Man, 2020. I’m a Pisces, right? So you bet I was all pumped up for that year. Everyone was talking about how the planets were lining up—big changes, big wins. I really thought I was going to crush it. I had this pretty sweet gig, running my own little consulting shop, focused on live events. Money was good. I was cruising, honestly. Got a nice new office, hired an assistant, thought I had finally made it big time. I mean, I looked at that new year, and I just saw success stacking up, year over year. No big deal, right? Just keep doing what I’m doing.
That cockiness? That was my first mistake, though I didn’t know it yet. Everything was great until about mid-March. I remember the exact day I knew the game was over. I was sitting there, mapping out a huge festival contract, when the news hit about the national lockdown. Suddenly, the phone stopped ringing. Not slowed down—stopped. That big contract? Canceled. The other three I had lined up? Poof. Gone in less than 48 hours. I went from juggling six clients and a full-time assistant to staring at an empty calendar and a hefty rent bill, all in the blink of an eye. Seriously, it hit me like a damn truck.
I spent the next three months in a haze. I tried to hang onto the office, burning through my meager savings just hoping the whole thing would “blow over.” It didn’t. I was a wreck. My wife kept asking, “What’s the plan?” And I had nothing. My ego was bruised, my bank account was zeroed out, and I felt like a massive failure. Everything I practiced up until that point had failed me. This wasn’t theory; this was the ugly, grinding reality of survival, and I was losing.
My Practice: Documenting the Pain and Pivoting
It was during those miserable weeks, sitting alone, dodging creditor calls, that I started the real practice for this post. I opened a new document and just started typing out every single failure point. I wasn’t looking for excuses; I was looking for the damn pattern. Why did my whole career structure collapse overnight? I broke down every decision I had made from late 2019 to March 2020. I listed the actions I took—or, more importantly, the ones I avoided taking—when the warnings started flashing. This exercise became the blueprint for what I eventually realized were the 5 Common Mistakes that almost ended me. I didn’t read some book; I just looked at the mess I made.
I realized I needed to scrap my whole approach. I slammed the brakes on my old way of thinking. I packed up the office furniture—sold most of it for pennies just to pay a couple of bills—and moved operations back to my tiny spare room. The actual practice wasn’t finding a new job right away; it was forcing myself to admit the structural flaws in my career. That deep dive gave me the insight, and man, was it painful to write down. But you gotta face the music.
Here’s the thing I dug up—the mistakes that people like me, the ones who think they’re too good or too settled, always make. I wrote them down, not as “tips,” but as a warning sign from Future Me to Past Me. I was an idiot, and I finally owned that idiocy. Once I owned it, I could fix it.
I realized the core problem wasn’t the event itself; it was my rigid structure. That’s how I finally boiled it down to the five traps I fell into that year. Check these out, because this is the stuff that saved my butt:
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Mistake #1: Being a One-Trick Pony (Relying on a Single Income Pipeline)
I was 100% reliant on live events. When that industry died, I was dead. I didn’t have any side hustles, no digital products, nothing. Now, I split my time between stable contract work and building up two small, completely separate online revenue streams. If one fails, the other two keep me eating.
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Mistake #2: Treating Networking as a Social Club (Ignoring Strategic Connections)
I only talked to people in my immediate sector. When I needed help pivoting, I had zero connections in the tech or finance worlds. I had to start from zero, cold-emailing strangers. Now, I schedule one non-industry coffee meeting a week. It’s boring, but it works.
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Mistake #3: Thinking I Was “Done” Learning (Refusing to Upskill)
I coasted on my old qualifications. I scoffed at digital marketing and coding bootcamps. When the world became digital overnight, I didn’t know the first thing about it. I had to scramble, learning video editing and basic web dev in my 40s. That panic studying is what landed my current stabilizing contract.
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Mistake #4: Ignoring the “What If” Scenario (No Real Emergency Buffer)
I had maybe three months’ savings. When the crisis lasted a year, I was wiped out fast. I spent money like the next check was guaranteed. I learned to treat every single cent that comes in like a potential lifesaver. I now have a six-month “lifeboat” fund that nobody touches.
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Mistake #5: Looking for the Easy Way Out (Taking Short-Term Fixes)
For a while, I kept trying to find a gig exactly like my old one, even though the market was dead. I wasted a month chasing ghosts. I finally swallowed my pride and took a less glamorous, lower-paying job in a completely new industry. It gave me stability and space to breathe, which let me plan the real comeback.
The Realization: Where I Ended Up
I spent the last half of 2020 doing the hard, ugly work. I contacted every person I had burned bridges with, admitted my failures, and rebuilt my network. I forced myself to learn new tools that felt stupidly complicated at first. I got a contract job in logistics tech—something I never would have looked at before. It wasn’t glamorous, but it was stable, and it taught me that I wasn’t just my old title; I was adaptable.
Funny thing is, about a year ago, my old boss, the guy whose company folded and left me hanging, called me up. He was talking about “getting the band back together,” the classic move. He sounded desperate, still trying to live in 2019. He was offering me some lame partnership deal. I just listened, calmly. Then I told him thanks, but no thanks, and hung up the phone. I’m not working for survival anymore; I’m working for structure, and I learned that lesson the hardest way possible. That old job is still struggling to get its footing. I’m stable, diversified, and looking ahead. That painful, documented 2020 mess is the reason why.
