Our Heroes

The heroes of My Next Season are the executives who have made the transition successfully and found happiness and fulfillment on the other side. We highlight a few of our heroes here but are constantly adding to our library in order to have many stories and reflections about the journey to share with our clients.

Bryanformer President of a Large Oil Company

Unfortunately, I didn’t do much planning for my transition to retirement. When the time came, I was mostly worried about how I would replace my intense 70-hour work week with other satisfying activities. Due to my lack of planning, however, I was unwilling to make long-term commitments until I figured out where I wanted to spend my time. I was offered several directorships with large corporations but was concerned that my hands-on style would be frustrating in board roles. Once I had time to discern all of my options, I ended up finding opportunities in the charitable world where I could make a significant difference. My priorities in retirement have included staying busy and feeling productive, making an impact on the organizations where I volunteer, playing an active role in the lives of my 10 grandchildren, becoming and staying physically fit, and taking the time to travel internationally.

Advice for future executives who will transition: (click to expand)
  • Think about how you want to fill the relational void that comes with retirement. I quickly learned that I missed the frequent interface with my colleagues and the camaraderie of working toward a common goal. To help with this new void, I spend a lot of time maintaining contact with a long list of former work colleagues.
  • Do some serious thinking about what you really want to do with this time in your life – what would give you satisfaction and enjoyment. One of the most rewarding aspects of being retired is the control it gives me over how I want to spend my time. Shift your mentality from focusing on the things you “should” do to the things you enjoy.
  • Think about your next season as refilling your life with a new job in which you have complete freedom to choose – find something which is fulfilling and purposeful.
  • Talk with and gain counsel from others who have already navigated their way into a satisfying retirement.
  • For me, it was important to “hit the ground running.” You know yourself best and can gauge how much activity you’ll need. I scheduled my time with new roles and activities quickly so there was little down time immediately following the transition.
  • Don’t underestimate the volunteer world. I have thoroughly enjoyed serving in an advisory role to the CEO of a not-for-profit organization. There are a vast number of very interesting challenges that can use your skills while making a positive impact on a good cause.

Jim, former Chief Human Resources Officer for International Corporations

I spent my entire career having a game plan. I was deliberate in strategizing each move, never leaving anything to chance. I always knew what needed to be done. For some strange reason, however I didn’t have a plan for how I would spend my time during retirement. I thought it would be a natural transition. I thought, “I’m passionate about everything, so I’ll find other things.” Well, retirement came and there was no soft landing.

Advice for future executives who will transition: (click to expand)
  • Plan your retirement. Have something to go to immediately. Process this upcoming season before it arrives. Don’t wait until you are already retired to figure it out. There are emotional ramifications that come without a plan!
  • Engage in activities or things that are mentally challenging and stimulating. Know what you need. You’ve been living in a challenging landscape for most of your life, and to lose this altogether can be extremely disheartening.
  • If you’re thinking you’ll start an abundance of new hobbies/activities post retirement, think again. If you are not already incorporating such interests into your life now, you probably won’t in retirement. Have realistic expectations and set goals before retirement arrives.
  • If you are an extrovert, schedule time to see people regularly. Be intentional about extending invitations to people with whom you’d like to be connected.
  • Use some of your newly available time to spend with those you love. I have gotten to spend more time with my grandchildren and it has been wonderful.
  • Anticipate the changes ahead – physically, emotionally, and mentally. Give yourself space and time to adjust to this new lifestyle and to feel the normal ups and the downs of the transition. Be gracious with yourself – you’ve earned it!

Karenformer Executive of Fortune 50 Company

When my company went through a restructuring, I found out that I would be transitioning sooner than I had originally planned. I still had some time to prepare, but I was afraid of what life would look like on the other side. My worst fear was waking up on the first morning after leaving, and realizing I had nothing to do. It’s terrifying to think of a life without any purpose or anything to look forward to.

Advice for future executives who will transition: (click to expand)
  • Take back control of your calendar. When my retirement came, I knew that I needed a break, but I didn’t want to completely give up work. In this new season, I have the option to work, but I can also work on my own schedule.
  • Take advantage of a second chance with your family. I spend more time with my children and grandchildren now and even volunteer at my granddaughter’s school. Look for new opportunities to connect.
  • Listen to others, but process the information on your own. Gather advice from friends and colleagues, network, and be open to opportunities but filter them according to what you really want to do in your next season.
  • Join an exercise class. It will keep you fit, and provide a great way to make friends, since you aren’t going to the office every day.
  • Rediscover an old hobby. I took a quilting class and finally learned how to use the sewing machine that had been gathering dust in my basement.
  • Learn how not to be in charge. It’s tough when you go from giving direction to being a participant. Let go of the frustration; it can actually be quite freeing.
  • Envision what type of day will be fulfilling to you and bring you joy. Create that day by including a variety of activities that will make you excited to get out of bed every morning.
  • Find a way to “pay it forward.” I really enjoy mentoring young executives, providing advice and guidance with their career and life goals. It’s something I didn’t have access to in the early stages of my career. Coaching some of the “rising stars” I’ve stayed in touch with has been a pleasure; I always walk away feeling energized.

Rich, former Private Company President and CEO

After working for seventeen years in public policy and moving to the corporate world for another twenty, I’m now ready for what my wife and I call “Life 3.0” I’d been working with my board leadership for five years on a strong succession plan, so I knew that they were in good hands when it was time for me to leave.

Advice for future executives who will transition: (click to expand)
  • When most people think about what they want to do after retirement, they think of themselves as an individual. For anyone who is married, however, these decisions are for both of you. It is very important that your spouse to play the role they deserve in your plans moving forward.
  • Do some research. My wife and I talked to a dozen couples and read several books, as we looked forward to our retirement. Many suggested that we ‘hit the pause button’ and take a sabbatical to refocus. We’re going to take three to six months off, do some traveling, and refocus on the things we want to pursue in “Life 3.0”
  • Embrace spontaneity. As I was about to retire, I was approached to lead a year-long civic project that was very important to our region and our state, so we pushed back our sabbatical. It’s been an enriching experience but required flexibility with respect to our initial plan.
  • Focus on your faith. My wife and I find our faith very important. It drives our life, so we’re using our new found time to engage more in faith based causes, in prayer, and studying scriptures.
  • Leverage your strengths. My wife and I have different strengths and weaknesses. As one team in this new phase of life, we can work off each other to be a more effective pair. I am called to be in a supportive role as she leads based on her strengths.
  • When you are approached with offers for things to do in your next season, many of them will be appealing and/or tempting. Don’t be afraid to say “no” to things that don’t fit with your schedule and priorities. Be discerning about your choices and recognize that you are seeking the ‘best yes’.

Jim, former President of a Large Canadian Oil Company

My departure was unplanned and was the result of a corporate reorganization. Despite the fact that I was caught off guard, I’ve been able to phase into retirement by slowly and steadily scaling back my responsibilities. Initially I worked as CEO of an organization and then switched to serving on five boards, two of which I chaired. Eventually I was ready to reduce my overall number of directorships. Board work allowed me to maintain my stature in the business community while progressively decreasing my time commitments. Despite the initial shock of the unplanned change, I have been delighted with the choices I’ve made and the opportunities that have come along.

Advice for future executives who will transition: (click to expand)
  • Prioritize your family. Be wary of taking on too many responsibilities that you’re unable to spend time with your family. I gain great satisfaction from the time I spend with my children and my wife of 40+ years.
  • Pay attention to your health. I have lost 50 pounds since retirement and I now work out regularly.
  • Continue to be mentally stimulated. Keep learning!
  • Find a way to use the skills that come the most naturally to you, though with progressively less time commitment than your previous career.
  • Be patient with yourself as you walk unchartered territory. Because I didn’t have any advance notice, it took me about a year to feel confident in my path. It takes time!

Patriciaformer Managing Director of Fortune 20 Company

I’ve really lived through two retirements at this point. When I initially transitioned out of my corporate role, I wanted to keep working but in a different setting, so I took a position as a university administrator. Now a few years later, I’m moving out of full-time work and discovering a new season for the second time. Retirement isn’t a “one-and-done” experience but a series of exciting choices and transitions.

