If I Could Start My Career Over, I’d Do These 3 Things Differently

One of the beautiful parts of getting older is the ability to zoom out and connect the dots to see how every twist and wrong turn somehow brought you here. But if I’m being honest, there’s also a flip side: sometimes you look back and cringe a little.

I’m not talking about the cringey outfits (although… whew). I mean the decisions I made early in my career that I’d handle so differently today.

I’m sharing three of the biggest ones here, not because I think we should dwell on regrets, but because I want you to have the tools I didn’t. Maybe these stories will help you feel less alone, more prepared, and more in control of your future.

They say you either win or learn. I’m so grateful I get to do both, and now you can too.

3 Career Mistakes I Made After College

I didn’t prepare well for my first interviews 

Picture this: I’m on a phone interview for my dream internship at a New York City magazine. The editor asks, “What was your favorite story we ran this year?”

Panic. I had no answer.

I hadn’t done my homework. I had not researched her, the publication, or the role. I was a smart candidate, but I was unprepared. That interview was going to slip through my fingers, and I knew it.

Looking back, I wish I had taken the time to:

• Research the interviewer and the company’s current work
• Prepare thoughtful questions to ask 
• Align my past experiences with their future needs

That rejection stung, but it taught me a lesson I never forgot. Interviews aren’t about being perfect. They’re about showing you care enough, and preparation is a big part of that. 

I didn’t start investing for my retirement Day 1

At my first job, I was earning $30,000 a year in New York City. Just enough to survive, at least that’s what I told myself. So I skipped the 401(k).

Had I invested $100 a month into my 401k for the first year of my career, that $1,200 would have grown to $21,345 by the time I am 65. Add in the match my employer offered at the time and it would have been $42,690!

That’s the power of time.

No one sat me down to explain compound interest or employer matching. But now I know: it’s not about having extra money; it’s about making money work for you, even in small amounts.

If you haven’t started investing yet, don’t panic. While the best time to start investing is as soon as you get your first paycheck, the second-best time is today.

Kickstart Your 401k With This Free Guide 

I let stress wreck my health

One Saturday, I was alone in my apartment when a sharp, stabbing pain brought me to my knees. I could barely move. I crawled into a cab and took myself to the ER.

The diagnosis? Nothing. They couldn’t find a cause.

But I could. I was running on empty: emotionally, physically, mentally. I was living alone, questioning my career, contemplating ending my engagement. I hadn’t built routines to take care of myself, and my body was begging me to stop and listen.

That was the moment I realized health isn’t a “nice to have,” it’s a foundation. Especially in the early career hustle.

Today, I move my body daily, take breaks, and check in with myself when I’m overwhelmed. I don’t wait for a breakdown to hit pause. I wish I had known that earlier.

Building a Foundation for Work, Money and Your Mind is Paramount 

Your first few years post-grad come with pressure…to prove yourself, make money, and figure it all out fast. But the truth is, most of us are just figuring it out as we go. Mistakes are part of it, but learning from them is where the magic happens.

If you’re looking to grow your career, protect your peace, and build a financially independent life, I share weekly tips and stories like this in my newsletter. It’s free, it’s real, and it’s written just for you.

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