The Entrepreneurs Pit of Despair

Michael Grimm
2 min readMar 24, 2021

Part 1

Some people live it. Some people beat it. Some people never make it out.

Many entrepreneurs experience, at some point in their journey, a pit of despair. This is the story of mine. My rise, my fall, and my journey back to the top.

Shit, I thought, “So this is how I die.” I looked down at my air gauge and the needle was in the red. My heart was racing, my brain firing on overdrive. Where was the group? Why did I leave my buddy? How long have I been under now? Shit, shit, shit. I estimated I had about two minutes of air left in my tank. Each breath I took was harder and harder to get out of the tank. “How did I think this was a good idea?” Sure, I had a few dives under my belt so naturally I felt like I was an expert now and was safe to leave the group and explore on my own. Dumbass. “It’s ok” I reassured myself, “I can rebreathe into my BCD and get an extra couple minutes, but that’s so cumbersome I knew it’d slow me down.” I was lost and almost out of air. “I think maybe the group went that way.” I turned towards a reef, “or maybe it was that way (another reef).” Shit.

I was scuba diving in Tulum, Mexico. This was at the peak before my fall. I was on a trip with some friends and clients. At the time I was getting paid to fly around and teach my methods. I thought I was such hot shit. Experienced business owners twice my age were traveling and paying to sit in a room with me for two days to learn how to grow their business. I was on top of the world. I was smart about it in the beginning too. Early on I learned to surrounded myself with advisors, investors, and advocates. But I took them for granted. I thought they’d be there forever. I never realized there was one lynchpin that could bring the whole thing crashing down. I was invincible and never thought that’d happen, until one day, it did.

Over my dark years in the pit my mental and physical health suffered, as did my relationship with my spouse, and relationships with friends and family. It wasn’t a good place to be. Depression, mania, apathy… you name it. But I’m not alone. Many people have been in the same place and unfortunately, like me, many have to battle it alone.

I was in the pit for three and a half years before I crawled out. I did make it out. I was one of the lucky ones.

--

--