person thinking

In a few months, I’ll turn 39. It’s an age that I’m approaching with mixed emotions. My thirties have been very good to me—personally and professionally. I got married to the love of my life and became a mom. I wrote a novel, experienced a few dream jobs, and cultivated a successful freelance writing career for myself. I approached all of these milestones with appreciation and a healthy dose of caution, and I really tried (and am still trying) to learn from every new opportunity and savor the lessons—even the ones that came when I got knocked down.

This is quite different from how I approached things in my twenties. When I moved to New York City, I was four days out of college—and 21 years old. Simply determined to “make it” in the cutthroat world of magazines, I thought I knew best and didn’t always listen to what my bosses were trying to teach me.

Now that I can look back on my experiences with a little more clarity, I see I could have made things a lot easier for myself. Believe me, I’m far from perfect and still consider my career and myself a work in progress. But I cringe a little when I think about where I was more than a decade ago—and the mistakes that I could have avoided. If I could jump into a time machine, here are the seven things I would go back and do differently:

1. I Never Officially Asked Someone to Be My Mentor

I’ve worked with a lot of incredible writers and editors in my career who know I look up to them and who I’ve gone to for advice numerous times over the years. But I never sat down any of them and said, “I really admire the career path you’re on, and it’s very similar to the plan I envision for myself—will you take me under your wing?” You know that old adage, “Ask and you shall receive?” There really is a switch that flips when you tell someone what you want from them and explain how they can help you.

Case in point, when I was a young entertainment editor at CosmoGIRL!, I was all set to interview John Mayer for a feature. At the time, he was my favorite singer and I felt like the lyrics from his first album were ripped out of my own diary. But a high school student who had asked our editor-in-chief to be her mentor was a fan, too—and wanted to develop her interview skills—so, my John Mayer interview was given to her.

Now, this is an extreme case, and not every mentee is going to get such a major opportunity handed to them from a mentor. But there is a huge lesson to be learned here: If you don’t ask someone to be your mentor, you’ll never know what doors it could have opened for you.

2. I Didn’t Keep in Touch With My Interns

It never ceases to amaze me how many of my former interns have gone on to basically rule the world. Often on their last day, I’d simply thank them for all of their hard work and send them out into the world, only to maybe hear from them for a job reference when they graduated.

Now that I’m a freelance writer who pitches a wide variety of publications and editors, I very often end up pitching former interns. It makes my heart happy to see them succeeding, but it would have been even better if I’d made an effort to keep in touch with them. It would make those “Hi, please assign me a story” conversations a lot less awkward.

And on that note—be nice to your interns. I always did try to treat mine with respect, but things get busy and it can be easy to take out your stress on them. Don’t do that—because if they’re going to be in a position of power one day and you were mean to them, they might just take pleasure in rejecting you.

3. I Spoke Back to My Superiors Sometimes

As a junior editor, there was one senior editor who edited a majority of the features I wrote. Our interaction went something like this:

Senior editor: “Do you think our readers care, like really care, about Britney Spears anymore? Should we change that reference?

Me: [Eye roll]

Senior editor: “So—what do you think?”

Me: [Long, drawn out sigh] “You really don’t know anything about entertainment or what I do as an entertainment editor if you’re asking me a question like that. Everyone loves Britney Spears.”

Senior editor: [Draws in breath and throws copy back to me, effectively ending conversation]

So here’s what happens when you’re blatantly disrespectful—you’re essentially hanging a sign around your neck that screams “Difficult.” The person you disrespected will always remember that when asked by another colleague about you or—and this is a biggie—when your professional paths cross again. And trust me, they always do. It’s very tough to redeem yourself (even if your excuse really was being an insolent 20-something who didn’t know better).

4. I Didn’t Negotiate

I was at my first job for five years before I finally decided it was time to move on. I was apprehensive about breaking out of my comfort zone and going somewhere new, but I was recruited for a job that seemed like the perfect next step in my career. The executive editor who interviewed me was very persuasive. That was great—but the job paid less money than I wanted, came with a title that was technically a step down, required that I sit in a cubicle instead of an office (I was coming from an oversized private space) and didn’t include any of the new responsibilities I wanted, such as managing a team or top-editing junior writers.

It had been so long since I’d interviewed for a job—and gotten an offer—that I was afraid to accept anything other than what was offered to me. So I got the offer and took it, no questions asked. I didn’t even try to get more money or find out if an office would be possible down the line. I left everything on the table and showed up for my first day of work with a massive pit in my stomach. I only stayed at that job for nine months, and every single day I wondered what would have been if I even tried to negotiate a little bit.
Here’s the thing—the very worst that can happen during negotiations is you’re told “No.” And if you’re told “No” to the things that you consider deal breakers, then you have the power to decline and wait for a better opportunity to present itself.

5. I Should Have Asked for Feedback Before My Reviews

After a few years at my first job, some changes took place and I had a brand-new boss. I thought I was doing great before she came on board and that I was on track for a promotion. And then, it was time for our annual reviews, and she told me how very presumptuous I was for thinking I was ready for more responsibility—that I had very specific things to work on before she would even consider it. Yes, my boss should have sat down with me before the review if she was that concerned about my performance—but I should have been checking in with her, too.

Let me empower you: It’s OK to check in with your boss every six weeks or so. It doesn’t even have to be a formal meeting. Just find a free minute to ask if you can review your latest projects or get feedback on how you’ve interacted with recent clients. Find out what your boss was impressed by and where you need to improve. Be bold enough to ask where she sees you in the next year and how she suggests you get there.

6. I Was Terrible About Managing My Contacts

Get in the habit of creating a Google spreadsheet with the contact info of everyone you meet. Update it with every business card you receive or contact information in the signature of every email. Store it in your Google drive, email it to yourself as a backup, and be diligent about updating it when someone’s information changes.

Please just trust me on this one—there’s nothing worse than having to dig for the contact information of someone you met five years ago. It may take five years until you need to reach out to people on that list again. That’s OK—it will save you a lot of time and energy if you can quickly pull it up on your computer rather than racking your brain trying to remember where you met that contact or how you think their last name might be spelled as you desperately search your email.

7. I Didn’t Always Speak Up After I Made a Mistake

Many times in the early part of my career, I made mistakes and I did not speak up. Luckily, I was never fired and none of my mistakes were so detrimental that they couldn’t be fixed. But there were a lot of close calls that created more work and unnecessary late nights for my colleagues and myself.

We are human. We all make mistakes. And if you have a boss who makes you feel like mistakes aren’t tolerated, then perhaps you need to find someone else to work for. However, what is unacceptable is not taking responsibility for your mistakes. Hiding from mistakes, lying about mistakes or throwing others under the bus because of your mistakes will catch up with you—and it won’t be pretty. Admitting something went wrong as soon as it goes wrong will suck, but the mess will be a lot easier to clean up and your reputation should come out unscathed.

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Updated 6/19/2020