Most business owners I’ve talked to over the years already work for a difficult boss. The catch is that the boss isn’t on any org chart. It’s the voice in their own head — the one that says they should be further along, should be working harder, should already have this figured out.
Firing the Bad Boss in Your Head
That was the idea that stayed with me after I sat down with coach Leah Zimmerman for episode 27 of Rebooting Business. Leah spent years as a classroom teacher before moving into executive coaching, and she’s spent a lot of time watching how people talk to themselves when no one else is listening. Her line was blunt: she’s coached clients to “fire the boss” in their head. Listen to how you’re speaking to yourself, she tells them, and then ask whether you’d stay one week with a manager who talked to you that way.
It’s a good question, because most of us wouldn’t. We’d quit. And yet we run our own businesses under exactly that kind of management, day after day, and call it discipline.
Leah traces a lot of this back to where the voice comes from. We learn it early — from teachers who made us feel worse when the work wasn’t done, from the assumption that struggle is our fault and excuses are forbidden. By the time we’re adults running a company, that internalized critic has hardened into a few stubborn beliefs: that there’s never enough time, never enough money, never enough margin for error. She calls it a scarcity mindset, and it does something quietly corrosive. When you believe there isn’t enough, you stop looking for more. You spend your energy confirming the shortage instead of finding the way out of it.
That mindset has a familiar symptom, and it’s one I saw constantly during my years mentoring small business owners through SCORE. People come to you wanting a single broken thing fixed. The website isn’t generating leads. The blog post doesn’t rank. The images won’t size right for social. They want the widget repaired. What they almost never ask is the larger question underneath it: what am I actually trying to achieve, and is this even the right way to get there?
Leah and I landed on the same diagnosis from different directions. Hers came from the classroom — the teacher who wants the copier fixed so they can run the same worksheets they’ve always run, without asking whether those worksheets are teaching anything. Mine came from years of clients who’d spend two hours sizing an image and another two writing a post that wasn’t working, when the real problem was that they were trying to do every job in the business themselves. The fix isn’t a better widget. It’s stepping back far enough to see the whole machine, and then deciding which parts are actually yours to run.
The hard part is that this kind of stepping back rarely feels productive in the moment, because we’ve been trained to value the immediate. Leah’s framing is that coaching, at its best, isn’t someone handing you answers — it’s someone asking the question that lets you find the answer yourself. People resist unsolicited advice because advice treats whatever you’re doing as a problem to be corrected, and we push back against the judgment buried in that. A good question doesn’t carry the judgment. It just opens a door.
Which brings it back around to the boss in your head. That critic isn’t asking useful questions. It’s only delivering verdicts — you’re behind, you’re not enough, you should already know this. Replacing it doesn’t mean going soft on yourself. It means trading the judge for an investigator: a voice that asks what you’re really after, why it matters, and whether there’s a path you haven’t considered yet.
Leah put the principle in a way I keep coming back to, and it applies well beyond business. You’re not responsible for producing someone else’s voice, she said — only the clearest version of your own. The internal boss spends most of its time measuring you against other people. The work, in business and in everything else, is to stop answering to it.
You can listen to the full conversation with Leah below using these links:
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