11 Things I Wish I'd Known at 30

(Still working on some of them, tbh.)

Welcome to the first installment of Hi Everyone with Hillary Kerr. I am so delighted you are here!

The year I turned 30, my life looked pretty great on paper. I was the co-founder of my own business, which was starting to thrive after three and a half years of intense work; my first book had just been published; and I was in a committed, long-term relationship. Living the dream—superficially, at least. But trust me when I tell you that things were not what they seemed.

I was wracked with doubts and insecurities. The aforementioned relationship was deeply unhealthy and would implode within the year. And I couldn’t stop comparing myself to my friends who were all getting married, buying houses, and having babies while I was living beyond my means, extremely stressed about work, and very lonely. I didn’t know how to negotiate for myself, I hadn’t invested in my friendships, and I didn’t know my self-worth. I just wish I could give younger me a hug. Or, even better, I wish I could give her some advice from the future.

Since that’s not technically possible, I’m happy to share a little of what I’ve learned, 10 years down the road. Perhaps you already know all of this, but if for some reason you don’t (I sure didn’t), I hope it helps in some small way.

1. If you don’t ask, you don’t get.

I host a (in my opinion, great) podcast called Second Life, where I get to interview brilliant, successful women about their work and the chances they’ve taken in their careers. One of my guests—the co-founder of Lord Jones, Cindy Capobianco—said this to me, and it hit me like a ton of bricks: “If you don’t ask, you don’t get.”

I don’t know about you, but I’ve wasted a lot of my time waiting for someone to give me things: money, promotions, respect, you name it. I figured they’d see my hard work or my worth and then just anoint me with whatever it was my heart desired. That is some fairy tale nonsense, and I highly recommend divorcing yourself from this garbage as soon as possible.

No one knows what you want. No one knows what you need. No one knows what you deserve. No one but you. It’s your happiness, your salary, your life; you are in charge. And you need to ask—clearly and calmly—for what you want. It doesn’t always mean you’re going to get it, or that you’re going to get it exactly the way you asked for it, but you need to state your intentions.

2. You are the CEO of your own career.

Here’s the truth: No one cares about your career as much as you do—and that’s great! You are the one who is in charge of the direction it goes, and like any good CEO, you need to have a plan for today, a plan for the future, and an idea of how you’re going to get there. It can be so hard to take that long view of your career when you’re bogged down in the day-to-day tasks of your current job, but it’s important to check in with yourself on a regular basis—whether that’s every quarter or every year is up to you—and make sure you’re planning your next moves.

That said, I don’t think you should get too fixed on a single plan or path, because things evolve and open up to us as time goes on. But having a plan, checking in with yourself, and examining your goals and dreams on a regular basis is absolutely critical to your long-term success.

3. Always keep a pair of tweezers in the car.

There’s something about the lighting that is wildly revealing. While I do not suggest doing a full brow groom here—you need a bigger mirror for that degree of work and more distance/perspective—trust me when I tell you that you will always find something somewhere if you look. (Need a new pair? These are my favorite.)

4. Don’t wait to be happy.

This is not romantic, but here is my truth: Having a family and a loving marriage hasn’t made me happier than when I was single and living alone. Don’t get me wrong—I adore my husband and my kids, but they do not make me happier than I was before. I was happy single; I am happy now. Is it different? Absolutely. But my point is don’t wait for the next phase of your life to be happy. You are responsible for your happiness today. That happiness will change over time, but I think it’s incredibly important to enjoy all the stages of your life when they are actually happening.

5. Treat your face right.

This doesn’t mean spending a ton of money on treatments! It just means take the time to figure out the best skincare routine for you, and then stick to it. When I was in my late 20s and early 30s, my skin freaked out, and I suddenly was having breakouts galore. I didn’t see a dermatologist or esthetician about it and figured I could just handle it on my own. Wrong. I ended up using way too many harsh anti-acne products that made everything worse.

When I finally found celebrity esthetician Shani Darden, the first thing she told me was that I was doing too much. I needed to edit my routine, stop using every maximum-strength product on the market, and use a few things that would give my skin a minute to reset. She was right. Oh, and wear sunscreen every day on your face, neck, and hands! There is literally no point in taking care of your skin if you’re going to damage it with the sun. Your future self will thank you.

6. Comparison is the death of happiness.

Stop comparing yourself to other people, especially your friends. I know it seems impossible, but the sooner you can stop, the better. It was really hard for me in my early 30s because just about everyone I knew was getting married and having kids, and I was not even remotely there. While they were planning baby showers and buying houses with their husbands, I was renting a new apartment by myself. It was hard not to compare, but I forced myself to remember that I don’t really know what anyone else’s life is like. They have problems just like I do. The problems are different, but they’re just as big and feel just as awful. And this dismal idea was weirdly comforting!

