Your twenties can feel like a constant guessing game. You’re a young adult alongside other young adults stepping into the real world for the first time. You’re armed with an overload of information and advice from family, friends, mentors, and the random stranger in the grocery store. You’re trying to figure out whether you’re making the right choices, whether your career path makes sense, and whether you’re wasting too much time on the wrong things. Reflecting back, there are so many things I wish I knew in my 20s.
If you’re in your 20s and you feel stuck, uncertain, or under outside pressure, I’ve been there. And if you’re in your 30s asking, “Am I where I’m supposed to be? What am I doing with my life?” I’m here to confirm… you’re not alone either.
As a Career and Leadership Coach, I’ve spent the past decade, working with early and mid-career professionals who’ve hit roadblocks, switched careers, or struggled with spending their time trying to reach people’s expectations. You cannot begin to imagine how common this is (I can’t emphasize this enough)!. Heck, I’ve also navigated plenty of detours myself.
Today, I’m going to break down everything I wish I knew in my 20s (when it comes to careers). The pieces of advice I’m sharing with you come from failing, making mistakes, pivoting in different directions, agonizing over the “right choice,” and realizing that the hardest things I went through were actually preparing me for something better.
My hope is that they’ll save you stress, encourage you to try new things, embrace new experiences, and help you make the best decisions possible, and remind you that your own path matters more than anyone else’s timeline.
You ready? Let’s dive in!
Things I wish I knew in my 20s (Unfiltered Career Advice)
1. Your career won’t be linear… and that’s Ok!
In my early 20’s, I thought a career followed a straight line: graduate from high school, go to college, get the “right” day job, and climb until you reach the top. Afterall, that’s the traditional path all young people were taught, right?
But the thing is… the real world is different. Industries collapse. Entire companies shut down. Fields that were hot a few years ago cool off. Over the past decade, we’ve seen industries that once boomed (like publishing or retail) stall out, while new skills and roles we couldn’t imagine in our 20s have exploded (hello AI).
And sometimes, it’s not just the job market… you change. Maybe you studied engineering because it seemed practical (or your parents told you to), but once you’re in it, you realize your old self chose security while your present moment self craves creativity. That doesn’t mean you made a mistake it means you’re human.
Honestly, I love this self discovery. It’s really powerful to recognize and admit when something isn’t working. That takes courage, self reflection, and a big dose of honesty! Not everyone is willing to follow through with all of that.
As a reminder, I’ve coached countless clients labeled as “job hoppers” or “career changers.” The truth? Those people aren’t failures they’re explorers. They’ve built skills in different directions, which often makes them more adaptable and resourceful.
If you realize that it’s time to try something different, it all starts with a plan and mapping out your big goals. You can do this digitally with the Goal Journal I’ve created! Check it out here!
2. It’s not always about the money
In my early 20s, money was the only thing that mattered. The title, the paycheck, the status, that was my measure of success. I told myself, “If I make this much money, if I get this title, I’ll finally feel accomplished.”
At 26, I became an Executive Director (and yes… I worked hard and grinded for that title), a title people don’t usually get until much later in their careers. On paper, I had everything. But behind the title and salary was someone exhausted, stressed, and disconnected from what actually mattered.
And I’m not alone. I’ve coached professionals making $300K, $400K, even $500K+ who have no peace of mind, no downtime, and no healthy habits left. They rarely see their families. They skip vacations. Their entire identity revolves around work.
By the way, I do understand that financial security is important because it can afford us certain opportunities and lifestyles, but the older you get, you begin to value your mental health and peace more. Because a paycheck without peace, calm, and fulfillment will drain you in the long run.
3. Focus on impressing yourself, not other people
This was one of the hardest lessons I had to learn… and it took me awhile. As a recovering people pleaser, I spent most of my time in my 20s trying to impress a lot of people, my parents, mentors, old classmates, even my friend group. I made career moves based on how they would look on social media and in a conversational exchange, not on whether they made me happy.
But here’s the thing I had to realize, those people weren’t living my life. Same goes for those you are trying to impress… they are not living your life! They won’t deal with the stress of a toxic boss, the exhaustion of 60-hour weeks, or the emptiness of a “dream job” that doesn’t fit. You will. So stop chasing approval from others and focus all of your energy on building a career that will impress your current and future self!
One of the biggest questions you want to ask yourself is, “does this fulfill me when no one else is watching?” This is one of the best ways to determine who you’re building your career for. If your answer is anything other than you… it’s time to go back to the drawing board.
4. Pursue big dreams (even if they scare the people around you)
When you share your big dreams, some people will cheer for you and some will panic. In my 20s, I let the fear of others shape my path. Teachers, guidance counselors, and even close friends said,
“Don’t do that.”
“Why would you do that.”
“Don’t give up that good job.”
Sound familiar? This is why its important to be able to discern who to tell the big dreams to and who to keep in the dark. If someone hasn’t done the thing you want to do, they will most likely tell you not to do it, based out of their own fears and insecurities. Don’t get me wrong, most of these people are trying to point you in the right direction… but it’s often based on a lack of knowledge and experience. From childhood, we’re taught to play it safe and stay between the lines.
But here’s the truth: safety can be overrated. Sometimes the best version of your life comes from stepping outside your comfort zone.
