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Entrepreneurs

Seven Things I Had to Give up to Quit My Job and Never Go Back

Quit My Job – Tim Denning

Photo by Charles Collingwood on Unsplash


A dream job sounded like the answer.

Becoming a young Gordon Gecko on Australia’s Wall Street seemed like a smart plan. I tried to pivot my career into stocks. I got close to my goal. But I discovered the world of tech and banking and did that instead.

Later, I realized I didn’t want a job after all of the effort. Here are the things I had to give up to quit my job and decide never to go back that can help you think through your own career.

Give up the pain of past failure

I only realized this recently: I took a job because of a bad entrepreneurial experience in the startup world that caused me to walk away from everything.

What I’ve never said before is I made a big mistake. Instead of getting a job, I should have started all over again as an entrepreneur. The reason I couldn’t is because I was afraid.

See, when we have one bad experience that blows up in our face it scars us. So we do anything we can to get away from it. That’s what I did by doing a complete 360 and going from a startup to a minimum wage employee.

I had to give up the idea that one bad failure should cause me to seek an escape and do the opposite of what I love. Failure means same direction, different route. Not wrong direction, do a u-turn.

Give up bad money habits

In my 20s I worshipped the gods of luxury. Stupid BMWs. Fine dining restaurants to look cool. New clothes every few weeks to show wealth.

My worst money habit was I had no safety blanket. I spent every dollar I earned. I liked buying audio software and giant keyboards with synthesizers attached to them. One could easily cost $5000.

Then I’d buy expensive microphones that would get used a few times a year so vocalists could sing on my music. My side hustle of music never made me any real money. Yet, I kept throwing bad money at it with zero return. I had to give up these terrible spending habits.

My mantra became: spend less than you invest.

Give up the fear

Most people will choose unhappiness over uncertainty — Tim Ferriss

Not having a job can be scary. There’s no way round it other than to accept the feeling. Otherwise you can end up in a job where you’re unhappy because you’re afraid of uncertainty.

Uncertainty goes down when you build yourself a safety net. That’s what your investing habit is for.

When you have a few financial assets to your name, it’s easier to stomach back-to-back months of no income while you figure out life without a job. Or if you discover your side hustle dream isn’t finished and needs a rework.

Feel the fear and do it anyway, says Tony Robbins. I’m glad I did. Give up the fear, or at least accept the fear and use it as motivation.

Give up the toothless excuses

Obviously not everyone will be better off without a job. But some of you will. What held me back were the excuses.

  • “I’m not ready.”
  • “I need to learn more before I quit.”
  • “I need a team.”
  • “I need more money.”

There are millions of excuses your clever brain can come up with. But excuses don’t create progress. They keep you in comfort which leads to regrets if this whole quit-your-job thing is something you really want to do.

Squash the excuses. Here’s how: you can always get another job again. Now you have a Plan B. No need for excuses.

Give up LinkedIn shame

Some of your colleagues will hate you. They’ll tell you they’ll keep in touch and then never speak to you again. If you’re on LinkedIn some of your connections will think you’ve lost the plot.

You’ll attend functions with old work colleagues and feel like an alien. You won’t be able to speak their language anymore. They’ll secretly laugh at you when you go to the bathroom to urinate. That’s okay.

Shame is only placed on you because of a lack of understanding. There are two possible reasons:

  1. The people who shame you wished they could quit their job.
  2. Or they can’t imagine a world without their job.

Both reasons are fine. You do you. Feeling shame for going after what you want just isn’t worth it. Your true friends will be revealed when you quit. The people who used you for your career status will be revealed, too. Move on.

Give up salary crack

The three most harmful addictions are heroin, carbohydrates, and a monthly salary — Nassim Taleb

A predictable salary is a drug I love more than candy. The consistency of it is nice, but I figured out it leads me to be paid a lot less as a consequence.

A salary is where you give up your leverage to a middle man who gets the upside in return for the comfort of the same amount of money each month. For plenty of people that works fine.

No problemo.

For me it’s a nightmare. I knew I was leaving a lot on the table. I didn’t want the extra money to buy a Lambo. No. I wanted the money to buy back time.

A near-miss with cancer in 2015 taught me to be fiercely loyal to time, because every day we’re slowly dying. So I gave up the gorgeous salary in return for lumpy paydays. Some months I earn money. Some months there are tumbleweeds rolling through my apartment because I didn’t work hard enough.

The solution is to keep money from the larger paydays to cover the times when there are no paydays and you’re figuring sh*t out. Proper money management sets you free from a job, if that’s your goal.

Give up being poked with a stick

A boss has one job: to poke you with a stick to get the most out of you. Motivation can be hard to cultivate. I had to learn to give up the brute force variety of motivation my boss gave me and to “self-motivate.”

Sounds easy. It’s not. The temptation to binge on YouTube and eat mango gelato twice a day is enormous. That’s why you need clear goals. Not cheesy self-help goals written on the wall that you place gold stars on like a 5th grader. I mean real goals.

Goals that move your work forward. I mean ranking what you do each day based on fake work versus work that leads you to pay utility bills, cover the cost of the roof over your head, and put tacos in the refrigerator.

And the biggest liar is yourself. The temptation to label something work that’s actually bullsh*t in disguise is high. So learn to be honest with yourself, otherwise you’ll end up right back at the cubicle with your boss’s stick lodged in the side of your rib cage.

Self-motivation over external motivation.

Final Thought

I hope to never see my boss’s yellow teeth or smell his horrible seafood breath again. But if I do have to call him up and ask for my job back, then at least I’ll know it’s because I managed this list poorly.

If you love your job then stay there and send me a smiley face emoji. There’s nothing wrong if you already love what you do 🙂

But if you hate the idea of a job then build a side hustle after hours that can replace your salary. That’s the smart transition path.


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Tim Denning
I am an Aussie Blogger with 500M+ views — Writer for CNBC & Business Insider. Inspiring the world through Personal Development and Entrepreneurship. You may have seen my work on Medium, LinkedIn, Bitclout, or Twitter.

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