Ep.109 / Dear Younger Me: Everything I Wish I Knew at 15, 18, 25 & 30
If you could sit down with your younger self... what would you say?
As another birthday rolls around, Josh reflects on the biggest life lessons he's learned by writing letters to himself at four defining ages: 15, 18, 25, and 30.
From growing up feeling different, struggling with confidence, chasing validation, this deeply personal episode is full of honest conversations we all wish someone had with us sooner.
Dear Younger Me: Everything I Wish I Knew at 15, 18, 25 & 30
If you could sit across from your younger self for just one hour, what would you say?
Would you warn them about heartbreak?
Tell them to invest earlier?
Encourage them to take more risks?
Or would you simply tell them that everything is going to be okay?
Every birthday has a way of making us look backward before we look forward. We think about the dreams we had, the mistakes we made, the people who shaped us, and the versions of ourselves we eventually outgrew.
For this special birthday episode of HOT AIR, I decided to write letters to the younger versions of myself. Not because I wish I could change my past, but because I think there's value in recognizing how far we've come—and in sharing those lessons with anyone who might need them today.
Dear 15-Year-Old Me
At fifteen, I believed fitting in was the goal.
Like so many teenagers, I spent countless hours worrying about what everyone else thought of me. Every awkward interaction felt catastrophic. Every mistake felt permanent. Every opinion from someone else somehow became more important than my own.
Looking back, I realize I wasn't actually trying to become myself.
I was trying to become someone everyone else would approve of.
The irony?
The things I spent years trying to hide—my creativity, sensitivity, energy, and enthusiasm—eventually became the qualities that shaped my career and connected me with others.
Sometimes the parts of ourselves we're most insecure about become our greatest strengths.
Dear 18-Year-Old Me
At eighteen, I thought I needed a perfect roadmap.
Society asks young adults impossible questions:
"What are you going to do for the rest of your life?"
The truth is, very few people have that answer.
Instead of waiting until I felt completely ready, I wish I'd trusted myself to take more chances.
Travel.
Say yes.
Apply for the opportunity.
Move somewhere new.
Confidence doesn't come before action.
It comes because of action.
Dear 25-Year-Old Me
Your twenties can become an endless competition.
Career.
Money.
Relationships.
Social media.
Fitness.
Success.
At twenty-five, I confused validation with ambition.
I thought accomplishments would finally make me feel enough.
But external validation is temporary.
Purpose lasts much longer.
One of the most valuable lessons I learned is that happiness doesn't arrive after achieving your goals.
It has to exist while you're working toward them.
Dear 30-Year-Old Me
Thirty felt like another beginning.
By then, I'd already changed careers multiple times.
Instead of seeing reinvention as failure, I finally began recognizing it as growth.
You are not one identity.
You're allowed to evolve.
You're allowed to outgrow old dreams.
You're allowed to discover new passions.
Your career is simply one expression of who you are—not the definition of who you are.
Confidence Is Built, Not Found
One of the biggest misconceptions about confidence is believing some people are simply born with it.
They're not.
Confidence comes from surviving difficult moments.
It comes from keeping promises to yourself.
It grows every time you try something scary and discover you can handle the outcome.
You don't become confident before taking risks.
You become confident because you took them.
Comparison Is a Losing Game
Social media has made comparison easier than ever.
We compare our real lives to everyone else's highlight reels.
Someone is getting married.
Someone bought a house.
Someone started a company.
Someone is traveling the world.
The problem isn't that other people are succeeding.
The problem is believing their success somehow diminishes your own.
Life isn't a race.
Everyone is running different distances toward different destinations.
You're Allowed to Reinvent Yourself
One of the themes that appears throughout my life is reinvention.
I've worked in multiple industries.
I've discovered entirely new passions.
I've built new careers.
I've launched a podcast.
I've become an artist.
I've continued evolving.
Too many people believe reinvention is evidence they failed.
In reality, it often means they're growing.
The Most Important Relationship
The longest relationship you'll ever have is with yourself.
Learning to trust yourself changes everything.
Learning to forgive yourself changes everything.
Learning to enjoy your own company changes everything.
Because eventually, external validation fades.
Achievements come and go.
Careers change.
Relationships evolve.
The person who remains through every chapter is you.
Growing Older Is a Gift
Birthdays often make people anxious.
We worry about getting older.
We wonder whether we're behind.
We question whether we've accomplished enough.
I've started looking at birthdays differently.
They're not reminders that time is running out.
They're reminders that we've had another year to grow.
Another year to learn.
Another year to love.
Another year to become ourselves.
Final Thoughts
If I could actually sit down with every younger version of myself, I wouldn't hand them a roadmap.
I wouldn't try to erase every mistake.
I wouldn't remove every difficult chapter.
Those experiences shaped the person I am today.
Instead, I'd simply tell them this:
Relax.
Keep going.
Trust yourself.
The life you're building will look different than you imagine—but in the best possible way.
And maybe that's the advice all of us need to hear.
No matter how old you are today, there's probably a younger version of you who would be unbelievably proud of the person you've become.
Maybe it's time to be proud of that person, too.