20 Things I Would Tell My 20-Year-Old Self

As I celebrated my 30th birthday this past weekend, I thought a lot about my 20s and what I’ve done in the first decade of my career. 

Yes, it’s very cliche to use a milestone birthday as an opportunity to reflect on your life and how you’ve grown and changed over the years. But I’m a writer; sometimes we like a good cliche.

I was 19 when got my first freelance writing gig, which I have always considered the official start of my career. After that, I completed several internships, earned a Bachelor’s degree in Media & Communications, and worked for two digital media companies before quitting to co-found my own marketing agency in 2018. 

Me, age 20, enjoying a Harry Potter-inspired Butterbeer at Universal Studios, while knowing absolutely nothing about the real world or real beer.

Like most people’s careers, there were a lot of ups, downs, and lessons learned in between those major highlights. I have no regrets about how I’ve spent the last 10 years, but there are some parts that might have been easier if I’d known then what I know now.

To that end, here are 20 things I would go back and tell my 20-year-old self, in the hopes that it might help someone else who’s standing at the very beginning of their career journey right now.

1. This “freelance thing” you’re doing can evolve into a full-time career. 

Right now, you see freelance writing (and tutoring NYC 4th graders, and working the customer service desk at Lowes) as a way to support yourself and pay the bills while you pursue unpaid internships. You actually have the potential to far out-earn your future corporate salaries if you stick with this and go after more freelance clients. 

2. Educate yourself on finance management and self-employment taxes. Like, right now.

Your dad told you to “set aside money for taxes” when you started freelancing. You didn’t listen and now you owe the IRS a whole lot of money you already spent. You’re about to get caught up in a vicious cycle of high-interest credit card debt for the next decade (but you will pay it off with a lot of sacrifice and self-discipline).

3. Chip away at your student loan debt while you’re in school.

 It’s stretching your already-limited budget, but those tiny payments you’re making every month (even though you technically don’t owe anything yet) will allow you pay off one of your loans by the time you graduate.

jar of coins turned over on its side
Image credit: Josh Appel / Unsplash

4. Your school has a lot of useful career resources that you’ll have to pay for in the real world.

People pay a lot of money for resume reviews, interview preparation, and career coaching. You have this at your fingertips right now, at no additional cost to you. Take advantage of it!

5. Start networking now.

Career success really is all about who you know. If a parent, mentor, teacher, or friend gives you an email address or phone number and says, “Ask this person about their career,” do it. At worst, you’ll walk away knowing what you don’t want to do with your life. At best, you’ll walk away with a job offer. 

6. You don’t need to say ‘yes’ to everything.

It’s good to stretch yourself and go the extra mile sometimes, but it’s also okay (and important) to have boundaries and ask that your bosses and colleagues respect them.

7. Respect your own boundaries or no one else will.

Similarly, if you don’t want people to email you over the weekend or hit you up with work questions while you’re on vacation, put up your out-of-office reply and STOP ANSWERING THEM ON WEEKENDS AND DURING VACATIONS. Spoiler: You’re still going to struggle with this when you’re 30.

8. Communicate, communicate, communicate.

So many problems in the workplace can be avoided or mitigated with clear, honest communication and setting the right expectations up front. Don’t make assumptions about what somebody wants or assume that they know what you want without having a conversation about it. Ask questions (even if you think they’re stupid) and offer feedback if someone doesn’t deliver what you asked for.

close up of woman holding and using a smartphone
Image credit: Paul Hanaoka / Unsplash

9. Responsiveness goes a long way.

Your fellow journalists will tell you you’re crazy for responding to every single PR email you get and explaining why you can’t use their pitch. Don’t stop doing it. You’re building strong relationships and some of those PR people will go on to become your clients.

10. Your coworkers can become some of your closest friends.

Even if you work remotely, you’ll inevitably develop some close relationships with the people you work with. Treasure and lean on these people, because they’re the only ones who understand your exact workplace challenges and dynamics. You also never know when you may be able to help each other, even after you leave the company.

11. It’s weird and hard to go from peer to manager.

You may end up managing people who used to be at your level. It’s an uncomfortable transition, you might have to walk back on some “friend” aspects of your professional relationship. Take it in stride and don’t be too hard on yourself if you overstep from time to time.  

12. ‘Venting’ does not equal addressing problems.

Never, ever badmouth a coworker, executive, client, etc. to your employees or peers. Find a professional, diplomatic way to communicate concerns directly to the person you’re struggling with. You’re going to mess this one up a lot. Keep working on it.

13. Don’t settle for a bad offer.

Whether it’s a salary or a client contract, there will always be people and companies who don’t want to pay you market value for your skills and experience. Push back and fight for a higher rate. If they still say no, it’s okay to walk away.

three women sitting at a table negotiating
Image credit: wocintechchat / Unsplash

14. Employer benefits aren’t everything.

You’ll meet a lot of people who are scared to leave their corporate job because they don’t want to lose their health insurance or 401(k). Don’t let that fear stop you — there are ways to get those things without having a corporate job.

15. Pay it forward.

You’re going to have a lot of help getting your career off the ground. When you have the opportunity and authority to help someone else get their foot in the door, don’t pass it up.

16. Running a business is really hard.

It’s absolutely worth it…but it’s going to take a lot of late nights, lost weekends, stress, and complicated tax and legal research to keep your business going. Find healthy ways to cope with that stress. Therapy helps

17. Running a business with your spouse/partner is harder.

Not every couple is meant to run a business together (you’ll learn that after your first failed business with your ex). Even if you can make it work, it will inevitably test your relationship. Don’t forget to be a couple and set aside sacred “no work talk” time. 

Sean and Nicole - wedding day selfie
Somewhere in between launching, running, and growing a business, we got married (Nov. 2019). Wedding planning was a good “non-work” project for us!

18. Don’t get too comfortable.

Always keep an eye on what else is out there. You never know when a big client will drop you or your company will be forced to make staffing cuts. 

19. With every new experience, you’ll learn something you didn’t know before. 

Never walk into a situation — an interview, a new job, a sales call, a client meeting, etc. — thinking you know exactly how it’s going to go. Keep your mind and ears open, and be ready to listen to whatever this experience has to teach you.

20. You’re not going to have all the answers when you’re 30.

Or 40. Or 50. Or ever. We are all works in progress, and nobody really knows what they’re doing 100% of the time. The best you can do is keep working at something and getting advice from others who have been there until you become confident in your own abilities. Then, pass your knowledge on to someone else and help them grow, too.

Me, age 30, still not knowing everything about the real world (but about to order a real, delicious beer).