Join me and 101,000+ others on my Substack to upgrade your life.

The Moment I Decided to Quit My Job and Do My Own Thing Forever

by | Sep 26, 2022 | Startups

The trend right now is to quiet quit or old-fashion quit a job.

Millions of people are rethinking their careers. The definition of work is changing. And people are wondering, is this all there is?

A reader asked me “what was the moment that made you decide to throw it all in and do your own thing?” This question has come up a lot lately. So let me answer it.

It wasn’t one moment that made me quit my job and do my own thing. It was a series of moments. Here they are.

The way tax works makes salaries a bad choice

Last year in my old job, I paid almost 50% tax on every dollar I earned.

Not once did I ever think that was a defect. Then I started learning more about how money works and what wealthy people do. I learned this…

A salary gets the tax taken first.

This means you don’t get to choose when to pay tax or how much to pay for a given year. Let me be clear: this isn’t about avoiding tax, it’s about having options around tax. Death and taxes are guaranteed.

When I started working for myself the game changed. I got paid for my work but the tax process was entirely manual. If I got a large amount of money I could increase my expenses to reinvest in myself or the business.

Or I could select how much tax to pay per quarter based on my estimates. Some quarters I may want to pay more tax than other quarters for cash flow reasons.

The tax rate also changed. When I became my own one-person business, I could pay 25% company tax on any income and then invest the money into assets. The other 25% of tax left over still has to be paid, but I don’t pay it until I sell the asset one day and cash out to my personal name.

My plan is never to sell assets. It’s to use assets to borrow money and buy more assets. Suddenly, a huge chunk of my tax bill is gone (legally).

Because I can delay when I pay tax, that money can be put to use in the financial markets until such time as I need to pay a tax bill.

My tax dollars are funding my investments instead of me having to do it all by myself with a salary.

Everything I just described gives you tax efficiency. Salaries are inefficient and tax is automatically deducted. Doing your own thing is efficient and you make tax decisions.

Bottom line: You can earn 50% less money working for yourself and still make the same money you did with your old salary.

I got sick of running in corporate circles like a circus animal

I started my career in banking. Then I later moved to work in tech full time. In both industries I dealt with almost all other industries.

I saw the same patterns repeatedly. The biggest one was being good at internal politics meant more than basic business skills.

I’d regularly encounter these mediocre leaders in my own organization or ones working for competitors, suppliers or customers.

  • They had no talent.
  • They could barely read a balance sheet.
  • They knew nothing about sales and marketing.
  • They micro-managed their teams into the ground.

Yet somehow they earned a boatload of money and got to make important decisions.

By the end of my 9-5 career last year, it hit me: they were weasels. In other words they were great at throwing people under the bus, back-stabbing, and being cruel to people.

They played the politics game and got good at it.

This made me feel like a circus animal. I had to put on an act for these leaders and pretend I didn’t know the game they were playing. It became exhausting. Being fake every day drains your energy.

rethink your career

Photo by Francisco Andreotti on Unsplash

I got sick of this one thing about business leaders

Running a business or having a successful career is hard.

To be good at business you need to be good with customers also known as humans. Most of the leaders I worked with never spoke to a customer.

So what happened is they made dumbass decisions that made my job ten times harder. Working for myself meant I could treat customers how I wanted to.

I could show empathy, respect, and a listening ear to customers and get rewarded when I did.

Businesses that plateau, or even fail, don’t speak to customers.

The workload always increased with no end in sight

Perhaps you can relate to this.

A key colleague leaves. The business promises someone else will come to pick up the slack, but until then, everyone has to work more.

The hiring process is slow and a comedy of errors happens. Or economic factors change and suddenly the business goes from employing new people to a hiring freeze.

So the new person doesn’t join. Or if by some miracle the new person is employed, another person has already quit so the work they pick up has little to no impact on yours.

This was my daily existence working for multiple employers.

Once I got settled in a new job and got good, the leaders above me would drown me in more work. So I’d come home late and not see my wife, and soon-to-be-born daughter.

