Life After Enough

Golden Handcuffs: They Pay You Just Enough to Keep You

Life After Enough

Show Notes

023 I've walked out of law before. Actually done it. I came back. When I did, I made myself a deal: take a corporate job for one reason, to carry me on a fixed schedule to my FIRE number, and then I'm free. The number landed in April 2024. But the day you become free on paper is not the day you feel free. The salary kept landing. Every month it landed, some part of me still couldn't let it go.

That's golden handcuffs and it's the one trap nobody examines, because it sounds too stupid and ungrateful to complain about. "I can't bring myself to leave a job that pays me really well." Who's going to sympathise with that? So you never say it out loud, never look at it head on, and never get free of it. The absurdity is the lock.

This is week two of Money month, and here's where I split from every other person who makes content about this. The standard advice is: golden handcuffs are a cage, be brave, value freedom over comfort, rip the plaster off and leap. I think that advice is dangerously wrong because I took it to the letter in 2016 and it nearly ruined me.

What this covers:

Why golden handcuffs are not one-more-year syndrome What the handcuffs are actually made of: the monthly pulse of the salary landing, and the foregone-income maths that reads as loss even when it isn't Why the standard "be brave and leap" advice is dangerous The distinction that reframes everything: I'm not addicted to being safe. I'm addicted to feeling safe. Those aren't the same thing Why you don't break golden handcuffs, you outgrow them and how building the other side is the only thing that actually works

This one's for you if:

You've hit your number, or you're close enough to see it, and you still can't make yourself leave You still get a hit of relief when the salary lands, even though you've been fine for ages You've said "just a couple more years" for rather more than a couple of years Every bonus or raise resets the clock and nudges the number up You know the difference between being safe and feeling safe and you suspect you're paying for the second one with your life You want to escape the rat race but realise there's nothing built on the other side yet

Question to sit with: If the money stopped landing tomorrow, what exactly are you afraid you'd feel? Name that feeling. Because that, not the money, is what's keeping you here.

Whether you're trapped in golden handcuffs you can't explain to anyone, wondering why you can't quit your job even though the maths says you're free, trying to figure out how to retire early when the salary keeps pulling you back, or realising that no number was ever going to be high enough because the problem was never the number, this is week two of the month-long argument that the barrier is never the money.

📩 Get the weekly email: one idea a week about money, identity, and what nobody tells you about life after financial independence.

🔥 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.

More from Life After Enough

Oct 18, 2026

040: I was stopping breathing 36 times an hour, all night, and I had no idea. If you snore, you wake up with your heart racing, or you live in a fog you've been calling stress, these are sleep apnea symptoms, and they're worth three minutes of your time. The year I turned 40 I was diagnosed with severe sleep apnea, and most of what I'd been calling my bad mood turned out to be broken sleep. If you're chasing financial independence and early retirement, you've modelled the money out to 90 and you know your withdrawal rate to the decimal. Nobody tracks whether you'll be awake enough, and well enough in your head, to enjoy any of it. This is the third episode of Health month on Life After Enough. For years I was waking in the night with the pillow soaked and my heart going like I'd run up a flight of stairs. I thought I was a bit overweight and I snored, and I treated the snoring the way everyone does, as a joke. The longest pause in my breathing was 80 seconds. The fog at my desk, the naps that made it worse, the short fuse, the flatness I'd put down to being nearly 40. All of it was the same thing, and roughly one in five men my age has it and hasn't been told. What this covers: The haunted room at 18 and the wet pillow at 38, and why they turned out to be the same thing What severe sleep apnea actually does to you 36 times an hour, and why eight hours in bed felt like two The symptom men never raise with their doctor, and the one that disappeared the week I started on the machine What the health reset did to the night: deep and REM sleep roughly doubling once the weight came off and the drink went The mind: why a brain woken thirty times an hour on adrenaline is not a calm brain the next day, and what's still not fixed a year in This one's for you if: You snore, you're always a bit tired, and you've decided that's just what your forties look like You wake up in the night with your heart racing and can't explain it Your partner stopped finding the snoring funny a while ago You've planned a retirement full of treks and second careers on four broken hours a night Question to sit with: When did you last wake up actually rested? Not caught up. Rested. If the honest answer is a while, or years, then that's the question for your plan. Everything you retired for runs on sleep, and you can't bank it at the weekend. If any of the first half of this sounded familiar, get it looked at. It's one night at home with a kit on. 🎯 WHEN COULD YOU ACTUALLY STOP WORKING? Run your own numbers in the free Freedom Dashboard and find your date in about five minutes. It'll also show you how much of your current salary your future still needs, which might be a lot less than you think. Nothing you type leaves your device. 🧭 FIND YOUR FREEDOM SCORE: Most people chasing financial independence assume money is what's keeping them stuck. It usually isn't. This free 2-minute quiz scores you across the five pillars of a real exit and tells you which one is actually holding you back. 📩 GET THE WEEKLY EMAIL: one idea every Monday about money, identity and what life after financial independence actually looks like. No fluff, no pitches. 🇸🇬 SINGAPORE LISTENERS: this one's for you. Small in-person workshops on the exact exit maths this show talks about. Find your freedom date in a morning, or take the full day and plan the years before it. Eight seats each.

