Why Job-Hopping Every Two Years Might Not Pay Off

Scott Kirkwood
Magenta
Published in
6 min readApr 18, 2018

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Once considered a sign of disloyalty or immaturity, job-hopping is now a favorite career tactic. But sticking around offers long-lasting benefits.

Illustration by Arley Valencia.

Back in the days when resumes were printed at Kinko’s, most workers tried to hold a job for a couple of years, if only so it looked good on paper. Today, Twitter bios rattle off short stints like badges of honor. And why not? The demand for tech designers makes job-hopping a no-brainer — you can quickly boost your title, your bank account, and your portfolio without ever suffering an annual review. Most articles about the topic actually encourage jumping ship, quite possibly because they’re penned by recruiters, who profit with every new job vacancy.

But the folks with the outdated ID photos generally have deeper professional relationships with colleagues, a better understanding of corporate culture, and an easier time navigating internal politics — all of which tend to produce more achievements. In this age of job-hopping, there are overlooked benefits to staying in place.

Emily Wengert, Group VP of UX at Huge.

“After working at Huge for nine years, I have enough history, credibility, and relationships with senior staff that people are willing to take a risk on me,” says Emily Wengert, Group VP of User Experience at Huge. “If I went to a new company and said I want to start working on artificial intelligence, they’d say, ‘I’ve already got someone who’s been doing that for five years,’ but at Huge, if I say, ‘My client wants AI and I want to lead the project and surround myself with people who can teach me how to do it,’ I’m given that permission. My longevity allows me to add things to my resume in a way that wouldn’t be possible if I’d jumped around every few years.”

That experience has allowed Wengert to craft a pop-up store for a skin-care brand in Tokyo, create a chat interface for a fast-food giant, and design a digital game for a global tech company — things that were well beyond her reach when she started designing websites a decade earlier.

“If you stay with one organization for a while, you’re able to discern the differences between a situation that isn’t working and deeper systemic problems that are more or less unresolvable.”

Derek Chan was also fortunate enough to get hired at a company in the midst of massive growth: When he started as a graphic designer at Airbnb in 2012, he was tasked with internal efforts including in-house conferences, interior design elements, and new city launches. Six years later, he’s gone from 170 coworkers to 4,000, and he’s tackling the company’s marketing and branding efforts along with photographers, videographers, and several creative directors. “I feel so fortunate that I’ve been able to time some of my own ‘growing up’ as a designer with the growing up of this company,” he says. “I’m not sure if six years at another place would’ve been the same — it’s just been great timing.”

In the early days, Chan benefited from Airbnb’s scrappy start-up mentality and the guidance of talented supervisors who asked the right questions and pushed his design thinking: “Most of the things I’ve learned here came from feeling a little uncomfortable with what I was doing,” he says. “At Airbnb, people often end up doing more than their role might suggest. I’ve learned a lot by pulling off things that seemed impossible with the budget that we had to work with.”

Chan has even been fortunate enough to work on projects with two of the co-founders — RISD grads who keep design at the forefront of the company’s culture — something that would’ve been highly unlikely if he hadn’t put in his time.

The Wisdom to See the Big Picture

“I’ve seen a lot of people in the tech world move around every one or two years, which is long enough to see problems in an organization, but not long enough to see any solutions actually come to fruition,” says Russell Maschmeyer, a product designer at Facebook. A year-and-a-half into his seven-year tenure at the company, he was promoted from product designer to manager — a move that nearly ended in disaster.

“I had never managed people before, and I really wasn’t prepared for it,” he says. “Because I wasn’t actively seeking mentorship and looking at the skills I needed for this new role, it was pretty obvious that I wasn’t building a cohesive team, and I was feeling pretty burnt out. At that point I did a lot of soul-searching and asked myself, ‘Have I screwed this up so bad that I should just bail and start over somewhere else, or should I dig in, ask for help, and really figure out what it means to be a manager?’”

Maschmeyer reached out to other managers and got an incredible amount of support to turn things around.

Like casual dating, job-hopping means never having to work through a problem. A long-term outlook may invite more short-term headaches, but it also provides the opportunity to work through those headaches. “If you stay with one organization for a while, you’re able to discern the differences between a situation that isn’t working and deeper systemic problems that are more or less unresolvable,” says Maschmeyer. “In my first year as manager, I just didn’t know what i was doing; it wasn’t that Facebook was messed up or failed to support me — I just needed to ask for help.”

An Airbnb tradition that Chan started at Airbnb: A line-drawing of every employee.

Creating Your Own Opportunities

Bigger organizations like Facebook naturally allow for more growth than smaller companies. For those who do work at smaller companies with limited opportunities (or supervisors who are less focused on their employees’ growth), Wengert suggests seeking out a “sponsor” — a senior employee who appreciates your talents and who can scout out new challenges.

“Find someone who knows your interests and can pull you into projects, and sit down with them for coffee once a quarter,” she says. “I’ve designed a lot of experiential spaces in the last few years, and I’d love to design a conference in the next twelve months. So I’ve tried to plant that seed with people who know what’s coming down the pike, so that there are more eyes and ears to help me identify that next big challenge.”

If you find yourself entertaining more pleas from corporate recruiters, consider a few questions before making the leap: Do my values match my employer’s values? Does the company generally groom talented workers for bigger opportunities? Does my supervisor care about my professional growth? Do I still have room to expand my skills? Moving to a new company always presents a huge risk, so take the time to assess the value in staying, because leaving is rarely the only option.

“I certainly don’t think everyone should stay at every job for nine years like I have — that would be terrible career advice,” says Wengert. “But when it’s a certain kind of place and you’re a certain kind of person, sticking around can be incredibly empowering.”

Magenta is a publication of Huge.

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Freelance writer. Formerly at National Parks magazine, National Geographic, and the Humane Society of the United States. www.scottkirkwood.work