A letter to anyone who left Big Tech a while ago, and isn’t sure it’s working out

You’ve done well. You left Big Tech a few years ago, and whatever you’ve done since, it isn’t working out the way you hoped. You’re not sure what to change.

I’m writing this to the person I was a few years after I left. I spent six years at Google, then two at Amazon in a job I wasn’t suited to. I burnt out, left in 2016, and became an independent consultant. For years after that I worked with founders and executives across Europe and the US, and I did my own sales and marketing, because nobody else was going to. After another burnout, I left consulting for coaching, and finally found what I love to do. I’m building that business now. It took me far longer than it needed to, and you don’t have to take as long as I did.

Some of it has been good. Some days, what you’re doing now has felt like the life you wanted.

Maybe you went to a startup. You got a bigger title and options that might be worth something one day. You were hired for what you knew at Big Tech, and half of it doesn’t apply. There’s no team to hand things to, and the plan changes every month.

Maybe you went to a corporate. Everything takes three times as long. When you explain how you’d have done it at Google or Amazon, the room goes quiet, and someone says, “We’re not Google.”

Maybe you went out on your own, fractional, advisory, or building something of your own. You have two or three clients, and one of them pays for most of it. Coffee chats fill the week but not the pipeline, and it’s feast and famine.

Or maybe you’ve tried more than one of these, and you’re between things again, wondering which to try next.

Wherever you landed, when people ask, you say it’s going well. To yourself, you say something else: you’re busy, but you’re not sure it’s going anywhere.

And there’s the money. You left with some stock, and you’ve held on to some of it. Most of what you’re worth is still in one share price, and you check it more often than your invoices or your payslip. Now and then you still work out what the stock you left unvested would be worth today. Your old total comp is the number everything gets measured against, and nothing since has matched it. Spending money on yourself feels like a bet. And you’ve started saying yes to things you’d have turned down two years ago.

For years, the name on your badge opened doors. Now you’re finding out which ones open for you. Your LinkedIn headline still says “ex-Google” or “ex-Amazon”, and you can’t decide whether to drop it. The recruiter messages are all for the job you left, and you read them properly now. In the alumni WhatsApp group, everyone else seems to be doing fine.

And underneath it all sits a fear you don’t say out loud: that leaving was a mistake, and that going back in might be the honest answer, even a level below where you left. On a bad week, a bigger question gets louder: who am I, if this isn’t working?

What gets in the way. You give it serious thought, usually on a Sunday night. Then the week takes over, there’s a deadline or a client or a board meeting, and the question goes quiet until the next bad week.

Everyone has an opinion about what you should do: your partner, your old colleagues, your friends. None of them is lying to you, but none of them can be neutral either. And if you’re on your own, your feed is full of people selling you an answer: the path to six figures, the funnel, the course, and the advice to niche down and post more. They all assume you want a bigger business. Nobody has asked whether you do.

Maybe you chose to leave. Maybe you were caught in a layoff, pushed out or handed a package, and the decision was made for you. Either way, you may never have decided what you were going towards, so you took whatever came.

For years you had a scoreboard, with the level, the promo, the scope and the headcount. You left it behind, then built a new one out of whatever your new world counts: a title, a funding round, day rates or followers. Somewhere along the way, the question shifted from what do I want? to how do I prove this was the right move?

As one of my favourite coaches says, following someone else’s playbook is like wearing someone else’s underpants. It might feel fine at first, but sooner or later you get a wedgie.

What do you really want, if nobody else gets a say?

What it looks like when you’ve worked it out. You know what you want, so saying yes and no gets quicker. The work in your calendar is work you’d choose, and the share price goes back to being just a number. Your LinkedIn headline says what you do now. And when someone asks how it’s going, you can tell them the truth.

If we work together, we start with what you want, and give it a full hearing before anyone asks whether it’s sensible. Then we look at what you already have: the work, the stock, the money, and what it needs to do, and by when. If what you want is a business of your own, I’ll help you sort out what it should look like to suit you and meet your financial goals. We try something small, see what happens, and keep what works.

I won’t tell you what to do, and I won’t sell you a six-figure plan, a course or a programme to hustle harder. Making where you are work is a real answer, and so is going back in, or something else entirely. You could spend another three years telling people it’s going well, but I’d rather you didn’t.

Richard

If you’d like to work it out with me, here’s how it works →