7 Lessons on Figuring Out Your Career When You Feel Lost in Your 20s
If you feel stuck, behind, or unsure what’s next, these lessons will help you see that uncertainty can actually be your biggest advantage.
By
Josh Felgoise, Host of Guyset Podcast
Oct 21, 2025
The Secret Life of Walter Mitty
1. Feeling Stuck Is the First Sign You’re Ready for Change
“Maybe you start to think, huh, I’m kind of stagnant here and I’m no longer really growing. There’s nobody here that I can learn from and I don’t really see a position that I can grow into.”
That moment of realization isn’t failure. It’s feedback. Feeling stuck means you’ve outgrown your old version of yourself. It’s uncomfortable, but it’s the first step toward something better.
When I stopped seeing “stuck” as a dead end and started seeing it as a signal, everything changed.
If you’re in that stage, read You’re There for a Reason (Even If You Don’t Know What It Is … Yet). It’s about finding meaning in the middle of uncertainty.
2. You Don’t Owe a Job Two Years of Your Life
“This two-year mark that you’re supposed to hit, that you’re supposed to wait out because someone before us decided it’s the mark of success.”
That rule was built for a different generation. You don’t have to earn the right to pivot. You just have to trust yourself enough to know when something’s run its course.
Leaving before you hit a milestone doesn’t make you flaky. It means you value alignment over appearances.
If that mindset speaks to you, check out How I Turned My Fears Into Reality (And How to Avoid the Same Mistake). It’s an honest look at what happens when fear drives your choices.
3. The Fear of Change Is What Keeps You Trapped
“It is so much easier to stay where you are because of all of the things that I have just said that you have to do to find another job.”
Fear loves routine. It tells you that staying safe is smarter than starting over. But every time you ignore that nudge to grow, you trade potential for predictability.
I’ve learned that fear doesn’t mean stop. It means you’re close to something important.
If fear is what’s holding you back, read How to Show You Care (Without Going Overboard). It’s a reminder that vulnerability and growth often come from the same place.
4. Comparison Will Convince You You’re Behind
“Why does it feel like they’ve had a promotion and a raise and climbed the ladder to success while I completely don’t?”
Comparison ruins clarity. You stop focusing on your own progress and start chasing someone else’s story.
I’ve done it too, watching other people post wins while wondering why my timeline looked slower. But growth isn’t supposed to be synchronized.
For a perspective shift, read 7 Lessons I Learned About Confidence from Talking to Girls at Bars. It’s about learning confidence by doing, not comparing.
5. The Unknown Isn’t Your Enemy
“You are at what I am calling the unconventional part. The part where you don’t know what you’re supposed to do or what you want to do or what’s out there for you.”
That uncertain middle space feels terrifying, but it’s also where you start writing a new story. The unknown isn’t against you. It’s where all the new possibilities live.
I’ve learned to see that blank space as creative space. You don’t have to have an answer yet. You just have to stay curious.
For more on showing up even when things feel uncomfortable, read How to Talk to Girls at a Bar (Without Making It Weird).
6. Reframe Uncertainty as Excitement
“I have no idea what I’m going to do tomorrow. How exciting.”
That quote from Night at the Museum reframed everything for me. Instead of thinking “I don’t know,” I started thinking “I get to find out.”
Once you turn uncertainty into curiosity, it stops feeling like a threat. It becomes fuel.
If you liked this reframe, dive into How I Turned My Fears Into Reality (And How to Avoid the Same Mistake) again — it connects deeply with this same theme.
7. Forward Is a Pace
“Forward is a pace. Forward is emotion.”
You don’t need a five-year plan to move forward. You just need to keep showing up, even when progress feels slow or invisible.
Momentum is built in small moments like sending that email, applying for one new job, or simply admitting you’re ready for change.
Explore more in Lifestyle for posts that help you build structure while staying flexible in your growth.
Final Thought
You don’t need to know exactly where you’re going. You just need to trust that moving toward what feels right is enough.
Want to hear the full story? Listen to The Unconventional Part: Figuring Out Your Career When You Feel Lost on Spotify or Apple Podcasts.
