The tyranny of time

"Still working. Still thinking." That's how I describe what I do now. It took me longer than I expected to be comfortable with that description.

I left my law firm nearly twelve years ago. It was the right decision. I had work lined up, consulting opportunities were emerging, and trustee roles were accumulating. On paper, the transition looked straightforward; in practice, it wasn't quite so simple.

The difficulty wasn't the work itself. Rather it was the gap between knowing I'd made the right choice and feeling comfortable with it. Knowing you've earned the right to step back doesn't make stepping back immediately comfortable.

I see the same pattern in our clients at Milestones. People who have thought carefully about their next chapter, who have made deliberate choices about what they want and what they don't. And yet they struggle with the space they've created. The time that was meant to feel liberating feels unsettling. The flexibility that looked attractive from inside a demanding career feels uncomfortably unstructured once they have it.

So why is this transition so difficult?

Part of it is identity. We define ourselves by what we do. "I'm a lawyer." "I lead X." "I work for Y." Take away the full-time role and the sentence becomes harder to complete. "I used to . . . ." "I was . . . " The past tense feels diminishing, even when the present is by choice.

Part of it is measurement. Full-time work provides external validation. There are deadlines, deliverables, feedback and you know whether you've had a productive day because someone else has told you. Step back and you lose that external gauge. You're left deciding for yourself what counts as useful, and that's surprisingly hard.

Part of it is expectation. You've stepped back but you haven't stopped. So what should you be doing? How much is enough? And when people ask "What are you up to these days?" what's the answer that doesn't sound like either frantic busyness or defensive idleness?

The difficulty is compounded by the language we use. "Productive." "Useful." Both imply measurable output. But useful to whom? On what timescale? And why does time need to be filled rather than simply lived?

What I've learned - both from my own transition and from working with clients navigating theirs - is that this takes time. Longer than most people expect. Knowing you've made the right decision doesn't make living with it immediately comfortable. The gap between knowing and feeling will close, but not as quickly as you'd like.

And even now, twelve years on, I still find myself measuring my time against old standards that no longer apply. Old habits persist.