— 2017 —

CHAPTER TEN

Why You Should Have (at Least) Two Careers

by Kabir Sehgal

It’s not uncommon to meet a lawyer who’d like to work in renewable energy, or an app developer who’d like to write a novel, or an editor who fantasizes about becoming a landscape designer. Maybe you also dream about switching to a career that’s drastically different from your current job. But in my experience, it’s rare for such people to actually make the leap. The costs of switching seem too high, and the possibility of success seems too remote.

But the answer isn’t to plug away in your current job, unfulfilled and slowly burning out. I think the answer is to do both. Two careers are better than one. And by committing to two careers, you will produce benefits for both.

In my case, I have four vocations: I’m a corporate strategist at a Fortune 500 company, U.S. Navy Reserve officer, author of several books, and record producer. The two questions that people ask me most frequently are “How much do you sleep?” and “How do you find time to do it all?” (My answers: “plenty” and “I make the time.”) Yet these “process” questions don’t get to the heart of my reasons and motivations. Instead, a more revealing query would be, “Why do you have multiple careers?” Quite simply, working many jobs makes me happier and leaves me more fulfilled. It also helps me perform better at each job. Here’s how.

Subsidize Your Skill Development

My corporate job paycheck subsidizes my record-producing career. With no track record as a producer, nobody was going to pay me to produce their music, and it wasn’t money that motivated me to become a producer in the first place—it was my passion for jazz and classical music. Therefore, I volunteered so that I could gain experience in this new industry. My day job not only afforded me the capital to make albums, it taught me the skills to succeed as a producer. A good producer should be someone who knows how to create a vision, recruit personnel, establish a time line, raise money, and deliver products. After producing over a dozen albums and winning a few Grammys, record labels and musicians have started to reach out to see if they can hire me as a producer. I still refuse payment, because making music—something that is everlasting—is reward enough for me.

At the same time, I typically invite my corporate clients to recording sessions. For someone who works at an office all day, it’s exciting to go “behind the scenes” and interact with singers, musicians, and other creative professionals. While I was in Cuba making an album, one of my clients observed about the dancing musicians, “I’ve never been around people who have so much fun at work.” That my clients have a phenomenal experience only helps me drive revenue at work, so my corporate and recording careers are mutually beneficial.

Make Friends in Different Circles

When I worked on Wall Street, my professional circle was initially limited to other folks in the financial services sector: bankers, traders, analysts, economists. Taken together, all of us establish a “consensus” view on the markets. And most of my asset manager clients were looking for something different: “Give me a contrarian perspective.” In other words, they didn’t want to hear the groupthink. I took this as marching orders to tap my Rolodex for people who could provide my clients a differentiated perspective.

— 2021 —

Flirt with Your Future Self

by Amantha Imber

It’s normal to get urges to try out different roles or career paths. But instead of doing something dramatic like jumping ship or enrolling in a two- or three-year degree, Scott D. Anthony, a global innovation thought leader, senior partner at Innosight, and author of the book Eat, Sleep, Innovate, is a fan of London Business School professor Herminia Ibarra’s suggestion to “flirt with your future self.”a

“The idea is that you consciously experiment and ‘try on’ different roles, and indeed leadership styles, to see what fits the best,” Anthony said on my How I Work podcast. “For example, I think that a natural next act for me someday would be to become a teacher. But will I actually like teaching? There are small experiments I can do in my current role that help me understand that better, which includes talking to people who have made similar transitions to see what surprised them.”

Try to get out of work mode and get into play mode more often. As Anthony suggests, treat it as a little experiment. Feeling inclined to make a new career move? Make a list of five people you can speak to who can provide insight into this career. For example, if you want to pivot into travel blogging, ask colleagues who they think the best travel bloggers are and reach out to them on LinkedIn or other social media channels for a chat. Turn up your curiosity, and make a list of things you want to know and questions you might ask. For example: How do they make money? How did they get their start? How many hours do they work?

As you think about switching jobs or careers, don’t do so blindly. Connecting with those who’ve “been there, done that” to learn about their experiences and listening to any advice they have can come in handy before making the leap.

a. Amantha Imber, “Global Innovation Thought Leader Scott D. Anthony on His Daily Creativity Ritual,” October 21, 2020, in How I Work (podcast), produced by Amantha Imber, https://www.amantha.com/podcasts/global-innovation-thought-leader-scott-d-anthony-on-his-daily-creativity-ritual; and Herminia Ibarra, “The Most Productive Way to Develop as a Leader,” hbr.org, March 27, 2015, https://hbr.org/2015/03/the-most-productive-way-to-develop-as-a-leader.

Adapted from “Career Advice from Wildly Successful People,” Ascend, on hbr.org, June 30, 2021.

For example, one of my clients wanted to understand what Chinese citizens were saying to each other. Because I am an author, I have gotten to know other writers, so I reached out to my friend who was a journalist at a periodical that monitors chatter in China. Not restricted by the compliance department of a bank, he was able to give an unbridled perspective to my client, who was most appreciative. My client got a new idea. I got a trade. My friend got a new subscriber. By being in different circles, you can selectively introduce people who would typically never meet and unlock value for everyone.

Discover Real Innovations

When you work different jobs, you can identify where ideas interact—and more significantly, where they should interact. “It’s technology married with liberal arts, married with the humanities, that yields us the result that makes our heart sing,” said Steve Jobs, who was the embodiment of interdisciplinary thinking.

Because of Hurricane Katrina, many musicians left New Orleans. In order to generate funds to help musicians in the city, I could have created a typical nonprofit organization that solicits people for money. Instead, I helped create a more sustainable solution: a brokerage for musicians that I described as “Wall Street meets Bourbon Street.” People wanting to book a musician for a party in New York could find a band on my organization’s website, which would then ask the booker to add a “tip” to be allocated to a New Orleans–based charity. The booker (who in some cases were my corporate clients) easily found a band for the party, the New York City–based musician got a gig, and the charity in New Orleans got a small donation. Because of my time working at a bank, I was able to create a different type of organization, one that has since merged with an even larger charitable organization.

When you follow your curiosities, you will bring passion to your new careers, which will leave you more fulfilled. And by doing more than one job, you may end up doing all of them better.

Adapted from content posted on hbr.org, April 25, 2017 (product #H03M9A).

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