I needed a salesperson. I hired a project manager.

Not so long ago, I had a conversation with a young founder that sent me straight back to 2012. He runs a small agency. Finding clients, doing the work, managing projects — all of it, mostly himself. When I asked what his biggest pain point was, he didn't hesitate: "Finding a talented salesperson. Ideally 100% commission."

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I smiled to myself. I'd said those exact words fourteen years ago.

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But as we kept chatting, the real problem surfaced. He didn't need a salesperson for growth, he needed one to replace the clients he kept losing. Delivery was slipping because he was stretched across everything. Clients left, he'd scramble for new ones to fill the gap. Classic cycle: no money → can't hire → do everything yourself → no time to grow → no money.

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I asked: "If you found that salesperson tomorrow, what would their first week look like?"

He replied. "Probably chaos, haha."

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I've always admired people who can laugh about everything being on fire. For me, back then, it was pure panic. This might sound funny, but through our conversation, an old Russian fairy tale came to mind. A hero arrives at a crossroads. Three roads, a stone with inscriptions.

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Go right — lose your horse, save yourself.

Go left — lose yourself, save your horse.

Go straight — lose both.

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No good option. Just different costs. That founder was standing at exactly that crossroads. And so was I, once.

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The same crossroads, twelve years earlier

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In late 2011, my business partner — the one responsible for sales — told me right before our New Year's party that there were no new projects. We'd need to let most of the team go within a month. By January, I was back at my desk doing sales — something I hadn't done since 2008, when we'd split responsibilities and I'd happily taken the ops and delivery side.

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Now I was writing bids on Elance, sending connection requests on LinkedIn, crafting proposals — while also writing status updates to clients, answering the team's questions, reviewing deliverables, resolving issues. Not switching between sales and delivery every day. Every hour. I had a small daughter at home, a mortgage, and I was the only one earning. The full set.

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Somewhere around February, I went to a meeting of a local entrepreneurs' club. Small group, a café on a freezing Friday evening. I sat there with a glass of wine, not in much of a mood to talk, mostly just warming up. And then I heard another founder describe my exact situation. His solution made me set down my glass.

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He said: "We realized that finding a new client costs way more than keeping the ones we have. So I focused entirely on sales myself, and we hired project managers to handle delivery."

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Not salespeople. Project managers.

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He was obviously an extrovert — sales came naturally to him. I couldn't say the same. I've always been on the shy side. Sales were a constant source of stress, and if I'm honest, I was subconsciously looking for someone to carry the part I didn't enjoy. But sitting in that café, I finally saw the crossroads clearly. There was no road without a cost. The question was which cost I could actually pay. The truth was simple and uncomfortable: at that point in time, nobody could sell our services better than me. I knew the work, the clients, the team, the tech. A salesperson on pure commission — even if I found one — wouldn't have any of that. And I couldn't afford an experienced one.

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What I could do was stop being pulled into delivery every hour.

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So instead of looking for a salesperson to replace what I didn't enjoy, I looked for a project manager to protect what I needed to focus on. Someone young, organized, willing to learn. Not a technical expert — just someone responsible and consistent, who could handle daily client communication, task tracking, and quality checks without pulling me in. I found that person. And I gave them a single Google Doc.

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Three sections: a checklist for starting a new project, a daily routine for managing active ones, and a template for weekly client reports. No framework, no system, no fancy tools. Just one document with clear steps.

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That Google Doc, looking back, became the seed of every system we built later. But in early 2012, it was just a way to stop the bleeding. The PM took over daily project management. Churn slowed because clients finally felt someone was watching their project consistently. And I could sit at my desk for a full morning writing proposals without getting pulled into "quick questions" every twenty minutes. The cycle didn't break overnight. But it cracked. And the crack was enough.

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The road nobody wants to take

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What I took from that crossroads keeps coming back to me in conversations like the one with this young founder. My instinct was to hire for the part I hated — find a salesperson so I wouldn't have to sell. But the uncomfortable thing turned out to be exactly what only I could do at that stage.

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The real unlock wasn't removing it. It was removing everything else that kept me from doing it well.

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Something to try this weekend:

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If you're in that same cycle right now — bouncing between selling and delivering — write down the two or three things that pull you away from the one activity only you can do at this stage. Then ask: which of those could a capable, organized person handle with a clear checklist and simple expectations? Not a senior hire. Not a perfect candidate. Just someone consistent. That's usually the first crack.

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So here's my question: what crossroads are you standing at right now? What's the uncomfortable road you keep avoiding — even though somewhere inside, you already know it's the one you need to take?

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Hit reply and tell me. I read every response.