Career Advice from a Serial Job Hopper

I’ve lived, worked, and studied across three different U.S. cities, six countries, and nine organizations, in a dizzying fourteen positions. My mother jokes that I am a “flight risk;” I have not stayed in any role for more than two years, or any organization more than three. And while some roles prioritize applicants willing to stay through the long-haul, this is not always a requirement. 

There are myriad ways job hopping antes up the benefit and value you bring to a new opportunity. Instead of overexplaining your decisions in an effort to downplay your professional history, think about how you’ll discuss the unique perspective and skill-set you bring from your varied background in a way that works for—not against—you. 

The good side of job hopping

If you’ve switched positions, sectors, or geographical locations, you likely bring a broader experience than someone who has worked one role for an extended period. 

Though longevity may yield a deeper understanding of and insight into organizational systems, it may also lead to complacency and resistance to change. Focus on what you offer as a job hopper and be ready to name the strengths you’ve developed through your experience:

• Broader and more diverse perspectives. Chances are you’ll offer a more flexible way of thinking and an ability to identify alternative ways to approach a problem. If a team is looking for someone who isn’t going to take a business-as-usual approach, you may be a fit. 
• Adaptability. Your resume shows that you’ve dealt with change. In most of my interviews, I show that I’m ready to support diverse populations by sharing stories about my experiences teaching four-year-olds English in rural Japan and working with oil executives in Melbourne, Australia. Talk about your adaptability in a way that shows you’ll take initiative and be prepared to overcome learning barriers with grace. Address your experience adapting to different cultures and environments, especially if you’re entering a new sector or type of organization. During an interview for a role that requires expertise I don’t have, such as fundraising, I might demonstrate that I am ready to acquire new skills, build meaningful partnerships, and adapt to a new function, thanks, in part, to my international graduate program. I’d make the case that, from conducting statistical analysis to researching the marketization of higher education, my studies prepared me to learn information with intention. Yes, I’d acknowledge the learning curve, but I’d also emphasize how these past experiences show I’m ready and eager to overcome it. 
• Ability to connect the dots in unexpected ways. As you consider new positions and sectors, think about the unlikely transferable skills and knowledge you bring. For inspiration, read this advice to a fashion designer who is looking to pivot into the nonprofit sector. 

Pro tip: When starting a new position, be sure to respect colleagues with a longer track record with the organization. Before you try to change anything, take the time to learn why things are how they are.  

Crafting your narrative and applying for positions

Confused about how your past positions fit together? So are hiring managers.

Set aside time to reflect on your experiences and note patterns in your levels of motivation, interest in new opportunities, and purpose for working so that you can speak to and write about your career trajectory in a compelling manner. Your goal is to tell a coherent story that highlights your unique skills and experience. To start, ask yourself: 

• How does everything on my resume tie together? What do English language teaching, account management, cultural curation, and faculty development all have in common? Well, at their bare bones, they’re about helping people gain access to tools and resources. At least that’s the common thread I’ve found best explains how my seemingly disparate roles overlap and connect. What’s yours? 
• Where should I begin? I recommend starting with your first role, even if it was some time ago, noting a) what drew you to this position, b) what you saw as your purpose, c) what you gained, learned, and enjoyed, and d) why you moved on. This process also sheds light on our own unexamined motivations. Learning that I am drawn to work that centers on people and increases access to resources has transformed my job search, both in narrowing my focus and keeping my own values front and center. Do the work and you’ll save yourself (and others!) lots of time. 
• What about the outliers? For plenty of reasons we sometimes take positions that are not a part of the larger puzzle. Spend some extra time exploring any positions that are misaligned with your overarching aims. What drew you there? What did you learn about yourself as a worker and how will this inform your future roles and actions? 
• Can I summarize my main findings in a tweet? With your patterns and hopes in mind, try to come up with your professional tagline. And don’t worry, it can be cheesy! This is a private statement just for you that will be sitting on the backburner through your search. For a long time, my tagline was “...getting folks the things that help.” This motto helped me see and share how I’ve been resourceful and service-oriented in various capacities. Whether you think of it as a brand or as a mantra, being able to succinctly describe your motivation and offerings will help make your case memorable and convincing.
• Share when you’re ready. Make sure your references understand you, your story, and the value you bring. This informs the conversations they have with hiring managers, and helps them better understand why you’re applying for another position, yet again. 

Prepare for these interview questions

Instead of thinking in terms of right and wrong answers, focus on responses that are honest, positive, and reflective of who you are. Embedded in your replies should be a case for how this position, at this organization, fits into your path right now.

• Why have you switched organizations so frequently?
• How long do you picture yourself in this position?
• What’s your five-year plan?
• Tell us about a time you had to navigate change or uncertainty at work. 

Even if these questions don’t come up, it's safe to assume the reasons behind your varied resume is of interest to at least one member of the hiring committee. When they ask you if you have any questions, address the elephant in the room, so that they don’t have to make assumptions after you’re gone:

• Are there any hesitations I can address about my candidacy? 
• How long are you hoping for someone to stay in this role? 
• What has been a typical tenure? 

Be honest and realistic with yourself (and others)

If you’re in a cycle of dreading your work and have started applying for positions that aren’t aligned with your values, goals, or interests because you so badly want a change of scenery, take time to pause, reflect, and draw a blueprint. Don’t apply for jobs you can already imagine quitting, and try not to leave positions before you’ve made your mark. This sort of job hopping isn’t beneficial to your spirit, resume, or future employer. 

If you’re leaving for thoughtful reasons and on good terms, you should use your diverse experience and perspective to your advantage at an organization that will be grateful to have you for any period of time. Consider it a compliment if they wish you’d stay longer. 

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