The Quest for Clarity: Navigating the Phases of Your 20s
Read Time: 5 Minutes
Today at a Glance
In this week’s issue, we’re diving into:
The three phases of life in your 20s (and why none of us know shit).
Why it’s okay to “fuck around” and focus on experiences.
How balance and self-awareness lay the foundation for a better future.
Let’s get into it!
The Three Phases of Your 20s
Your 20s are often painted as a chaotic blend of self-discovery, ambition, and the pressure to "have it all figured out." But through reflection, I’ve noticed three distinct phases most people seem to navigate:
Phase 1: The Initial Focus Phase (21–24)
This is the time when everyone seems hyper-focused on something. For many, it’s climbing the corporate ladder, starting a business, or finding “the one.” There’s this palpable urgency to lock down big milestones early—as if missing them now means missing them forever.
For me, it was the opposite. I wasn’t focused on traditional goals like promotions or relationships. I was focused on experiences: traveling, meeting new people, and saying yes to random opportunities. My peers were diving headfirst into careers or serious relationships, but I wanted to explore the world and figure out what mattered to me.
What I Learned:
Life is richer when you prioritize breadth over depth early on.
By stepping away from the “traditional” path, I gained perspective on what I truly wanted—not what I thought I was supposed to want.
Of course, it wasn’t without challenges. People questioned my choices, and there were moments I doubted myself. But looking back, this phase gave me stories, skills, and self-awareness that shaped the person I am now.
Phase 2: The "I Don’t Care" Phase (25–27)
This is when the shine wears off. You’ve been in the workforce for a few years and start to realize that things in the world don’t operate the way you thought they would. Maybe you’ve been passed over for a promotion, or your salary increase hasn’t kept pace with your expenses. Life starts feeling a bit like a hamster wheel.
The Shift:
At this stage, many people stop striving as hard. They’re less worried about climbing the ladder or finding a partner and more interested in enjoying life. It’s a period of exploration—going out, trying new hobbies, and focusing less on big milestones and more on day-to-day pleasures.
For me, this phase was about doing things I had always dreamt of but was scared to try. I realized corporate America wasn’t going to deliver the life I wanted, so I embraced remote work, traveled as a digital nomad, and let go of the fear of getting fired. Worst-case scenario? I figured I could work at a bar or hostel. Honestly, that didn’t sound so bad.
What I Learned:
Sometimes, “not caring” is a healthy reset. It gives you space to reevaluate what truly matters.
This phase is a chance to explore without the pressure of expectations.
Phase 3: The Quarter-Life Crisis (27–30)
This is where things get real. As 30 looms closer, panic can set in: “What have I been doing with my life?” Suddenly, you’re hyper-aware of all the milestones you haven’t hit—career achievements, financial stability, relationships—and it feels like time is running out.
The Reality Check:
At this stage, people often scramble to “catch up,” whether that means finding a serious partner, saving for a house, or accelerating their career. But the truth is, this panic is less about actual lack of progress and more about comparing yourself to others—or worse, holding yourself to the expectations you set at 13 when you really didn’t know shit.
What I’m Preparing For:
Approaching this phase with intentionality rather than panic.
Focusing on how I spend my time in areas of importance rather than chasing arbitrary achievements.
Building skills, hobbies, and habits now so that when the time comes, I’m ready for the next stage of life. - Don’t be that guy that has no hobbies.
The Case for Fucking Around
"You have your whole life to work. Why are you rushing now?" – My Mom
When I was 16, I wanted a cool car so badly that I considered getting a part-time job to afford it. My mom shut it down with one sentence: “You have your whole life to work.” She was right. Once you start the grind, it never stops.
In your early 20s, you don’t need to have everything figured out. In fact, this is the best time to mess around and have fun. Take that spontaneous trip, live abroad, or work a random job like at a winery in Italy or a pig farm in Oregon just because it sounds interesting.
Here’s why it matters:
You Build Stories and Skills: The more experiences you have, the more interesting you become. If you want to be an interesting person, you have to do interesting things. Everyone works, golfs, plays pickleball, loves dogs, and drinks espresso martinis—you’re not special.
You Realize What You Don’t Know: The more you explore, the more you’ll see how little you understand. And that’s a good thing. Meeting people who’ve lived wildly different lives can open your eyes to opportunities you didn’t know existed.
You Discover What Actually Matters: Fucking around doesn’t mean being reckless—it means exploring your options and learning what brings you joy. Try new activities, hobbies, or experiences. Maybe you’ll find your next passion or talent.
Laying the Foundation for the Future
Now, I’m not saying you should completely throw caution to the wind. There’s a balance to be struck between having fun and building a life you’re proud of. Truthfully, I went a little too hard in the last bit of the "I don't care" phase, and it put me in a dark place. Looking back, here’s how I would approach it:
Set Boundaries for Yourself: After this bodybuilding prep, I plan to let loose a bit, but I’ll keep clear boundaries. For example, I’ll only go out on Saturdays or limit certain activities to make room for personal growth.
Invest in Skills, Not Just Fun: Use this time to pick up skills that will serve you later. Whether it’s learning how to cook, starting a side hustle, or reading about relationships, these investments compound over time. Pick something you enjoy, so it doesn’t feel like work.
Create Space for Reflection: Take time to reflect on what you’ve accomplished, what makes you happy, and where you want to go.
Reflection Question
Where are you in your 20s journey?
Are you in the hyper-fixation phase, the “I don’t care” phase, or staring down a quarter-life crisis?
What experiences have taught you the most about yourself so far?
Are you balancing fun with building a solid foundation for your future?
Recommendation Zone: The Defining Decade
This week’s recommendation is The Defining Decade by Dr. Meg Jay. It’s a must-read for anyone navigating their 20s and trying to make sense of life.
Why You Should Read It:
Learn how the decisions you make now set the stage for your 30s and beyond.
Gain insights into relationships, careers, and self-discovery.
Shift your mindset from “waiting for life to happen” to creating the life you want.
Parting Thought: Embrace the Unknown
Your 20s are a time for exploration, mistakes, and growth. Don’t be afraid to fuck around, but don’t forget to learn from those experiences. The more you try, the clearer your path will become.
This week, focus on one thing you’ve been avoiding—whether it’s a new experience or a lingering task. Take the leap and see what it teaches you.
Stay curious, stay bold, and keep chasing the dream.
– Quest