A letter to anyone still in Big Tech, and not sure this is still it

You’ve done well, and you’re still inside Big Tech. You’re just not sure the next step is yours.

I’m writing this to the person I was when I was still inside the Big Tech bubble. I spent six years at Google, working on ads and maps, then two at Amazon in Luxembourg, leading a team of over 100 people. From the outside, it was what I’d been working towards. I got there by trying harder, which worked until it didn’t. It took me ten years and two burnouts to work out what I actually wanted, and you don’t have to take as long as I did.

On paper, it’s going well. Your mother beams with pride as she tells her friends about the job she doesn’t understand, at the company everyone has heard of. Your uni friends envy your equity and title, and your younger self wouldn’t believe where you’ve ended up. And there’s plenty you like about it: the people, the problems you get to solve, and the feeling when something you helped ship actually works.

But something has just shifted. Maybe it was a reorg, a new skip-level, or an “org update” that appeared in your calendar with no agenda, and this time you were on the wrong side of it. Maybe it was the edict from above that “AI-driven impact” is now part of everyone’s review, and nobody can tell you what that means. Are you meant to automate yourself out of a job, or someone else out of theirs? Or is it just an exciting development, with nothing to worry about? Everyone around you sounds sure, and nobody is. Maybe an offer came in, and you’re not sure you want it. Or maybe you made the level you’d been chasing, and found nothing above it that you want.

And there’s the money. It’s good money, but not enough to retire on. Your Financial Independence number is still three years away, and it’s been three years away for a decade, and you’re always waiting on the next vest. You’ve modelled “half the money, half the hours” more than once. Maybe you even made a version of the trade, and found the question came with you. Meanwhile, you’ve looked at that vineyard in Portugal so often that the ads follow you into meetings.

You wouldn’t call it burnout. You’d say stamina, or a plateau. But you took a week off as a fire break. You needed a plan just to do nothing. And every win lasts about an hour before the machine in your head says “next”.

You’re not unhappy, but you’re not sure this is it. And when you mention any of this to someone outside the bubble, they say, a little wistfully, “I wish I had your problems.” So you stop mentioning it.

What gets in the way. You give it serious thought, usually somewhere between your last Google Chat or Slack message of the day and falling asleep. Then your VP’s next fire drill lands, and you tell yourself “one more year”, as you have for five years running. Everyone has an opinion about what you should do: your manager, your family, your peers. None of them is lying to you, but none of them can be neutral either.

You’ve done everything right, and that might be exactly the problem. For years you had a scoreboard, with the promo, the scope, the headcount and the OKRs, and you got very good at it. Somewhere along the way, the question shifted from what do I want? to what’s the smartest move? And underneath both sits a quieter one: without the logo and the title, who would you be?

As Howard Thurman said, “Don’t ask what the world needs. Ask what makes you come alive, and go do it.”

What would make you come alive?

Maybe you stay, but on your own terms. A different scope, a team you’d choose, or the same job with less of the noise.

Maybe it’s another job, somewhere that fits who you are now.

Maybe it’s the thing you want to build, the one in your Notes app, with the domain name you bought and told no one about.

Or maybe it isn’t a company at all. A portfolio of advisory work, or the thing you always said you’d do “one day”.

Whatever the answer, you can say it out loud without immediately explaining why it’s unrealistic, selfish, or something you should already have done.

What it looks like when you’ve worked it out. In the half-second before you speak, you used to run the calculation: how will this land? Then one day you notice you’re doing it less. You’ve stopped managing how you come across, so you say what you think and disagree when you disagree. Your shoulders come down, and you realise you hadn’t known they were up.

The life you built wasn’t a mistake. It got you here, but it doesn’t get to decide what comes next.

I won’t tell you what to do. You could spend another three years thinking about this, but I’d rather you didn’t.

Richard

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