Advice for future executives who will transition: (click to expand)
  • Accept when it’s time to move on. I could feel myself losing intensity towards the end of my corporate career, and I knew I needed a slower pace of life. I could have hung on for a few more years, but I did what was best for me at the time.
  • Consider doing some self-assessment. I talked with my friends and former colleagues and also attended an intensive executive program designed to assist in career transitions. This helped me focus in on what I really enjoy doing as well as what I am good at.
  • Working at a University can be a nice balance between the corporate world and a not-for-profit. It is often run more like a business in that there is more structure; but it also has the not-for-profit mentality where the focus isn’t as concentrated on efficiency and the bottom line.
  • Keep your expectations realistic when joining a not-for-profit. Your experience as a top tier executive will be valued, but you will need to be sensitive to the organization’s employees, policies, and experience. Don’t expect to make changes on the first day; there will be a lot for you to learn as well. Listen before making decisions.
  • Know that even though working with a not-for-profit can be extremely rewarding, it can also be frustrating. It may not be as stressful as a corporate job, but resources are limited and the pace of decision-making can be slow.
  • Do something that you are excited about every day when you wake up. This is a season of life where you have more flexibility, so do things that makes you happy.
  • Don’t be afraid of having days where you have nothing on the schedule. With this free time I’ve visited museums, gone to the movies, met up with friends, or just stayed in to read a book. Don’t worry about boredom: you can counter that if and when it comes.
  • Allow yourself the freedom to change your plan if it’s not working out. I know I have a hard time quitting something once I start, but, at this point in life, I think it is more important to enjoy what you are doing. Make the most out of this new season in your life and every experience you choose to create.

Sam, former President of a Large Oil Company

Thanks to my wife, I was prepared to make a smooth transition to retirement. My wife encouraged me to think about post-retirement six years before I made this transition. Because of the advanced planning, we decided to restore a historic house that is now our new home. Before both the move and my retirement, we started spending holidays in the area of our new home and got to know the surrounding community. I also became very active in industry associations before retirement, which set me up for board positions. This brought continuity and ease to the transition.

Advice for future executives who will transition: (click to expand)
  • Start planning your retirement well in advance and be intentional about building your community.
  • If possible, start getting involved in post-retirement activities before you retire so that you have a smooth transition.
  • Establish a new home in a different location well in advance so that you not only have a fresh start, but you have a social network established.
  • Have a good partner – worth her weight in gold!
  • Start making external contacts beforehand. Network while you work so that you have a better chance to get on boards or pursue other opportunities of your choosing.
  • Continue to learn. As a CEO, I juggled a lot at once and was constantly learning and growing. I knew I’d be bored if I wasn’t challenging my mind or taking on some sort of responsibility.
  • Even retirement can have different phases. What you want to do and how you want to spend your time may change as time goes on. As I approach 70 years old, I find myself leaning more towards not-for-profit and educational work, rather than corporate boards. Allow yourself the freedom to change your focus.
  • Make the time to attend family events. Now is the time when you have more free time than you’ve ever had. Use this time to be around the people you love.

Vickiformer Executive Vice President of a Fortune 500 Company

After working for the same company close to thirty years, I needed a change of pace, so when the company went through a major restructuring, I decided to leave. Moving forward I seized new opportunities as they came along, eventually leading several large not-for-profits. You need to have a plan as you begin your transition, but don’t be afraid to adapt to unexpected adventures life brings to you.

Advice for future executives who will transition: (click to expand)
  • Follow your heart when working for a not-for-profit. I became quite interested in inner city poverty through my marketing work for a city, and that’s what led me to my first large philanthropic position.
  • Bring your skills from corporate America into the not-for-profit sector. The industries may differ in a lot of ways, but many of your best practices can cross over. Paint a vision, lead your team, define a strategic plan, and set up metrics just like you would in a corporate position.
  • Protect your free time. I still work full time, but now I guard my free time with dedication. I don’t work on Sundays, I try not to stay in the office late, and I spend more time with my family. If you want to work in your next season, try to find balance.
  • Do your research before jumping into a leadership role with a not-for-profit. People think that charity jobs are easy, but they can be just as demanding as a corporate position because of their limited resources. The reward is great, but make sure you know what you’re signing up for.
  • Reach out to those who are less fortunate. There is a strange belief that those in worse circumstances are vastly different than us, but through my work around the world, I can tell you that people want the same things everywhere. You can make difference by helping out.
  • Figure out your passions and follow them because that is what will help you succeed and love what you’re doing.

Ed, former CEO of a Large Oil Company

My corporate DNA and training for deliberate analysis and planning contributed to thinking through my retirement well in advance. I retired at age 55 and was fortunate in being able to choose the timing myself. Because of a two-year restriction on board memberships, I used that time lecturing at my alma mater, overhauling personal finances, and embracing a new hobby: photography. After the initial two years, I joined four boards and volunteered with four non-profits, which occupied 50% of my time. Even though I was very careful about which board positions I accepted, the workload was a bit much. I miss the intellectual stimulation of making complex decisions and the quality of my colleagues, but I am really enjoying spending more time with my family. I hope to start focusing on my physical health – good thing I still have time to work on this!

Advice for future executives who will transition: (click to expand)
  • Leave your career/company when the timing is right for you. If you can, make the decision for yourself.
  • Have a plan to be busy/active on day one and start some of your planned activities before you retire.
  • Develop a rainy-day interest. Most of the activities people talk about are outdoors and don’t work when the weather is bad. Have some activities that are versatile.
  • Join outside boards before you retire if they add to your skills while working. After you retire, consider adding boards that will expand your learning.
  • If you desire to get involved with non-profits, be aware that they have fewer resources, which results in you doing more work yourself. It’s a different experience than corporate boards.
  • Get used to self-initiation. The pace of life is changing and you will no longer be fighting to stay ahead of the fire hose.
  • Simplify your life!
  • Don’t feel the pressure to travel, especially if you traveled often during your career. My wife and I decided to pay for our children and grandchildren to come see us twice a year, so we still get to see the people we love without leaving home.

Billformer Fortune 50 Operating Company President

In retirement I have spent a lot more time with my wife and I have really come to enjoy my time with her. I have loved having more time and flexibility to schedule things that are of interest to me.

Advice for future executives who will transition: (click to expand)
  • Think about retirement as a project and think about something that you can move into the day you retire.
  • Think critically about how you want to spend your time when you’re retired—find what you’re passionate about.
  • Commit to things that aren’t long term.
  • I decided to build a house in the islands and kept a home on the west coast. I wish I had made the move immediately to be closer to my son which I have now done, 10 years later.
  • Where you live has tremendous long term implications.
  • One of my biggest learnings was that weekends are important and that you need to establish a regimen that gives you a break from work otherwise you’ll never stop – even in “retirement”.
  • You shouldn’t wake up each morning asking yourself what you’re going to do. You need to wake up in the morning excited for the things you will do.
  • I cannot emphasize enough that this is a very important step in life that requires a lot of thought.
  • Physically moving was very helpful for us because it stimulated new patterns of behavior and made the transition TRULY a NEW transition.
  • At the end of the day, the skills that you acquire through your job are your skills you will take with you wherever you go. Wherever you can use those skills and be a true asset is where you should take your time and talents.

Michael, former Fortune 100 President/CEO

I made the transition from President/CEO to Vice Chairman and that was a very difficult move for me. When I decided to address some problems within the company, I did not enjoy the support from the board. I was promptly asked to retire and was given a generous package. I realized I needed to sever my emotional relationship with the company because it was eating me alive. It has continued to anger me for years after leaving and now I have ill feelings toward the company I spent my entire career with.

Advice for future executives who will transition: (click to expand)
  • I wish I had thought more about the transition process.
  • You need to focus a lot on personal relationships because they get shortchanged during your career.
  • You need to realize that there are certain things you can control and others that you cannot.
  • Retirement is good. For some it is a death sentence. It is good to retire healthy so you can truly enjoy your next season. Don’t look back. Create a new future for yourself.
  • Spend time enjoying the things you love to do. Don’t empower those in your past to control how you feel in this important phase of your life.

Robert, former Fortune 200 Operating Company President

I decided to retire because I found I was not spending nearly enough time with my family. I took 2 years to prepare the company and myself for my retirement. From the company standpoint, my transition went really well because I gave myself enough time to prepare for my next season. The timing was perfect considering the company was coming off of a strong financial year, successfully coming out of the challenges caused by financial meltdown.

Advice for future executives who will transition: (click to expand)
  • Overall, I wouldn’t have changed a lot. Take time to prepare yourself and the company.
  • As I have watched others retire, I have seen that those who are successful accept that life is going to be different during retirement than it was before.
  • Filling one’s life with something purposeful is the beauty of retirement.
  • Those who feel useless or guilty that they are no longer working are unsuccessful in retirement. This is probably because they haven’t filled their lives with a retirement activity equally as engaging as the workplace. Some people do find an equally engaging substitute. Others don’t. I had a friend who was planning to play a lot of golf during retirement and ended up playing so much he got burned out and didn’t enjoy it anymore.
  • For me, the horizontal breadth and diversity of activities has successfully taken the place of the vertical engagement of the working years.
  • Retirement is the “jubilant” phase in life! Try to celebrate every opportunity, and make others have happy moments.
  • To be jubilant in retirement however, one needs to have a strong foundation, which starts with a solid financial plan. “Financial security” is a necessary but not sufficient condition for success.