7. Figure out your exercise situation ASAP.

Embarrassing but true: I was pretty active through high school, but after that, I basically didn’t exercise with any regularity—save for dancing in bars—until I was in my early 30s. After a long-term relationship exploded right before my 31st birthday, I was looking for anything to help me with the anxiety and depression that followed the end of that situation. And to be honest, I was looking for distractions to fill my time after work because I was so lonely. I ended up joining a dance-cardio class that saved me. Those workouts often were the only hour in a day I could get out of my head, when I wasn’t thinking about how sad I was. Having that frequent dose of endorphins changed my outlook on everything.

8. It’s never too late for love.

After going through that previously mentioned breakup, I remember being so scared to start over, wondering how I was going to ever meet anyone when everyone around me seemed already paired off. I felt like my window was closing, and it terrified me, even though I didn't even know if I wanted to get married or have kids! I just knew I wanted the option, and it felt like I was starting the process five years behind everyone else.

I wish I could go back in time and tell my younger self that this breakup was the best thing that could happen. It was an opportunity to meet myself again, to reevaluate what I really wanted in a partner, and once I got over the heartbreak, it was one of the happiest periods of my life. By the time I met my now-husband, I was in such a good place. I’d had time to focus on my career, work on myself, have really wonderful experiences, and my world was full of amazing friends. Even better: I knew what I deserved, and was able to recognize my husband was everything I hoped for in a partner.

9. Even the best change comes with loss.

Monica Padman, the incredible co-host and co-creator of the podcast Armchair Expert, said this to me when I was interviewing her for the show recently, and I loved it so much because it gave words to a feeling I’ve experienced frequently over the years but never really understood.

I felt it keenly when my husband and I moved in together after we got engaged. I was so madly in love and so excited to marry him, but there was something bittersweet about knowing that I was never going to live alone in my single-girl apartment again—that this wonderful progression in my life also meant a new level of accountability and sharing. I worked really hard to get to the place where I loved my life as a single person, and that era was coming to a close. I remember feeling so confused by the fact that a tiny part of me was already nostalgic for the past, even though I was in the best relationship of my life. Being comfortable with change, with evolution, with difference is a hard thing for me. It’s something I’m still working on, and I wish I’d gotten comfortable with it earlier.

10. Work on it when it’s a small problem.

When I was in my early 30s, if there was an issue—with a friend, with my health, with someone on my team at work, whatever—I tended to brush it under the rug. I’d wait and see if the problem would resolve itself on its own rather than deal with it head-on.

Now, a decade later, I handle small problems very differently. A perfect example is my teeth. I had braces as a teenager, followed by a permanent retainer until my early 20s, but never had a retainer or any follow-up after that. Years went by, and my teeth were fine… until they weren’t. I noticed that my front teeth were shifting in ways I could see both IRL and in photos, and even though it was super subtle, I decided to ask about fixing it.

I talked to my dentist, and he told me that a) the movement wasn’t going to get any better, b) it would never resolve on its own, and c) the longer I waited, the longer it would take to fix said teeth. So I invested in Invisalign.

The best part of it? Because I addressed it early, I got a fast-track treatment plan that only took 11 weeks; it’s literally the shortest option available. Whereas if I’d let it go another five or 10 years, I’d have a very different treatment timeline. Is this a silly example? Yes, but I do think it’s applicable to a lot of things. Deal with issues when they’re small because the fix will be easier. Period.

11. Leave the way you want to be remembered.

I didn’t want to believe this when I was younger, but the way you behave during the last few weeks of a job, relationship, or friendship is the way people will remember you.

As a co-founder who has hired hundreds of people over the last 15 years, I have noticed that there are two kinds of people: the folks who give it their all right up to the end and the ones who stop the second they turn in their resignation notice. I get it; if you’re on to the next, it’s hard to put in effort. But every industry is small, and people will talk to your boss and colleagues as you go forward in your career. And they will remember how you left things.

The same is true for relationships and friendships. If your time together has run its course, that’s totally fine, but I think there’s something to be said for respecting the good times you had together and leaving with honesty and dignity. (Of course I’m talking about relationships that have simply run their course, not relationships that are toxic or abusive.)

And that's it for my very first newsletter! If you're still reading this, thank you for being here, and thanks for sticking around. If you have any questions or concerns, or want me to touch on any topics in particular, I'm all ears. Leave a comment on Hi Everything's Bulletin or DM me on Instagram—I'm @hillarykerr—my inbox is always open!

xxHillary