Big decisions

Hello again my friend,

If you’ve ever worked a job with a toxic boss, or had that itch to go and do your own, or just felt stuck you’ll be familiar with this. The context is different. The pull you feel now is from how the upcoming change will impact you. But in those cases, the pull to make a move is from the consistent drag. People who don’t mind a toxic job and just suck it up and continue are the same people who will fear AI but not actually make a move.

In my opinion, now’s the time to make a move. The changes coming are too powerful. It’s not just AI, it’s also the disposition of most companies. Think about it. How are you going to negotiate a salary increase when you (and they) know AI can do half your job?

Hello again my friend,

With all the talk of AI taking jobs and companies restructuring, it's natural to feel uneasy. I still feel uneasy, even after spending serious time figuring this stuff out. But this isn't the first time I've felt this way, and if you’re more than a few years into your career, it’s probably not yours either.

If you've ever had a toxic boss, felt the itch to go do your own thing, or just felt genuinely stuck, it’s so similar to how AI is creating pressure today. You know the feeling. That low hum of knowing something has to change but not knowing exactly what to do about it (yet).

Before, it was the slow drag of a bad situation. Now it's the weight of incoming change. But here's what I've noticed: the people who tolerated a toxic job and never made a move are the same people who will see and feel the AI pressure and still do nothing.

I don't want that for you.

So this one is personal. I'm going to walk you through three decisions I've made that scared the hell out of me, pushing management for a raise, leaving to do my own thing, and eventually blowing up my career entirely. I’ve always tried to write from personal experience, the stuff I’ve really lived, and I think those decisions will creep up on many of you if they haven’t already.

What I thought I'd regret. What I actually regret. And what any of it has to do with the moment a lot of us are facing right now.

Let's lock in.

I've asked for raises well over a dozen times in my career. I’ve gotten some.

Most of them were clean. You make the case, they see it (or they don’t), you move on.

But a few of them, at one job in particular, left a mark that had nothing to do with the money.

I remember presenting numbers, which were related to my bonus. It should have been a straightforward conversation. Instead it created friction that spilled into my earnings. I walked out of that room with a specific, new, feeling. That we both knew it wasn't working anymore.

Not the job. The relationship. My boss had built what he did from the ground up. I'd grown fast, faster than anyone at that company, and somewhere in that meeting it became obvious that there would be some resentment.

I lost something that couldn't be negotiated back. Was it the most professional way to go about it? Nah. but these things happen.

Asking for what you're worth is always the right move. Stretching further than what seems reasonable is also fine, and a normal thing. But it's not just a financial negotiation. You're also revealing something about yourself, your ambition, your self-awareness, how seriously you take your own value.

Some managers respect that. Others quietly resent it (or worse). The ones who resent it were never going to be your long-term allies anyway. The friction just surfaces what was already true, and would’ve blocked your progress.

Now think about the current climate.

There’s a window in place right now. AI is good enough to do half our jobs. But not everyone knows how to use AI yet, and even if they do, that doesn’t mean they work hard or know how to prioritize. They also don’t have the context you do. Your still capable, but the conversation is changing.

AI is already being used to justify leaner teams, flatter structures, and slower salary growth. The moment companies have a clean, defensible reason to hold the line, they'll use it. That reason is coming faster than most people think.

It’s not going to be negotiating a salary increase as AI can do more of our jobs every day. If you've been sitting on that conversation, now might just be the time.

I left a stable job to start a newsletter. It didn't work out.

The decision itself wasn't dramatic. I just realized one day that if I didn't try, it would bother me forever. That felt like enough. Looking back, I was only half right. Yes, I genuinely wanted to build something. But I was also exhausted. Same arguments, same unresolved issues, same confusion about what we were doing. It just wasn’t a good fit anymore.

Both things were true. I just wasn't honest about the second one until much later.