Amy, former Executive Officer of a Fortune 50 Company

My transition went very fluidly because I had worked so intensely for so long that I was ready for more breathability, flexibility, and rejuvenation. I had a lot of pent-up energy that I wanted to use to explore interests beyond my corporate career, while still drawing upon the skills and experiences that I had gained. Retirement gave me the opportunity to try new things and engage in different and more creative activities.

Advice for future executives who will transition: (click to expand)
  • After retiring, I began to do consulting as well as work with corporate and not-for-profit boards.
  • These were great avenues to use the skills I had honed in my corporate career while still maintaining more personal freedom.
  • Explore creative opportunities that you couldn’t while you were working. Since retiring, I’ve begun a writing project, and have taken up gardening: two activities I love but didn’t have time to enjoy before.
  • Use your experience to mentor younger people. I have been able to coach a lot of talented younger individuals who are just starting off in the business world. They are eager to hear your wisdom, and you can be a powerful influence in their lives.
  • Save time for family. Retirement really allows you to be available for your loved ones. Be sure to cherish the gift of that time together.
  • The best part of retiring is having the opportunity to make more choices about how you spend your time. Don’t limit yourself. Be open to exploring new possibilities.
  • Explore a range of activities and don’t jump right into just one thing because you could be closing yourself to a lot of interesting opportunities. I have ended up with a diverse portfolio of work which I love.
  • Everyone needs structure, but try to distinguish between structure that confines and overcommits you and structure that allows you to explore new things. Don’t box yourself in.
  • The notion of a My Next Season Bucket List can be helpful. It is a way to identify new kinds of goals and experiences that can be fun, creative, and fulfilling.

Frank, former Fortune 100 Director

I spent the last five or six years of my career thinking about what I wanted to do next. My company hired a lot of consultants, and I thought that might be something I would like to do. After working for one company for so long, I wanted to see what else was out there.

Advice for future executives who will transition: (click to expand)
  • Use your connections to help you find something for after retirement. Networking and marketing yourself will take a lot of time, but they will pay off in the end.
  • Use the skills that you already have in your life post-transition. You can use the talents you utilized in your corporate job in a different environment after retirement.
  • Spend a lot of time thinking and preparing, so that retirement is in the back of your mind for a number of years before you actually retire. You can’t start thinking about retirement, the day you’re packing up your box and leaving the office.
  • Do a self-assessment of your skills so you can really see where the best place for you is and decide ahead of time how productive you want to be.
  • Take a little time off in between your work and your next job, but not too much because it can be seductive to do nothing, but you will end up stale and sluggish.
  • Broaden your interests and find a good balance in your life. You need to leave time for your family, work, hobbies, spiritual life, health, and time to just have fun.
  • One benefit of the technological age is that you can work from anywhere. You can work from vacation and no one minds as long as you get the job done. I take calls looking at the ocean.
  • Talk to others. Don’t try to do the transition alone. Get advice from your family, your spouse/partner, your friends, or even others in the business field. Sometimes they can see things about you that you can’t see.

Peter, former President of a Large Oil Company

As a result of a merger and subsequent corporate reorganization, I agreed to my retirement date about a year in advance and my transition was very smooth. My priorities for retirement have included improving my health through regular exercise, staying intellectually stimulated through a few corporate boards, managing my own money, spending time with grandkids, and enjoying the outdoors to fish and golf. For me, the key has been to stay active and not let myself get bored.

Advice for future executives who will transition: (click to expand)
  • Really pay attention to your physical health. I have been surprised by how many of the executives I see on boards do not take good care of themselves.
  • Be prepared to miss your executive assistant. You may be surprised to find out just how valuable your assistant was when you were working. Thankfully, board work often includes access to administrative support.
  • Think about how you want to use both your money and your time. You have worked hard to get to this place, yet this freedom in choice can be overwhelming at times.
  • Weigh the pros and cons of board work carefully. Think about if it will be difficult for you to serve in an advisory role versus a management role, as well as how much time you are willing to devote.
  • Stay active and don’t resign yourself to a stagnant lifestyle.
  • Spend time outside. No longer are you cooped up in meetings, lunches, and work trips. Take advantage of this available time to enjoy nature.

Richard, former Executive Officer of a Fortune 50 Company

My transition was somewhat of a shock. I was not prepared for life outside of my corporate job. You go from having 15 meetings a day and 100 people trying to get on your calendar to having absolutely nothing to do. It’s a huge change and you have to prepare for it.

Advice for future executives who will transition: (click to expand)
  • You need to have more plans than just a broad generalization like “I want to travel” or “I want to play golf.” What are you going to do when you wake up and then the hour after that?
  • There are lots of advisors who can help you with your finances or your health in retirement. You need to think beyond that, however, and plan what you’re going to do with your time as well.
  • Most people nowadays don’t want to retire in the classic sense. They just want to be able to do something completely different. I started a second career as a coach and advisor so that I could use my skills in a new way.
  • Just because you aren’t working at your company, doesn’t mean that you can’t still be friends with your coworkers. A lot of my colleagues have become my close friends, and I still see and talk to them regularly.
  • Try new things. The best part about retiring is having the luxury of doing things I couldn’t do before.
  • Spend time with your family. As an executive, I had to miss a lot of important events in the life of my family.
  • Retired, I had the time to become reacquainted with my spouse and witness all the milestones in my children’s lives.
  • One of my most difficult adjustments was not having an executive assistant to book my travel and meetings for me. Everyday tasks became a little bit harder when I had to do it all myself.
  • Take self-assessment tests. Sometimes after doing one thing for so long, it’s hard to even remember what your interests are outside of work.

Charles, former President and CEO of Fortune 100 Company

I was not ready to be done working at the time my company asked me to retire, so I began to look for opportunities to work even after retirement. I wanted to do something truly new and different, so I joined boards in industries that interested me, but in which I did not have a lot of experience. I looked for places where I could find opportunities to learn, work, and grow.

Advice for future executives who will transition: (click to expand)
  • Make the best use of your time and realize that retirement is not your last transition but is instead the beginning of a series of transitions for which you need to prepare.
  • Retirement gives you the freedom to manage your own time and priorities, and to discover what those priorities are. Don’t let that time go to waste.
  • Find things that interest you and in which you have skill and expertise. If you can determine what those subjects are, you can use them to have a great retirement.
  • I didn’t know what I wanted to do immediately, so I took a summer to relax and begin to wrap my mind around the future. Planning ahead is key because these decisions are important ones.
  • Spend time speaking with people who have already gone through these transitions.
  • They have great advice and their wisdom has significantly benefitted me during my transition.
  • When planning, listen to your spouse and/or family. If I’d been a better listener, I would have been able to accommodate their needs better and sooner.
  • Find a strong financial advisor, because your finances are crucial in making your transition a smooth one.

Wayne, former Director at Fortune 100 Industrial Company

I wanted to get involved with not-for-profits while I was working, but I traveled so much that I didn’t have the time. After retiring, I got involved in a lot of efforts within my community, which supplements my activity level and I really enjoy.

Advice for future executives who will transition: (click to expand)
  • Ground yourself outside what you do at work so that your identity is not only tied to what you do for a living. Take pride in the many roles you play. You’re a lot more than your former job title.
  • Try to stay grounded when you are a CEO so that when your corporate perks are taken away, you still have things to keep you happy and motivated.
  • Assisting your replacement as a consultant is a great way to ease out of corporate life.
  • Manage everything with your spouse or partner.
  • In many cases, they struggle just as much as you do and need help transitioning as well.
  • Use your free time to leave a legacy to your children and grandchildren. One of the things I’m doing for them is writing a book about where I’ve come from and what I’ve done.
  • Enjoy your freedom. You get to do your own planning. Stay busy, but save time to relax.
  • Get a doctor and a financial planner younger than you so that you have them for the long run.
  • Be comfortable in your own skin and the person that you will be after retirement—at parties you are no longer an executive, but you are a grandfather of four and an active board member in your community.

John, former CEO and VP of Fortune 10 Company

One of the best aspects of my transition is that I can spend more time with my children and grandchildren. Retirement allowed me to take trips with my wife and kids to places that we had always wanted to go, but that we couldn’t because of my work schedule. Now that family is my priority, I can be a powerful influence in the lives of my wife, children, and grandchildren.

