I've Reached the Mountaintop. Why Am I Still Anxious?

Every work email, text, and call since buying my first business spiked my blood pressure by 10 points. I've been pulled out of picturesque moments on beaches, mountain trails, and scenic drives, all from feeling that tiny buzz in my pocket. What the hell am I so anxious about? I'm in the dream scenario I pictured while inking my first purchase agreement. I'm no longer needed for the day-to-day operation of the business. I routinely put in less than a day of real work each week. I go into the office once every week or two, in between stints at our little house in the mountains. I have the type of flexibility I would have killed for while I was working in big tech. And yet, even with this objectively great lifestyle, I still feel my chest tighten whenever my phone chirps. There are remnants of the last four years rattling around in my nervous system that will probably be there for a while. **Let the Battering Begin** I closed on my second acquisition in September###-###-#### Another small hood cleaning business 10 miles away from our office. They had great customers, a reputation for high quality work, and an owner who I genuinely liked. Seemingly the perfect fit. A great first step to kick off my rollup vision. After six months of personality conflicts, political maneuvering, and deceit, the operations manager from the newly acquired business put in his notice. The following week, four technicians put in their notice. I would later find out they were all hired by a company we sub-contracted for, who was now competing with us. That triggered a lawsuit that took two years and more than $100k in legal fees to settle. And we no longer had the capacity to service our existing customers. (Note: maybe don't give a newly acquired employee, who hasn't earned your trust, unrestricted access to your now largest client.) A month later, we were served our own legal notice. An employee caused an auto accident in a company truck. The other party had substantial injuries, and a legitimate claim that would far exceed our auto policy limit. Luckily, this one only took nine months to resolve and the insurance company footed the bill. (Note: Do not decline extending the umbrella policy over your auto insurance to save $15k, just because the previous owner did.) That's two existential threats in as many months. And after doubling our debt with the second acquisition, business failure would also mean personal bankruptcy. Then we lost a large, long-time customer to the newly formed competitor. We were bleeding revenue and things were looking bleak. That fall, I decided it was a good time to attempt a complicated reverse merger. A much larger fire sprinkler business in a nearby city went up for sale. My grand idea was to put it under contract, find an equity partner to take majority stake in the combined entity, clear my personal guarantee, and keep a piece of the larger platform. I put it under contract. After six months, I received an LOI from an investment firm, racked up $30k in due diligence fees, and then the investor pulled the plug. The sprinkler company's pipeline dried up when a large "sure thing" contract anchoring their next few years fell apart. (The threat of impending doom clearly wasn't enough excitement for me. I needed to add a song and dance routine for the private equity bros to really get me going.) **Some Light Drowning** Now, to be clear, over this period we didn't just weather a barrage of shitstorms. We made real progress while taking our licks. I'm lucky to have a great management team that made this possible. They're extremely competent, hard-working, and most importantly, willing to put up with me. (While we're on the topic of people willing to put up with me -- my wife deserves her own truckload of flowers for being the biggest reason I got through this. She had to watch me struggle through all of this while also dealing with the threat of losing everything herself. With more compassion than I probably deserved.) Looking back, we accomplished a lot of good stuff. Our technician team was back up to capacity two months after we got hollowed out. Now free from our saboteur, the company quickly got back on the same page; infighting basically disappeared. Two more months and we migrated two ancient customer databases living on the server/shin heater under my desk into a modern field-service platform. We also launched our new fire suppression service, which became a crucial part of our growth strategy. These were real wins that should've been celebrated. Each took a lot of time and effort to land. I should have done a better job letting everyone know what great achievements these were when they happened. Unfortunately, when you feel like you're drowning you don't have time to celebrate each gasp of air. You just get to stay alive a little longer and keep fighting for your next breath. This was the pattern for more than two years; I would bob up, breathe for a moment, then get pulled back under for more struggle. All the while, depositions, motion filings, and legal fees were grinding me down below the surface. At some point, my body decided that moving forward with my head above water was no different than thrashing in the deep. It makes sense why the anxiety spike keeps happening. If you can get pulled back under at any moment, you're constantly preparing to hold your breath. The feeling of dread became permanent. (Yes I realize this is a lot of water-based metaphors in a post about a mountaintop. But you go where the current takes you. Shit, there's another one.) **Get Out of the Water Dummy** During all this flapping about in the water, I realized something. I am, in fact, a human -- not a whale. I mean that in the obvious biological sense (I have kneecaps, not fins), and in the even more obvious sense that I'm not the titan whose breathtaking rollup strategy will be written about in business books. My ego and ambition really wanted me to be that guy. Take on all the risk, make the brilliant moves, and be rewarded handsomely for my grit and shining genius. But that's not me. I don't have the pathological work ethic or the resolve celebrated by entrepreneurial media. It's not a sacrifice worth making just to feed my ego. (That's what this post is for. I can't let my ego starve completely.) So I've decided to step out of the water and dry out on the shore. Right now, it's time to go risk-off, relax a little bit, and let the tides bash some other poor schmuck for a while. The anxiety won't magically go away because I'm not in the water -- a rogue wave could drag me back out at any time. But the stress is a lot easier to carry when I'm not actively piling on the risk. Maybe I haven't really reached the mountaintop. I didn't even know what it looked like until recently. The journey isn't over, but it's shaping up to be different than the one I set out on. I'm sure I'll end up in the water again before it's all over. But now I know it's not the best way to get where I want to be. There's still a lot of work left to get to the mountaintop. Getting to the summit will take growth externally (sustained business stability, risk reduction) and internally (working on my delicate flower of a psyche). Acknowledging that I've been trying to swim up a mountain is a good start.