I had always expected to be an Entrepreneur. As an American, we are born into a world where your safety and health depends on having deep pockets when (not if) an emergency occurs.

Around the turn of the century the safest road was being a "company man." Stay on the rails: Work hard in school, go to a good university, work at a big company... and 10-15 years later after 60 hours a week of mind-numbing work, corporate politics, with your body (and soul) deteriorating you would no longer be "pay-check-to-pay-check". 10-15 years after that you might even pass for successful.

This was the narrative of success, and it sounded terrible to me. For better or worse, I was born with a chip on my shoulder, impatient, idealistic, and with a deep curiosity about how the world really works. To me, high school was the ultimate prison. The thought of staying "on the rails" to a "successful" corporate career, was just an extension of that prison.

So I prepared myself and learned "the way" of the entrepreneur. Make hay. Be resourceful. Hustle. Be creative. Only the paranoid survive. Be your own boss.

Then, to use the words of Tolkien, a thing happened that [I] did not expect...

Millennials had all been given the same advice to stay on the rails BUT the world we came into had changed. The financial crisis and technology cleared out the entry level positions we were all counting on. Liberal arts, or soft science degrees became worthless overnight.

**The reality settled in- the student loan payments didn't give a shit about recessions or mega corp entry level hiring... the ticket to a middle class life wasn't on those rails anymore. **

At the same time the greatest force of change since electricity had finally come into play - the internet! And the internet needed people to build it! Unlike previous revolutions though, the internet needed divergent thinkers, and a lot of them. Thus began the arms race for talent!

This isn't the story of the internet. You know that one.

The arms race for the creative, technical, talent needed to build this new world was immense. And the "capital holders" made a concession to get the talent: All the things we hated about the previous 100 years of corporate life were done away within 10 years.

Suits? Lmfao. Most of the people I now work with have never owned one. 60 hour weeks? How about 40 but with free lunches, yoga sessions, "20% time" and off-sites. A boss responsible for driving efficiency? Ha! Bosses were now there to retain the talent, not get the most out of them. The job was to make working at the company pleasant so you wouldn't go looking for a new gig. Need to run an errand during the day? "Why are you telling me? I'm your boss. not your mom"

The whole paradigm had changed... it wasn't just tech companies either. The tech companies created a vacuum - and all the other companies had to follow suit or be completely drained of talent.

What a bizarre change of fate...

Suddenly the world I had been avoiding had evolved into something nice? and the world I had trained for was very very different. Entrepreneurship looked nothing like it had... American companies were eager beavers to outsource everything to Latin America, Eastern Europe, and India. Zero interest rates let companies an entrepreneurs and established firms gobble up markets and take wild bets.

There was still plenty of money to be made but you've got a 5% chance of an exit worth ~$10M to $30M and its going to take 10 years. If you're smart you're using the IRS upper limit for salary: ~$148K (or whatever it is now) and putting every extra penny into your business.

10 years.

10 years of 70-80 hour weeks.

10 years of MAX $148,000 salary in a costal metro.

10 years of employees or contractors treating you like crap... but you need the talent, so you deal with it.

10 years of customers treating you like crap... but you need the revenue, so you deal with it.

...and that is if everything goes well. 95% of the time it won't.

I still did it. I went after it... and I did fine surprisingly. I was able to pay my rent in SoCal living on the beach. I was able to pay my student loans. I didn't get rich but built a business!

...but I had all the headaches - 60 days late on a Net 30. Ugh. My stud contractor decided he just didn't feel like finishing the project. I still haven't heard back from him 12 years later. The late nights trying to turn my service into a product... lol just kidding, I've got 90 hours of continuing ed to do because wordpress had another security vulnerability and I need to switch that site to rails and the latest rails made a lot of changes.

At least I was my own boss!

Wait no I wasn't. I had tons of bosses - customers, employees, contractors, vendors. Myself.

Some of my bosses were great! Some of them were terrible... just like when I was an employee.

Who the hell said Entrepreneurs get to be their own boss? Everyone has a boss.

2.5 years into my business one of my friends sent me a referral to a company. They had skateboards in the office, happy hours, and craft beer Fridays.

"I think it would be a good a good fit for you." He said after listening to me bitch about a client for the 12th time.

"Nah, I'm okay, I like being my own boss" I said.

That week 2 of my clients told me that they weren't going to pay their last invoice. One guy got in a motorcycle accident and the other guy wasn't happy with my work... 1 out of the last 40 customers, thats actually pretty good... just really bad timing. $4500 gone. Poof. Ouch. I could make it work, but where is this going? You don't get rich like this.

The company from the referral- those guys were good people. They seemed like they would be good bosses... Imagine not having to do taxes? that would be nice. I haven't had my teeth cleaned in 2 years - I hope I don't have a cavity? And entrepreneurs never talk about the loneliness. Its super lonely. You are always fake it till you make it with people because that confidence grows your business.

So I fired some customers, kept the good ones... and added a corporate job. Since that point I have been doing corporate work AND part time entrepreneurship (Note: This saved me and my family during covid when my corporate job shut down. And I'm proud of the work I do. I NEVER do my business on the clock for my W2. Thats morally bankrupt in my book).

I've changed my mind...

Now a days, I don't separate entrepreneurship and employment into buckets like I did - they are different, but like I said everyone has a boss and its still work.

Corporate work changed, so did entrepreneurship. They are different than the were in 1999.

Had I known a principle engineer at Google or Jane street can make more than a GREAT entrepreneur over that same 10 years, with a fraction of the risk. I'm not sure my path would have looked the same. But thats also why the world looks like it does right now and its not great. We need the best and brightest people building companies, spread out on different problems, and building a better version of the future. They shouldn't be working to grow the mega corps.

The good news is that I think things are changing. I would be terrified to be a Mega Corp right now... LLMs are changing the power dynamics yet again. Capital and head count are starting to look like disadvantages not advantages. I hope you spent some time learning entrepreneurship... You might need to go get some more bosses.

The only rule is change.