In North America, there’s a lot of pressure around the concept of retirement. It’s held up as a mark of success, a milestone worth bragging about, a destination everyone is supposed to be racing toward.
Some people arrive earlier than they intended. Some people arrive exactly as planned. Some people never arrive and suffer for it. And some people never arrive because it’s simply not something they ever desired.
Before you read any further, I want you to do something.
Define what retirement means to you. Not the textbook version. Yours. Take a moment, jot a few words down. Notice the moods, the emotions, the physiological reactions that show up when you sit with that word. And ask yourself: who have you watched retire that shaped the definition you’re carrying right now?
Merriam-Webster defines retirement as “withdrawal from one’s position or occupation or from active working life,” and retired as “having concluded one’s working or professional career.”
Plain. Clean. Completely devoid of the weight most of us actually feel around it.
If you did the exercise, you probably noticed a significant gap between that definition and your own. There’s also something worth naming in the distance between what you think you should want and what you actually want.
This is where it gets interesting.
Every founder I’ve ever worked with has a completely different relationship to this word. Unique as a fingerprint. A whorl away from anything that can be templated or mapped onto someone else’s formula.
When we excavate it together, here’s what we sometimes find.
Fear of losing an identity that has been built over decades. Fear of redundancy. Fear of emptiness. Fear that meaning will simply evaporate. Sometimes its a lack of worthiness, despite having achieved incredible success and defying the odds they started with. Maybe it’s worry about what to do with free time and how to sustain self worth and value.
And sometimes, underneath all of it, we find something else entirely. We find that the business was an expression of meaning that had never been fully identified. Think about a business that takes off like wildfire – the right service or product at the right time and place and exponential growth. All the departments, the teams, the vendors, the clients, the problems being solved, a founder go go going while the going is hot, doesn’t necessarily take the time to reflect on meaning or purpose.
The business became the identity. The identity became the business. As founders approach retirement, taking time to reflect with a neutral sounding board is the greatest gift you can give yourself. To witness and acknowledge what sits in the gap between you and retirement.
When external pressure arrives, from a spouse, family members, peers, or competitors, telling you it’s time to simply “retire,” it can trigger a fight so powerful you’d think we were fighting for our lives.
Because we kind of are.
If retirement feels like someone else’s dream, it probably is. And that’s worth knowing.
And if you see retirement as a chance to reinvent yourself or reconnect to your worth and value, to define how you’ll express yourself in the world moving forward, that’s worth knowing too.
If you’re a founder sitting with any of this, the tension, the identity questions, the external pressure, you don’t have to sort it out alone. That’s the conversation I have with founders every day.
PS… I am this work, so retirement for me will look like more of who I was born to be as long as I have the health to keep going.
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