What to do when you’ve done literally everything to succeed, but didn’t?

I’m actually asking.

The Fumbling Generalist
4 min readAug 23, 2021

The alarm screamed “Six Foooorty-fiiiiive!” and thus begin another day of what I have, sarcastically, called: MY LIFE.

Those two words should have never been put together. These days are neither mine, and “living” would be the last thing I would call whatever it is I am doing every day.

I drag myself to the bathroom, where I flawlessly execute muscle-memory moves that would see my body all cleaned and decent-looking in 20 minutes. No brain activity would ever be required for that.

(Although, on not too few occasions, I caught some deep insights into what would have been billion-dollar ideas…had I acted on them. But you know me, I hate self-development.)

A couple of minutes more, I would be coming down the stairs, in my work clothes, straight to the machine that dispenses the coffee. Usually, the TV would be on the news or a YouTube compilation video of something mundane, like people slipping on shiny surfaces.

But this very morning, the TV would be silent as I walk to the table and slunk onto my favorite chair.

(My mornings are never like the ones they show in the opening scenes of films where there’s a soundtrack and the main character dances and prances around the house as he or she prepares for work.)

“It is especially quiet today,” my brain hissed.

I take my caffeine drip and wonder…

Photo by Christine Isakzhanova on Unsplash

I wondered if there are other people in this world who work at a job they absolutely hate but come in day after day anyway.

I wondered if, like me, they also hate half their co-workers but can’t bear upsetting them because the bloke might get promoted first and you might need a favor from him.

I wondered if they also think their boss is a privileged idiot with no redeeming qualities. Mysteries of mysteries, nobody can’t figure out how this fella got to be in a position where he is allowed to make important decisions.

I wondered if others also think that their company is BS — that it’s all marketing, bells-and-whistles and that if clients knew what goes on behind the scenes, they wouldn’t trust those people to walk their dog or water their grass.

I wondered if they also feel like a poser at work — perfectly competent on the outside, but on the inside, screaming, “I don’t even know what I’m being paid for! My actions don’t make a difference!”

I quickly snap myself out of these caffeine melodramas and proceeded to my morning commute. In 90 seconds, I am looking at the rearview mirror as I hear the click of my seat belt.

(Pretty sure that I live with other people, but I never seem to run into them.)

I drove my Toyota a few miles and straight into…of course, a traffic jam. But I’ve learned to live with it. No sense in blaming politicians for the state of the roads this morning. The lull however gave me some time to engage with more thoughts.

I wondered where I would be at that exact moment had my life taken a different turn.

Had I succeeded with my dreams, where would I be?

Because make no mistake, I’m not your boilerplate graduate who immediately turned corporate after getting his diploma. No, I gave the “Follow Your Dreams” bit a real shot. (I even had that poster!)

My start-up was supposed to be the next unicorn. I was gonna sell informational products online.

I followed my passion and was working from home even before virtual became a virtue or Work-From-Home arrangements became standard. I was not some naive dreamer, you see. I knew it wouldn’t be easy. Nothing worthwhile ever is. So I worked long hours…longer than if I were in an office.

I sacrificed time with my family, romantic relationships, and social life. But I told myself, “Someday, it will be all worth it.” (Think: Jeff Bezos in his garage, with hair.)

I did everything business gurus said I should. I cultivated contacts, watched my finances, and had a great team. I had awesome mentors and a good product.

But then 2 years became 3, and 3 became 5. I failed and stayed motivated, knowing success might be just around the corner. I pivoted the business a couple of times, dusted myself off, and learned the lessons from every failure.

Until…the only lesson left to learn was that “Final Notice” does not mean the banks would stop bugging you after that.

I had no choice. If I am to keep body and soul together, I need to earn money. So I went corporate. I went to work for somebody who started a business…and made it.

And so here I am this morning, stuck in traffic, waiting for the wheels of my car to turn. Honestly, I don’t know what I’m gonna do next. I’ve done the “Let’s be Elon Musk!” thing. That was what my 20s to my mid-30s were all about. I have nothing, but poor health, to show for it.

Now I’m in the thick of the “Let’s be Don Draper!” phase, and to be honest, they both feel the same. Soul-crushing.

I did my best then. I am doing my best now.

In half an hour, I’d be stepping inside an office building where security screening would search me to the bone. And I would play along by raising both my arms.

I don’t wanna raise them so high…like I’m surrendering or giving up. I wanna raise them, just enough…like an open-palmed, clueless shoulder shrug.

Because that’s me right now. Clueless.

“What now???”

Any ideas? I’m all ears.

Please use the comment section.

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The Fumbling Generalist
The Fumbling Generalist

Written by The Fumbling Generalist

I write about random things that I feel suddenly passionate about. And I’m man with many passions. (About 204,753 of them…and counting!)

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