Four Hard Truths About Moving Into Your Late 20s That No One Told Me About.

Reflections on my Defining Decade (so far).

Photo by Johannes W on Unsplash

The PlayStation 2 is now 23 years old.

If that doesn’t throw you into a spiral of nostalgia, I don’t know what will.

Turning 28 years old this year means the runway to my 30s is fast approaching.

Here are a few hard truths I am grappling with as I move into this new decade of my life.

#1: You come to realize your parents are humans too

My childhood ended when I realized my parents were human.

Sounds silly, doesn’t it?

But growing up, you think your parents are superheroes who have everything figured out.

Witnessing my parents get divorced, and the messy process that ensued ripped that Bandaid right off.

I saw them as emotional, insecure, and scared about what the future holds.

I finally saw them as humans.

I could now connect with them in a deeper way, not just in a parent-child relationship.

As I get older my parents have become my friends. We can chat about anything and everything.

As a result, my relationship with my parents has become 10x better in my late 20s.

One day, your parents won’t be around.

That’s something that always hurts to think about. But you get to decide what type of relationship you have with them in the interim.

#2: You’re just as lost as you were in your early 20s, just with slightly more experience and more tools to handle the uncertainty.

There will never be a feeling of arriving.

Where you’ll wake up one morning and feel like everything in your life is settled and you’re perfectly content. That’s a myth.

I often use to say, “When I am an adult I’ll have my career and money figured out.”

Now that I have become said adult, I can report that I do not have my career and money figured out.

Maybe I never well. And that’s okay.

The goal in life is not to get rid of uncertainty but to learn how to deal with it better

Instead of trying to pave the thorny road of life with leather, I’ve used that leather to create better-fitting shoes.

#3 Most people never grow up… and maybe never will

I have an ex-friend that was an extremely popular and attractive person in high school.

She got all the attention from the boys, and sometimes, quite creepily, from the older male teachers too (nothing ever happened).

She got invited to all the parties, could dictate what was ‘cool’ or ‘lame’ at the drop of a hat, and could create fashion trends out of nothing.

Think Regina George from Mean Girls.

But while high school was more than 10 years ago, and we’ve all moved on to bigger and better things, she’s still trying to play these high school games.

It’s quite sad to see.

Despite the early promise, she hasn’t progressed far in life. She’s a drop-out, works a mundane job and is surrounded by exactly the same people she went to school with.

Since her powers are fading, she’s resorted to other tactics. She manipulates people for her own gain, sucks up to those who can serve her wants and needs, and disposes of them once they’re no longer useful.

That’s when I realized:

Most people never grow out of high school mentality.

They are trapped by the games that they excelled at and want to keep playing.

But just like musical chairs, the music stops playing at some point. And all you are left with is a creeky chair with broken legs to sit on.

Let go of those games, or be prepared to be dragged by them.

#4 Success is something you start to define for yourself

Your late 20s is when you start to define what success is for you.

Prior to this point, you’re given a pre-determined script of what you need to achieve to be considered successful by standard metrics.

  • Get a degree.

  • Get a job.

  • Get a promotion.

  • Make six-figures.

  • Marriage and a crippling mortgage.

  • Work until you’re 75.

  • Enjoy your life with arthritis.

But when you’ve been punched in the face by your 9–5 job, worked for a few bad bosses, dated around, traveled around the world, and made new friends, your worldview dramatically expands

You start to realize that you don’t want what everyone wants.

You see the facade of ‘security’ or ‘settling down’.

You want to start making your own path in life and building something for yourself.

While most of my friends are settling into a cozy 9–5 job, buying houses to settle down, and looking to get married, I’ve decided to do the exact opposite.

I’ve quit my 9–5, started multiple businesses, have decided to remain single, working as a digital nomad, and plan to be a digital nomad full time in the next couple of years.

I’ve traded security for uncertainty, and I couldn’t be happier with my life.

Define success for yourself, or it will be defined for you.

The takeaway

As I enter the twilight years of my 20s, I am filled with optimism and hope.

From all accounts, life gets better in your 30s.

You’re more confident in yourself, you have more skills and have a higher level of financial security.

Rather than cling to the youth of my 20s, I am embracing aging. I am training my mind to view it as a gift, not a curse.

As Sean Kernan once wrote:

As I see more people getting sick and passing into whatever awaits, I’m reminded that aging is a gift — and it isn’t given to all.

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