Emotional Milestones of Transition

Emotional Milestones of Transition

By Peter Lichtenthal, MyNextSeason Advisor and Former Global Brand President for The Estée Lauder Companies

Retirement isn’t just a career transition; it’s a deeply personal journey with its own emotional arc. Some people move through it with excitement and ease, while others find it more challenging. Wherever you fall on that spectrum, it’s important to recognize that certain moments in the process tend to stir strong emotions. These milestones are universal, yet the way each person experiences them is entirely individual.

1. The Decision

Whether you are choosing retirement on your own terms or being asked to step into it, the first big moment comes with the decision itself. It’s the point where the future stops being abstract and becomes real. For some, this brings relief and excitement; for others, it stirs concerns, doubts, or even fear. This is where the hope for what’s next meets the reality of closing a chapter.

2. The Announcement

The next milestone comes when you share the news—with your team, your board, your colleagues, or your company at large. The announcement makes your retirement public and increasingly real.

Suddenly, it’s not just your decision anymore; it’s a moment that invites reactions from others. You may be met with praise, surprise, questions about your plans, or concerns about what it means for the people you’ve led. All of these reactions can heighten your own emotions and reinforce the reality of the change ahead.

3. The Celebration

On the surface, a retirement celebration sounds joyful—a well-deserved recognition of your work and impact. And for many, it is. But it can also bring unexpected discomfort.

Being in the spotlight, giving a farewell speech, or receiving praise can stir complicated feelings. Some worry they’ll become too emotional when speaking; others feel uneasy about being celebrated at all. The mix of pride, gratitude, vulnerability, and finality can make this moment quite complex.

4. The Last Day

The final milestone is the actual last day. Turning in your badge, closing out your computer, and leaving the building are all tangible signs of an ending. For some, this day is filled with relief, joy, and a sense of freedom.

For others, the physical act of leaving can feel heavy, marking the closing of a space that has held meaning, relationships, and routines for years. The sounds, sights, and emotions of this day often linger long after it’s over.

5. The First Morning After

Then comes the first “workday” when you wake up and realize you’re no longer going to the office. There are no emails waiting, no calls to return, and no meetings filling your calendar. For many, this quiet can feel liberating. For others, it’s surprisingly jarring—a sharp contrast to years of structure, deadlines, and demands.

The absence of a packed calendar can feel unsettling, leaving you wondering how to shape your day. That’s why it helps to plan ahead. Line up a project you’re genuinely excited to begin, schedule a few social activities or trips, and give yourself touchpoints to look forward to.

Even as you’re still discerning what your next season looks like, having something to transition toward makes those first days feel less like an ending and more like the beginning of what’s next.

Honoring Emotions, Embracing the Future

Each of these five touchpoints has the power to stir emotions that go beyond logic. Your mind may tell you this transition is right, but your heart may still wrestle with a combination of feelings, including fear, sadness, anticipation, excitement, or uncertainty. This interplay among these feelings is natural.

What matters most is preparing for these milestone moments and acknowledging what you’re feeling rather than pushing it aside. Yes, explore opportunities, network, and set new goals. At the same time, give space to both your heart and your mind so you can step into your next season not only prepared but also grounded in who you are and what matters most.