Why I Pivoted Away From Everyone Else’s ‘Money Dream’ — A Different Way Of Living And Working.

Image Credit: Unsplash

Recently I’ve told a lot of people about my career change. Whether we like it or not, our career is tied to our money dream.

Money dream definition:

  1. What we’d do if we had lots of money
  2. How we associate the work we do with the money we earn

Society has a pretty clear money dream for us all. That’s what many of us follow.

Here are some examples:

  • Get a good job that has a 6-figure salary
  • Buy a big house with lots of rooms (including a Theatre Room)
  • Once you have your first house, start saving for investment properties on interest only loans
  • Once you have equity in your home, buy another property
  • If things go well, buy a second home by the sea as a holiday house
  • When you can afford to, trade in your modest car (like a Toyota) for a luxury car like a Mercedes
  • Buy a boat, or a caravan, or a jet ski, or a motorbike

Many of these examples above form part of the majority of people’s money dream.

We’re told that this is the dream we should aim for. Somehow money will make us feel amazing. All we need is another house, another object, another job promotion.


I discovered my money dream the hard way.

I had all the money I could ever hope to have thanks to a startup that did well. As I ticked off different goals that I thought mattered, I felt more and more empty.

Image Credit: Guy Hepner

The money dream that was supposed to set me free made me feel trapped. It was like a nightmare, not a pleasant dream where everything felt good and I was on Cloud 9.

I spent years literally trying to figure out why my money dream was so messed up. None of what I had was better than the days when I had nothing.

Somehow the days sitting in an office by myself trying to sell to people who would hang up on me seemed more fun.


Then a career change added a twist to my money dream.

After I’d discovered my original money dream was seriously flawed, I had a point in my career where I’d hit the top of the food chain (so to speak).

Companies were throwing stupid amounts of money at me to come and work for them and spread some positivity, harsh truths and sales wisdom.

The reality of my money dream hit me again. I could take the money but what would I do with it?

An investment property?
More shares?
A bit of crypto?

None of these things made any sense the first time. The second time I faced this harsh vision for my life, things seemed a lot clearer.


I started negotiating.

I had an epiphany one night. What if I took all the generous offers from companies I was getting and did an experiment?

What if I took an “I don’t give a fuck” attitude and negotiated with them?

Here’s what I told each company:
• “I want money to do random acts of kindness.”
• “I value time, not money. Give me time.”
• “Give me opportunities to inspire others.”

These three thoughts came to me after a lot of deep reflection. These were the three things I valued that made me come alive. Money just didn’t move the dial in any way what so ever.

“Many of the companies began to realize that I was unconventional. Instead of walking away from weirdness, they leaned in”

I asked for four days work-weeks.
I asked for remote working. 
I asked to take staff to homeless shelters.
I asked if my team could learn public speaking.

Image Credit: Henrique Lima

All of these requests were met with stunned looks. Some companies couldn’t work out why my money dream was so messed up. They were thinking quietly to themselves:

“Doesn’t he just want a huge salary, equity and a shit hot bonus like everyone else?”

The companies that thought like this were crossed off my list. The old money dream they were trying to sell me had expired. I’d been there and done that.


Not everyone has the chance to test their money dream as I have.

That’s why I wrote this article. I want you to see another way of life. I want you to question the money dream you’ve been sold.

I’m willing to bet that if you test my theories enough for yourself, you’ll see what I saw: Our current money dream is broken.

I’m hoping through my example you can question what you’re doing in both your life and your career. Experimenting with my own money dream has been one of the most rewarding lessons of my life.

It’s taught me to think differently and test what works for me rather than trying to fit the mould that the business world wants me to fit into.

Image credit: Artem Pozdniakov a.k.a. 360brain

It’s not easy.

Nothing good in life is. Testing your money dream can blow up in your face. You can seriously piss companies off sometimes. You can damage your valuable reputation. You can look like a spoilt brat.

Anyone that thinks this way about you is not worth working for anyway. People that don’t understand the subtle differences between each of our money dreams are only fooling themselves.

“Companies that understand the ever-changing money dreams of the human race are thriving. Companies that don’t get it are dying”

This money dream challenge will not be easy. You’ll have to deal with a lot of shit, but at the end of it, as I’ve realized, you will see it’s all worth it.

Challenge your money dream. Invent a new money dream. Do what you’ve always wanted to do.


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