Advice for future executives who will transition: (click to expand)
  • Examine your personal priorities. I was putting my work ahead of my family. Now, I live closer to my grandchildren, and I am able to play an active role in their lives.
  • Make up for the time you lost with family and friends while you were an executive.
  • Give back to the community. I’ve become more active at my alma mater, which has allowed me to connect with other graduates and rekindle relationships with people who attended school with me.
  • Leave a legacy to those in the next generation.
  • I got involved at a local high school. I teach the students there about business and help to get them real-world experience.
  • Travel. I gained a lot of new perspectives while traveling to meaningful places with my family and church.
  • The more involved you are, the easier the transition is.
  • Spend more time with your family and be visible to them. Family is something a lot of executives overlook during their careers, and retirement allows you to change that.
  • Do what you love to do for fun.

Norm, former President of Business Unit of Fortune 100 Company

When I had major back surgery, I decided it was time to retire. I had originally wanted to help build homes for those in need, but the surgery prevented me from being able to do this. I found a new unexpected calling working for a not-for-profit. It helped me make my Next Season a productive one, as it allowed me to greatly contribute with the skills I had gained in the corporate world. It really consumed my days and nights—and how I spent my weekends. I have felt like, through this effort, I was making a difference and giving back.

Advice for future executives who will transition: (click to expand)
  • Don’t just sit around. Initially I followed the stock market on television and bought groceries.
  • Then I began to open my eyes to really ask myself, “What will my Next Season be? What do I want to do?”
  • Being at home without a plan is not a sustainable way to spend retirement. You need to seek more activity.
  • Take the skills you have learned in your years of business and apply them to new situations.
  • Business people can really help not-for-profits if they find a not-for-profit that might fit what they want to do.
  • Retirement is a great time to spend more time with your loved ones and make memories for your children and grandchildren.
  • Plan activities for you to be involved in by yourself.
  • Family is important, but everyone has their own individual schedules and lives. People think family, golf, and travel, but a lot of time you need something more to fill up your days and give you purpose.
  • Having a well-thought-out plan of what to do after retirement is paramount. If an individual thinks they have everything figured out by only having a date to retire by, they have already lost the battle. You need to put a lot of thought into the level of activity you want to have upon entering your Next Season and where you specifically want to be involved.

Vanessa, former CEO and Chairwoman of Fortune 100 Company

I had been planning towards and thinking about retirement for years before the date actually arrived. I wanted to be on boards and do consulting work, but first needed time to relax and think. Staying positive and enjoying the fruits of my labor was really important, because I’d worked hard for years. Now was my chance to reflect on all the good I’d been able to do for the company and the individuals I worked with. I also wanted to slow down a bit from my frenetic pace.

Advice for future executives who will transition: (click to expand)
  • Take time to reflect on your accomplishments and consider your options before jumping in to new endeavors. Waiting a little while can give you a fresh perspective and new doors may open to you in the meantime.
  • Try and find a way to utilize your talents: You can stay busy and make some extra money without having to put in seventy hour work weeks.
  • Take the opportunity to try new things. I’m now serving as a trustee on a university board and I’m loving the experience. I love interacting with the college students, mentoring young people, and being involved in shaping so many people’s lives.
  • The best part of retirement is the ability to pick and choose what I want to do, which I think is the dream of everyone with a Type A personality. I get to decide how I spend my time, and I have more time for the people who matter to me.
  • Create a new structure for yourself, because you’re used to having a structured life. Just make the structure more open so you have more freedom within your order.
  • Get involved with projects that give you energy. I love working with young people because it energizes me while helping to create a lasting legacy.
  • Add value to whatever you do. Don’t just show up.
  • Take all of the extra worries off your plate. I wish I’d sold my big house sooner, because I worried about it more than I needed to.
  • A lot of retirement is keeping your energy up and staying positive. Get up. Get involved. Get going.

Nancy, former Not-for-Profit Board Chair, Leader, and Consultant

I’ve never fully retired; I just keep reinventing myself as I move through the seasons of my life. I’ve worked in banking, as a finance professor, as a leader of several not-for-profits, and as a development and education consultant. The key to a successful transition is to be open to new experiences, think positively and be resilient.

Advice for future executives who will transition: (click to expand)
  • As I reflect on my life, I can honestly say that through prayer, faith-filled friends, and circumstances the Lord has led me to challenging and rewarding opportunities that I never would have imagined. If you are a person of faith, I encourage you to pray before making any firm commitments. Ask God for guidance and discernment as you consider plans for your retirement.
  • Reflect on your life and do a lot of “self-studying.” When I transitioned, understanding my personal preferences, talents, and strengths helped me decide where to focus. Reading books on self-assessment and taking personality tests can be helpful when seeking a new direction in life.
  • A key to a healthy transition is having a strong support system. Mine would not have gone as smoothly without my husband, adult daughters, and friends encouraging me.
  • Be patient and allow yourself time to explore new opportunities. You never know what new activities you might enjoy or where your skills are most needed.
  • After you’ve reflected on your strengths, values, and past experiences, there comes a time when you need to stop looking backwards and start moving forward. You need to face the future with joyful anticipation, and you can’t do that if you’re fixated on the past.
  • Try to find that elusive balance in life of helping others, enjoying your family, and developing yourself.
  • Use your relaxed schedule and freedom to explore opportunities for service to a non-profit organization. I am helping three non-profit organizations find funding from foundations to support projects for the poor and disabled.
  • Find activities that you and your family mutually enjoy. My husband and I travel more and have even reconnected with friends from our youth.
  • Do something just for yourself. I devote more time to strengthening myself physically, mentally, and spiritually. I take exercise classes, work out on my own, and read fiction, non-fiction, and spiritual literature to keep my faith strong and mindset positive.

Markformer Executive of Fortune 10 Company

When my company and I decided it was time for me to retire, I was ready. I’d spent thirty years with the same company, and there really wasn’t any place left for me to grow there. When you get that high up in a corporation, open seats become harder to find. A number of head-hunters tried to recruit me right away to do jobs I’d already done, but I wanted to try out some new things.

Advice for future executives who will transition: (click to expand)
  • I’m a learner and an achiever, so I knew I wanted to go back to school after I retired. The experience has been extremely rewarding and refreshing after so many years in business.
  • Use this time to give back. I volunteer with several organizations I wouldn’t have been able to serve with during the height of my career.
  • The best preparation for retirement is to not define yourself solely by your work life. If you can maintain a focus in other areas of your life, then leaving your job doesn’t seem like such a huge blow.
  • Talk to as many people as you can about your transition. They’ll often have great advice to share.
  • I’m still probably just as busy as I was at my old job, but now I get to decide 100% of what is on my calendar. I get to go to school, volunteer, serve on boards, and spend time with my family all on my own time.
  • Make sure to use your freedom to get in sync with your spouse/partner. My wife and I sit down with our schedules every week and plan things together.
  • Stay in shape. I try to exercise at least four times a week so that this next season can be a healthy one.
  • Take your time before you jump right into something. This is your first chance in decades to look at your life and decide what you want to do. Use this as a chance to rescript your life and do something new. Executives have the tendency to always want to be doing something, but sometimes it is best to push your pride aside and just reflect before moving forward.

Eliformer Vice President of a Fortune 500 Company

I retired because I wanted to do something new and different, so I gave ten months’ notice to my company and began the next chapter of my life. All I did was relax for a few months, but I was looking for new ways to use the skills and expertise I gained during my career, so I transitioned into consulting. After a few months of that I transitioned into business start-ups. Retiring doesn’t mean you have to be done working, and if you enjoy what you are doing it isn’t really working anyway .

Advice for future executives who will transition: (click to expand)
  • Leaving a corporate position can be a dramatic change. After living within a certain routine for years, transitioning to something new can be daunting. Mentally preparing can make everything easier.
  • Make plans and have goals, but don’t put on blinders. Move into your next season with some forethought, and be open to new experiences and opportunities that might not arrive until after your transition.
  • Take the opportunity to volunteer. Since leaving my corporate position, I’ve had more time to serve at my church and on the board of a local museum, both of which have been rewarding.
  • The best part about being retired is being able to do what I want when I want to do it. Don’t paint yourself into a box with too many commitments right away.
  • The world is full of interesting people and new doors to open. Take advantage of both in your next season.
  • Writing down your goals and reviewing them can help you stay on track. Having a concrete mission can help you avoid saying “yes” to things that you will regret later.
  • When you retire, people want to know how you plan to spend your time, but don’t be in a hurry to answer that question. Take time to think and relax before jumping into your next phase of life.


Tomformer Primary Care Physician

While I had loved my years working as a physician, the practice of medicine had changed greatly in the years leading up to my transition, and I felt ready to retire. I started cutting back two years before my last day of work and spent that time planning for what my next season of life would look like.

