OP #290: The Best & Worst Career Advice I Ever Got

Continuing on my theme of reflections, I dive into what is some of the best and worst career advice ever given me.

Author

Darren Herman
March 11, 2025

Happy Tuesday,

I woke up in Manhattan today and am excited for a day full of meetings with various portfolio companies and partners. I will head back to Boston later today.

I am energized coming out of last week.  Why? We launched the first 2025 event for Silicon Alley Sports, an organization that I chair and founded over 18 years ago.  In just the first week of selling tickets, we’ve sold 26% of our golf tickets, 58% of our pickleball tickets, and a handful of schmoozer tickets.  I think that this is pretty great.  If you are in the digital ecosystem, which I imagine many of you are, and are in the NYC area, you should give a Silicon Alley Sports event a shot. Even if you do not play a sport, you can still come and schmooze with an awesome crowd.  I welcome any reader of The Operating Partner community and may even have a secret gift for OP members who attend.  Register for a ticket here.

If you work in Private Equity or any other investment field, you know that Bain & Co (no relation) has a seminal PE report they release each year. Well, they just released it for 2025 and it’s chock full of information. If you are interested in the PE space, it’s a great read. And since AI is such a hot topic in the OP, I will link directly to the AI component of the PE report.

In other news, I’ve been fascinated with synthetic data in marketing intelligence over the past six or so months. Imagine using an LLM to replicate your ICP or target audience and use it to ask questions, surveys, focus groups, etc. Yes, instead of asking humans, you’re asking the LLM who is replicating humans. Scary? Yes. Weird? Maybe. Helpful? Absolutely.  

There’s real value in this. The time it takes to field a survey is marginal now. The cost comes down dramatically. And survey burnout by takers? Non-existent.  

One of the companies in the space, Aaru, just got a big investment from Accenture and was recently featured in this article. I’ve also used Evidenza and the output is fascinating. The craziness is that this can go well beyond just marketing and into product, research, and many other areas.

Last, fingers crossed for New York Knicks Jalen Brunson who suffered an ankle injury playing the Lakers.  Hoping for a lot of rest so he can fully recover ahead of a NYK playoff push.

Here are some articles to get us started:

Thank you for subscribing to the OP. I truly appreciate your time and attention that you spend with this each week. As always, please feel free to reach out. If you received this by someone forwarding it to you, you can subscribe for free here.

Darren

The Best & Worst Career Advice I Ever Got

I’m on a retrospective roll with these OP letters, and it seems to be working. Maybe because I’ve recently seen Noah Kahan and Matt Nathanson in concert, and their unapologetic lyrics are rubbing off on me.

I’ve gotten a ton of advice from friends, mentors, parents, uncles, aunts, bosses, peers, speakers—you name it. Some of it was gold. Some of it, well… not so much. So, I figured I’d share some of the best and worst career advice I’ve received. And I’d love to hear yours, too. Send me what stuck with you—good or bad—and I’ll compile a running list to share in the next OP.

Best Advice: Build Momentum (Or Go Where the Momentum Is)

This one is twofold. First, go where the momentum is. Find an opportunity (a job, project, company, industry, workstream) that already has the wind at its back. Have you ever tried running against the wind? It’s exhausting. When you have momentum behind you, things move faster, and you can push through blockers with less resistance. It’s why startups with product-market fit scale quickly, while others burn capital trying to force something that isn’t there.

Second, and more importantly: build momentum. This is something I preach constantly. I like to use a Northeast winter analogy—building a snowperson. At first, rolling the base takes effort. But as the snow packs on, it gets easier. Soon, that little snowball has enough mass to stack another on top. The same applies to your career, your team, and your business.

Momentum is the process of transferring potential energy into kinetic energy. It’s why in sports, you hear coaches yell, “Keep your feet moving!” It’s not rocket science: just keep moving. When you’re stuck, don’t look for the perfect move—just make a move. Small, compounding actions lead to outsized results over time.

Worst Advice: Follow Your Passion

I hear this one all the time. And sure, it sounds great. But I’ve learned firsthand that sometimes, turning your passion into your job can actually ruin the passion.

Back in college, a few friends and I started a company helping musicians with the business side of their careers—touring, booking, contracts, marketing, photo shoots. It filled a huge gap in the market. Most musicians are brilliant artists but aren’t wired for business. I was a huge music fan, had been to more shows than I could count, and figured this was my dream job. Follow your passion, right?

Except… I quickly learned that the music industry had an ugly underbelly. Guns and drugs backstage with a well-known hip-hop group? Check. Getting stiffed by venues, which hurt our artists and nearly sank our business? Check. Bands missing their set times because the lead singer was nowhere to be found? Check.

The experience changed the way I saw the industry. I used to warn friends, “Don’t come to shows I’m working—you’ll never see music the same way again.” What was once a passion became a job. And that job drained the joy out of the passion.

I think people say, Follow your passion because they assume it means you’ll love what you do. But here’s what I’ve learned: You can find enjoyment in unexpected places.

I never planned to work in an advertising and marketing agency. I had a stereotype of what it was like—one that turned out to be dead wrong. I stayed for nearly a decade, and I loved most of it. I never saw myself working in PE because I had my own assumptions about that world, too. And yet, I’m closing in on ten years at Bain Capital, and I truly enjoy what I do.

Instead of following your passion, follow opportunities where you can build momentum. Passion often follows mastery, not the other way around.

Below are a few articles I came across this past week that I found interesting. While I may not agree with everything in each one, I think they're worth a read. If you stumble upon an article you think I or the Operating Partner community would enjoy, feel free to share it with me. Of course, I reserve the right to decide what gets featured in the OP.

Legibility and Liquidity (Joni Rechtman)

Thank you again for subscribing to the OP. It was a ton of fun to reflect on good and bad advice and write this OP #290. I encourage you to reach out and let me know what you liked or didn’t. It’ll help me get better. Or if you just want to say hi, ping me.

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