The newsletter never really got off the ground. It took too long to generate any income, and then a family situation came up that ate into my runway faster than I expected. I didn't run out of money dramatically, it was quieter than that. More of a slow fade than a crash.

What I got wrong had nothing to do with the idea. It was the transition. I left with a blank state. No audience built up beforehand, no marketing in place, no real bridge between the stability I had and the thing I was building. I had a job with reach and credibility, people knew me, respected the work, and I barely used any of it. I could have been building in public the whole time. Quietly sharing, growing, documenting. I wasn't. I was too worried about what people would think.

That's the regret. The way I left.

AI is making it genuinely easier to start something than at any point in history. An app, a service, a brand, the barrier to building has collapsed. A lot of people who've been sitting on an idea are about to pull the trigger. And a lot of them are going to make the same mistake I did. They'll leave too fast, too soon, without building the bridge first.

If you're considering it, don't wait until you're ready to quit. Start now, while you still have the platform and the stability. The jump is always easier that way, and I wish I’d done that.

This one was the hardest to explain because from the outside, it genuinely looked like a mistake.

I turned down a job offer from someone I knew personally. More money, better perks, familiar industry, familiar faces. They wanted me on the team and made it clear. Turning it down was awkward in a way that lingered, you don't easily walk back from saying no to someone who went out of their way to say yes to you.

Instead I went to beehiiv. A startup most people hadn't heard of at the time. Starting from zero, in my thirties, in a new space. My family wasn't excited. The people in my life who knew the other offer thought I was being naive at best, reckless at worst. beehiiv wasn't a known quantity then. It is now, but not then. I had responsibilities, and it looked like a big risk.

What nobody tells you about starting over in your thirties is how disorienting it actually is. You've spent years building something like reputations and networks. Then, you're the new person again. You have to earn everything back from scratch. That requires a specific kind of humility that not everyone has or wants. It really hit my confidence.

What I didn't expect was how clarifying it would be. Strip away the title, the familiar context, the borrowed credibility, and you find out quickly what you actually know. Turns out I was more capable than I thought. Turns out beehiiv was exactly the place to find that out.

Now think about what's happening in the job market. A lot of people are about to be pushed into a restart whether they choose it or not. Layoffs are accelerating. Entire categories of work are being restructured. For some that's a crisis. For the ones paying attention, it's the best possible time to make a deliberate jump into something new. I’ve talked about this at length in previous posts.

The roles being built around AI are still early. The people getting in now, even from zero, will have a significant head start on everyone who waits until it's all settled and competitive. Starting over is only a setback if you're heading back to something old. If you're pointing yourself at something growing, zero is just the beginning.

In so many cases, going to a company that’s perhaps a bit old fashioned and showing them you can do three people’s jobs with AI is actually a great case to hire you. Most people can’t use AI that well yet.

The decisions themselves are rarely what you end up regretting.

You ask for the raise, you leave for something new, you bet on the unfamiliar thing, and it works out sometimes, you work hard and keep your priorities straight. It’s not always clean, not always on the timeline you wanted, but it works out. What actually stays with you are the things around the edges. The transition you didn't plan. The audience you didn't build. The work you were too cautious to show because of what someone might think.

I spent years worried about the wrong things. Worried about the big moves, when it was the small hesitations that cost me.

AI is going to force a lot of people's hands in the next few years. Some will get laid off. Some will see their roles quietly hollowed out. Some will decide to jump before they're pushed. All of those are versions of the decisions I just described, asking for more, betting on yourself, starting over.

The bold move tends to work out. The hesitation around it is what costs us. At least, it cost me. It’s better to be bold.

So if you're sitting with one of these right now, the raise you haven't asked for, the thing you want to build, the role that doesn't make sense on paper, I'm not going to tell you it'll be easy. I'm going to tell you that the version of you who doesn't make the move is the one who ends up with the real regrets.

In a world moving this fast, doing nothing is its own kind of decision.

Thanks, as always, for reading.