What risk actually looks like is not doing something, that you will spend the rest of your life regretting — Sam Altman
Regrets drive a lot of decision-making.
I quit my job last year to have less regrets. I tried entrepreneurship and built an online business again after a devastating startup failure in 2011 that sent me to the corporate world in exile for a decade.
Now I’m having a baby girl because I can’t imagine dying without experiencing the gift of parenting. Maybe I’m crazy.
Here is a list of things you should do at least once in your life to limit deathbed regrets you’ll never be able to change.
Give your lunch to a homeless person
I saw Keanu Reeves do this once in LA. Sweet guy.
Giving your lunch to a homeless person isn’t about virtue signaling or high-fiving whatever god you believe in. It’s about showing a stranger kindness. When you do, it can completely change their life. They can be reminded that people care and it can do a world of good.
Bonus advantage: sharing your food shouts to your brain “I have enough.”
Start a side hustle
Don’t wait for the holidays or when you have spare time to work on a passion project. Life is too short not to take a chance on doing what you love.
The beauty of a side hustle is it’s de-risked. Your job pays the bills while your side hustle fuels your imagination and helps you explore your curiosity.
Maybe something happens, maybe it doesn’t. But at least you’ll know by trying side hustle experiments. Any monkey can do it. Why not you?
Launch a Twitter/TikTok account
TikTok will be the death of me.
Occasionally, I open a link in TikTok and my brain is depleted of dopamine as the 15-second video I watch auto-plays into another viral video. Before I know it my brain is cooked. But I’m a 30-something grandpa with tinnitus and a hearing aid. Don’t mind me.
Before you die dare to publish your thoughts online. TikTok and Twitter still have the viral loop built in. You can find an audience, and find your tribe.
You can help strangers through content and give your life more meaning.
Fall in love
Not everyone finds everlasting love that lasts the rest of their life.
That’s okay. My point is you got to try. It’s an experience worth having. When we’re drunk on love we’ll do anything for the other person. It empties out our selfish tank and fills up our selfless one.
Some of the best lessons come from failing in love too. When a breakup happens you realize the other person was a mirror of you.
The things they did wrong were problems in your mind and not necessarily with them.
Let love teach you a thing or two.
Experience a flow state
Some people will tell you going to bed for a good ol’ fashion bonk is the greatest ecstasy humans can experience. Not really.
Flow states are what power the science of achievement. The best in the world have all mastered this superpower — some realize it and some don’t.
Flow states make you feel like Wonder Woman or Superman. Imagine feeling like that every day? You can.
Learn about flow states and apply them to your day to do the best work of your life.
Do gym for 90 days straight
If meditation upgrades your mind’s software then the gym upgrades your body’s hardware.
So many people I see at the gym never get to experience the magic. They can’t escape their phones and end up doing distracted, low-quality workouts. A great workout that’ll convince you to do it forever and never give up is done in the present moment.
Great workouts require you to sweat and experience exhaustion. When you do, you cross an invisible threshold and get the post-gym rush of endorphins.
The only reason I go to the gym is because I’m an endorphin junkie. The stress relief superpowers plus the relaxation I get help fuel my flow states.
Get addicted to exercise.
Your future mind and body will thank you. You won’t get older and become as stiff as a plank of wood, therefore leading to regrets about how poorly you treated your body.
Ask an influential person a question at a conference
I’m sure you’ve been to a conference before.
At the end of a presentation from a successful person there’s often a chance to ask questions. Most of us don’t. We sit there frozen, too afraid to ask. Yet we can think of a question we’d love them to answer.
Don’t leave conferences with regrets.
Get up in front of hundreds/thousands of people, go red in the face, think your question is dumb, and ask it anyway.
These are the moments courage is built. And courage breaks down every Berlin Wall we face in life.
Cruise through Halong Bay in Vietnam on a boat
Nature teleports our minds into the present moment.
One of the most beautiful places I’ve ever been to is Halong Bay in Vietnam. I first saw it in a James Bond film and had to go. The only way to describe it is majestic. There are hundreds of islands. Some of them you can enter.
I went to one island where we walked into the middle of a forest, only accessible through underground caves. As a 6-foot giant I had to bend my skinny arms and legs to squeeze between the crevices.
Once we got into the open it felt like we’d gone back to the age of dinosaurs. Everything was untouched by humans. It was a glimpse of centuries past.
Do yourself a favor and go to a world heritage site to experience unmessable nature at its best. You’ll connect with your animal ancestors when you do.
Get a year’s worth of expenses saved up
Then take some time off and do whatever the heck you want.
Jump on a plane without a plan. Drop in on an old friend without telling them you’re coming. Spontaneity is lost when we become adults. A year’s savings can help you find this childlike beauty again.
Plus savings relieve stress, especially during a recession.
Quit a job at least once
You weren’t born to work the same boring job for the rest of your life. Even if it’s good, quit. It’s only the best based on the jobs you’ve already had.
Maybe there’s a better job or career you just haven’t worked yet. Don’t wonder. Try another career for fun.
Oh, and every time you quit a job you get a pay rise. Nice.
Sit in a nightclub alone with a lemon water
Done this plenty of times.
When you do it you’ll see how everyone is trying to escape reality by destroying their bodies. Life will never be the same.
Alcohol will look like the devil in a red Prada dress.
Dance in the rain to Moby’s “Raining Again”
Dancing in the rain is something few people do before they die. They don’t want to ruin their outfit.
As a 20-something broken man I went to a dance music festival. The weather went from sunshine to heavy rain. I went to hide under an umbrella. Then I saw everybody else take their shoes off and dance in the rain as the artist, Moby, played his famous “Raining Again” song.
For once in my life I said “screw it, I’m dancing in the rain.”
I got completely drenched and ruined my brand new outfit I’d bought for this New Year’s Day party. I didn’t care.
For the first time in my life, dancing in the rain made me feel completely free. I hadn’t felt like that in a long time. Try it.
Face a cancer scare
Like don’t go sit next to a power line or anything and get cancer intentionally. But experience a major health scare. Or watch someone else experience one.
Notice how it makes you feel. Now pretend it’s you. Magic.
You’ll never waste time again.