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8 Pieces of Advice I’d Give My Twenty-Something Self

Now that I possess all the infinite wisdom that comes with being 30 years old (kidding, of course), I’ve been thinking a lot about what life was like in my twenties.

Graduating from college, entering the real world, starting a career, discovering new passions, going on bad first dates — it’s all par for the course as you navigate your twenties. 

But as I’ve turned a new decade, it has been fun to think back on the trivial (and not-so trivial) things that caused me oh-so-much angst in my twenties. As I’ve grown older and matured, I’ve learned so many life lessons about what matters, and what truly doesn’t.

It feels freeing to be in a place where I can look back at something that would have ate away at me for weeks as a 23-year-old, and laugh it off as a 30-year-old. 

If I could, I’d go back to that sweet, naive, newly-minted college grad, and give her the following pieces of advice. If you’re in your twenties right now, hopefully this advice will help you too.

Now that I possess all the infinite wisdom that comes with being 30 years old (kidding, of course), here are eight pieces of advice I'd give my twenty-something self.

1. Your first (or second, or third) job will not be your last

When I got my first “big girl” job out of college, I imagined I’d stay there for several years, working my way up through the ranks. Imagine my surprise when just a year and a half into my role I discovered a new opportunity I wanted to pursue.

I agonized over leaving a job after such a short amount of time. After all, in college, we’d been warned that “job hopping” doesn’t look good on a resume. I almost didn’t go for it, but after days of indecision, I figured there was no harm in simply applying. Thank goodness I did! That next job turned out to be an incredible four-year learning experience, and the catalyst that led me to start my own business.

Your first job isn’t your last. No one expects you to stay for years — if you do, and that works for you, fantastic! But more often than not, you’ll experience many jobs throughout your life, perhaps never settling into one for the long haul.

2. Find a way to be a mentor to someone

When I think back on my career and life, I remember multiple mentors, professors, former bosses, teachers, relatives, etc. who no doubt had a massive impact on me.

That’s why finding a way to serve as a mentor to someone else is incredibly important — plus, it’s the right thing to do. 

And selfishly, there is nothing more rewarding than seeing former interns, colleagues and students shine bright as they grow in their own lives and careers, knowing that maybe, just maybe, I’ve played a tiny part in that growth. 

3. Develop a side hustle or passion project

Repeat after me: You are not your job. Now repeat it again for good measure. Your value and your worth do not come from your salary or your job title. 

In the beginning of my career, I got wrapped up in my job, and quickly realized I no longer had any hobbies or much of a personal life.

That’s when I started this blog, and it became a huge passion. Of course, it eventually turned into a side hustle and now my business, but it still serves as a huge passion, and one that gives me purpose and drive every single day.

Find something that makes your eyes light up — and hold onto it tight.

4. Watch your facial expressions in meetings and social scenarios

Rewind to a middle school choir concert. Expecting a big hug and congratulations after the show from my parents, I was shocked when I was admonished by my mom for “making faces” that made it clear I was not happy to be standing next to a certain someone during the concert.

I’ve always worn my emotions on my face — and that’s not always for the best.

I thought I left that bad trait behind in seventh grade, but apparently it has stayed with me, despite my best efforts. I was mortified when a former boss pulled me into his office to remind me to watch my facial expressions as it was completely obvious when I was irritated or upset in meetings. Yikes.

Gotta work on that poker face! A lesson I’m still learning to this day.

5. Chill out about dating, OK?

This, this, this.

Easier said than done, but man, the hours I spent agonizing, dissecting, discussing and overanalyzing. If I could get those hours back, think of all I could have accomplished.

Of course, and I can’t take back those hours, and I wouldn’t, because it’s all part of growing up, but I wish I had relaxed a bit on the “needing to find love” front.

Because it will happen. It did happen. And I didn’t believe anyone when they told me to relax, but it did, and it will for you too. 

6. Your friendships will change

Perhaps the most difficult lesson to face on this list, friendships change, and people come and go. I can’t say I was prepared for this.

I left college with a strong group of friends — some I still speak with regularly, and some I haven’t connected with in years. I struggle with my friendships changing, to this day, and finding friends only becomes more challenging as you get older (although thanks to social media and Bumble BFF, I’m discovering new ways to meet likeminded people). 

There are a few friendships I wish I had put more effort into, but there are also some that I’ve learned to be OK with letting go of. Not everyone is meant to stay in your life forever.

7. It’s OK to live at home to save money

I lived at home until age 28 when I moved into my beautiful Chestnut Hill apartment

I admit I’ve always been a bit of a late bloomer, and I truly loved living at home with my family, but it was also a smart and strategic move.

However, it wasn’t always a move that other people in my life conventionally agreed with — there were people who would try to make me feel ashamed of living at home. Sometimes I sadly let them get to me.

But looking back, man am I glad I stayed at home as long as I did! That smart financial decision allowed me to pursue my dreams much faster than I ever would have thought possible.

Do what you need to do to set yourself up financially — for me, that meant living at home. I have no regrets about it.

8. You can’t please everyone

I’m sure this is a life lesson I’ll continue to learn time and time again as I grow older, but truly, you can’t please everyone.

Despite best efforts, there will always be someone who doesn’t like you or doesn’t agree with your decisions — you might even encounter haters.

And that’s where you come in. It’s more important to love yourself than to be loved by others. It’s more important to find happiness and contentment within yourself than to allow yourself to constantly give all of that to others. 

Sometimes you’ll have to make difficult choices — ones that only you might understand in the moment. You’ll find the confidence to be okay with this, and to push forward, knowing that only you know what is best for you.

Tell me! What would you add to this list? What would you tell your twenty-something self? Or, if you’re in your twenties now, is there anything you relate to here? Leave your thoughts in the comments below.

*Photo via Pexels

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Meet Jessica

I live by the saying “Life begins at the end of your comfort zone” and help others do the same to reach their biggest, brightest goals. Read my story here.

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