024: In twelve months I walk out of corporate law for good. This is the first in a monthly check-in counting down to that date, documenting whether I'm actually ready, one pillar at a time. Not from the safe side after it all worked out but from inside it, while I still don't know how it lands.
The number landed in April 2024, years of saving all pointing at the moment I'd finally be free, and I felt nothing. So I did the predictable thing: decided it wasn't enough, picked a bigger number, marched back to the desk I was meant to be leaving. Hit that one too. So this episode isn't a man working out whether he can afford to leave. It's a man still in the suit, twelve months from a door that's been unlocked the whole time, finally asking why he won't go through it.
About this series: Five pillars make up a real "enough" - Health, Money, Identity, Relationships, Purpose. One check-in a month to 24 June 2027. This is Check-In #1: Money - the pillar everyone assumes is easy for me. It isn't, just not for the reason you'd think. Next month: Identity, the one I'm most afraid of!
What this covers:
- Why hitting your number isn't a finish line
- Rich on paper, stuck in practice - why net worth isn't freedom, liquidity is
- The repositioning: 18 months of cash, a bucket strategy over the textbook 4% rule
- How a partner who keeps working changes the whole shape of sequence-of-returns risk
- Walking away from $30K in unvested shares and arranging my life around the vest date anyway
- The one cushion that's actually real (the visa), and the long line of ones that aren't
This one's for you if:
- You've hit your number, or you're close, and still can't make yourself leave
- You're rich on paper but not liquid
- You keep recalculating a plan that comes back "safe" and still doesn't fix the feeling
- You catch yourself adding cushion after cushion and calling it prudence
- You want the honest, unedited version of the final year before FIRE - including the parts that don't look good
Question to sit with: What's the cushion you keep adding that you don't actually need? What would it cost you to admit you don't need it?
📩 Get the weekly email: one idea a week about money, identity, and what nobody tells you about life after financial independence.
🧭 Find your Freedom Score: most people chasing financial independence assume money is the thing keeping them stuck. It usually isn't. This free 3-minute quiz scores you across the five pillars of a real exit - health, money, identity, relationships, purpose. It then tells you which one is actually holding you back, and the specific thing to fix first. Fast, free, and a little too honest!
🔥 Escape Plan: Are you a lawyer who's done the maths but still can't make the leap? The Escape Plan is an 8-session 1:1 coaching program for lawyers navigating the identity, purpose, and transition work that spreadsheets can't solve. Founding pilot now open.
📊 Free Coast FIRE Calculator: figure out when your money can do the work, so you can start designing a life worth being present for.