Man, September 2018. Feels like a lifetime ago now, right? But it’s one of those months that still kinda pops into my head sometimes, especially when I’m just chilling and thinking about how things turned out. I remember it because, well, I’m a Virgo, and September is, you know, my time. Always makes me double down on evaluating everything, maybe a bit too much, if I’m being honest.
Back then, I was stuck in a job that was… fine. It wasn’t bad, it wasn’t great. Just there. I was doing my thing, clocking in, clocking out, paying the bills. But deep down, I felt this itch, this nagging feeling that I was meant for something more, or at least something different. My brain, being the Virgo brain it is, was constantly sifting through details, analyzing every little thing, trying to find the “perfect” next step. And that, my friends, was probably my biggest mistake.
I remember this one gig that landed in my lap. A friend, who was already running his own small design studio, called me up. He was swamped, needed someone to really take the reins on a bunch of new client projects. This wasn’t just about cranking out designs; it was about managing the whole thing, talking to clients, even figuring out the project scope himself. It was a big step up from just being a cog in a machine. My friend, bless his heart, told me he saw something in me, that I had the organizational chops and the eye for detail to nail it. He offered me a spot, not as an employee, but as a partner on these specific projects, with a hefty cut of the profits.

Now, my immediate thought wasn’t “Wow, what an amazing chance!” Nah, my brain went straight to the risks. What if his business tanked? What if I screwed up and ruined a friendship? What about health insurance? Retirement savings? All those sensible, grown-up things. I started mentally listing out every single thing that could go wrong. I grilled my friend with a gazillion questions, probably drove him nuts. He was super patient, tried to answer everything, but I just couldn’t shake off the “what ifs.”
Overthinking My Way Out of Opportunities
I spent probably two weeks, maybe even three, agonizing over it. I drew up pros and cons lists, I charted potential earnings versus my current salary, I even tried to predict market trends for design work. Typical Virgo stuff, right? Trying to control every single variable before taking a leap. I talked to my family, my other friends, everyone had an opinion. Some said go for it, others said play it safe. My internal compass was just spinning.
While I was busy overthinking this, another opportunity popped up. A recruiter from a pretty cool tech company reached out. They were looking for someone to help streamline their internal documentation and communication. It sounded less glamorous than design, but it was a well-funded startup, growing fast, and the role had tons of potential to evolve. They wanted someone who was super organized, a real self-starter. Again, my Virgo nature was a perfect fit on paper.
But again, the same thing happened. I looked at the job description, it didn’t perfectly align with my “ideal” next step. The company was in a city a couple of hours away, which meant relocating. More unknowns. More variables to calculate. I started thinking about apartment hunting, setting up new utilities, leaving my current comfort zone. My brain just hit this wall of “too much uncertainty.” I went through the initial interview, but I didn’t push hard enough. I didn’t show the enthusiasm I should have. I was too busy assessing the potential downsides, picking apart every little detail, instead of just embracing the possibility.
What did I do? I ended up politely declining my friend’s offer, saying I needed more “stability” at the time. And with the tech company, I guess my lukewarm attitude shone through, because they eventually went with someone else. I stayed exactly where I was, in that “just fine” job.
The Realization Hits Harder Now
It didn’t feel like a big deal then. I thought I was being responsible. I thought I was making smart, calculated decisions. But looking back now, especially after seeing how my friend’s studio absolutely blew up, or seeing that tech company become a household name, I just cringe a little. I didn’t just miss a couple of job offers; I missed the chance to really stretch myself, to learn new skills at a rapid pace, to be part of something growing and exciting. I missed the chance to fail, too, which is just as important for growth.
I was so caught up in the details, in mitigating every single risk, that I completely overlooked the bigger picture – the chance for significant personal and professional evolution. My Virgo tendency to analyze everything became a roadblock. It wasn’t about being practical; it was about being paralyzed by potential imperfection. It’s a tough lesson to swallow, realizing sometimes you just gotta jump, even if the landing isn’t perfectly mapped out.
So yeah, September 2018. What opportunities did I miss? Pretty much the ones that could have kicked me out of my comfort zone and into something amazing. It taught me that sometimes, the most analytical approach isn’t always the best one, especially when growth is on the table.