Oct 11, 2026

039: Five months ago I quit drinking, and it was only meant to be a three-month break. If you're sober curious, sick of the hangxiety on a Saturday morning, or quietly asking yourself "am I drinking too much?" while you chase financial independence and early retirement, this is an honest account of what happens when a completely normal drinker stops. My last drink was a glass of champagne on a flight home from Hong Kong, a big weekend behind me and a short break planned as part of a health reset. I haven't had one since. This is the second episode of Health month on Life After Enough, and it's about why quitting alcohol turned out to be the biggest thing I've ever changed, in a life I didn't think had anything to change. Here's the part worth saying up front. By any standard I'd have used a year ago, I was a completely normal drinker. Brunches, dinners, work events, a few on a Friday. Nobody at my table would have looked at it twice. There was no rock bottom, no intervention, and I'm not telling anyone to stop. What I found is that the only question anyone ever asks is "am I an alcoholic?", and because the answer's no, nothing changes. You never get to the useful questions. What is this actually doing for me, and what's it costing me? For me, the answer was most of my weekends, for most of my adult life. What this covers: Grey area drinking: the huge space between no problem and a serious one, where most people I know actually drink The fake fun test: could you stand in that room for four hours on a Diet Coke and still enjoy it? The weekend tax: how a medium Friday night quietly cost me every Saturday, and why that matters more than the money Hangxiety, alcohol and sleep, and why a "normal" drinker's nervous system never gets to reset What surprised me five months alcohol free: no cravings, a dial turned slightly down, and the strange return of old memories This one's for you if: You'd never call yourself a heavy drinker and you've also never asked what the drinking is doing for you You've spent a decade buying time back from the job, then handed half your weekends over on a Friday night You've thought about a break from alcohol and keep finding a reason not to You want an honest account of quitting drinking that isn't a recovery story and isn't a lecture Question to sit with: Look back at the last month. How many of your Saturdays did you actually get to use? And next time you're out, test if you would still be having a good time on a soft drink? 🎯 WHEN COULD YOU ACTUALLY STOP WORKING? Run your own numbers in the free Freedom Dashboard and find your date in about five minutes. It'll also show you how much of your current salary your future still needs, which might be a lot less than you think. Nothing you type leaves your device. 🧭 FIND YOUR FREEDOM SCORE: Most people chasing financial independence assume money is what's keeping them stuck. It usually isn't. This free 2-minute quiz scores you across the five pillars of a real exit and tells you which one is actually holding you back. 📩 GET THE WEEKLY EMAIL: one idea every Monday about money, identity and what life after financial independence actually looks like. No fluff, no pitches. 🇸🇬 SINGAPORE LISTENERS: this one's for you. Small in-person workshops on the exact exit maths this show talks about. Find your freedom date in a morning, or take the full day and plan the years before it. Eight seats each.

