How to (Really) Quit Your 9–5 Job If That Is Your Goal in Life

Tim Denning

If having *no* boss is what you call freedom, then here’s how to get it right away.

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There are people who find 9–5 jobs a giant pain-in-the-ass.

When you hear them describe their job, it sounds like a prison sentence with roadside manual labor and the ol’ shackle and chains. Their job makes them a prisoner and they hate it.

Others love their 9–5 job. They go to work and enjoy that they have zero ownership in the company and can walk away at any time without any liability.

I’ve lived many work lives. The first half of my 20s were spent starting seven businesses that all failed miserably and one that was an overnight success (that I later walked away from). I then had a corporate gig in a bank and wore a suit to work. The lobby was like a hotel and the language used never contained the F-Word. My next gig was a hybrid between startup and corporate with a people leadership role.

I eventually settled for what I have now: a 9–5 job four days a week, and my side business two days a week. My side-hustle means that I can leave my 9–5 job whenever I want. I have chosen not to because it’s fun and I learn a lot.

Falling into the trap of a 9–5 job you hate is easy.

Getting out is the challenging part. But if you have made up your mind that you never want to work for a boss again, then you can choose to transition out. Here’s how to really quit your 9–5 job if that is your goal.

Start with an interest.

I was on a call last week with someone who kept saying “divine purpose.” It sounded like a phrase from a religious cult. I felt all spiritual like I wanted to get on my knees and pray while simultaneously chanting Hallelujah.

Purpose is too grandiose. If you want to quit your 9–5, then you’ve gotta go small. Replace the mythical word of purpose with interest.

What are you interested in? Some people are not sure. An easy way to find out is to write down everything you did this week. Where was the bulk of the time spent? There’s your hint. What do you get pissed off at when you miss it or can’t do it?

If I said you can’t go for a run today would you get angry? My former boss would. He would chase you down the street with a pitchfork if you told him he couldn’t go for a run in the woods, or as he calls it a “forest bath.”

Content creation is the seed.

Once you know your interest, then you need content creation. Content creation is part of any side hustle.

Content is how you find people.

That’s the number one question I get as a young entrepreneur: “How do I find people who will pay me money so I can leave my 9–5?” Well, you let people find you through content.

Every day I wake up to messages from people who like the same things I do: writing, entrepreneurship, and personal development. Content is the magnet that brings these people into my life.

All of my current mentors have been attracted to me through content too. A simple “I loved that video” or “that piece was powerful” turns into a conversation. The conversation helps you find mentors and prospective customers.

If you’re not creating content then you are missing out big time.

Remove your filter and say what you think.

One negative side of a 9–5 job is that we’re taught to filter what we say. Because telling the truth in the corporate world can get you in trouble or cause you to lose your job.

I spoke to a LinkedIn connection of mine yesterday via a video call. I asked her why her profile said that she no longer worked in finance for a big bank. What followed took me by surprise.

She started a year ago posting inspiring videos on LinkedIn. Her videos gained a lot of traction and she began charging money for public speaking. The senior leader she reported to heard about her LinkedIn success and pulled her aside.

“You’re growing too big Tania. I need you to stop doing what you’re doing.”

This leader forced her to decide between posting videos and her 9–5 job. While thinking about what he said she described to me a day at work. Random people would smile at her in the lift because of her videos.

People would pull her aside in the kitchen at work and thank her for sharing her thoughts. A father emailed her while in a meeting and said that he burst into tears in front of his nine-year-old after he and his daughter watched a video about a trip to Peru and a drive through a town struck by poverty. What made him cry was this line:

“I’m sorry dad for being so ungrateful. I promise to change.”

That was all the motivation Tania needed. She told her boss she was leaving and took a three month holiday to America. Since then, she has gone on to create a Mastermind, publish daily videos, do one-on-one coaching, and speak on stage. Let me put this into perspective for you.

She now gets paid between $50,000-$100,000 USD per speaking gig after twelve months of posting on LinkedIn.

If you don’t see what is hiding deep inside of you because of your job, you may never feel what it’s like to truly live.

Find a way to be helpful.

Helpful people leave their 9–5 jobs.

It has taken me six years to realize that. Without being helpful, nobody will pay you a dollar. The act of being helpful allows you to find out what you’re good at and what problems you can help people with.

Helpfulness is customer research.

Many people try to skip this step and end up stuck in a world of selfishness and personal branding. Don’t do it. Work hard on finding how you can be helpful and you’ll have endless ways to charge for your skills.

The way to fast-track how you can be helpful is to start for free.

An easy way is to join a Facebook Group in a niche you care about. Let’s say you love sports cars, then find a sports car group on Facebook and join. Find questions within the group and answer them. Watch the feedback you get like a hawk.

Do people say “thanks!” or “that was so helpful?” If so, you’ve found a way to be helpful. If not, keep searching until you can be helpful to one person.

Find a way to make $20.

I made this mistake early on. I wanted to go from zero to hero too quickly.