Advice for future executives who will transition: (click to expand)
  • Try to find a cause or organization that you love that you can pour your time into. Since retiring I’ve become much more involved at my church. I’ve joined the governing body, started singing with the choir and praise band, and led several major construction projects, work that has made a difference in the community.
  • The gifts of retirement are that of time and choice. Now I have plenty of time and the ability to choose my own ways to fill it.
  • Financial security and good health are two huge advantages in retirement. Don’t take these for granted if you have them.
  • Make sure to have a clear place to spend your time after retirement. Are you going to put in time on a board, at the church, at school, at a second job, traveling? Don’t retire without a plan.
  • I’ve really enjoyed reading more during this season of life. I have more time, and can spend hours with a book now, where before I could only read for brief snippets of time if at all.
  • Use the skills you learned during your career in new ways. Since I was a doctor, I now volunteer with Hospice, which has impacted so many people during such a difficult time during their life.
  • If you are religious, use retirement as a time to grow in your faith. I’ve become a much stronger and more committed Christian during this phase of life.
  • Take this opportunity to improve your health. Spend time focusing on your physical health as well as your mental and spiritual health.

Jeanformer Executive Officer of Fortune 50 Company

Several difficult life events influenced my retirement. As a result, my focus was entirely on family health situations with little time for intentional thought on what I’d do next. When things settled down, I decided to pause and contemplate my life path before eventually deciding to begin the next chapter in my life. I’ve always been adaptable, and this was an opportunity to adapt again and try something new.

Advice for future executives who will transition: (click to expand)
  • Deepen your roots and connections wherever possible. Since I’d moved countless times for my career, I decided that for this new chapter I wanted to become more engaged with family and friends, planting roots in my community.
  • Get advice from others. When you’re deciding what to do next, talk to your friends and see what suggestions they might have. Then do the same for others when they are beginning their own next chapter.
  • Take some time to pause and reflect. This may be the first time in a long time you have not been dictated by non-stop activity. Take advantage of the calm. Accept that your daily life will change, but drive the change yourself.
  • Keep some structure, but make sure that you leave time to be flexible as well.
  • Think of how you can draw on your skills and experience in other environments. I have found coaching young professionals to be very energizing. They truly listen and are very interested in what you’ve learned. I help out in a local school one day a week, and it is so rewarding to have an impact on the young students.
  • Invest in the people who mean the most. Enjoy and value those relationships. Touch base with former colleagues and let those friendships deepen in a new environment.
  • It’s ok to try something new. There is no better risk to take than taking a risk on yourself. Jump in and do it!

Kathyformer Partner, Management Consulting Firm

My transition was wonderfully smooth because I spent a lot of time planning ahead. After thirty years of traveling for business, I was ready for a change in lifestyle. I’ve always known I wanted to retire early, so I’d been thinking about the transition for a while. I gave my company ten months’ notice so that I could finish well and plan a great new beginning.

Advice for future executives who will transition: (click to expand)
  • You’ve planned financially for retirement. Put similar effort into planning how you’ll spend your time.
  • A good friend gave me terrific advice when it comes to timing: Write a six month plan for the period before you leave your company so that you can end well. Jot down all of the things you know you would like to do in retirement. Use that list to shape a nine month plan for after the transition so that you can start well.
  • Define a purpose for your next season. Going in, I knew I wanted to spend time with family, spend time returning to college, and spend time volunteering. Over the past few years, I’ve thoroughly enjoyed all three.
  • After years of a packed calendar, I found having at least a little structure in place helped me. I started with two recurring commitments on my calendar.
  • Balance structure and flexibility. Flexibility is the best part of retirement for me. I feel so blessed that I can take advantage of opportunities on short notice.
  • I still consult and add to my list of things I want to do during retirement, and it has become somewhat of a bucket list for this chapter of my life.
  • If you are used to traveling for work, then always staying home, although a blessing can feel a little strange. Take a few road trips.
  • Sample things before committing. I tried out a number of volunteer opportunities before picking a few I wanted to stick with.
  • Start adjusting the elements of your life to fit your new chapter. Within a month or so, I was rearranging my closet and re-organizing my office to match my new roles as a student and a volunteer instead of a management consultant.
  • Explore your city and neighborhood and all they have to offer.
  • Ask others for advice. They can help you find ways to put your skills to work and pursue your interests. Be open to their ideas and try new things.

Markformer Executive of a Fortune 30 Company

At the height of my career it wasn’t uncommon for me to have six or seven work-related calls to take on both Saturday and Sunday. I didn’t have control over my time, I wanted to spend more time with my family, and I wanted to give back to the community. A year in advance, I began to plan for my retirement and think through how I wanted to spend my time and resources.

Advice for future executives who will transition: (click to expand)
  • Don’t be afraid to move on. I wanted to be able to give back in new ways and I couldn’t do that while working in corporate America, so I needed to try something new.
  • Think deeply about your transition: not just what you want to do next, but your strengths and weakness, where you want to be, and who you want to spend your time with. The more fully you understand yourself, the smoother your transition will be.
  • Leave well. After having a long career with my company, it was important to me to facilitate a smooth transition and maintain strong connections with my co-workers.
  • Use your skills in new ways. I’ve been able to use my financial, risk, and global team management skills to help several not-for-profits. It’s extremely rewarding to use these skills to help others. Strong leaders are in high demand in the not-for-profit sector; you might be surprised to learn how the skills you’ve developed over your entire career, and perhaps take for granted, might be used for good.
  • Mentor young businessmen and women. Individuals at the beginning of their careers can benefit greatly from your wisdom and advice.
  • Be intentional about maintaining and building relationships, whether to friends or colleagues. I try to schedule two lunches and a breakfast with different individuals each week to maintain these relationships.
  • Take time to make decisions. Pause, detox, and reflect before jumping into something new. You might not even realize the level of stress at which you’ve been working and living. It might be tempting, but don’t skip the pause – it will give you time to connect with family and friends, explore new possibilities, and gain important perspective.

Jimformer Chairman, President, and CEO of a Large Technology Company

I began to consider my retirement a year before I actually left my company. It was a good time for me to transition out, both for me and for the company, so I gave them notice in advance and worked harder than ever to finish well for my successor. As strange as this sounds, I think going through a company buyout earlier in my career helped my transition a lot. I wasn’t nervous or apprehensive about the unknown, because I’d already experienced it before, and I knew I’d be fine.

Advice for future executives who will transition: (click to expand)
  • Spend time evaluating and even trying options in different fields. I worked in private equity, managed assisted living facilities, and returned to a corporate job before I eventually created my own company.
  • Don’t lock yourself into doing something you don’t want to do. I made sure that my new position contained the aspects of being a CEO that I loved without those I didn’t enjoy.
  • Work with people you like. Whether it be a for-profit board, not-for-profit organization or your Alma Mater, make sure you are with people with whom you want to work and enjoy.
  • Take an almost clinical approach to understanding what you enjoy and why you enjoy those things. Sometimes taking an assessment test can help define your skills in a new light.
  • Talk to as many people as you can. Sometimes others understand what you need to be satisfied better than you do.
  • Find a hobby you love but haven’t spent time doing in a while. I enjoy landscape photography, but didn’t have a lot of time to do it at the height of my career.
  • You can have your cake and eat it too. I’ve started my own company, serve on boards, work with not-for-profits, and serve at my church. In this season you don’t have to limit yourself to one job or purpose.

Harryformer Executive of a Fortune 50 Company

When I retired, I’d spent nearly forty years working and was ready to transition when a new CEO took control of my company. I was lucky because I got to transition out slowly to help the CEO’s new staff. When you’re slowing down from 100mph to 30mph, take any opportunity to taper that you can get because it facilitates a smoother and more gradual transition.

Advice for future executives who will transition: (click to expand)
  • Be specific. Don’t just say that you want to “spend more time with family.” Actually plan specific ways that you’re going to do that, because otherwise you won’t get the results you desire.
  • Figure out what your talents are. When you’ve worked at the same company for decades, you have a warped view of your skills because you’ve probably been working with people who have a lot of the same talents as you. Ask people outside of work to help you discover what those might be and how to use them.
  • Only join a board if you can make a difference. Many people want to join a board just for the money or the title, but it’s really a waste of time for both parties, if you can’t make a meaningful impact.
  • Work with a not-for-profit whose mission matters to you – this is the season! I volunteer with the Wounded Warrior project because I was in the military myself, and I understand the sacrifice that these individuals have made.
  • Try being an advisor to a small company. You get to use your business expertise in ways that produce a huge impact. Your advice could make or break a company. I like to use the term “Angel Advisor” because I do it without pay and expectation.
  • Rediscover an old hobby. I’ve been spending a lot of time working on cars, which I love to do. In fact, sometimes it seems that I’ve become the neighborhood mechanic. It’s been an unexpected way to connect.
  • You and your spouse will be used to spending time apart after working for years. Make sure to plan time away from one another into your schedule. It’s healthy to determine what you’ll do together as well as what you’ll do separately.

