Illustration: Oscar Ramos Orozco

Turn Your Wandering Career Path Into a Secret Weapon

For those of us who’ve experienced the adventurous-yet-agonizing wanderlust of a post-college career journey – six months here, nine months there, never settling for long – there is nothing more fearsome than being interviewed and hearing the hiring manager ask this question:

So… You have quite the background! Youve done so many things. Tell me about that… 


Yikes, youre all over the place. These are cool experiences but… too many things. This is not giving me confidence in your stability.

You understand their concern – you’ve bounced around before, and you’re likely to keep doing so. So why should they hire you?

In the year after I graduated from college, I worked for eleven different companies – some simultaneously, some on projects, some full time. I did everything from ecotourism and outdoor education to business plan writing and information design consulting, including some pretty unglamorous things in between (installing energy-efficient home insulation and building rain barrels). During that saga, I got asked the “What’s the deal with your bouncing around?” question a lot. So much so that I decided to make my answer to that question my primary strength – my secret weapon.

Don’t be fooled, it may feel like there’s no winning response, but that isn’t the case. Don’t miss the opportunity to turn this knuckleball into a homerun.

Follow these steps, and you’ll make them glad they asked:

1. Don’t shy away from your past. Embrace it.

You walked your path for a reason. Even if you were anxious and lost or undirected for much of it, you don’t need to talk about it that way. Think back on it as a grand adventure, full of twists and turns and intrigue – the stuff of legends! Talk about it with pride, with confidence, with a slight smile. 

“Yeah, those were the good old days! Some of my fondest memories, for sure.”

2. Find the common threads, and use them to tell a good story.

No matter how random or varied your experiences, there is always a common thread. An interest you have, or an experience you were seeking, or a skill you were trying to develop. So think hard, and find that thread. Use it to tell a story that says something about you as a person – something more compelling than just having “put your time in” at one job for several years.

“Absolutely. Well, I think the best way to describe that time was that I was searching for the best way to develop my creative side in a way that made sense, in a way that actually benefited people and I could feel the impact. It definitely took some time to find that.”

3. Sell your versatility.

That background is your proof that you can handle uncertainty and come out better for it. They don’t have to take it on a leap of faith that you can dive into new things and get your bearings quickly – the proof is right there. In a world where every company and organization is moving quickly in a changing landscape, and every hiring manager needs you to onboard quickly and as painlessly as possible, these are great traits to have. Use that as a source of confidence for yourself.

“I’m sure I can come up to speed on this quickly. The situation seems similar to when I did XYZ – and that project went well in terms of bla bla bla. I’m also reminded of my time at ABC where the main challenge we faced was [insert here] – just like this role/project.”

4. Explain why they are the exception to the rule.

Especially if you’re using the narrative that you were searching for something, that’s a perfect lead-in to telling them why they are the company who can tame your wild heart once and for all. Do your homework, and be able to describe to them in detail why you think they’ve got what you’ve been searching for. The more specific, sensible, and heartfelt you can be, the better.

“I’m glad you asked. I think why I’m so excited about [their company here] is because I can tell that you guys have the mix of X and Y that I’ve been looking for, and in a setting where I don’t have to settle with regards to Z. To me, that’s the holy grail. It’s literally my dream job.”

If you play these cards, you should be in good shape. And relax, everyone’s career path is winding and jumbled these days – so it’s much less of a liability than you think. Just make sure you know how to defend it correctly.

How about you?

Do you have a wandering career path? How have you handled it?

More insights on: Self-Marketing

Nathaniel Koloc

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Nathaniel is the co-founder of ReWork where his team is determined to change the world by helping people find work that they love.
load comments (36)
  • Patrick Bowen

    I graduated from college in December of 2005. Since then I have worked for 8 companies as well as freelanced. While not as many as mentioned in the story above I have definitely received this question. Here’s how I handled it:

    1. I used my various experiences to craft my resume for each job ensuring I had the experience and also showed minimal employment gaps. This almost always got me in the door for the next job interview.

    2. I set my freelancing up with an official business name and business registration, so I could list that as work without having to look like I was just getting by.

