The Five Businesses Exercise
- 4 days ago
- 2 min read
Here’s an exercise I give to about half the leaders I work with.
Even if you have zero intention of leaving your corporate career, I want you to do this:
Brainstorm five businesses you could start or buy.
Not as a plan. Not as a resignation letter.
As a discovery.
I worked with a leader who’d spent twenty years in corporate life
and was starting to wonder — seriously, not as a fantasy — about other possibilities.
She came back the next session with a list that surprised both of us.
Two of them were directly related to her expertise, just in completely different contexts.
One was a franchise model she’d never considered.
One was a business she could buy from someone who was retiring.
And one was a wild card that made her light up when she talked about it.
She didn’t quit her job. But something shifted.
She realized her skills were valuable in contexts she’d never imagined.
That the corporate ladder wasn’t the only structure in the world.
And that choosing to stay in her role was a choice — not a default she’d never examined.
That’s what the exercise actually does. Not career planning.
Perspective.
The other thing I’ve noticed: what people put on the list is revealing.
When someone who’s spent twenty years in supply chain management
puts ‘woodworking studio’ on their five businesses list —
that tells you something about what’s missing in their current life.
Not that they should open a woodworking studio.
But that creativity, making tangible things, that need exists and it’s not being met.
Your list will tell you something.
Try it. Five businesses. Anything.
No filter, no practicality test, no business plan required.
What did you put down?
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