One of the hardest parts of retirement planning is that most people have never done retirement before.
We can build projections, analyze spending, estimate healthcare costs, and stress test portfolios. But what retirement actually feels like — emotionally, psychologically, even socially — is much harder to model.
I think about this often because years ago, I went through my own version of a retirement transition long before traditional retirement age.
At the time, I was already established in my career as a financial advisor. I had earned my MBA, CFA, and CFP® designations, and my husband and I were both working full time while raising two young daughters. From the outside, life looked successful.
But internally, I felt increasingly disconnected from my own life. One day, I had a realization that hit me hard: our nanny was living my life.
While I spent most of my waking hours working, she was the one spending time in our home with my children — feeding them meals, organizing their days, caring for them when they were sick, witnessing the small moments that make up family life. She was wonderful, and we loved her. But I suddenly realized how absent I felt from my own daily existence.
Eventually, I made the difficult decision to leave my job. At first, I thought I might never work again. What followed was not just a career break, but a complete reassessment of my priorities, my identity, and my relationship with time.
What surprised me most was how uncomfortable the transition initially felt.
Like many high-achieving professionals, I had spent years structuring my life around productivity. My days were organized around deadlines, obligations, and constant motion. Without that structure, I felt strangely untethered.
When I finally had quiet moments to myself, I had to actively resist the urge to immediately clean a closet, organize paperwork, or otherwise make myself “useful.” I realized how deeply conditioned I was to equate busyness with value.
That adjustment period was uncomfortable — but important. Over time, though, something shifted. I had a third child. I became a better cook. I got to know my children more deeply. I slowed down enough to become more present in my own life instead of constantly managing it from a distance.
And eventually, after about three years, I realized I did want to work again — just differently.
I was still passionate about financial planning, but I no longer wanted work to consume my entire life. So I started building my own firm gradually, beginning part time and growing slowly in a way that allowed work to fit into my life instead of forcing my life to fit around work.
Looking back, that experience fundamentally shaped how I think about retirement planning.
Many people assume retirement is primarily a financial question:
- Will I have enough?
- Can I afford healthcare?
- What withdrawal rate is safe?
Those questions absolutely matter. But there is another set of questions that can be just as important:
- Who am I without my work?
- What will structure my days?
- What kind of pace feels good to me?
- What relationships, interests, or parts of myself have been neglected?
- What am I moving toward, not just away from?
For many professionals, retirement is the first time in decades that life is no longer organized around external demands. That freedom can feel exciting — but also surprisingly disorienting.
Which is why we often encourage clients to think about retirement less as a single event and more as a transition period or experimentation phase.
Some people continue consulting. Some volunteer. Some help care for grandchildren or aging parents. Some start businesses. Some rediscover hobbies, friendships, travel, or creative interests that had been crowded out during their busiest working years.
And many discover that what they really want is not necessarily to stop working altogether, but to have a different relationship with work.
That is part of why the idea of being “work optional” resonates with so many people. Often the goal is not complete withdrawal from meaningful work, but greater flexibility, autonomy, and alignment between how you spend your time and what matters most to you.
In many ways, retirement planning is not simply about accumulating enough money to stop working. It is about creating enough financial flexibility to build a life that feels intentional, sustainable, and connected to who you actually are — especially once achievement and busyness are no longer the primary structure holding everything together.