You don’t need everyone’s approval. Find mentors, communities, or even good books that align with your vision. Surround yourself with people who believe in your dream, even when it feels like the hardest thing you’ve ever attempted.
5. Don’t be afraid to fail
In my early 20s, I avoided failure like it was the worst thing that could happen. I saw it as embarrassing! So, I overanalyzed every next step, waiting for the “perfect” time. But I later realized that perfection is a myth and waiting wastes a lot of time.
Failure isn’t the end. It’s feedback. Every mistake teaches you something you can apply next time. The people you admire most? They didn’t avoid failure they learned from it.
6. You’re allowed to change your mind
This is one of my favorite lessons and the older I get, I become even more comfortable with it. When I was in my 20s, I thought my biggest goal was to become a CEO of a Fortune 500. I worked tirelessly, climbed the ladder, and got into executive leadership. And then… I realized it wasn’t what I actually wanted.
At first, I felt ashamed. Would people think I’d failed if I stepped back into a mid-level role? In reality, the worst case scenario would be that someone asks me “why.” But here’s the truth: you’re allowed to realize that what you once wanted isn’t right anymore.
Life circumstances can make your mind change too. After being in a long-term relationship and working on major projects outside of work, I realized I valued time spent in my creative zone. I also realized that travel brought me the most joy and many of my clients in high ranking roles didn’t have time for that. That was confirmation for me, that it wasn’t my lane!
7. You are not defined by your title or paycheck
This is a staple for things I wish I knew in my 20s. Actually, can we say this louder for the people in the back? I wish I could shout this from the rooftops. I’m sad to admit that I’ve seen way too many highly skilled professionals crumble after layoffs or career shifts because their identity was tied to their title or income.
Seriously, most professionals go into major depressive episodes and cannot function. People get so wrapped up in the titles, bonuses, salary, and playing the hero in the workplace.
But you are not your job. You’re not your salary. You’re a human being with values, strengths, and passions that exist beyond your business card. Your job is what you do, not who you are.
P.S. I’m willing to bet, you’re pretty amazing outside of the office! Remember that!
8. Ask better questions during interviews
A lot of professionals end up working in toxic environments, for bad bosses, and in roles where they aren’t doing what they applied to do… all due to the lack of asking the right questions! When interviewers ask, “Do you have any questions for us?” that’s your chance to learn about culture, not just logistics. Don’t waste it asking, “When will I hear back?”
Ask questions like:
- “What’s your management style?”
- “What kind of employees thrive here?”
- “When was the last time you implemented employee feedback?”
- What do you expect me to achieve in my first 3 months here?
- What is your big goal for this role?
These tell you far more about whether a company is supportive or toxic. Specific questions you ask can reveal whether a job will support you or drain you. Don’t be afraid to ask!
9. Trust your gut
I don’t think our instincts get enough credit or respect! Your intuition is a built-in support system. If you walk into an interview and the energy feels off, don’t ignore it. I’ve accepted jobs where I felt red flags and every time, my gut was right.
It’s also ok to trust yourself! Your feelings are valid and you should ALWAYS take them into high consideration and avoid making up excuses or gaslighting yourself.
10. Your coworkers aren’t your best friends
You may have a great time bonding with coworkers, happy hours, inside jokes, baseball game outings. But most of those friendships are situational. When promotions or layoffs happen, dynamics shift.
It doesn’t mean people are bad. It means the workplace isn’t built for lifelong loyalty. If you find a true friend at work, cherish it but don’t confuse colleagues with family.
Be kind, but also be aware. Don’t believe me, I wrote a whole article breaking it down for you here: 12 Reasons Why Your Coworkers Are not Your Friends.
11. Keep your plans private
If you grew up in my household, you would’ve heard this phrase often, “stop telling all your business!” This became one of the biggest lessons I learned as an adult, not everyone needs to know your next move. If you’re job hunting, planning a side hustle, or considering graduate school, keep it close. Sharing too much can backfire.
Because the sad truth is… not everyone is cheering for you. Most of the time they don’t care or could even be jealous and find ways to sabotage you. Plus, remember, your plans don’t need public approval. You just need to feel good about them!
12. Advocate for yourself
Another common phrase in my household growing up was, “a closed mouth doesn’t get fed.” In plain language, if you want opportunities, you need to speak up. Whether it’s learning a new skill, stepping into a different direction, or aiming for the next step, let people know.
Bosses, mentors, and trusted colleagues aren’t mind readers. Often, they want to help. but they can’t if you don’t ask. Self-advocacy is the bridge between where you are and where you want to be.
Final Thoughts
How are you feeling after reading about all the things I wish I knew in my 20s?
I hope relieved, enlightened, and empowered! Your 20s are full of little things and big dreams, mistakes and wins, detours and lessons. You’ll face outside pressure, experiment with side hustles, and wrestle with people’s expectations. But every experience even the messy ones shapes you into the best version of yourself. And although it may seem hard and stressful, your these are truly the best years of your life. You’re being molded and shaped into the person you’re meant to become.
So take risks. Change your mind. Learn from the hard work and the setbacks. And most of all build a career that gives you peace, not just a paycheck. I hope you take these life lessons and pieces of advice as you map out your journey!
All my best and cheers to your growth my friend!
– Chelsea Jay
