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Investments to Make in Your 20s, 30s to Avoid Regrets in Your 40s, 50s

by | May 16, 2022 | Money

Time speeds up as you get older.

Ask any adult and they’ll tell you. As a child, life goes painfully slow. You’re dying to grow up as fast as you can so you can watch horror movies and the odd nude scene.

By the time you become a teenager you want to be old enough to get drunk and party hard. The urge to be of legal driving age increases too.

Three months before I became old enough to own a car the wait became painfully long. Every weekend I’d meet up with my friends and we’d talk about all the things we were going to do when I could drive.

When the date finally arrived I drove everywhere a car could go — and even places a car shouldn’t go, like through floodwaters and extremely deep mudflats. Within a year the novelty of driving wore off.

I was onto chasing the next shiny toy: becoming a famous DJ.

The best rewards don’t come from silly pleasures. They come from goals you invest heavily in for a long time.

These are the investments I’d make if I could relive my 20s and 30s. Folks in their 40s and 50s that I admire have done these and never regretted them.

1. Invest in yourself

It might seem dumb to start with this one. Hear me out.

I ignored investing in myself for most of my life. My mental health deteriorated to the point of ruin. I didn’t even recognize myself any longer. I didn’t even trust gravity.

Some days I would question the ground I walked on and feel like it was moving (when it wasn’t). It became clear I needed help. But I couldn’t dare do it because of embarrassment. Plus I had zero time.

I was working myself into an early grave and I knew it.

I was a 20-something grandpa with no energy who always felt sick and couldn’t attend family dinners or social events at work because of an eating disorder.

Finally I had enough.

I got help. I started investing in myself. I turned off the news full of fear. I paid for a psychologist with the little savings I had. I started exercising. I began to eat better food and stopped stuffing hamburgers in my mouth.

The ROI of the investment paid off slowly. I’m proud to say after all these years, I’ve healed from all the trauma I created for myself because I invested in myself.

Do this

Invest in your mental health, food, exercise, sleep/relaxation, healing. It’ll be hard but it’ll pay dividends for the rest of your life.

2. Invest in buying your time back

Your 40s and 50s will be damn hard if you don’t learn to invest your money early. I saw it way too often as a banker.

People would be stupid with money in the hope they’d make it all back by retirement. Instead of a solid investing habit they’d developed an out of control spending habit.

Every promotion, every bonus, every new business — all led them to make more dumb purchases to demonstrate status to the tribe.

Screw status.

Status doesn’t make life good. Owning your time to do whatever the hell you want with it is the ultimate status — it’s true happiness.

Do this

Learn how to invest in financial assets. Then invest at least 20% of everything you earn using the dollar-cost averaging technique. If you do, it’ll protect all the time you gave up to earn money, from nasty inflation.

3. Invest in relationships (not dumb networking)

Capitalism accidentally teaches us to view others as transactions we could one day make. Just open your messages on LinkedIn.

You’ll be right-hooked in the face with pitches for all kinds of stuff out of nowhere. Too many people trying to cash in. Not enough people trying to build career-long relationships.

A relationship starts with a conversation, not an ‘ask.’ Read that again.

Invest in building relationships with interesting people you come across. I love to build relationships with quiet people. They see the world differently and their humility lights a fire in my brain that’s infectious.

Do this

Start random conversations in elevators. Direct message your heroes and share something they’ll find helpful or interesting.

Walk through life with zero agenda — you’ll drown in opportunities if you do.

4. Invest in the weirdos that make up your family

Many of the corporate big knobs I worked with previously used to tell me candidly how they wish they’d spent more time with their families.

I ignored my family for years.

My brother and I fell out of touch. The ball was in my court and I didn’t chase after it. Now I know that’s stupid.

You only get one family. Spend time with them. You’ll miss them even more when they’re gone. As a man about to have my first kid, I don’t want to make that mistake. I want to be there for my newborn daughter.

I want her to know who her daddy is.

I don’t want the only image of me to be through a Zoom call with her mother while I travel the world and live out of a suitcase to keep some dumb business happy as I meet clients. That could have been me.

Then it hit me: being consumed by your job is a scam.

Do this

Spend time with your family. And go ring grandma tonight while she’s still alive. The older our relatives get the less chances we have to see them before they’re gone.

Work can wait.

5. Invest in a side hustle

This one isn’t meant to sound cool. I’m not trying to invisibly high-five the bros. A side hustle is a strategy.

It’s a way to have a job and do the work you really want to on the side with zero risk. Once the side hustle starts to become a bigger part of your income, you can slowly transition from a job to work you love.

It’s what I did. I invested a lot of time before and after work to make it happen. I can now say it’s easily one of the best investments I’ve ever made.

Do this

Work on a side hustle between 6-10 pm. Commit for at least a year. Invest time into learning about online income streams. Experiment heaps.

6. Invest in publishing bite-sized content

Twitter should be illegal. It’s one of the best life hacks I’ve found. It’s where the cool kids hang out if you follow the right people.

All you need to do to unlock its superpower is post a few one-sentence tweets every day. People and opportunities you could have never dreamt of will enter your life out of nowhere.

Now you know my secret. Steal it.

Do this

One single-sentence tweet per day, every day for a year.

7. Invest in reading about the lives of others

99% of us will never be friends with the greats of history.

They’re either dead or have huge iron gates out the front of their homes that keep out stranger danger. You don’t need to know wildly successful people though. A good book can teleport your brain into the life of another.

One person I learned a lot from was Victor Frankl. He ended up in a concentration camp during World War 2. He could have been taken to the gas chambers at any time. He came close a few times.

Yet somehow he survived in the harsh conditions to tell the story. What’s weird is how he explains the difference between those killed and those who survived.

It all boils down to this: the ones who lived chose a positive attitude. They didn’t let their minds defeat them, even though that’d be perfectly normal given the situation.

This is the closest I’ve come to a holocaust survivor, thanks to reading. There are simply no stories as powerful as this that I come across in everyday life.

Do this

Read more biographies about unusual people. Not Elon Musk. No.

I mean bizarre people who have lived uncommon lives you could never imagine. The non-cliche types. The oddballs. The obsessive. The ones who attach balloons to a gardening chair to see what it’s like to fly.

8. Invest in the one place no money book tells you to

I read a lot of money books. Never read a single one that says to invest in your local homeless shelter.

I don’t mean invest with money either. Nope. Invest with your time.

Dare to spend time with people who’ve got left behind by society. It’ll help you understand the real problems. We’re only a few bad days or weeks away from becoming homeless ourselves. Few understand.

Ask people who had their livelihoods taken away by the 2008 recession. Could easily become any of us in the next recession caused by the aftermath of coroni.

Do this

Dare to serve food at a homeless shelter. Warp your mind.

Closing Thought

The perception of time slows down when we make smart investments. We don’t become so reactive and society doesn’t control our thoughts as much.

Invest well in your 20s and 30s, and your 40s and 50s will be a blast with fewer regrets.

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