Joeformer Senior Vice President of an International Company

I’ve always set goals for myself: physical goals, mental goals, career goals. When I felt like I had accomplished everything that I wanted to in my career, I decided it was time to retire and focus on some other aspects of my life. In this new season, I have goals as well, and because of these I don’t feel unproductive. I’m still working towards something.

Advice for future executives who will transition: (click to expand)
  • This season of life is a great time to see the world. Traveling for longer than a couple of days is now possible, and my wife and I take advantage of the opportunity, sometimes for weeks on end.
  • After I retired from my corporate position, I continued to teach as an adjunct college professor. Teaching can be a great way to add structure to your life and make some extra money without having the time constraints of a regular job.
  • Take up old hobbies. I used to fish when I was younger, but hadn’t picked up a rod in years. I took a refresher course at a local college and have loved getting back on the water.
  • Do what you love. I love golf and now I play more than the occasional game. I practice at the driving range, play with friends, and have even traveled around the world to play some of the more prestigious courses.
  • Think outside the box and try something new. I’ve always been fascinated by bridges, so I took an art class to learn to draw them. Now I’m planning to write a kids book about bridges.
  • Write down your goals so that they become more tangible. Try making lists like “50 Things I Want to Do in the Next Ten Years.”
  • Stay active to keep in good health. I go on daily walks with my wife, but I also do yard work, go get the groceries, work out, and play golf. Exercise doesn’t have to be dreaded.
  • When I worked, even Saturdays were not free. Now I’m like a 10-year old on summer vacation; the time is mine, and I get to make the decisions on how I spend it which has been a wonderful gift.

Tobyformer Physician and Professor of Medicine

For years I’d let my work consume a large portion of my life. I worked long hours in the hospital and didn’t trust others to handle my responsibilities while I was away. I couldn’t even relax on vacations. It took me a little while to allow myself to relax in retirement, but since I have, I have found my next season to be a rewarding and healthier one.

Advice for future executives who will transition: (click to expand)
  • Don’t continue to work just because you are afraid of what lies on the other side of your transition. At a certain point, fear of retiring may keep you from making the choice that’s better for your family, your health, and your mind.
  • When I started to think about retirement, I had a lot of apprehension and separation anxiety. While this may be natural, it’s important to push through the apprehension thoughtfully, to plan for your transition, and to understand you are making the right decision.
  • Although I suffered some guilt for not being at work for the first few months, the transition was easier than I expected. You just have to keep moving forward.
  • Keep learning. I’ve been a lifelong learner. I’ve loved learning about patients and diseases, and I didn’t want to stop learning so I’ve been taking classes at seminary and reading to stay sharp.
  • Don’t let your health go. When I retired I had a bad knee, but instead of sitting around and letting the knee grow worse, I’ve taken up an exercise rehab regimen that involves a lot of walking, swimming, and water aerobics. Now my knee is much better and I haven’t lost my mobility.
  • If you are a type-a person who is worried about feeling unfulfilled, then plan ahead so that you have something to do when you retire, just make sure they are things you want to do and not just things you have to do.
  • Music is a wonderful thing to rediscover in retirement. I’m taking piano lessons and a lot of my friends are picking up their old instruments as well.
  • This season of life has been a happy, healthy, and purposeful one for me. I laugh, smile, and sing more. Sometimes you don’t realize how wonderful relaxing is until you give yourself time to do it.

Marthaformer Executive of a Fortune 50 Company

After narrowly escaping a large executive level lay-off at my company, I realized that I needed to start planning for transition to early retirement on my own terms. My daughter was nearing the end of high school, and I wanted to spend time with her before she left for college. I had also committed to a couple of non-profit board positions that I knew would keep me engaged.  While I thoroughly enjoyed my career and my airplane seats aren’t as good as they used to be, I have fully embraced my new life.

Advice for future executives who will transition: (click to expand)
  • Plan not only for your exit but for your entrance into your next season. Before I retired, I agreed to deepen my service on a couple of non-profit boards. After retirement, I extended my volunteer work through my church and into education, both areas where I had a great deal of passion. I consciously booked my time early on doing things that were meaningful to me.
  • Your new-found free time is not endless and will be quickly absorbed by people and organizations who want to tap into your talents. Decide how you want to spend your time – and be comfortable saying “no” to things that fall outside your areas of interest.
  • Even if you think that you want to continue to work, resist any temptations (or calls from search firms) to immediately jump back into doing the same thing at a different firm or something new. Take some time for yourself to really understand what you want your next season to look like.
  • Think about the skills you have developed over your career and how you might be able to use them in a new way. I was able to transfer my financial, strategic planning, due diligence, and mentoring skills into a new role as officer and board member of one of the largest not-for-profits in the United States. The change is exciting, and it is also fulfilling to use the skills I spent years developing.
  • Strengthen and renew your friendships. Now that you have more time, develop your bond with others. I rarely had the time to take a leisurely lunch or a long walk in the neighborhood with a good friend. It is a true gift now that I try to embrace as much as possible.
  • Many people are afraid of retirement, because they are losing a long-developed identity. It took me at least a year before I stopped telling people what I “used to do” – as that somehow validated my worth. Establishing your new identity may feel uncomfortable, but this is a chance to redefine who you are. Take full advantage of the opportunity, and embrace the “new you.”

Joeformer Executive of a Fortune 50 Company

When my company reorganized their management structure, I was asked to step down and sign a non-compete. While I didn’t have much time to prepare before the transition began, not working gave me time to cool down, refocus my priorities, and decide what I ultimately wanted to do. Sometimes patience is the key in discovering the next chapter of your life.

Advice for future executives who will transition: (click to expand)
  • Remember when you were entering college, many moons ago? Many thought they knew what they wanted to study and the profession they wanted to pursue. Most, like me, changed majors a few times until they found what they enjoyed and felt would be the foundation for their professional career. I’ve found that considering what to do next is similar, it isn’t a straight path and may be opportunistic or may have a direct route. Patience and flexibility are in order.
  • Take time to travel. If you have the means, explore the world with your friends or family. You will never run out of fascinating destinations and experiences, and combining leisure trips with not-for-profit work can be rewarding as well.
  • Focus on those who matter most to you. In corporate life, your family often takes the back seat, so use this time to show them you care. I’m in better health than my wife so I’m glad I have the time to care for her.
  • Give back. Volunteer with a not-for-profit whether that be on the board, as an employee, or a volunteer. You can change the lives of others while learning new things about yourself.
  • People often put on blinders when they transition. Try to be open to new possibilities so that you don’t get stuck in a rut. Don’t be quick to say “no” to opportunities that may seem outside your comfort zone. This may be your season to say “yes.”
  • The best part about this season of my life is having free time. Pursue things you’ve always wanted to try, but have never had time to do before.
  • Share your expertise. Sometimes retirees are afraid to share their knowledge and experience in a new setting, but know that your guidance may be invaluable to others.

Benformer Vice President of a Fortune 50 Company

When I was a young man I had the opportunity to serve others through not-for-profit work in Japan. Working the majority of my career in corporate America, I always knew that when I retired, I wanted to find a way to give back. Having a plan made my new season something I looked forward too and now I can use my skills to dramatically impact the lives of those less fortunate.

Advice for future executives who will transition: (click to expand)
  • Look to your past to find inspiration for your future. My transition was about returning to an area of work that I hadn’t been able to be involved in full time for years. Whether it be going back to school or taking up an old hobby, your next season can be a great time to revisit your past.
  • Give back through not-for-profit work. There are so many people around the world who could benefit from your help. Find a way to lend a hand.
  • Repurpose your old skills. I use the administrative and management skills I gained working for a corporation to more effectively lead a not-for-profit, even though those fields are very different.
  • Obviously your financial situation should be high on your list of things to consider as you decide the options you have in your next season.
  • Enjoy the time with your family. I have five children and a number of grandchildren that I want to spend time with, so I make sure that my life isn’t so hectic that it cuts away from my time with them.
  • Your next season will not just happen in the same way that your career didn’t just happen. You have to work hard and plan for this new chapter in your life just as you did the previous ones.
  • Figure out what you are passionate about and what will satisfy you as you move forward. Make the most out of this new exciting time in your life.