You probably won’t start something tomorrow and be earning 6-figures next month. Sorry to tell you that but I’m not here to lie to you.

What rocketed my journey forward was to sell something for twenty bucks.

The $20 was validation that my writing skills had value and people would pay me to use them for the benefit of their business. When I stopped setting the bar so high for myself, my bank account was flooding with $20 deposits. Those $20 deposits add up pretty quickly. And when they do, you now have the start of a sales funnel that you can sell more expensive, helpful products and services to.

Charging a small amount of money starts your sales pipeline for whatever you want to charge money for.

Learn how to treat people.

You won’t make it out there on your own in the big bad world, away from your old 9–5, if you don’t know how to treat people.

You need other people to quit your job and earn money online.

Those people will run away from you if you don’t treat them well. You have to do the following:

  • Be friendly.
  • Be as nice to the trolls as you are to your friends.
  • Give a piece of yourself before expecting anything in return.
  • Negotiate fair prices.
  • Be humble.

People underestimate the power of this step. I’ve seen people quit their 9–5 jobs, shame everybody for not doing the same, start a business, treat everybody like dirt, have the audacity to ask for money to get a simple one-sentence response to an email (their time is so gosh-damn important!) and destroy the relationships they had before they’ve begun.

Freedom from a 9–5 job requires other people.

Learn to treat people well and you’re going to discover lots of people who can help you make more money than you would have ever made by yourself, while rotting away at the core from loneliness because you no longer get to socialize in the office anymore with your work colleagues.

Become obsessed with the phrase “revenue share.”

Pool your resources.
Pool your skills.

The phrase “revenue share” is huge. I first learned this phrase when I sold an online course with two people I met from the company Mind Valley.

They wanted me to create an online course about writing for publications. I thought I would have to pay them for their help but they made my life incredibly easy by saying, “let’s just do a revenue share.”

In practical terms, the revenue share looked like this: a person buys the course, the money goes to the payment provider (Stripe), and then the money gets split in realtime equally between the two of them and me.

It was genius to see this revenue share model play out. I got to use my writing skills, and they got to use their IT and digital marketing skills. It was a revenue share match made in heaven. We all got to do well.

You can make your skills go further when you revenue share the money you earn with people who have the skills you are lacking.

Work towards the tipping point.

What I have said so far all happens while you’re working away at your 9–5 like a good little worker bee.

If you spend enough time outside of work hours, during lunch breaks, and on the weekend, doing the work associated with your interest, there will be a tipping point. You will create enough value that the money you earn starts to make your paycheck have less value. It’s an awesome feeling.

There’s one catch: it takes longer to reach the tipping point than you might imagine. And when you get there, you want to set up a buffer so that you are not racing back to your 9–5 when you stumble across the tiniest of setbacks (and you will).

The good news is that it shouldn’t be hard to work away at your interest in your free time, because you would have done it anyway, even if this idea to quit your 9–5 hadn’t come across your email inbox.

How to Stay Away from Your 9–5 Permanently

You might make it over the prison wall, away from your 9–5. But whether you get caught again and have to go back is up to you. This is the step I have seen people from corporate land screw up time and time again. They leave their job and end up right where they started, often worse off.

Anyone can escape a 9–5 job; staying away is the hard part. The way you stay away from your old 9–5 is to do this:

Invest instead of save.

Staying away from your 9–5 job requires three investments:

  1. An investment in yourself. The money you make has to be invested back into yourself in the form of learning and further skills acquisition. If you’re not learning, then you stop growing and the opportunity you’ve been given dies. Without investing in yourself, you get ahead of yourself. Learning reminds you that you have so far to go and that you’ve come so far already. Growth is learning. Maintaining what you’ve built is disrupting yourself, consistently.
  2. An investment in assets that make you money. Take some money off the table and hide it for a rainy day. I have seen many people get wiped out in recessions because they didn’t put money aside for a rainy day, month, year, or couple of years (due to an invisible disease). Choose your poison: stocks, bonds, gold, digital currency, or real estate. If you save your money rather than invest it, money printing by governments, inflation and the temptation to buy stuff you don’t need will make you go backward financially — and eventually, right back to your 9–5.
  3. An investment back in to your money-making vehicle. If your blog makes money, you have to put money into it. If your website makes you money through the sale of goods, you’ve got to invest in it. Many people make money online and then don’t reinvest some of the profits back. Investing the profits helps you minimize tax and grow your audience.

The Time Is Now

Don’t read any more blogs. You’re not getting any younger or better looking, so you might as well start right now. (Like this minute).

If you identify as someone that thinks of their 9–5 like a prison, then it’s time to climb the prison walls and do work related to an interest you have.

I’m begging you not to waste another minute. Once you get started you will feel the incredible power of momentum.

Earning an alternative living outside of a 9–5 job has changed my life. It has allowed me to live with passion, stress less, relax more and not let a recession destroy my dreams. The same is possible for you.

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Aussie Blogger with 100M+ views — Writer for CNBC & Business Insider. Inspiring the world through Personal Development and Entrepreneurship


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