Ask Khe: How do I choose the right career in my twenties?

Should they switch?
Should they switch?
Image: Reuters/ Jim Young
We may earn a commission from links on this page.

 FWD: Thinking is Quartz’s podcast about recreating your career. In it, host Khe Hy talks to bold professionals who’ve challenged the status quo. Now he wants to hear from you. Whether you want to stretch in your current role or launch your own company, Khe is here to answer your all of your career questions. Email him at

Dear Khe:

I’ve gotten conflicting advice on how to find a career fit. I’m in my twenties and have worked in media, tech, advertising, and nonprofit. On one hand, people advise me to try out different jobs for size. “You’ll never know unless you try it.” I like this iterative process to career design, but I think it also creates a lot of strife. On the other, people say it matters more how you approach your job than what job you’re approaching. I want to find a good fit for me, but don’t what to be comparing and contrasting all my life. How do I know whether to double down or keep exploring?

Sincerely, A drifter

Dear Drifter:

How many times have you told an employer “It’s not you, it’s me?” Can we start by first getting crystal clear about the motivation behind each job change? Have you ever left a job because:

  • You struggled to get along with co-workers
  • You perceived a disconnect between your title and skills
  • You thought you were underpaid
  • You sought a more prestigious brand name
  • The “new-ness” wore off (aka shiny-new-toy-syndrome)

How well do you know yourself?

Now these are all valid reasons to leave a job. But if your plan is truly to discover the right career, you need to ensure that you’re honest with yourself about your motivation. Every time you change jobs, you risk putting a “ding” on your resume; having many jobs invites a future employer to ask some additional questions. And while the label of job hopper will vary wildly by individual and industry, “Ask a Manager” columnist Alison Green wrote that employers are “wary of people with a track record of jumping around from company to company every year or two.”

Trying on for size without quitting

Next, have you considered how you could “try different jobs for size” without constantly changing roles? I know what you’re thinking, “He’s gonna tell me to start a side project.” Double eye roll. But hear me out. Side projects are low risk endeavors that enable you test out new skills without the professional (or financial) risk.

Take Tom Critchlow, a former VP of operations at the marketing agency Distilled who dabbled in the programming language Python. In his blog post titled The Importance of Launching, he wrote how coding “276 lines of Python” launched a small music discovery project called F*ck Yeah Spotify which then landed him a job at Google. And as technology parades through pretty much any industry, the possibilities for experimentation expand drastically: You could start a tea company. You could even try your hand at Soundcloud rap.

Double-down or keep exploring? More options exist

LinkedIn founder Reid Hoffman thinks that it’s okay to try on a career for size. In his book The Alliance: Managing Talent in the Networked Age, Hoffman introduces tours of duty – two to four year career engagements at LinkedIn. Hoffman describes these tours as a win-win for both employee and employer:

The company got an engaged employee who worked to achieve tangible results for LinkedIn and who could be an advocate and resource for the company if he chose to leave after one or more tours of duty. The employee transformed his career by enhancing his portfolio of skills and experiences.

Upon completion of a tour, LinkedIn employees can sign up for another tour, preferably with LinkedIn but often with another company. Can this approach be applied outside of LinkedIn?

Time to take a tour internally?

Lisa Shalett, a former Goldman Sachs partner and Board Member of Brookfield Property Partners thinks that it makes sense to pursue tours of duty within your company. Over her 20-year career at Goldman Sachs, she’s held senior roles across seemingly disparate functions: international equities, global compliance, brand marketing, and digital strategy. On the Rad Awakenings podcast, Shalett told me that “people tend to define their skills by the context in which they’ve used them to date” and so any career reinvention should begin by widening the aperture on your own skills. But that’s not enough, reinventing yourself (both within and outside your organization) requires you to “own [your] story” in describing it others, like a future employer:

“You’re asking someone to make that leap along with you. Because typically, people will default to the story of ‘oh here is what this person has done before, and thus this is what they will always do.'”

Hopefully this expands the set of options beyond doubling down and continued exploration. And irrespective of the specific path, if you honor the integrity of relationships (read: don’t burn bridges) while pushing yourself to keep learning, there’s a good chance that you’ll end up—as Shalett says—”where you’re supposed to be.”

Do you have a career question?

Email us your questions at and be sure to include:

  • A specific question; we know every situation is unique yet strive to make the answers as universal as possible
  • A brief description of yourself including your years of experience, role, and industry

Subscribe to FWD: Thinking on Apple Podcast, Google PodcastSpotify and Stitcher

FWD: Thinking is a new podcast about bold professionals who have challenged the status quo to recreate their careers. They’ve grown out of the cracks in the org chart, punched above their titles, and when all else failed, started their own companies. Hosted by Khe Hy and created by Quartz, this podcast traces the blueprints that lead to a more fulfilling work life. Subscribe on Apple Podcasts or wherever you get your podcasts.