Oct 4, 2026

038: Thirty thousand hours. That's roughly how long I've spent sitting in a chair since I started work, and early retirement won't give a single one of them back. If you've been in a corporate job since your twenties chasing financial independence, you're on a similar number, and there's a ten-second sitting rising test in this episode that shows you exactly what it's cost. Most people on the road to early retirement have a plan for their body, and the plan is this: hit the number, hand in the notice, then get healthy. I had that plan too. This is the first episode of Health month on Life After Enough, and it's about why, for anyone who wants to retire early, that plan is the wrong way round. Here's the thing nobody tells you about a desk job. Nothing hurts. A smoker knows what they're doing to themselves. Nobody at a desk thinks they're doing anything at all. So while you've been checking your portfolio every month for twenty years, a second health account has been running in the background, and it only goes one way. I found out about mine under a loaded barbell, the day my hips wouldn't open and my lower back took the whole load. That was the first I'd heard about thirty thousand hours. The body you retire with is being decided now, in the chair, on the ordinary Tuesdays. The exit date doesn't reset it. What this covers: The thirty thousand hour sum, and why compounding works exactly the same way in reverse for your body Why "sitting is the new smoking" is wrong, and the one way it's actually worse What's happening in your legs at 3pm on a Tuesday, and why your 6am gym session doesn't touch it Why "get healthy after I leave" is worse for early retirees than for anyone else The sitting rising test: ten seconds on the floor that measures exactly what the chair has taken off you This one's for you if: You've spent years optimising your withdrawal rate and never once thought about the other account You train hard and still can't work out why your back hurts and your bloods are off Your after-retirement list is full of treks, climbs and cycling trips, and you've never checked whether your body will pass them You've told yourself you'll sort your health once the number's done Question to sit with: What's the physical thing you're saving up for when you're free? The trek, the climb, the long trail. Do the sitting rising test today. Would your body pass the version of it that trip needs? If the answer is no, or probably not, don't wait. 🎯 WHEN COULD YOU ACTUALLY STOP WORKING? Run your own numbers in the free Freedom Dashboard and find your date in about five minutes. It'll also show you how much of your current salary your future still needs, which might be a lot less than you think. Nothing you type leaves your device. 🧭 FIND YOUR FREEDOM SCORE: Most people chasing financial independence assume money is what's keeping them stuck. It usually isn't. This free 2-minute quiz scores you across the five pillars of a real exit and tells you which one is actually holding you back. 📩 GET THE WEEKLY EMAIL: one idea every Monday about money, identity and what life after financial independence actually looks like. No fluff, no pitches. 🇸🇬 SINGAPORE LISTENERS: this one's for you. Small in-person workshops on the exact exit maths this show talks about. Find your freedom date in a morning, or take the full day and plan the years before it. Eight seats each.

Sep 27, 2026

037: Everyone chasing financial independence pictures the quiet day at work as a win. Well paid, nothing on fire, nobody chasing you, and you got paid anyway. This week I had exactly that day and it was unbearable, and once you retire early or hit your number, I think it happens to you too. This is the final Purpose check-in on Life After Enough, and it's about the strange moment when financial freedom quietly flips a good day at work into the worst kind. On Monday I sat at my desk and waited for an email that might land at eleven, might land at six, might not land at all. That was the whole day. Not hard, not stressful, just a full day of my life I couldn't spend on anything, held available for something that never came. It landed worse than any of July's late nights, which makes no sense until you see what actually changed. The work didn't get worse. I stopped needing the thing the day was paying me in. When the money's already built, the scale tips, and the trade at the centre of every job gets priced properly for the first time. What this covers: Why a quiet, easy day at work can feel worse than a brutal one once you've hit your number The trade behind every salary, and why financial independence flips it overnight Borrowed purpose: how your job quietly runs on meaning borrowed from your mortgage, your number, your school fees, and what happens when that loan gets repaid Why lifestyle creep isn't really a spending problem, it's a job going looking for a new reason to exist Why the fix was never a better role, a different job, or a four-day week Where the countdown stands now that I can finally see the trade for what it is This one's for you if: You're close to your number and a quiet Friday has started to feel wrong in a way you can't name You've told yourself work gives you purpose and aren't sure anymore whether that's true You hit your number and felt nothing, and wondered what was wrong with you You catch yourself eyeing a bigger house or a bigger buffer to give the job a reason again You want the honest version of the final stretch, including the parts I'm not allowed to tidy Question to sit with: What's lending your job its purpose right now? The mortgage, the number, the school fees, someone you look after? Find it, then ask the harder half. What happens on the day that loan gets repaid? 🇸🇬 SINGAPORE LISTENERS: this one's for you. Small in-person workshops on the exact exit maths this show talks about. Find your Freedom Date in a morning, or take the full day and plan the years before it. Eight seats each. Dates 👉 https://luma.com/lifeafterenough 📩 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! 📊 Free Coast FIRE Calculator: figure out when your money can do the work, so you can start designing a life worth being present for.

Sep 20, 2026

036: Everyone thinks early retirement is the moment you finally escape the cage, and that financial freedom on the other side of the number will feel like pure freedom. Here's the warning nobody gives you. The people who escape the cage are the ones who quietly build a new one, with better views, and call it purpose while they're doing it. I know, because I'm still employed and I'm doing it right now.

See all episodes →