Reflections on Time, Identity, and Fulfillment After Early Retirement
At 36, I sold the fintech company I had dedicated years to building and walked away with an eight-figure exit. No client needed an answer. No product roadmap demanded a decision. No inbox confirmed that I was useful. I thought it would feel like freedom. Instead, it felt like an identity crisis.
As CEO, I had been time-starved but important. My calendar dictated where I needed to be, and my business card defined who I was. Then both disappeared. Although I had achieved the exit many entrepreneurs dream about, I had never paused to ask how I actually liked to spend my time.
It took therapy, experimentation, motherhood, and eventually founding another company to understand that the goal is not simply to have more time. The true goal is time choice: the ability to decide how your hours are spent before someone or something else decides for you.
Don’t Wait for Retirement to Discover What Makes You Happy
During my first year with abundant free time, I treated life like a research project. I learned chess, attempted sewing, tried yoga and Zumba, and even took MasterClass courses for no practical reason at all. I wasn’t trying to earn credentials, impress investors, or turn hobbies into side hustles. I was simply exploring what brought me joy.
This exploration was surprisingly uncomfortable. Entrepreneurs are trained to value activities with measurable returns, and time invested purely in joy is difficult to quantify. Still, it’s essential to find out what lights you up now. Schedule leisure with the same seriousness you give a board meeting—joy deserves that priority. You don’t need an exit to start getting curious about yourself.
Being Needed Is Not the Same as Being Valuable
Eventually, there comes a time when no email demands your attention. This might happen after an exit, a career change, or retirement. If being needed has been your primary source of identity, the silence can feel destabilizing.
I had to separate my value from my speed at solving other people’s problems. Therapy helped, as did embracing new experiences where I was a novice. Pole dancing classes didn’t care that I had been a CEO. Singing lessons humbled me—I don’t sound like Taylor Swift, even when I breathe correctly. No art gallery called about my adult coloring attempts.
Each experience taught me something about myself and added a layer of confidence. None of these activities advanced a business objective. They simply interested me, and that was enough.
Schedule Joy Before Life Schedules Over It
My mother died when she was 65, shortly after taking her first flight in first class—something she had delayed until the timing felt right. Her death taught me that “later” is not guaranteed. Yet, I kept planning my time reactively.
Becoming a parent made this lesson concrete. Within a year of selling my company, I welcomed a child, and my calendar filled again—this time with sleep schedules, feedings, and household duties. My time abundance vanished, but the insight remained: joy does not protect its own place on your calendar. You have to plan for it.
Spend Money to Buy Back Time
At 41, I returned to entrepreneurship with a provocative question: Are wealthy parents happier?
The answer is yes—when money buys back time. Harvard Business School professor Ashley Whillans found that couples who paid for housekeeping, meal delivery, and other time-saving services reported happier relationships. What mattered most was how they used the hours they recovered (source).
I had lived this research firsthand. A night nurse gave me sleep. A nanny gave me patient time with my children. Grocery delivery, meal preparation, and laundry help preserved my weekends. I was investing in the energy to enjoy the life I had built.
Delegate the Thinking, Not Only the Doing
This understanding inspired me to found Peacock Parent, a company centered on delegating at home without guilt. After speaking with thousands of parents, I learned something unexpected: many were overwhelmed not just by doing household tasks but by anticipating and planning them, even when the tasks themselves were outsourced.
I felt it too. I worried about forgetting details and wanted future needs flagged before they landed on me. I also felt the strain of the sandwich generation, caring for an elderly parent while missing my own mother’s support.
The lesson for anyone buying back time is to hand off the mental load along with the task. When outsourcing, delegate the remembering, scheduling, and follow-up as well—whether to a person, a shared system, or a tool. If you still keep track, you haven’t truly bought back much time.
Choose How You Spend the Time You Buy
Buying back time only works if you are intentional about how you use it. I will gladly pay an extra $50 for an in-home appointment so someone else does the driving. I skip the rush out the door, traffic, and parking hassles, and get my lash extensions at home in pajamas. I’m buying calm as much as convenience.
Then I decide what the recovered time is for. Sometimes it’s adult coloring, an audiobook, or a hip-hop lesson. Sometimes it’s posting on social media—but only when I have something meaningful to share, not just to feed an algorithm.
Don’t wait for retirement to decide how you want to spend your life. You can start planning for joy today.
Key Takeaways
- More free time does not automatically bring fulfillment. You have to learn how you like to spend it.
- Money improves happiness when it buys back time and you decide deliberately where that time goes.
