Have a Winding Career Path? How to Explain it With Ease

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A few years ago, I was transitioning from one job to the next. I went from education consultant to  risk management consultant to recruiter, at which point I decided I wanted to move into human resource management. Explain that one, Roland, I thought to myself.

Although I knew that what I wanted next made sense on some inexplicable level to me, I didn’t know how I was going to convince my friends and family—not to mention interviewers—that it was a logical move. In order to get others on board, I knew needed to be able to communicate my past in a way that actually made sense on a non-psychic level.

My solution—and the solution for anyone in a similar boat? Telling a really good story about your experiences.

A story isn’t a list of your awards or accomplishments—that’s your resume. It’s what lies between the lines. It’s not the individual jobs you secured in the past, but the challenges and decision points that shaped their chronology.

Want to put your story together to make some sense of your winding career path? Follow the steps below, and you’ll be on your way.

1. List What You Loved—and Hated—From Each Job or Experience You’ve Had

This love-hate list will tell you what you chose to carry with you into your next experience from the last and what you chose to simply leave behind. You can start to put it together in this way:

I wholeheartedly loved _______, _______, and _______ about that role.

_______ didn’t speak to my passion for (or ability to) ________.

Although I excelled at ________, ________ wasn’t for me.

2. Reframe What You Hated Into What You Learned About Yourself

This is a key step because it turns those negative, “stuck” points in your career into reasons behind your movements. For each “hated” item in your list, note at least one thing that you learned from that experience that moved you to look into something new.

That project taught me that my real strength was in ________, and I decided to take action in that direction.

Although the work was fantastic there, I realized that ________ was very important to me in my work environment, and that led me to ________.

3. Bring in Thoughts About Who You Are as a Person

What is it that has shaped who you are today? What influences—or influencers—have informed your passions and interests? Have you always loved burying yourself in a good book, or picking up the latest trends, or documenting an event? Are these passions that you’re looking to bring into your everyday work?

A lot of times we discount this part of our story, but you absolutely shouldn’t! After all, how can you tell a great story about yourself without injecting a big dose of what makes you tick? What makes this step difficult is that there isn’t always evidence for these kinds of things on paper, like there is for your work experiences, so it may feel soft and unofficial. But it’s also what makes you human, and what makes you the person that your potential employer will want on his or her team.

As a child, I immersed myself in ________, and I know it’s time for me to follow that lead. What comes naturally works best!

Until now, I’ve ignored something my friends, family, and teachers always said about me: I ________.

My core belief is________, and I apply that to every role I take on.

4. Connect Your Dots

At this point, it’s time to pull together why your answers to the steps above make perfect, logical sense with what you’re asking for right now and where you’re headed in the future.

Connect the specific things you’ve loved and learned from your past experiences, as well as things about who you are as a person, to specific possibilities in your new venture.

I learned ________ and ________, and I’m eager to put that to use going forward, specifically in ________.

Everything I’ve learned until this point, especially ________, ________, and ________, has prepared me for this next step.

While ________ may not seem to apply to this role, I really think the understanding I gained about ________ will help me succeed.

Remember that your story is in the in-between. It’s the “why” behind your leaps and jumps. And, the more seemingly arbitrary or diverse those experiences, then all the more important it is to capture your story so that you can communicate it to others.

Now, here’s the final step: Speak your story out loud—where you started, what you learned along the way, and where you’re headed. Once the story feels right to you? You’re ready to go out and tell the world.

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