You'll Never Feel Ready for FIRE If You Keep Doing This
The one habit that quietly resets your finish line every time you get close
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As I was wrapping up my last weeks in consulting in Dubai, a Senior Partner - someone who had been at the firm nearly 20 years and making north of a million dollars a year for most of them - told me he wished he could retire like me. I had been there seven years. Surely if I could retire, he could retire three times over. I told him as much. He looked genuinely surprised. “It’s not all that it seems,” he said. “Money is tight. My calculation is another eight years.”
I spent the next few months trying to understand what I was missing (or what he was missing).
He almost certainly has more money sitting in his accounts than I have invested. And yet he can’t retire. Two mistakes explain almost everything.
The first: he lives his private life the way the consulting firm runs his professional one. The firm puts him in the Ritz-Carlton and flies him business class. After enough years, there’s no mental separation between what the firm covers and what he covers. The standard just travels home with him.
The second: he plans to retire into the exact same lifestyle. Same villa, same schools, same flights. He’s not planning a different life - he’s planning to fund the current one without a salary. Which is why the number never feels like enough.
Here is what that lifestyle actually costs.
The family had been renting a four-bedroom in The Meadows at AED 280,000 a year - comfortable, well-located, good community. When he made partner, they bought a five-bedroom in Mohammed Bin Rashid City near the peak at roughly AED 15 million. Finance AED 12 million over 25 years and you’re at AED 65,000 a month in mortgage payments - more than double the rent, for a house he’s barely in because he spends most weeks in Saudi Arabia.
Two kids are at exclusive high schools at around AED 120,000 each per year. Two are in US boarding schools - one at Deerfield Academy at $74,000, another at a similar New England institution. Total annual school fees: roughly $210,000. What exactly elite high schools delivers over a high-performing moderately-priced private school at a quarter of the price is unclear. As a partner, it’s simply what you do.
Two nannies and one house help at home. The kids, with a dedicated adult for every need, are building exactly the kind of learned helplessness that creates more work for the parents later. His wife stopped working when he made partner, seven years ago. She wants to go back now, doesn’t feel sharp anymore, and is struggling to re-enter the market. They permanently lost a second income, and she lost something harder to replace.
Every school break the family travels. He joins for a few days when Riyadh allows. His wife and the two younger kids fly business class; the nanny who travels with them flies economy - the other stays home. When the two older kids can make it from the US, they fly business to wherever the family is going rather than picking up a summer job or staying to build any independence.
Take a Maldives trip - three rooms at a resort that suits a consulting partner family: an overwater suite for the couple at $2,500 a night, a room for the older kids at $1,200, a suite for the younger kids and nanny at $1,800. Seven nights at $5,500 a night is $38,500 before anyone has eaten or done anything. Business class for four people runs $2,500 each - add the nanny in economy and the two older kids flying in from the East Coast and total flights land around $20,000. A Maldives trip for this family is $60,000 to $65,000. They take three or four holidays a year.
Now the contrast. A partner I know in London - similar title, but paying 40%+ in UK income tax, so considerably less in net compensation - has $11 million invested and could retire tomorrow. He rents a good flat in Clapham, his kids go to strong state schools, his wife works. He flies economy on anything under four hours. He rides his bicycle everywhere and is in good shape. His counterpart is not - always in a car, barely moving.
Cut the London partner’s assets in half and he could still retire well. His lifestyle was never inflated, so the number needed to sustain it stays low.
Every decision that trapped the partner I spoke to falls into one of two buckets: convenience or status.
Good convenience enhances something you genuinely value. I drive five miles out of my way to charge my car for $10 instead of $30, and I run there and back - ten miles a week I wouldn’t otherwise do. That’s convenience working for me. Harmful convenience makes you passive, sedentary, dependent. Three household staff and a car for every errand aren’t convenience. They’re atrophy with a price tag.
Status spending has no good version. It’s what you pay so other people register something about you. The school no partner questions, the villa in the right neighborhood, the cars at the right price point. As we explored in Tradition and the Cost of Outsourced Thinking, most of it isn’t even chosen - it’s inherited from the environment. And as we wrote in Leave Your Emotions at the Door, pride does most of the driving without announcing itself.
If you are building toward FIRE, you are already building real wealth. You don’t need to signal it. Spend on what you actually love. Cut the rest. The gap between what you earn and what you genuinely need - that’s where freedom gets built.
Till next time!