Maryformer Executive of a Fortune 50 Company

After working a number of years in a large international corporation, I decided that it was time to leave and begin to fulfill my dream of working for a not-for-profit. There are so many great organizations that need help, and I knew that my skills in management and finance would be useful. I told my boss why I was leaving, and over the next year, I transitioned out of my old company and into a new season of life.

Advice for future executives who will transition: (click to expand)
  • If at all possible, try to leave your company on good terms. While this won’t work for everyone, it allows for a smoother transition for both you and your employer.
  • Know what you need as a person. I’ve always been a very intellectual individual and so I wanted to work in an environment that would stimulate me mentally. The not-for-profit that I ended up working for focused on educational research which was perfect for me.
  • Find a place where you can make a difference. You can serve not-for-profits in hundreds of capacities but find one that fits your skills. Since I’d worked in finance, I decided to help a charity that hadn’t really managed their endowment; that was a place where I could make a difference.
  • Retirement is not your final transition. I transitioned from a full-time corporate job to full-time not-for-profit work. Now I’m transitioning again into philanthropic work with a lesser time commitment to focus on other pursuits. I’ll probably transition again.
  • Maintain a portfolio of activities. I’ve always been one to like a schedule, but I also live variety and this is the perfect season of life to fill your schedule with an array of activities. Don’t be afraid to try something new.
  • Be a lifelong learner. There are hundreds of opportunities to attain knowledge wherever you are. Visit museums, concerts, or shows. Take classes. Read new books. Don’t stop learning just because you may have stopped going to the office.
  • Have good conversations. Don’t be afraid to sit and talk with your family and friends even after dessert. Use your free time to get to know those you love and don’t cut the conversation short.

Thomasformer Entrepreneur and CEO

You could say that I retired twice. After a long career with a corporation that I bought and lead as CEO for a number of years, I decided it was time for me to transition into my next season. Several years later, however, the board asked me to return as an interim CEO while the company underwent some management changes. I agreed and so transitioned into and then out of a CEO role for the second time. You could say I’ve had a lot of practice retiring!

Advice for future executives who will transition: (click to expand)
  • In life there is a time for everything. Embrace working as an executive during that time in life, but don’t be afraid to embrace a less hectic season of life as well.
  • Serving on a university board can be a great way to use your experience. I’ve really enjoyed serving on the board of my alma mater as a way to use my expertise and give back without the stress of sitting on a high profile corporate board.
  • Try taking up some hobbies that are engrossing and enjoyable without being stressful or unhealthy. I love gardening because it lets me be creative and gets me out into the fresh air.
  • Follow your gut. When you wake up in the morning and can hardly wait to do something, than stick with it. If you dread it though, maybe you should rethink your commitment.
  • As an executive, a lot of your time is consumed by other people’s demands. Now is the time to focus on your own needs and desires instead of the company’s.
  • If you can, help to grow your successor and viable candidates for management roles. That will ensure that your company stays strong even after you’ve left.
  • Try to transition your personal life before you transition out of your job, that way everything isn’t changing at the same time. Spend more time with your family in the months leading up to your transition and discuss what life will be like once you’ve retired.
  • Don’t be afraid to let others take charge in your next season. You don’t have to run the not-for-profits or boards you are a part of. Contributing your own perspectives and experiences can often be enough. Recognize the difference between governance and management.


Rick, former President and CEO of Private Corporation

The way my work contract lined up with the calendar, I knew that I could leave the company near my 65th birthday. Knowing my potential retirement date ten years in the future gave me a long time to consider my options and thoroughly prepare my management team and my successor. I retired at the end of my contract and was then able to join the Board, which allowed me to see out the transition.

Advice for future executives who will transition: (click to expand)
  • Take control of your transition by thinking ahead and positioning yourself in a way that creates several desirable options.
  • Increase the amount of vacation time you take in your last few years. I ramped up mine in order to better transition myself and the company into a period where I’d no longer be present.
  • Stay healthy. Every morning I go to the gym; a huge motivator is my love of traveling. I want to be able to see the world firsthand.
  • Don’t just talk about traveling, actually do it. You don’t have to be afraid.
  • In the afternoons I split my time between volunteer work and assisting small business owners. You’d be surprised by how much someone with your skill set can help those in smaller organizations.
  • Find a way to add value to your life and stay active. Don’t just twiddle your thumbs.
  • Fill out your time reading instead of watching TV. If I’ve ever got spare time I pick up a good book that will keep my mind sharp.
  • Work on your negotiating skills. When you run a business, everyone has a tendency to agree with you. In the real world, however, you’ll need to do more convincing and compromising.
  • Find a way to give back. For a number of years, I volunteered at a Children’s Hospital and loved giving a little bit of joy to such sick kids.

Lauraformer Executive Vice President of a Fortune 30 Company

In the years before I retired, I spent a ridiculous amount of time traveling. I was flying across the country multiple times a month, and got to the point where I didn’t feel like I was even participating in my own life. I felt like I had groomed my direct reports well and that I had been successful, so I knew it was my time to transition. I wanted to focus on the things I didn’t have time for before, and I wanted to use my skills to give back to the community.

Advice for future executives who will transition: (click to expand)
  • Transitioning can be a bittersweet pill. It was a great relief to be with my family, but I didn’t realize how structured my life as an executive was until that structure was gone.
  • Release the pressure. I put a lot of unnecessary guilt on myself for doing ordinary things once I retired. I got upset when people made the assumption that I slept in, because I didn’t want to seem like a slacker. That pressure dissipates over time though, so try to relax and enjoy this new season.
  • Your planner doesn’t have to be full. I created a parallel world for myself after my transition where every minute was spent with tasks I’d created liking reading a crazy number of newspapers. Not every second has to be planned though. Enjoy the flexibility.
  • Try a little of everything. I have done some consulting work, served with not-for-profits, and sat on a for-profit board. Check it out and see what fits your new life best.
  • Being an empty nester gives you some great opportunities. I travel with my husband now and we call it “dating with money.”
  • The best part about being retired is being able to maximize your time, even if you’re just relaxing. When you are an executive, every second is filled up, but a lot of time is tied up in red tape that leaves it tedious. Being retired, I can get things done efficiently and use my time in ways that make me happy.
  • Accept that there will be difficult days even in the best transitions. You have to go through a grieving process when you leave a chunk of your life behind, just know that it will get better.
  • Don’t let your ego get the best of you. During your career, your ego is constantly fed and you can always compare yourself to your colleagues. I had to learn to gauge my success based on myself instead of based on the outside world.
  • Create a community for yourself. That comes automatically during your career, but you need to replace that community with new connections in the new parts of your life.

Tedformer Executive Vice President of Fortune 500 Company

My prior company set their mandatory retirement age for senior executives at sixty-five, so I knew that I’d have to leave when I hit that arbitrary number. So-called retirement age has not caught up with people living healthier lives and being mentally active well into their eighties. I know that a lot of people look forward to the traditional retirement age and having an abundance of time for golf and travel, but I enjoy the current balance I have between family and work.

Advice for future executives who will transition: (click to expand)
  • You can travel and work at the same time. Many people want to retire to travel, but I get plenty of opportunities to travel through my work. You just have to be intellectually curious and combine business with meeting new people and diving into local life. People are fascinating, find out what makes them different and what motivates them.
  • Anticipate what you might like to do next. A slow transition into retirement or your next career might not happen. You have to be ready for a swift shift.
  • Stay relevant. Many people think that once you retire, you are outdated, but you don’t have to be. Don’t just golf. Study, find a new job, volunteer, work in a political campaign, lecture, write, add value.
  • I saw a movie poster the other day that said “experience never gets old,” and that is so true. Seventy-five is the new sixty-five. If you have something to give, use that skill. Your experience is no less valuable now that you are another year older.
  • I get a surge of energy when I am going to work at 630 in the morning. Don’t feel like you have to give that up, just because the culture asks it of you.
  • If your company retires you and you aren’t ready to retire, then try a new job. Your experience, judgment and energy are valuable.
  • Stay fit and maintain a healthy weight. Run, walk, bike, hike, stay on the move!

Jimformer Executive Vice President and CFO of an International Corporation

My company had a mandatory retirement age, so I knew when I’d be retiring years before the actual date came. I thought a lot about what I wanted to do, but ultimately the “where” trumped the “what.” My wife and I wanted to move across the country to a warmer climate, and so I decided not to look for new responsibilities until we found a new home. Eventually I got both.

