Everyone says you should do what you love, or at least what you’re best at, but how do you know what that is? How do you know what career to pursue? The choices can be mind-boggling. Let me explain how it works, and how it doesn’t:

I spent summers working on Wall Street in college. It sucked. That’s how I knew that banking wasn’t for me.

A BS in physics landed me in a bank vault earning minimum wage and living back in my old bedroom in my folks’ Brooklyn apartment. While I loved physics (don’t ask), making a living was a different story.

My girlfriend’s dad, who ran a semiconductor startup, gave me the idea to go back to school and get an engineering degree, which I did. Why? I met some of the engineers working at his company. They were having fun, running their own projects and making good money. That sounded good to me. That’s how I broke into the high-tech industry.

Chip design was OK and, while I was promoted to manager, I wasn’t moving up fast enough at a big company, so I went for the “big fish in a small pond” model. A sales exec saw how I interacted with customers and said I would make a great sales guy. I was skeptical, but interested in gaining one-on-one negotiating skills, so I went for it and took a step back from management to carry a bag.

Sales exposed me to lots of companies and ultimately led to my first executive job, running worldwide sales for a startup. After the IPO, I got fired (again, don’t ask) during a recession, and while I loved sales, I couldn’t find a job. Money was running out, so I applied for a director of marketing job at a public company and talked my way in. That’s what got me into marketing and Silicon Valley.

Marketing turned out to be my thing: I rose through the ranks and, as they say, the rest is history. When I couldn’t take the corporate grind and politics any longer, I started a management consulting firm. When I was asked to blog for CNET, I figured the exposure couldn’t hurt, so I went for it. That was nearly a decade ago. Today I’m a consultant, columnist and author. Who knew that was in the cards? Not me, that’s for sure.

The thing is, you never know up-front if you’re going to love something, how good you’re going to be at it, or if anyone will pay you good money to do it. And you certainly don’t know what will get you promoted and ultimately make you successful. You have to try it out, make things happen, and work at it to find out if it works for you. It’s all about experience, trial and error, and making the best decisions you can.

My advice: Don’t overthink your career. Forget about money and success. If you overanalyze things and stare at books and screens instead of paying attention to what’s going on around you, opportunities will pass you by. Instead, be aware, listen for clues, build relationships, keep your options open, and if it seems to make sense at the time, go for it. When it stops making sense, consider a change. Keep moving forward, never backward. That’s how you do it.

  • I dig you (Uber notwithstanding). Always read your posts.

    I just wanted to be a guitar player. Played for a ‘living” for 21 years (or, as my wife said “my husband works in the non-profit sector.”)

    • Steve Tobak

      Ha! I think you and my wife would get along famously; she’s also into the “non-profit sector,” if not unintentionally. 😀

  • SamHanson

    That’s the same advice you’ve given me a few blog posts ago in the comment section.
    It has helped and things are shaping up!

    • Steve Tobak

      Good to know I’m consistent … and at least occasionally right. 😉

  • Dirk Duden

    One the other side of the pond, I keep enjoying your blog posts and re-reading . Curious about the second book you’re writing. Heading for a big exec meeting next week, can’t think of any better prep. Recently former CEO of Andrew Corp. (Chicago) passed away. Floyd was a good friend of mine. He would have subscribed to every message of yours, Steve. Respect. You’re smack on the money and on quality of life. Must be your German-Austrian ancestors 🙂

  • Dirk Duden

    One the other side of the pond, I keep enjoying your blog posts and re-reading Real Leaders Don’t Follow. Curious about the second book you’re writing. Heading for a big exec meeting next week, can’t think of any better prep. Recently former CEO of Andrew Corp. (Chicago) passed away. Floyd was a good friend of mine. He would have subscribed to every message of yours, Steve. Respect. You’re smack on the money and on quality of life. Must be your German-Austrian ancestors 🙂

  • Gary Dumais

    Very helpful advice – thanks! It’s important to keep in mind that people’s preferences, perspectives, etc. change with time (especially over the course of a lifetime). So, doing “what you love” is likely to change as well. In other words, I think it’s wiser to focus on how to be adaptive (and evolve), rather than trying to determine that “one big interest” that will lead to fulfilling career. Embrace change!