    3. I kept a common personal thread. For me it was creating great interactive experiences from a brand and UX perspective. Every job I did I made sure to constantly jot down notes on how I was accomplishing that.

    4. I kept a common business thread. For me this was effectively helping companies out of hard spots. My contract gigs were usually catching other creative firms up. My freelancing was helping small businesses. My full time employment was usually focused on solving big problems. Again keep notes while you are at these places so you can create a better resume.

    5. Don’t burn bridges. I had a ‘gift’ for getting bored after 6-9 months at a place. If I noticed relationships souring I would find a way out without burning bridges. This gives you a ton of great references.

    6. I was always honest in interviews. Every time I said something that I thought might push the boundaries of an acceptable answer (something that might be construed as negative) I would back it up with a positive solution. Seemed to work for me.

    I’ve been at my current job for almost 2 years and love it. Just because I jumped around doesn’t mean I will forever (like mentioned above). So, yeah, this article just about hits it on the head. I think the most important part is to keep track of what you do where and how that could be used in the future… don’t just hope to be able to remember those things ‘when the time comes’.

  • Marco Puccia

    I’ve definitely been in this boat! This article is nails on. Last year, Allen Lim’s talk at TEDxMileHigh gave me some good perspective on the common thread element. He talked about how all of these disparate experiences can make you feel out of your depth or lost, but when you look back at things or take a birds eye view you can start to see the common thread — what he refers to as a core identity. Once that clicked in my mind, it made all the difference in the world. I could actually tell a great story when people asked about about my background and what brought me to law school! Anyways, great post!

  • Josh

    This is one of the best articles I’ve ever read at 99%. Extremely practical, with examples after each point. Original content addressing a real problem. Well done, sir.

  • Dr. Davis

    This is exactly what I had to do with my scholarship in academia. It was “all over the place” and everyone kept asking me what I was ACTUALLY interested in studying. “All of it” was not the answer they wanted. If this post had been around then, I would probably have found a full-time position sooner. I had to figure it out on my own.

    Good plan for making the most of what many will see as a problem.

  • Pete R.

    Great advice on embracing the wandering path with a very usable example. :) Thanks for sharing your tips here Nathaniel.

  • Yanina Wolfe

    I think it would also be an effective addendum to discuss how to present this on a cover letter. Usually seeing that type of resume, however wanderful (get it?) it may be might make HR go “yikes! you’re all over the place” and spend their precious interviewing time on someone else. If you can address the bouncing on the cover letter, you’re already soothing worries right from the start.

    • Patrick Bowen


      I think item #2 (the common thread) is the key to crafting an effective cover letter that gets around the HR. Start with an intro sentence or two that sums up your career focus. Use the next couple of sentences or a paragraph to provide examples of how your work helped you follow that common thread. Here’s what I started out with once:

      “I am an experienced media designer educated in audio and interactive media design who focuses on user perception and experience. My work experience at Company X gave me the opportunity to learn consumer marketing strategy which I used as a base for my design work at Company Y. This base of marketing and design tied in with my work at Social Organization Z has given me an excellent foundation to understand the human and design elements of marketing which I feel will enable me to hit the ground running for your organization.”

      Also, remember you don’t have to list every place you worked on your resume. Take 2-3 that best fit the current opening you’re applying for. To get around gaps this may leave you can creatively design your resume. Instead of saying October 2009-January 2011 at Company X and June 2012 – Current at Company Y (has an 18 month gap) you can just list Company X: 2009-2011, Company Y: 2012 – Current.

      • Mackenzie Sullivan

        Also remember there is no substitute for networking AHEAD of when a cover letter/resume lands on a HR person’s desk. From my experience as a career coach, if that is the first time the organization has ever heard of you — good luck! — even if you have the best Res/CL ever. With orgs still getting 100’s of applications for every job, you really need to network to tell you story BEFORE your app hits HR’s desk,.

      • Nathaniel Koloc

        100% right – networking is arguably more than half the battle for most hiring situations. Luckily tools like LinkedIn are making this element of job search easier, but it’s still important to invest time networking way in advance to start to build your connections. This is a case where taking a long-term view pays real dividends.