Advice for future executives who will transition: (click to expand)
  • Plan! You plan for every other phase of life, so make sure you also plan for this new phase – especially the non-financial aspects. Start with something basic like where you’d like to live or whether you want to work full time, part time, and/or give back to a not-for-profit? Making those initial decisions helps make settling on the specifics much easier.
  • There are multiple phases of retirement. After moving and settling in I began working for a private equity firm and traveling a lot for work, but after a few years, I transitioned into a more leisurely lifestyle.
  • Help the organizations that helped you. My college years were extremely formative for me, so I decided to give back to the school by serving on some of their committees and helping fundraise.
  • Use your free time to travel. If you can afford to, travel with your entire family. We’ve thoroughly enjoyed spending time away with our kids and grandkids. You’ll make memories that will last a lifetime.
  • Stay active. Be disciplined about engaging in things that interest you and learning new things.
  • Take advantage of the control you now have. The best part of being retired is channeling your skills and abilities in whatever direction you want. You get to manage your schedule. You get to decide what you do and when.
  • Make a lists of things you want to do in your next season before you transition. One should be productive things, the other fun things. You’ll be surprised by how many overlap.

Lesformer Chief Human Resources Officer for International Corporations

For most people one retirement is probably enough, but I’ve had two. I was fairly young when I retired the first time and after three years of part-time consulting and not-for-profit work, I felt called back to full-time work. When I retired from that position a few years later, it was much different. I was more relaxed and prepared for what was coming.

Advice for future executives who will transition: (click to expand)
  • Be thinking about your retirement in a broad sense even if you think it’s years away. The first time I retired, the timing was more than a year earlier than I’d expected. I was not nearly as prepared as I would have liked, but that didn’t have to be the case.
  • Don’t feel the pressure to be constantly busy. I felt like I had to fill every second of every day the first time I retired so I could feel useful. The second time I realized that you can take some time for yourself. It’s ok.
  • Undertake a project you’ve always wanted to try. I’ve written several books since I’ve transitioned and have thoroughly enjoyed the process.
  • Don’t be afraid to go back to work if it’s what you think is best. When I got an offer to work full-time, both my wife and I thought I was ready for it. She liked the idea of having me out of the house, and I was still young enough where I felt I could work full-time.
  • To stay intellectually engaged try serving on a board or being an advisor for a startup. They will be able to use your expertise and skills without requiring you to work full-time. It’s a great way to use your expertise.
  • Stay healthy. Retirement becomes much more restricted once you have health problems, so take care of your body. Eat right. Maintain a healthy weight. Exercise regularly. Simple things can add years to your life.
  • Being married to a psychologist helped me make great life and career choices. Your spouse can be a great counselor no matter their profession – leverage their expertise and listen to their advice. After all they know you better than anyone.
  • After I transitioned I had a lot more control over the various spheres of my life. Make sure to spend time on your physical, intellectual, relational, emotional, and spiritual wellbeing. A happy life is a well-rounded one.

Jamesformer Executive Officer of Fortune 50 Company

The first time I retired, the transition went smoothly. I planned to leave months in advance and even stayed on as a consultant for a few months to ease into my new life. After a few months, however, I got antsy and returned to my company in a new role. I knew almost immediately that this was a mistake. Although I didn’t realize it, I’d come to enjoy my less hectic lifestyle, and my company had moved on without me. I should have mentally prepared and embraced the transition the first time to save myself the headache of a second retirement.

Advice for future executives who will transition: (click to expand)
  •  Find ways to be intellectually stimulated. My biggest reason for returning to work was that I got bored with no new problems to solve, and my wife didn’t appreciate me trying to solve hers. Keep your mind active by volunteering, taking classes, or picking up a new hobby.
  • Plan ahead mentally. Look for possible roadblocks that may detract from you enjoying your next season and try to eliminate them. If I’d anticipated the boredom better, I would have saved myself from a difficult return to work and later second retirement. I ultimately used consulting and board work to satisfy my need to be active intellectually.
  • Allow yourself time to transition. You will not be completely acclimated to retirement on the first day, but that doesn’t mean you should hectically make rash decisions. Give your mind and body time to adjust to a slower pace of life.
    Build relationships outside of work. Non-work friendships are the source of great advice and often the people you become closest with after you leave the corporate world. Try to establish some of these friendships before you retire.
  • Exercise is a non-negotiable. Stay active in whatever ways you can. I walk four miles every morning to stay in shape.
  • Give your spouse space. Corporate spouses are usually self-sufficient so let them keep parts of their life for themselves. My wife and I usually do different things during the day but spend the evenings together.
  • Take full advantage of your time. You may spend upwards of twenty years in this new phase of life so don’t putter it away. Make it worth something.

Barry, former Private Company Founder and CEO

After starting and growing my own company, I was ready to move on to new adventures while I was still relatively young and in good health. Since the company was operating smoothly and I was ready to leave behind the challenges of running a business, I sold it and embarked on my next journey.

Advice for future executives who will transition: (click to expand)
  • Embrace your faith. Your next season can be a great time to focus on the direction and peace you can find in God. Be intentional about spending time exploring this area of life.
  • Don’t feel guilty. When I sold my company and took on a more relaxed lifestyle, I didn’t want to be idle and needed to be constantly doing something. After a stressful job, a normal level of stress may seem like laziness, but it’s actually healthy.
  • Take where you want to live into consideration. Think through the logistics and plan ahead. I haven’t been able to do everything I wanted, because I couldn’t sell my house immediately, which meant that I couldn’t move automatically to a new life.
  • Become an expert at something new. I decided I wanted to learn about market trading and make my own trades. I got some advice and coaching by others and did plenty of research online to better understand the subject.
  • Go on adventures! Get out of your comfort zone. Travel to a new place, go sailing, learn surfing, or do something crazy like hang gliding.
  • Stress can be addictive. So many people get adrenaline from the thrill of the hunt often associated with a busy corporate environment. Recognize that your frantic pace was your old norm and allow yourself time to adjust.
  • Focus on what you like and are good at. People might expect you to be on a board or volunteer at a museum, but if your passion is surfing or gardening or writing a memoir then spend your time there.

Mark, Brigadier General USAF, (Ret)

After spending over 30 years in the aerospace industry, I wanted to have some different experiences. I went from the Air Force to taking a year off to being the President of a public company to owning a Chick-fil-A. My mantra was “I’m not making a decision for the rest of my life. I’m just making a decision for what I’d like to do next.” I decided that I would try something for three years and if I didn’t like it, I would try something else. I have no regrets. Instead, I have stories that I hope will help others.

Advice for future executives who will transition: (click to expand)
  • Slow down and think about what you really want to do. Give yourself time to process the transition both intellectually and emotionally.
  • Don’t rush into anything. This is a significant life transition. Take the time to assess what has made you feel fulfilled in the past, what you do well, and where there is a need. It can fit together like a puzzle.
  • Balance contemplation with action. You’ll know when you are ready. Don’t overthink or wait for the perfect opportunity. Remember that you are not making a life-long decision. If you are interested in something, try it for a while. If you don’t enjoy it, try something else.
  • Get out of your normal routine to open your mind to new possibilities.
  • YOU have to make it happen. No one is going to figure out this next stage for you.
  • Think about how you can give back. Everyone has something different to contribute and offer.
  • Don’t just drift into something. Once you make a decision and head in a direction, opportunities will present themselves.
  • Enjoy the flexibility. Time is your asset.

Jerry, former President of a Large Oil Marketing Company

The timing of my retirement was exactly right. After I had completed some significant milestones and the job was starting to feel a bit “old,” I realized I was ready to retire and initiated the discussion one year in advance of when I wanted to leave. Although I had a great career and achieved more than I could have ever wished for, I never thought that I was defined by my work. I was ready for a break from the corporate world and have zero regrets about leaving when I did.

Advice for future executives who will transition: (click to expand)
  • Find what you really ENJOY and do it. There is no other time like this in a person’s life for such an opportunity to do what you love to do.
  • Don’t miss out on this time in life because of the time/energy demands of continuing to pursue stature or recognition.
  • Stay in touch with the people you think you will miss. A significant part of the transition is losing the camaraderie of colleagues. I’m thankful I can still maintain relationships with those that I choose.
  • Support your spouse. They have been by your side for all these years; now is a great time to support them and their goals/priorities.
  • Get involved in your grandchildren’s lives. With two parents working in many families, there is a unique opportunity for grandparents to play a significant role in their grandchildren’s lives.
  • Stay intellectually active. Continue to challenge yourself. I joined an Institute for Foreign Affairs which motivates me to stay up to date with world affairs.
  • Seek out the best medical advice. This is often overlooked during busy careers, but now is the perfect time to take care of yourself this way.
  • Get involved in a different area of life. My wife and I are very active in the arts, and now I have more time to give to this interest area.