Entrepreneurs

Freedom *Isn’t* What You Want. A Part of Being Human Is Doing Things.

Tim Denning Freedom

Photo by Nighthawk on Unsplash

You think you want freedom. But freedom can be a bad thing.

Quitting your job, or being a digital nomad, or living the laptop lifestyle won’t solve all of your problems.

How do I know? Last year I got fired and spent most of the year being an online blogger and doing nothing else. My friend said to me “Mate you must be loving life, eh?”

Not really. Spending the day on the computer and writing was nice for a few weeks. But when you do it each and every day to survive and put food on the table it changes everything.

Freedom from a normal job isn’t a bad thing, though. It’s just not worth becoming so obsessed with the idea that your life sucks until you achieve it. When you do achieve freedom from a 9–5 job you start to see the world differently.

A fellow blogger I follow online is Nat Eliason. He hasn’t had to work a normal job since March 2016. Like me, he found that freedom from a job or a typical life didn’t solve any of his problems.

As soon as you get that freedom, you realize that a fundamental part of being human is doing things — Nat Eliason


The Start of Freedom

It starts out being fun. You take what you love doing and do it full-time. Seems straightforward. Nothing in life ever is.

I spent the first few weeks waking up late and binging on takeaway Chai Lattes. Life was great, for a minute. Pretty quickly I figured out that life without work was boring. “I know, I’ll write every day,” said my brain.

It was a great idea. I’d learned in the years leading up to this full-time freedom phase of my life that I could in fact make money as a blogger. Writing could buy food and keep the taxman happy. Taking what you love and making it your job can take some of the shine off it though.

Writing started to feel like a chore real quick. That’s not how doing what you love is supposed to feel, is it?

Those Around You Can Warp the Idea of Freedom

This idea of freedom I was living was borrowed.

A friend of mine went from being a snake handler in the Australian desert to moving to Santa Monica with his laptop and being a blogger. I watched where blogging took him and fell into a whole new world. His idea of freedom tantalized me before bed. “I want to do that,” I said.

It took me years to learn that his life away from a normal job wasn’t so great at all. He admitted to getting caught up in many standard life problems. He also got divorced from the love of his life within fourteen days of getting married. It was a dream, and a nightmare, all in the same sentence.

I didn’t need to live in Santa Monica or have a life perfect for Instagram.

Chasing Rainbows

So you get your boss off your back and don’t have to take orders from anybody. Suddenly you’re going to be doing happy dances every day to McDonald’s, right? Nope. Not even close.

I thought my boss was my problem. While he was a dictator asshole who loved to use the phrase “mortgage motivation” he wasn’t really what I was escaping. What I wanted to get away from was having to delay my happiness for some future moment all the time. It was exhausting.

You can spend your entire life looking forward to retirement and it won’t do anything for you. As Nat said, “a fundamental part of being human is doing things.” If you get your freedom and do nothing then you’ll become miserable, fast. A 30-something retirement won’t change your life.

In fact, in the next 1–2 years, if I wanted to, I could retire as a 30-something-year-old. I’m not going to.

A new version of retirement

What if you thought about retirement differently? The way I think about retirement is that it’s a period in my life where I don’t have to do work that grinds my gears anymore to pay bills.

Freedom isn’t getting rid of the need to have a job.

Freedom is the ability to choose work that pays for enjoyment without thinking about how much I’m getting paid.

The guy I sit next to at work laughed when I said this:

“I want to reach retirement so I can quit the technology industry and go and work for the government on minimum wage. I’m fascinated by what it would be like. Then 12 months after that I want to work at an airport for shits and giggles to see what that’s like. Every 12 months I want to change industries and defy the boundaries of a resume.”

Maybe the wild choice of changing careers every twelve months is a better form of retirement. Maybe choosing work for shits and giggles is another form of retirement.

The Ability to Just Play and Goof Off

When I lived this digital nomad life last year everything became far too serious. Nat reminded me that you should never underestimate the ability to just play and goof off.

If all you do is obsess over passive income and becoming more ‘nomad’ by the day, you’ll have a nervous breakdown when the slightest setback creeps in. I found the separation between work and play disappeared. If I was watching a movie it had to be for money-making purposes. If I went for coffee it had to be with a mentor or somebody who could talk my ear off about business.

I couldn’t relax because my hobbies had made me a prisoner to them.

Have Multiple Sources of Meaning

Writing gave my life meaning. The problem was I depended on writing like a crack addict to give me my next hit of meaning.

Your life needs more than work to give you meaning. Meaning comes from helping other people. Meaning comes from falling in love. Meaning comes from spending time with your family. Meaning comes from travel. Meaning comes from learning about history. I forgot all these sources of meaning and so I relied solely on a blogging audience to give it to me. When they didn’t, I felt empty and alone.

Diversify where you get meaning from so you spread your risk.

The False Reality of Travel

It’s nice to travel. Travel is one reason people want to quit their jobs and become a digital nomad. I love travel too. It’s nice to explore the ancient ruins of Rome like I did two years ago. You know what’s weird?

After you travel a lot you start to hate it.

Two weeks into my trip to Europe everything began to feel the same. A city was a city. An ancient building was an ancient building. A bowl of pasta was just another bowl of pasta. A tourist attraction was just another place full of tourists who took photos of everything and didn’t know why. Many of them would never view a single photo they took ever again (I haven’t looked at any of my Italy travel pictures since).

Traveling the world won’t save you from yourself.

Traveling the world won’t suddenly make your life awesome and solve all of your problems.

What You Really Want

I realized that I didn’t want a lifestyle or material possessions at all.

Freedom was simple: I wanted the ability to have choices.

That’s what freedom is. It’s not quitting your job and never working again. Doing things is part of the human experience. Choosing what things you do and don’t do is a powerful experience. It shows you what is possible and acts as a compass that points to your next opportunity.

Now I’m back working a traditional 9–5 job again, four days a week. I don’t plan on leaving corporate life, yet. What has changed between last year and this year is that I work a normal job because I choose to, not because I have to. I’m aiming to ensure in each area of my life that I have choices.


Leaving work behind for good isn’t the answer. Turning your hobbies into passive income isn’t the answer either.

The answer: Replace the idea of freedom from work with the ability to have choices to do whatever work you choose.

Tim Denning
Tim is a thought leader in the personal development, entrepreneur and startup fields.Outside of blogging, Tim works for a large organisation helping fast moving technology companies come to Australia as well as helping Australian tech companies go to the world.
1 Comment
  • Krishna Teja Nov 19,2020 at 6:50 am

    Great article.. please write an listicle about ECOSIA..

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