8 Things I Wish More People Knew in Their 20s

And what so many older folks are still missing.

Sean Kernan
Jan 20 · 5 min read
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Source: pic via Adobe Stock

When people make these list articles, they often overstate the obvious:

  • Work hard.

These things might be good reminders, but they don’t really add to the conversation.

Even further, they don’t really produce meaningful insight for people to better their future.

If more people understood these eight things sooner, they’d be happier, more efficient, and endure a lot less pain.

1. Don’t back yourself into a corner that’s hard to get out of.

I knew their relationship was trouble from the get-go. They never got along. They had nothing in common. There was always drama, complaining, and tears.

And here they are, sixteen years of suffering later, with three bandaid babies, and a messy divorce to get through.

All because neither of them was strong enough to walk away.

Another friend is in over his head with debt problems. He made a bunch of assumptions about his future earnings and spending (which is often the case with money problems).

The lesson? Hangovers can be fixed with a good night's sleep. Bandaid babies and debt problems cannot.

Get to your 30s with as little baggage as possible.

2. You are paid by how expensive you are to replace

I graduated college with this misguided idea that a good degree and hard work would make me invincible.

Everyone would hire me and I’d get a raise every year.

All it takes is a company downsizing or a manager that doesn’t like you.

Our pay and job security are directly tied to how many other people are willing to do our job. This isn’t an opinion. It’s economics.

You either make yourself indispensable to a company. Or pick up skills and qualifications that make other companies want you more. Otherwise, plan on getting yanked around and low-balled.

As an extreme example, my friend skipped college and worked his way up to senior-level tech support with a camera company.

Now, at 38, his company is bankrupt and he’s out of the job with marginally transferrable skills.

3. Stare down your tough conversations.

One of my most cowardly acts came at the age of 21.

I broke up with a girlfriend over the phone rather than in person. On a 10-scale of How Poorly This Could Go, her reaction was a solid 9.8. Thankfully, I didn’t have to learn this lesson twice.

Someone once told me, “How far you go in life will be determined by how many difficult conversations you’re willing to have.”

That wisdom becomes more apparent with age. I’ve seen so many problems boil over into new and more troubling dilemmas because we lack the conviction to confront the issue in a timely fashion.

4. You are powerless without a cushion

My girlfriend often asks me why I’m so into saving my money and investing.

  • “Why not take more trips?”

Having savings is about power. It gives you options and control.

My best-tip: save enough money to cover a year of living expenses, as fast as possible. Then, keep extending.

Saving isn’t just about giving yourself an eject button from a bad boss. Having that money gives you a sense of security. It eases your anxiety.

But yes, having the option to rage quit is a nice card to own.

A full 69% of Americans don’t have $1000 of savings. Don’t leave yourself at the mercy of debt or living in your parent's basement.

Invest as soon as possible. Time is your friend. Put something away each month. You’ll be shocked at how quickly it adds up.

5. Your tribe is your future.

I always wondered why my parents interrogated my friends. It seemed a bit harsh — but it was with great meaning.

My grandfather once said, “Show me five of your closest friends, and I’ll know a lot about you.”

In your early 30s, the divergence of your cohort becomes particularly apparent. Some will be stepping out of med school while others are still stuck at the bar, putting off finishing college.

Whether we want to or not, we adopt traits from our peers. It’s intrinsic to our nature. Surround yourself with people who represent the person you’d want to be.

Just because someone wants to be your friend, doesn’t mean you should be buddies.

You can be a kind and generous person — but also selective in who you spend your time with.

6. Happiness has a very boring formula.

We develop this very childlike vision of happiness that involves lots of glory, fairy tales, and Wanderlustian adventures in foreign lands and resorts.

Meanwhile, as I get ready for my 40s, I’m never more content than when I go to bed at a normal time, work hard, and maintain good relationships. This comes with a caveat though.

Humans are programmed to seek contradictory things: novelty and consistency. It’s normal to constantly feel a bit restless.

I find that pursuing novelty is healthiest when attached to goals:

  • Going on a vacation after a successful venture.

Unearned cheap thrills are for amateurs.

7. Your career will break your heart at some point.

Our early careers bring a tough adjustment period where we reconcile an idealized expectation with operational reality.

Years of grinding lead many of us to a crossroads. I was eventually brought to that point. I’d realized I was just going through the motions. I couldn’t see my future in the field.

I went through this terrible transition, that was very akin to a hard breakup.

It’s OK to have a few jobs you hate. Explore what you are passionate about. Don’t spend your time wondering what you want to do. Try stuff out and learn new things.

And don’t be jarred if you feel the calling to make a radical change.

8. Lastly, most relationships have expiration dates.

People come and go as you get older. Relationships end. Social circles shrink to a core group of friends and family that belong there.

Cut the toxic people out of your life. Make it a point to preserve the connections you value most. Career, family, living, has a default state that pulls you away from people you were once close to.

Start deciding who you want in your life thirty years down the road.

Nurture and protect those relationships — or risk the loneliness of old age.

The Ascent

A community of storytellers documenting the journey to happiness and fulfillment.

Sean Kernan

Written by

Quality over quantity. That guy from Quora. Enjoy? Follow for more. https://seanjkernan.substack.com/ Open to gigs seanjkernan@gmail.com

The Ascent

A community of storytellers documenting the journey to happiness & fulfillment. Join thousands of others making the climb on Medium.

Sean Kernan

Written by

Quality over quantity. That guy from Quora. Enjoy? Follow for more. https://seanjkernan.substack.com/ Open to gigs seanjkernan@gmail.com

The Ascent

A community of storytellers documenting the journey to happiness & fulfillment. Join thousands of others making the climb on Medium.

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