The same money for an ever-increasing workload stopped making sense to me, so I just said “fuggit, I’m out.”

The guy that temporarily took over from me still doesn’t have a replacement and works like a dog without a bone — proving my point.

Zero ownership in the business you’re growing

Some of you who are on my email list know that right before I quit, I won a $12m deal for my employer. That was 12x my sales target for the year.

What I didn’t tell people is I got exactly $0 of that win.

I quit my job because I grew tired of having no ownership in the business I was growing. If I wanted a piece of a financial win, like the one above, I had to beg at the end of the year. And most times I didn’t win.

Now I earn a living where every action I take grows my net worth and I own 100% of all the work. No one can screw with me or poke my eyeballs out with BS excuses that steal money from my unborn daughter.

You should own the work you do every day. A job outsources the ownership to a fat cat.

I wanted to serve a bigger mission than just hitting stupid revenue targets

In every company I’ve worked out there are an ungodly amount of discussions about revenue. I got sick of it.

Chasing revenue is for 4000-year-old apes.

I wanted my work each day to mean something more. Now I help people write online which unlocks enormous opportunities for them.

This work creates a generational shift that will be felt long after I die. This is the type of work I’ve waited my entire life to do. Many of you reading this feel the same.

Do meaningful work or die trying.

The enormous level of inflation that devalues your salary year on year

Inflation is a fancy word most people don’t understand.

Inflation is simply a measurement of how much the currency your salary is paid in has decreased. So when you hear “inflation is 8.3%” what all employees on salaries should hear is “my salary just went down by 8.3%.”

Don’t worry, I didn’t understand it for years either.

But as soon as March 2020 struck and I saw the inflation lie, I thought, “Holly crap Timbo, you get paid in this worthless piece of garbage.”

Now, I haven’t escaped getting paid in dollars. But I have many different ways to protect myself from it. And my retirement fund is also safe and isn’t managed by an employer anymore.

Inflation matters because if you’re not getting a pay rise your salary is going down. I didn’t get an inflation-adjusted pay rise for 2.5 years.

When I looked at the damage I got a (roughly) 20% pay cut. Screw that.

Inflation is making your 5, 6 and 7-figure salaries look tiny.

I got sick of asking for permission all the time

During the end of my last job ever, I had to argue with many different departments over a $4 latte expense.

I couldn’t spend one dollar without a million different departments asking for permission slips. It got ridiculous. If I wanted to book a customer meeting I had to tell my boss. If I wanted to come in late I had to tell him.

If I didn’t want to attend another dumb office social event full of idiots drinking alcohol, I had to explain for the 100th time that I don’t drink because I don’t want to kill brain cells and experience a hangover that stops me from working for a few days.

My employer didn’t get it.

“Don’t you want to work overtime for free and get paid in bottles of alcohol that turn into bright yellow piss?”


Doing your own thing is how you enter the permissionless economy.

Too many god damn meetings

My job required endless meetings.

The 280,000 employees at my company had the same reality. I wasn’t alone. My previous employers had too many meetings, too.

I just want to take action, not procrastinate my entire life with strategies that’ll be dead because the market moves too fast. And all the meetings meant the real work of talking to customers couldn’t happen.

Meetings are mostly a social event to check boxes.

The most effective meetings never happen and occur via email with a group of colleagues who trust each other to execute. That’s the harsh truth.

Opt out of meetings to spend more time with family.

Wrapping up

Those are the moments that made me quit working jobs forever and do my own thing.

When I sent them to the reader who asked the original question of this article, he said “it’s funny how you literally have just written my daily life.”

I get this same response all the time. More people are having the same realizations as me. The world of work is changing. More people will do their own thing.

Own your future or be owned.

Are You Operating With Maximum Energy?

For those who are tired of dragging through the day, who want to get back the fire they once had, who are ready to reclaim your natural energy… this is your book.

Unleash the fire within