      • Nathaniel Koloc

        Great points Patrick, getting that summary of career focus is a great opportunity to plant the narrative seeds in the hiring manager’s mind.

    • Nathaniel Koloc

      Hey Yanina – I think Patrick and Mackenzie bring up good points. Cover letters (And resumes for that matter) don’t have to include all the stepping stones you took. It’s also smart to find in-roads and introductions to the company (hiring manager, if you can get it) rather than depending on CL + resumes to tell your story. Most hiring managers prefer not to take cold calls about positions, but few will turn down the request for a 15 min call if it comes via a mutual contact/friend – so use the power of LinkedIn to see who you know in common.

      That said, even if/once you do chat with someone, they’ll likely still need your docs on file – so you still have an opportunity to standout in further reviews. I see cover letters as your chance, more so than your resume, to control your own narrative. After looking at your resume they should feel that you meet the background requirements. After reading your cover letter they should have a very clear tagline for you in their minds – one that you put there – e.g. “Yanina – she’s the talented product manager from Texas who’s been trying to move to NYC for awhile but has been waiting for the right thing.”

      Note that powerful narratives include personal AND professional elements. Human beings want to hire other human beings, not resumes. So include a personal thread to your narrative to help them feel like they understand your motivation. That usually goes beyond summarizing your job history with a common theme.

      A few other points that I usually recommend to people:
      – Keep the cover letter informal-yet-professional. Most people get overly stuffy and stiff when writing in this setting, and it sounds oddly unnatural. You’ll stand out if you’re writing as if you were confidently speaking. Try that style and have friends read it to make sure it comes across well.
      – Once you finish your draft, read it over and ask this question: “Could someone else have written these same words?” If the answer is even maybe yes, re-write it with more of you personal voice coming through, and with more details. Anyone can write that “I have a lot to offer your organization,” but only one person could write “Overseeing communications for the Houston Public Libraries for the last two years has taught me everything I need to know to approach this role with the right mentality.” See the difference?
      – If you’re really serious (which you should be, right?) have some people read your CL first and see what narrative they are getting from it – then evolve it until they tell you what you were intending to hear. Then you know it’s ready to go to the hiring manager.

      Thanks for the comment!

  • Richard Arte Digital

    This is quite an interesting article! Especially for self-thought people like me. Thanks for sharing your knowledge through this site. Keep up the good work!

    • Nathaniel Koloc

      Thanks Richard, glad you found it helpful.

  • Dave

    I am about to retire from my present job but am seeking a new one in an interesting and uncharted field. Great article to start my journey!

    • Nathaniel Koloc

      Best of luck!

  • Cesar

    Thanks for sharing, Patrick!

  • Chrystian Tigeleiro

    Sounds like my career in a nutshell.

    A few months ago, I landed a position at a good company after 7 months unemployed. I constantly got asked about my “bouncy” 5-year job history during job interviews. Although I did leave two jobs for greener pastures, two companies laid me off in cost-cutting moves. I had no control over it.

    Still, it was held against me, whether Hiring Managers wanted to admit or not. A lot of the Manager felt I was either a bad employee or looking for something better all the time. Wasn’t true one bit. I just had some bad luck.

    When I interviewed for my new company, I used the job history proactively as a “I’m able to do anything” versus being trapped into a corner about it like I had allowed myself to be in prior job interviews. I got an offer one-day later.

    This article is great advice.

    • Nathaniel Koloc

      Chrystian, that is great to hear. Sounds like a good example of evidence that it’s all about context, and hiring managers really can appreciate the strengths that are shown through tough times / career journeys. Thanks for sharing.

  • Sean Blanda

    Awesome comment Patrick. Thanks for sharing!

  • Mackenzie Sullivan

    I am a career coach who works with business students and clients looking to get into social ventures, sustainable businesses, and non-profits. Often these students/clients have what look like “wandering” backgrounds. Often with a little digging, the client and I DO find a common theme. So if you are struggling to find your thread, think back on why (besides that you were desperate for a job!) you took each position. And share you career path with someone else – sometimes they will see themes you don’t.

