Turning the Page on My Twenties
My thirty-before-thirty challenge and how I’m turning my thirty-year panic into purpose.
The idea of turning 30 next year is a little surreal.
I don’t feel that old—whatever that even means anymore—but I recognize the weight of the milestone. My twenties have been a decade of evolution: filled with triumphs and faceplants, joy and grit. I’ve lived in two states, rented seven apartments and bought a house, purchased my first car, and traveled through dozens of states and countries.
Every moment—good, messy, beautiful, and brutal—has helped shape who I am today.
But hang on—we’re not done yet!
I’ve still got a full year before my “dirty thirty” rolls around next August, and rather than coast into the next chapter, I’m choosing challenge over cruise control. What started as a few ambitions turned into something more intentional: a 30-before-30 challenge.
Much like my annual Go for Growth exercise, this list is packed with variety—some goals push my physical limits, others stretch me creatively, professionally, and personally. It includes standout items from my Living List and feeds into my broader pursuit of purpose and progress.
And in the spirit of accountability, I’m putting it all out here on my blog. I’ll be checking in every few months and posting deep dives into some of these goals along the way.
Like personal development coach Joe Vitale once said, “A goal should scare you a little and excite you a lot.”
Learning & Growth
Write a Book of Poetry – Tell my story through 30 poems inspired by my first 30 years.
Write a Screenplay for a Series Pilot – Craft the first episode of an original show, idea and all.
Write an Illustrated Children’s Book – Let Oscar become the hero in my first picture book adventure.
Inventory All the Books I’ve Read and Add 10 More – I’ve read hundreds of books in the last ten years. Time to
Become a Power User with AI – I’ll sharpen how I use AI to create, think, and push projects forward (and, no, Copilot didn’t help me write this one)!
Connection & Community
Reconnect With 30 People Who Changed My Life – I’ll reach out with thanks and appreciation through dinners, calls, or handwritten letters.
Help Build a Habitat for Humanity House – At best, I’m a novice when it comes to home improvement, but the purpose and community of building a home for someone in need feeds my purpose.
Send a Surprise Gift to Someone I Haven’t Seen in Years – Delight someone just because.
Apologize Authentically Where I’ve Left Loose Ends – Make peace and close the loop.
Ask 3 Thoughtful Questions to 3 Trusted People – Seek insight from those who know me best—and then grow from what they share.
Become Friends with a Stranger – Time to turn a passing moment into a real connection.
Take a Road Trip and Meet 10 People on the Way – Meet people where they are and document what I learn.
Host a Themed Party for Friends – I’ll throw a party full of personality—and yes, costumes are required.
Creativity & Expression
Create Something Physical – I’ve always wanted to try sculpture—perhaps this is the chance.
Build Something Out of Legos – Not sure what yet, but it’ll take me back to one of my favorite childhood activities.
Curate a Visual Timeline of My 20s – I’ll showcase this decade through images, milestones, and stories.
Record My Year – Capture life’s highs and lows, then edit into a short birthday film.
Build a Ten-Year Time Capsule – Preserves memories for my 40-year-old self to unpack.
Challenge & Adventure
Complete a Physical Feat – I’ve run seven marathons, but have always been intrigued by Spartan Races, Triathlons, and other bold endeavors.
Reach a Strength Milestone – I’m in the best shape I’ve ever been, but it’s time to take it up a notch.
Take on a Fear-Conquering Activity – Face a fear head-on—bungee-jumping, perhaps?
Go on a Multi-Day Hike – I’ll disconnect and take on nature, one step at a time.
Say Yes to an Unplanned Weekend – I’ll hand over control to friends or family and embrace the unknown.
Eat Something I Wouldn’t Normally Try – Time to surprise my taste buds and challenge my food boundaries (those around me know seafood and eggs aren’t historically my cup of tea).
Reflection & Inner Work
Do a Weekly Hard-Truth Reflection – A year of raw, constructive insights—one per week.
Spend a Full Day in Silence – Disconnect to reconnect—with no talking or texting.
Tackle a Stubborn Habit or Limiting Belief – Confront a lingering blocker and finally chip away at it.
Write a Guide to Being 20-Something – I’ll share what I’ve learned—the wins, the missteps, and what I wish I knew ten years ago.
Create a North Star Document – I’ll define the principles, values, and vision that guide my life.
Define What “Enough” Means to Me – Clarify what fulfillment looks like—in wealth, time, and impact.
It’ll be a busy next year before the page turns on my twenties, and I wouldn’t have it any other way!
This challenge is ambitious, personal, and overflowing with purpose. I’ll be checking in with progress, stories, and reflections along the way, so stay tuned. And if you’re searching for inspiration to build your own Living List, don’t miss my other post and free starter file to help kick things off.
Time to tackle my 29th year!