When You Realize Your Work + Life Are Fully Intertwined

Last time, I said this about making transitions as an entrepreneur:

Adjusting our business and our lives to new dreams and realities is a challenge every entrepreneur faces at different inflection points—and we ignore it at our peril.

“Winston” knew something needed to change: in his mid-fifties, he was feeling stuck. He craved more time off for travel adventures with his spouse, but he also wanted to create more meaning in his work without shutting off the financial spigot.

The problem? He was bored.

When we dug into the day-to-day work occupying Winston’s time, it was clear that almost all of it was work his “competitors” could do equally well.

Over time, he become stuck in his zone of excellence, competing with a bevy of others for the same handfuls of marquee clients.

It wasn’t until a new client pushed for—and embraced—his personal genius that the light bulb went off. If there was one client like this, surely there were more…

That realization was the spark that lit Winston’s fire to re-visit every assumption he had made about his work AND his life:

How they entwined together in ways he hadn’t been aware of.

How he could re-craft his business to also serve himself in new ways.

How he could re-energize himself for his next chapter.

We worked together to define his version of a “life well lived”, using the 8 facets of my Business + Life assessment as the starting point.

While he’s still experimenting, Winston now knows exactly what living and working in his genius zone looks like, his own definition of “enough” (with his financial advisor deployed to keep him on track) and a step-by-step plan to fine-tune his results.

He’s figured out what most brings him joy, meaning and contributes to the personal legacy that he’s decided is important.

Here’s the thing: Winston didn’t just listen to his inner voice telling him it was time for a transition—he took action.

And that’s where the magic lies…