  • Nathaniel Koloc

    Thanks for the kind words Pete!

  • Nathaniel Koloc

    Hey Julie – I’m glad you brought up being a learner – that is actually a very powerful driver for a lot of people, and it’s a very valuable trait to have in new employees. So you’ve got a great narrative/fact there in and of itself. Very cool.

  • Nathaniel Koloc

    This is good stuff – I especially like the bit about putting multiple side gigs / project under one business umbrella. I’ve seen this done effectively be just calling that period of time “Freelance Project Manager” or something – if you didn’t have a business entity from the beginning. Thanks!

  • Nathaniel Koloc

    Thanks Marco! Hope all is well with you.

  • Nathaniel Koloc

    Thank you!

  • Eric Walesh

    Great article. spot on. I have always used my various jobs in commercial real estate due to layoffs as having varied experience and being able to quickly react to changing circumstances outside my control. I signed up for your newsletter

    • Sean Blanda

      Thanks for the kind words!

  • Steve L.

    Interesting article, and very practical. I have the opposite problem of not staying in one place long, however. My problem is my resume is filled with jobs where my shortest tenure with one employer is three years. I’ve been with my current employer 13 years. I sense that my “loyalty” is actually working against me as I look at other career opportunities.

    Some people have told me that a resume like mine is looked upon worse by prospective employers than one with lots of short-term jobs. It certainly wasn’t that way when I started my first job out of college. What do you think Nathaniel?

    • Nathaniel Koloc

      Hey Steve. I’m surprised to hear that people said longer tenures are looked upon worse than shorter ones. It may be true that this last 13-year stay is a bit long, but it’s all about context. If you can explain how you evolved while you were there, what core competencies you gained and developed, and why you want to leave now (assuming you do) and not sooner, you should be fine. It’s the narrative that counts.

      I would imagine that in 13 years you’ve had many experiences that would be applicable in new settings and at other companies. Pick the top three that you feel “define you” and practice articulating them to various audiences until you’re confident in the way you tell the stories. That should give you some ammo for when you need it.

      As long as you explain the timing and highlight your strengths and accomplishments (the same way everyone has to), I don’t think you’re at a disadvantage. The one thing to look out for may be allowing yourself to be pigeon-holed into whatever your current role/industry is. Be vocal about why you’re interested (and well suited to make) a change, so that people don’t assume you want more of the same.

      But again, I don’t think that’s a structural disadvantage. I hope that’s helpful!

  • IK

    good to see and common element aspect is more likely to adopt

  • Maria

    A must-read article for a lot of people I know, and very encouraging. The problem is that not all companies/organizations want to hear a “story,” from an applicant, a lot are still out of date and are looking for 100% predictability, and/or intentionally look for less dynamic people because they don’t understand them/value them. In addition to prospective applicants changing their approach, HR in a lot of places I have encountered needs a culture change in order for this to really start working.

  • jeanvatchara

    Thank you for writing this article, It has given me confidence to start my job hunt. I am often told that if you are a jack of all trades, your are a master of none. Why cant we be a jack of all trade and master of some? Other than the HBR article, “Hail the Generalist”, published in 2012 by Vikram Mansharamani, I have not read an article of this kind since!

    Only graduated from college in 2010, I have already worked in architecture, advertising, illustration and graphic design. I thought I was in trouble being a creative wanderlust.

    Thank you for such a brilliant and inspring article.

  • jeanvatchara

    Thank you for sharing, Patrick!

  • AlDavies

    Just stumbled across this article and I must say it has answered the only question that I struggle to answer in an interview! Could be my dream ticket in two days time

  • Nathan Nelson

    Very useful article. I have encountered this question several times in interviews and I particularly agree on finding common threads. A useful exercise for job hunters with mixed CVs is to build an alternative skills-based CV, setting aside the chronological information in favour of pulling these threads together under broad skills headings. The CV starts to make a lot more sense and you are better able to articulate what has driven you through your career.

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