14 Things I Wish I Knew In My 20s

Career Discoveries, Personal Growth, Interesting Fashion Game-Changers & More

Emily Steele
7 min readAug 19, 2022

The 4–5 years after college (basically all the years you think you’re old when you’re actually just 23 and you can still get away with jokingly saying you’re “adulting”) were rough for me.

I struggled professionally first, which snowballed into struggling personally (or perhaps — more likely — the personal issues were always present and were merely unearthed by my “career” woes), and I felt like I was going nowhere and building nothing as I bounced from part-time job to part-time job.

I eventually started my own business which only barely ever paid the bills (which was exactly how I measured not only the success of my business but also my self-worth; see above: “personal issues.”)

I’m not quite out of the weeds (are we ever? do the weeds just morph?) but as I enter the last year of my 20s, I feel the most peace and understanding with the timeline of my life than I ever really have.

As I think back on that tangle of messy, uncomfortable, anxiety-ridden-but-nevertheless-fun years, bits of wisdom come to mind postmortem (as wisdom tends to do) and I can’t help but wonder what would have been different if I truly internalized these things when I needed them most.

1. You can like what you do and still not want to do it everyday.

When I finally got to a place where I was working for myself and paying the bills, I was confused to discover there were still days I dreaded going to work. How could this be? I was finally here! Working for myself, owning my time, picking and choosing my own clients. I should have no reason not to want to work today, right? What was wrong with me?

It’s a bit dramatic to say never, but the underlying sentiment remains true: sometimes, you can love what you do but just not feel like doing it. That’s okay. And it’s not some sign from the Universe trying to tell you to change careers. You’re just a normal, working person who doesn’t feel like working today. You’re fine.

2. You don’t have to have just one “job.” Your work can be a mosaic.

Maybe it’s the “What do you want to be when you grow up” question that frames our perception that we must “be” when we “grow up” is a singular thing, maybe it’s the palpable judgement we feel when — once “grown up” — we are asked, “What do you do” and we respond with a laundry list of income-sources, but either way, I can’t even explain how much self-consciousness and stress this realization would have saved me if I had believed sooner in the plurality of jobs in my 20s (and beyond.)

3. The traditional concept of “a career” is dead.

Echoing the above, the idea of a “career” that our parents (Gen X, Baby Boomers) have is dead. “Work” is different for us. Financial and lifestyle goals are different for us. It doesn’t make sense to try and structure our professional lives the same way people did 30 years ago.

4. The job you end up having might not be a job you’ve ever seen or heard of before. In fact, it’s entirely possible you create or make up a job for yourself.

Last year, my “job” was: personal trainer/teen girl mentor/graphic designer/writer/marketing consultant.

Today, I’m a writer, freelance marketing consultant, graphic designer & creative director for a law firm.

Don’t remember seeing this among the career options in the college career readiness class.

5. There’s no magic about making 6 figures. You only need to make enough money for the lifestyle you want. Figure out what that looks like, and go from there.

Instagram loooooves to tout this ~SiX fiGuRE~ income like that’s what we should all be aiming for and once you cross the threshold from $90k to $100k your life will somehow be drastically different.

The reality is: a comfy salary looks different for everyone. For the van-dwellers traveling the U.S., six figures isn’t really necessary. For the 2-story homeowners in San Fran — six figures prolly won’t even cut it.

Everyone is different. Make the money you need to make to support the lifestyle you want to have. Not someone else’s lifestyle.

6. Things might not start happening until you’re in your 30s and that’s okay. Your 20s are for laying the groundwork. Enjoy this part!

I thought I needed to have “the answers” in my 20s. Now that I’m cresting 30, I want to hug my 23-year-old self and remind her these years are for the searching. And the more searching, exploring, trying, testing, and dabbling you can do in your 20s, the more likely you are to stumble upon that perfect combination of unique things that will make you happy in your 30s.

Your 20s are not about the answers at all. They’re about the asking.

7. A lot can happen in 5 years. A lot can happen in one. Where you are right now is not where you’ll be forever.

In the thick of it, it feels like it will be this way forever. But when I look back at everything that has happened in 5 short years, it’s mind blowing. I am a completely different person. I have a completely different job. I am married. I live in a different state! I have nieces and even genuinely think about having a child of my own these days.

A lot can happen in a relatively short amount of time. Today is not forever.

8. It’s not that easy to just “start a business.” (And it might not be fun for you, either. That’s okay.)

Instagram made it super trendy to just sTaRt a BuSinESs and I feel like it’s really scamming millennials on how that whole process works.

Starting a business is easy. Maintaining and growing a business that does what, I’m assuming, you set out to do with that business (i.e. provide an income) is not that easy. (But boy does IG make it look that way.)

Additionally, entrepreneurship just isn’t for everyone. And that’s okay. Social media also tends to look down on more “traditional” forms of employment and can make you feel untalented, uncreative, and unmotivated if you don’t want to work for yourself.

The hustle culture rose and fell in popularity like a failed rocket launch. We’re over it. If you don’t want to hustle — don’t do it. If you want to clock in and clock out everyday and enjoy your off-time guilt-free — DO IT.

9. You’re allowed to enjoy working for someone else.

See above.

10. If you have to convince yourself to like it while you’re still in the store — don’t buy it.

Shoutout to Sandra Bullock’s character from The Blind Side for this one.

Could have saved myself a lot of money on clothes if I understood this one.

11. When deciding what to wear for any occasion, always choose the outfit that makes you feel the way you want to feel.

Seems trivial, but it makes a big difference in the way you show up.

When I would get dressed for dates, parties — even just class — I would often imagine how others would look at me in an outfit. What would they think? What conclusions would they draw about me?

In the last couple years, likely thanks to my increased self-confidence and decreased need for the approval of everyone in the room, I discovered the best way to pick out an outfit was to simply pick the thing that made me feel the way I wanted to feel. Do I want to feel sexy? Confident? Comfortable? Pretty? Relaxed? Professional.

This has changed the game for me.

12. If what you like doesn’t seem like it’s “in style” or “popular,” you just haven’t found your people yet. Keep looking.

There’s a tribe out there for everyone. I used to try to just morph my tastes to whatever was popular at the time, only to be embarrassed to have done so upon finding the people who liked what I truly liked in the first place.

I would pretend to like music, clothes, colors, activities because it seemed trendy, and then I would somehow stumble upon a crowd who wore/listened to/liked the things I liked to wear/listen to/do and feel like super bummed I had camouflaged myself with the other crowd when I should have just kept looking!

13. Your greatest asset is actually the combination of the things you do well, not just one single thing.

Similar to creating a career “mosaic,” I firmly believe the greatest, most powerful thing each of us has to offer is that irreplaceable overlap in the venn diagram of things we love and do well. The weirder, more niche that overlap is — the better.

I can only imagine how much art I could have made by now if I had capitalized on this sooner instead of constantly trying to do one thing really well and “be” that one thing.

14. Even love is work.

Jobs you love. Friendships you love. Marriage.

Even love is work. Just because it’s fun and beautiful doesn’t mean it won’t also be trying and challenging. Just because it’s free and easy doesn’t mean it won’t also be scary and anxiety-filled.

I made love and work mutually exclusive for too many years, and so much peace opened up to me when I realized the two could (and often do) overlap.

Like my work? Follow me on Substack. Want to explore more? Find me here.



Emily Steele

lifter of heavy things: thoughts, words, weights, burdensome beliefs