A few years ago, I was working with the founder of a 200-person company who was badly burned out.
He'd checked all the boxes he thought he needed to be happy.
He'd built a respectable business.
Yet everyday, he still found himself waking up unhappy.
↓
He'd checked all the boxes he thought he needed to be happy.
He'd built a respectable business.
Yet everyday, he still found himself waking up unhappy.
↓
When I asked him what would happen if he redesigned his work so he actually enjoyed it, he laughed.
Then he paused.
Then he realized: The things he hated doing were the ones most out of alignment with who he was — and what the company truly stood for.
Then he paused.
Then he realized: The things he hated doing were the ones most out of alignment with who he was — and what the company truly stood for.
The next 3 months became an experiment in "What if my only job is to enjoy my job?"
He started by mapping every task onto buckets:
1. Love it – work that lit him up.
2. Could love it – work that might feel good with a tweak or two.
3. Delegate or delete – everything else.
He started by mapping every task onto buckets:
1. Love it – work that lit him up.
2. Could love it – work that might feel good with a tweak or two.
3. Delegate or delete – everything else.
Slowly, a pattern began to emerge.
Every chore he dreaded—the endless status pings, the Monday finance huddles, the product reviews he kept rescheduling—was also where the company was slowest or most error-prone.
Low enjoyment, it turned out, was a sign of inefficiency.
Every chore he dreaded—the endless status pings, the Monday finance huddles, the product reviews he kept rescheduling—was also where the company was slowest or most error-prone.
Low enjoyment, it turned out, was a sign of inefficiency.
So he made two moves:
1. He reassigned or eliminated the “delegate/delete” tasks.
Some went to colleagues who genuinely enjoyed them; others got automated or scrapped.
1. He reassigned or eliminated the “delegate/delete” tasks.
Some went to colleagues who genuinely enjoyed them; others got automated or scrapped.
2. He fixed the root cause of the “could love it” pile.
Usually that meant one of 3 things: tighter ownership, a clear metric, or a decision-making window.
When those pieces were in place, the urge to micromanage evaporated. Trust in the system replaced the need for control.
Usually that meant one of 3 things: tighter ownership, a clear metric, or a decision-making window.
When those pieces were in place, the urge to micromanage evaporated. Trust in the system replaced the need for control.
What happened next:
- Real-time dashboards slashed his “Just checking in…” messages by 70%
- Teams reorganized themselves around enthusiasm, and voluntary turnover dropped by a quarter.
- With fewer bottlenecks, product velocity jumped—and so did revenue.
- Real-time dashboards slashed his “Just checking in…” messages by 70%
- Teams reorganized themselves around enthusiasm, and voluntary turnover dropped by a quarter.
- With fewer bottlenecks, product velocity jumped—and so did revenue.
I’ve seen the same arc with individual contributors, freelancers, even artists.
The moment you treat enjoyment as a leading indicator, output and impact climb together.
When work aligns with genuine desire, it stops needing to be managed and starts pulling itself forward.
The moment you treat enjoyment as a leading indicator, output and impact climb together.
When work aligns with genuine desire, it stops needing to be managed and starts pulling itself forward.
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