A colleague of mine has an idea she returns to often.
Her own private practice she believes would bring back a sense of energy when she heads out the door in the morning.
She has the vision.
A small, leased space already picked out.
A name and logo she designed, with just a little help from AI.
⏳ That was 18 months ago.
Today, she is still in the same role.
The job is pretty stable. The income is good enough. The schedule is predictable.
But she is restless and feels “stale”.
There is no growth.
No room to shape her practice style.
Her current ideas are met with indifference, while the job expectations remain fixed: 20+ encounters, day after day after day.
It feels like clinical Groundhog Day.
I didn’t tell her what to do.
Partly because that goes against how we are trained.
Partly because I didn’t want to carry the weight of her outcome.
Instead, I offered her a different idea.
Using current actuarial data, a U.S. female born in 1983 or in her early 40s can expect to live into her early 80s.
Roughly four more decades if everything works out.
So, I asked her to zoom way out.
Picture yourself at 82.
Looking back on your career.
What more would you regret?
Opening that practice—with your name on the door and risking that it might not work?
Or staying exactly where you are for the next 25-30 years, knowing you never tested the dream that kept returning?
Choose the path that minimizes regret.
That is the entire framework. Not everyone can handle the anxiety of risk.
But there is risk with either decision.
Yes, we are living in a time where financial decisions are much heavier.
Stability matters.
But there is another kind of risk we all face.
☕ The risk of never starting.
There is a line often repeated:
A ship is safe in the harbor, but that is not what ships are for.
And a famous founder once put it more plainly:
“I knew if I failed, I wouldn’t regret that. But I might regret not ever having tried.”
Some of you did the math on your own life expectancy timeline while reading this.
Next week, we’ll look at something else related. Why does time feel like it’s speeding up, and what can we do about it for ourselves and our clients.