18 months I should've decided faster

I've been working on something lately that's turned into an unexpected time machine. A timeline document — every major moment in 20 years of running my agency. Financial records, old P&Ls, my personal spreadsheets and calculations, status newsletters I sent to the team, recorded company meetups, our Confluence knowledge base. It's monotonous work, honestly. Digging through old emails (most didn't survive server migrations), sifting through documents I haven't touched in years. But every time I hit an artifact — a photo, a message, a spreadsheet — the memories flood back. Not facts. Emotions. The joy of wins. The bitterness of losses.

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And I keep catching myself falling into "what if."

What if I'd decided faster? What if I hadn't waited so long?

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Because the last few years of that timeline? Those haunt me. There's this image I keep coming back to when I think about those years.

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I've always loved driving through mountains. The winding roads, the elevation changes, the views. But there's always that moment when you see something in the distance — a lake on a slope, surrounded by peaks — and you know your car can't get there. Especially not a comfortable one. You could park and hike. But that means leaving the warmth, the safety, the familiarity of the machine you've built. So you keep driving past it, looking through the window, telling yourself "one day."

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That's exactly where I was with the agency.

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I'd built a beautiful machine. It ran smoothly, didn't break down much, carried me comfortably. I was looking at life through the glass — everything seemed fine from inside. But the real life I wanted? That was outside. On that slope. At that lake.

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I remember one afternoon driving home from the shooting range. It was mid-week, middle of the day. The drive took about 90 minutes, the session about three hours. I'd get back near end of day. I'd finally achieved a dream — time and money for an expensive hobby I'd wanted for years. Guns, ammo, gear, range fees. I could do it mid-week without anyone asking where I was or what decision they should make. And I felt this weird cocktail of emotions.

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Euphoria that I had this freedom. This thing I'd always wanted. And sadness that I didn't care what was happening in the business anymore.

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I realized I didn't even know what the company was doing. Something was being built, something was being sold. Developers were being resold. Our CIO told me about automations we'd implemented — I didn't even know we had them. That's how disconnected I'd become. I'd spent my whole life following the advice "do what you love and you'll never work a day." And it was true for so long. But somewhere along the way, it stopped being true.

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The hobby was great. But it wasn't moving me forward. I felt stuck. Not developing in the thing that had driven me for decades. That's when the doubts started creeping in. I saw an ad on YouTube — some guy selling course creation services, talking about how "you already have knowledge people will pay for." And I thought: that's what I'd actually be interested in doing. I'd always wanted to build products. We'd tried so many times in the agency — comics, games, apps. We built successful products for clients but could never make our own work. I started thinking about why. Marketing, obviously. We'd tried ads, SEO, had a whole marketing department. But that was for the agency.

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The one who was stuck? Me.

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That's when I first seriously considered the term "personal brand." But I'd run from social media my entire life. So I started learning. What is a personal brand? How do you build one? I used AI to write content and posted it — pure garbage, obviously, but I posted it anyway. Then I saw Dan Koe talking about how he started on Twitter. How you need to write. And learn to write well. I dove into that. And honestly? I stopped thinking about the agency almost entirely. There was still stuff to do there, sure. It started annoying me because it pulled me away from what felt important.

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But I couldn't let go. It felt like betrayal.

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What kept me there

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So I started cutting the tail off piece by piece. Didn't renew projects. Sold teams to clients. Stopped actively looking for new work. Started reducing headcount. But some people stayed. And I invented work for them — internal projects, product ideas. Even though I could see the wave of AI and automation coming and knew it wouldn't last long. I was running at a loss, keeping people I couldn't sell or place on client projects that were ending. I lived that parallel life until 2024. And then I realized: enough. I had no focus. I was just thrashing. Nothing was actually happening.

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What kept me there for 18 months? Sunk cost. I'd invested so much — money, time, energy, reputation. How could I just walk away? Responsibility. These people trusted me. They'd followed me. I couldn't just abandon them. Fear. What if this personal brand thing didn't work? What if I was wrong? Normalcy bias. It had always been good. Surely it would keep being good. Those weren't reasons. Those were chains.

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In early 2024, I met a consultant who helped me structure everything I'd been doing. More importantly, he helped me package my messy ideas into a clear offer that resonated with something deep inside me. Only when I saw "this is what I want to do, and here's what I need for it" did I realize: the agency doesn't fit anywhere in this. And I definitely don't want to continue it. That's when I could finally let go. Because until the very end, what held me was that feeling of responsibility. To the team. To the people who'd trusted me. I'd chosen to sacrifice my own dream and desire to move forward for that feeling of obligation.

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Sounds noble, right? Except the market was changing dramatically. I didn't want it anymore. And I was bleeding money keeping people employed out of guilt. I told my mom first. She's a journalist, worked at a small paper for years, comfortable with words in a way I'm not. I showed her my writing. She supported me. Everyone else — including my now ex-wife — laughed at me. "What is this nonsense?"

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And yeah, it was nonsense. But how else do you learn if you've never done it before? Starting to write publicly was terrifying. I had no idea what I was talking about or how to say it.

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The real cost of waiting

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Those 18 months cost me. Money, obviously. Payroll for people I kept out of guilt. Taxes, overhead, operational costs that didn't go away. But the real cost? Time. And focus. That's what I'll never get back. The first year or two after I left were brutally hard. I had savings, but I thought results would come faster. Had to take off a lot of rose-colored glasses.

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Marketing in 2005 vs 2026? Completely different worlds. AI slop flooding everything. You struggle over one piece of writing while someone else pumps out dozens of posts. Sure, maybe they get no results, but it buries you in the noise anyway. I tried Twitter first, then moved to LinkedIn because the audience was closer to my ICP. You can write actively there and actually expect responses. I tried automation, templates, AI shortcuts. All bullshit. I changed my positioning several times. Tried being the all-knowing expert. Eventually landed on what works now: founder with scars, sharing personal experience, helping people who find it interesting and useful. Not chasing, not insisting, not trying to sell.

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That's when things shifted. People started subscribing. DMs became real conversations. People reached out with questions, asked for calls.

I thought it would be faster. It wasn't.

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Here's what I wish someone had told me 18 months earlier: The forces holding you in place aren't logical. They're emotional, psychological, cognitive. And from inside, you can't see them clearly. I couldn't. Not until someone outside helped me see the cage I'd built.

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One thing you can try this weekend:

Ask yourself one uncomfortable question: "If I was starting from zero today, would I choose this same business?"

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Not "can I make it work" or "should I fix it." Would you choose it?

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If the answer is no — or if you hesitate — write down why you're still here. Not what you tell yourself. What you actually say out loud when someone asks.

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"I've invested too much to quit now."

"The team depends on me."

"I don't know what else I'd do."

"It's comfortable."

"What if I'm wrong?"

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Those aren't reasons. Those are the forces holding you.

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And here's the hard part: you probably can't see them clearly alone. I couldn't. So tell someone outside your business — a friend, a spouse, someone who isn't invested — what you're thinking. Not asking for advice. Just explaining the situation. Then listen to what they say. Don't defend. Don't explain more. Just listen. Because when you're inside, you can't see the cage. You need someone outside to point at the bars.

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And I am genuinely curious: What decision are you delaying right now because leaving feels harder than staying? Hit reply and tell me. I read every response.

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P.S. That timeline document I'm still building? Every time I add another piece from those last few years, I see the same pattern: I knew what I needed to do. I just couldn't admit it yet. The knowing and the doing — that gap cost me 18 months. Don't let yours cost you more.