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6 Things I Know I’d Regret on My Deathbed

by | May 22, 2023 | Life

Regrets are worse than herpes.

They linger around until the end of your life. On the day your life is all over, they ruin the beautiful party and send you to the after-life with bitter anger.

The simple solution to limit regrets forever

In the early days of the internet Jeff Bezos quit his hedge fund job to start Amazon dot com.

In order to have the balls to do it he projected himself to age 80. At this ripe old age he wanted to have the least amount of regrets possible.

When he did this exercise he knew there’d be no way he’d regret starting an online business. He thought the internet would become a big deal and he loved every part of it.

He knew even if he failed he wouldn’t regret trying. But he knew if he ignored his dream he’d live with the pain of regret every day and become a grumpy, bitter, twisted old man like the ones you see playing the pokies.

Jeff’s formula is known as the regret-minimization framework.

It teaches us to make decisions based on whether we’ll regret not doing them later on. Author Morgan Housel says it best:

We spend so much time trying to quantify risk when the answer is just figuring out what you will or won’t regret.

I’ve applied this formula to my life and it’s helped me make some hard decisions. Have a read of this list and see if you can relate. Then change course on areas of your life where you know you’ll have regrets.

1. Working a career that was 10% of my potential

Never working a job again is definitely one of the hardest decisions I’ve made. It seems stupid.

Once you quit the job world people assume you’ve checked out. It’s often seen as an act of war. “He’s not one of us anymore.”

If the experiment fails then you’re forced to re-enter the workforce. Considering all the mud I’ve thrown at 9–5 jobs, I probably won’t be welcomed back with hugs and kisses to an employer ever again.

That used to scare me. Now it inspires and motivates me.

I knew 18 months ago that if I didn’t quit my job I’d always wonder “what if?” I’d always have thought “could I have had a career as a writer?”

So I took the plunge and now I know. Yes, I can make writing a career. Luckily I did it when I did — before I had the obligations most 30-something year olds have.

Creative dreams should always be chased. A lack of creativity will cause you to die inside faster than a solopreneur failure ever will.

2. Not having a kid

In my 20s, I thought I’d never have kids.

I could barely take care of myself. How would I ever care for a small human? Over time I changed my mind. I knew kids were a lot of work but I knew not having one would hurt me more.

Who would I leave all my stuff with? Who would take any of the wisdom I’ve acquired when I’m gone after AI destroys the internet?

The highlight of every day is seeing my daughter smile. It’s my biggest achievement in life so far. And the fact she has such a gentle personality and temperament makes me think I must have done something right.

Kids are strange. They seem like a disaster. They’re quite the opposite — but no one can ever prepare you to have them.

3. Never publishing a sentence on the internet

The first time I wrote anything online I felt terrified.

My biggest worry was that my boss would find out and tell me to delete the content. I published in secret for a while. When my boss eventually found out he didn’t get mad at all. In fact he insisted I do more of it.

And he got me a secondment to work in the social media department of our company. When you publish inspiration on any topic it comes back at you ten times harder.

If I never wrote on the internet, I’d regret the lack of purpose I’d now have.

4. Never owning a home

The debt is enough to rip your face off.

When I open my home loan app and see the huge debt number, I need to take a cold shower to cool off. The moment you apply for the loan they calculate how much you can borrow based on current and past income.

What nobody thinks about is what happens if your income goes down in the future or gets wiped out in a recession?

Still, I’ve always wanted to own a home. There’s this freeing feeling that no landlord or real estate agent can kick you out on your ass. The house is yours. You can make whatever changes you want.

The best part is, every week you make a payment, the house slowly gets paid off. Versus a rental property where you’re making some fat cat rich and staying poor every day you rent.

Homeownership is bizarre. It’s a love-hate thing.

5. Embarrassing daily exercise

I go to the gym and stand out.

I don’t have big arms and I can’t lift the big boy weights. Frankly, some days it’s embarrassing. I’m sure the gym bros are laughing under their breath.

Going to the gym is a pain in the ass.

It takes up lots of time, there’s traffic, you’ve gotta get changed and have a shower. But I know I’d regret not exercising.

It’s easy in this work from home culture to sit at a desk all day staring at a screen and living a life that’s worse than smoking a pack of cigarettes a day. The pain of exercise is good for me.

I get stronger and I feel 10x better when I leave the gym.

The energy after a workout carries into the rest of the day and produces the best flow states I’ve ever experienced.

Don’t underestimate exercise as a form of momentum in other areas of life.

6. Jumping on planes to chase insane goals

I should have flown to more places.

But in my teens and 20s I was petrified of flying. All I could ever think about was how the plane was gonna crash. I knew if I kept this view of the world I’d never leave Melbourne and have huge regrets.

So I got on as many planes as I could over a 2 year period.

I flew to new countries to chase romantic crushes. And I flew to America to meet venture capitalists and learn about Silicon Valley startups firsthand. I’m so glad I did. It’s made every part of my life better.

In every new country I’ve discovered a new way of life. I realize humans all kind of live the same if you pay close attention. It’s made me say “there’s one race: human.”

Travel makes humans less racist.

I know I won’t regret that truth bomb.

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