Solo Entrepreneurship Is Causing High-Performance Workers To Quit Their High-Paying Jobs In Their Prime | by Tim Denning | November 2022

Here’s What This Explosive Trend Means For You

Photo by Austin Distel on Unsplash

People no longer want to be told what to do.

A modern job is full of promises that are rarely kept. As you advance in your career and perhaps become a high achiever, you are faced with an existential crisis.

  1. Stay comfortable and qualify for a long service leave
  2. Go out alone and try to build something that belongs to you.

Option two used to be very scary. Not anymore.

I have been a top performer in a finance career for many years.

I spent more time in the office than I should have to get ahead. I gave up romantic relationships, blocked good friends, didn’t take vacations for 7 years, and hit every KPI I could.

Performance review day was my favorite of the year.

As I ranked up, I had to deal with more and more meat heads. Office politics exploded. “Are you with me or not Timbo?” I had to choose sides. They asked me to spy on people.

Even if I did all these tasks, my future was uncertain.

Maybe it would suit me. Or maybe you’d get stuck in a redundancy or restructuring spreadsheet. Then all my hard work would be gone. I also smoked too much of the “find your passion” weed.

So I left finances to work in social media.

At 6 months I was fired for no reason by a beer gut warrior who missed out on a job for Elon Musk. It was so easy. It took 5 minutes.

I got another job (eventually) and also became a high achiever. But he left me screaming in my head “is this all there is?” I felt empty and had a very deep feeling in my gut that is hard to explain.

He had a well-paid salary working at the intersection of finance and technology, but there were no guarantees.

So I quit at 35, right in the prime of my career.

If I were to stay at my old job, I’d probably be a stone’s throw from the C-Suite right now, drinking Starbucks lattes like it cost a pretty penny. But I did not. That life sucks.

I’m not the only person who quits in the prime of their career to become a solopreneur.

Justin Welsh is well known in American tech.

He held several senior positions working for software companies. But after the 2020 health crisis, he also resigned.

He went out alone and began:

  • sale of digital products
  • establishing communities
  • be a business advisor
  • and working to the rhythm of his own techno track

The He says he knows over 10 people in his career who looked around and saw all the unhappiness too, and quit to run sole proprietorships.

Marketer Andrea Bosoni discovered Same thing, with a little more nuance. He says that 10 years ago his dream was to quit his job and start a big business that turned into a unicorn and competed with Mark Fuckerberg.

He now says that most of the people in his network talk about quitting their jobs to become solopreneurs (an entrepreneur with no employees).

Workplace Expert Khe Hy I observe the same trend in your network. And in my neck of the woods here on Australian soil, the same trend is on the rise.

I went to look at several WeWork offices to rent for my online business and noticed entrepreneurs everywhere.

I asked the WeWork salesperson about it:

“Ahh that’s the trend mate. We now have more one-person businesses than multi-person businesses.”

A normal job has so many limitations.

Many workplaces continue to beg employees to return to the office. Some are forcing them.

The average employee likes working from home as it reduces travel time and does not require them to rent/buy property near a big city.

Saving time and money is an addictive drug.

Independent entrepreneurs are also not limited by borders. Most of them have online businesses that they can operate from anywhere. So the cost of living goes down as they leave the big cities to live somewhere affordable.

A solopreneur’s schedule also evolves. Instead of being stuck in hell every day, they can take back their time and decide which dates they go on. I found that most business topics are best discussed through written emails.

Articulating an idea in writing requires more effort to make thoughts clearer.

Workplace Santa isn’t running around handing out pay raises.

Especially not in a recession. The money you can earn at a job is limited. You can only go so far, and that becomes even more true when you decide that the upper management life is not for you.

Solopreneurship has many more ways to increase your income.

You may:

  • bring affiliates
  • Add new sources of income
  • Hire freelancers to do some of the work.
  • Partner with similar companies to create new products

Everything you build as a solopreneur belongs to you. Web3 started this trend and now it spreads like a virus.

We no longer want to give our ideas, thoughts and content to social media companies for free. We want to own the house in which we live. We want to own our savings without inflation destroying them.

We also want to own the fruits of our labor and make them worth something. When you have a sole proprietorship, one day you may sell it.

But you can’t sell your work. And a job has zero guarantees… other than a short notice period when you’re fired due to whatever excuse they can come up with to dump you on the sidewalk like a worthless piece of trash.

Earning more money to work the same hours is a great attraction of individual entrepreneurship. There is no surprise there.

There are good bosses, don’t get me wrong.

But most of them suck. They are told to work as hard as possible so they can cash their bonus check and get promoted. It’s not personal, it’s business. Being told what to do like a baby gets tired.

Still, most employees know more about their jobs than their bosses.

There comes a point in life where you want to take your experiences and use them to create something. For many people like me, this is when we reach the position of high performance in our work.

Not surprisingly, bad bosses have contributed to the rise of individual entrepreneurship.

Hope for?

It’s all sauce. I hate the entrepreneur label (or any form of it) because most people feel like they’re not cut out for it.

It is a limiting valve of human progress.

Unless you believe a label applies to you, you won’t experiment with its features and benefits. So you’ll never know what you’re missing. A better label for this lifetime is probably race owner either self employed person.

The other reason I hate the label entrepreneur is that it carries a lot of elitism.

I had businessmen as clients when I was working in banking. Many of them were holes. They would find some Uber-like model of economic extraction to take advantage of people and ruin society… and think they were king.

Or they wanted you to kiss their butts because they created an Airbnb copycat company. It drove me crazy.

Solopreneurship is not about status. It’s about freedom and time.

Let’s be practical.

If you decide that solo entrepreneurship might be for you, it’s a bad idea to tell your boss to go away and quit tomorrow.

Most of us are not born solopreneurs.

  • We discovered solopreneurship by accident.
  • We see someone else become a solopreneur and we try to emulate them.
  • We hear about solo entrepreneurship, but we don’t know where to start.

This is where after-hours side projects (also known as side hustles) come in. You can try this different career path while still working a job.

That’s what I did for about 7 years, though most people can have their aha solopreneur moment long before I did.

Through the process, you can test ideas and see if they lead to new sources of income. If they don’t work, you stay at your job. If they work, he slowly reduces his work days/hours until he has fully devoted himself to the individual venture.

A job where you have nothing is becoming unattractive. High performance in a race can be used to build an online empire of your own.

Leave a Comment