How to Turn That Hole in Your Resume Into a Story

Written by on 15 Dec 2015

If you look really, really, really closely… my resume has a 9-month hole.


Who am I kidding? 9 months?! You don’t really have to look that closely…


It's more like a crater than a hole.


And, it’s pretty damn obvious.


If you had asked me 5 years ago how I might react to a 9-month hole in my resume, I would have had the following responses in this order:


  1. Freak out.
  2. Lie.
  3. Freak out for lying.
  4. Apologize for freaking out and lying.
  5. Hope that the Pratfall Effect is still a thing.


For some reason, I had been brainwashed to think that any sort of jog or left turn in a resume meant doom to my career. Clearly, a hiring manager or a potential employer would see the hole, realize I was a slacker, and quickly toss me into the garbage can.


My resume, that is.


Isn’t that how we were all educated on career and resume? You must show one, over-arching theme. Make it runs throughout everything you do. Definitely double check that there are no gaps-- all your time must be accounted for.


And God forbid, no holes!


That’s all well and good when you’re planning your career, but what happens when you encounter something unexpected. You get laid off. You get fired. Your start-up hits the skids. You have to move home for a family emergency.


What happens when you do what I did and quit a job with no plan and no prospects because you were just that miserable?


How do you make that hole in your resume make sense to other people?


Better yet, how do you make it make sense to yourself so that you can embrace it, use it, and move past it on to bigger and better things?


The answer?


Turn it into a story.


There are lots of reasons for the creation of a story. The biggest one is that people love stories. They engage and identify best with stories. There won’t be one hiring manager or potential employer who can’t identify with a good story.


They probably have their own stories to share with you, as well.


More important than the “why” in this discussion of story is the “how”.


How do you craft a narrative that makes your time off, your unemployment, your vagabonding, your [insert random hole in your resume here] into a cohesive story?


You have to build a bridge.


All that matters to these people who are scrutinizing you and scrutinizing your resume even further is the bridge—how did you get from where you were to where you are now.


Take my story, for instance.


My 9-month hole in my resume jumps from Finance to Talent Development. From Wall Street to working from home. From 100,000 employees to 2 employees.


At first glance, this is a chasm. The likes of which would need a bridge double the size of Lake Pontchartrain to cross. It seems nearly impossible.


But let me show you how it’s done.


First, you have to define where you were.


For two and a half years, I worked at a Wall Street firm in Stamford, Connecticut. I was a salesperson on the high yield and distressed credit desk and had a permanent seat on the largest trading floor in the world (depending on who you ask). I covered over 150 institutional accounts and facilitated the trading of millions of dollars of assets every single day. I also engaged in the recruiting and mentorship of other analysts.


Then, I left.


Second, you have to define where you eventually landed.


When I started working again, it was for a woman who owned her own consulting firm. She had written a best-selling book, parlayed that book into a successful speaking career, and parlayed that speaking career into a training and development business. When we started working together, she was based in Houston and her company had grown enough to where she needed some help running the business, managing sales and marketing, and supporting on content and development. I had the opportunity to be her right-hand woman.


Then, I took it.


Third, you build the bridge.


It might look something like this:


My time on Wall Street was great for many reasons, but horrible for many more. Yes, I learned the inner-workings of the financial system, spent time with countless brilliant minds, and socked away some serious cash, but the reasons I left were even more appealing. Minimum 12-hour days that consisted of sitting in one chair, staring at four computer screens, getting yelled at by both colleagues and clients, all while nursing a Ny-Quil hangover was just getting to be too much to bear.


That was not a great behavioral fit for me, and there’s nothing wrong with that. I knew that I could (and should) find work that I love doing and that allowed me to serve using my gifts, so I went in search of it even though I didn’t have a precise plan.


As I was exploring other options, I came across an amazing opportunity. I overheard a fellow coworker talking about how his son had just returned from a Semester at Sea. I wasn’t quite sure what that was, so I googled it, and sure enough, it’s exactly what you might think.


4 months. On a boat. With undergrads. Studying. And traveling.


That sounded like Heaven compared to my Ny-Quil Nightmare.


I convinced the Powers That Be at Semester at Sea to allow me to attend the trip as a post-grad, and starting in January of the following year, I was off to the ocean.


During that time, I studied design thinking and global sustainable entrepreneurship under the best and most-forward-thinking minds in that space. I worked with a start-up incubator and 12 different entrepreneurs. I met and learned from mentors ranging from the founder of Priceline to Archbishop Desmond Tutu. I traveled to 30 different countries and experienced countless cultures. I made life-long friendships.


But most importantly, I did some serious self-discovery.


What was I gifted at doing? What had my education taught me? Where was my heart? Who did I want to serve? What was I going to do, next?


And I got some serious answers.


Speaking, writing, and teaching. Psychology. Service. People in transition.


Talent development.


I realized I wanted to grow things—to grow people. To help people become the best version of themselves. To inspire people to stop settling for what’s good and start shooting for what’s great. To motivate people to reach and exceed their potential.


To help people do what they were created for… now!


Now, all of that was well and good, but I don’t remember seeing a job description anywhere in that diatribe.


But at least, I had a plan. Or better yet, the semblance of a plan.


So when I returned, I went on the hunt with a renewed vigor. I knew how to advocate for myself. I knew what opportunities were worth exploring (business development at a start-up) and which ones were easy to say “no” to (financial analyst at Merrill Lynch). I had a new sense of direction. I had something to put out into the universe so I could get something positive back.


And boy did I get it back, in spades.


9 months after my departure from the bank, I got an email. It was from an author I had written to almost one year prior. She had written a book that I found really inspirational, so I wrote to her in the hopes that we could connect. She wrote me back, apologizing for the delay, and hoping to speak to me soon.


I called.

We talked.


After one hour and a whole lot of story-telling, she offered me a job. Not just any job. A job, working right alongside her, in the talent development industry, in which I could write and speak and sell and use all those gifts and skills to impact people in precisely the way I had hoped.


She offered me my foot in the door into the industry in which I wanted to build a career.


So I moved back to Texas and started working for her.


And that, ladies and gentlemen, is my bridge.


Define where you were.

Define where you went.

Build a bridge in between.


Remember, you’re talking to human beings in an interview. They understand the trials and tribulations of a career. They understand that not every resume has a pretty bow on it. They understand that you’re human.


But it’s your job to make it make sense to them.


Do that by making it make sense to yourself.


Now, go. Write your own story.


I can’t wait to hear it.

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