Turning your complex career path into a coherent story

By Anna Ranieri

It’s hard when you’ve had a non-standard career trajectory and you want to re-enter the work force, move to a higher position, or enter a new field. 

Will a marketing firm see you as a good leadership candidate if you’ve always been a professional fundraiser and small business owner? Would a medical devices company view you as capable of learning their product line if you’ve worked in the automobile or hospitality industries? Will a corporate hiring manager take you seriously if you’ve spent the last 10 years mostly volunteering? 

In these cases, you may not be the slam-dunk candidate. But you’re more likely to convince an enlightened hiring manager, venture funder, or board member if you can articulate how all of your varied experiences and skills actually make you a better candidate than the conventional applicant.

How do you do that? You tell your story in a way that connects the dots. Unlike a more typical candidate, you have to assure that your audience can identify the thread that runs through your career narrative and make sense of your varied skills, training, experiences, and choices.

First, if others are ever going to understand your trajectory, you have to make sense of it yourself. Identify the themes that run through your professional life. This will take some concentration and reflection. In fact, it may be something that a long-time friend, colleague, or family member identifies before you do:

“You’ve always liked building things, ever since you got a set of wooden blocks for your birthday.”

“You never settle for the status quo; no matter where you’ve worked and what you’ve done, you’re always looking to create something new.”

“You motivate people, whether you’re running the PTA, leading a team at work, or finding people to join the town council.”

Not long ago I recognized a coherent theme in my working life and I’ve shared it with my career-coaching clients as an example of how to capture that story. I’d taken Latin all through high school and loved translating the ancient tale of the Aeneid into something resembling modern English. I majored in literature in college, reading in Italian and French, and almost accepted a job as a translator after I got my degree, but went to work as a fundraiser for my university instead. I went to business school a few years later and then worked in marketing. Soon after I returned to institutional development (the uptown name for fundraising) while getting degrees in counseling psychology. When I finished my PhD, I continued my private practice — but also added career counseling and executive coaching to my professional mix.

Told like that, it seems like a trail of somewhat disconnected experiences. But what ties it all together is the process of translating; translating a text from one language to another, translating the significance of an academic program to a potential donor, translating the benefits of a product to consumers, translating a client’s concerns into possible ways forward, and helping clients to translate their own feelings, thoughts or capabilities to others. Eureka!

Ask yourself: what are the kinds of tasks that I like to do? Consider the kinds of processes and activities you’ve enjoyed most in school, at work, as a volunteer, a family member, or friend. Think about, or ask others, what may tie these together. Without a nod to a specific position or title, you may find that the general motif is being an effective listener, building relationships, solving complex problems, re-thinking standard ways of operating, creating a new vision, or motivating people to take action. This is what you’ve most enjoyed (and therefore tend to do well, because you’ve spent time at it). This theme that emerges from your experience may tie together a wide variety of activities with a common thread that unites them all.

Once you’ve identified your own theme, the next step is to tell your story. Craft it and take any opportunity to share it with those who can help advance your career: hiring managers, funders, colleagues, publicists, or the acquaintance you meet at a networking event or a local barbecue.

Forget titles, positions, and industries. Focus on what you’re best at, using terms that pull together your diverse experiences, those seemingly unrelated industries and the serendipitous opportunities you’ve had to learn something new. Don’t be humble: Leave off the: “Well, I’ve never done exactly this before, but…”. Instead, say with confidence, “Here’s what I do well”.

A few examples:

“I’m a relationship builder, and I’ve always been commended for my ability to listen to people’s needs and help craft a solution for them.”

“Complex problem-solving is exciting to me. I love to delve into thorny problems, work hard at teasing out the issues at hand, and get to the heart of the matter.”

“I thrive on creative thinking, whether I’m coming up with a new product or a new way of working. It’s impossible for me to settle for the status quo when I see that my team can create something better.”

You can talk about previously-held positions or companies later. First, establish the theme you want your audience to understand before they get stuck wondering, “But does he/she have enough time/experience/training?” You’ve connected the dots so they don’t have to.

This theme can then become your proverbial calling card. Include it:

  • At the top of your resume, at the beginning of your elevator pitch, and in your descriptions to recruiters and in job interviews.
  • In your pitch to possible funders, your marketing materials, and conversational openers.
  • In your request to your boss for a promotion.

After all, you want to assure that others understand your competencies and the crystal clear rationale for your landing that job, that funding or that promotion. You can’t expect anyone else to do that for you, though: you have to connect the dots.

This article first appeared at HBR