Celebrating the Non-Linear Life

When did being a "Renaissance Person" become a role you kept off your resume?

I met up with a long-time friend recently whom I met in a different career era, at one of my first jobs out of college in New York City. I was a grunt at the time but still had to look like I made decent money because we worked at one of the top media companies in the world, and this era being more than 20 years pre-Covid, stylish business dress  really was a thing. I think that era was the last in which I would see my friend, Jim, wearing a suit.

Back in our media company days Jim was “on the business side,” but his friends knew of his diverse talents and numerous side hustles. An avid photographer, one of his many occupational facets, he staged and shot editorial pieces for major national women’s magazines. I recall an occasion walking past his office at the company where we met, him motioning me in, then holding up a magazine from a competitor company, pointing to a page with a sleek image on a white background and mouthing silently, “I did that.” 

He was an entrepreneur, having launched a line of products for kids stimulating their creativity, and an inventor, developing and patenting many product concepts, most notably a razor with an additional blade for a notoriously hard-to-reach spot on a man’s face (which he eventually sold to the top player in the category). He liked to entertain, and when he did you could not help but notice his penchant for collecting scrap-metal and industrial-style antiques. Point to one and he could tell you its history–the shop, garage sale, or street corner where he’d acquired it.

Much has happened since our days in New York City: I moved to San Francisco to pursue building a startup (not yet the one I co-founded), and Jim arrived a few years later, seeking a fresh change in his life and career . He had worked in leadership roles in several companies since and was ready for something different. He had talked about relocating for some time, but I knew he was serious when he unloaded an elephant’s weight of collectibles to come West. 

Since his move, now nearly 20 years ago, he’s held BD and strategic partnership roles in marketing and digital agencies, built and launched a content marketing practice for a multinational media company in LATAM, invented multiple new products, added to his photography portfolio, kindly agreed to photograph my wedding and regularly take my professional headshots, volunteered to help at friends’ professional events that intrigued him (including my own), became a competitive sailing racer, held numerous yard sales in an attempt to reduce the footprint of his still-growing picks from the streets of San Francisco, created a  garden at his apartment building (in a deal he cut with his landlord, who complained about the overflow of trash gathering in the shared yard), became a focused caregiver to his mother, and shot a TV show pilot of his exploits salvaging urban treasure.

Oh and did I mention he started a side business during Covid that spawned from referrals of friends he helped with home-improvement projects?

So it surprised me and it didn’t when Jim shared that he was struggling with updating his resume in a way that “told his story”.

“You see,” he explained, as he took out a random scrap of paper, something he did often to ensure he captured inspirational thoughts or ideas in real-time. “Here’s what a resume is supposed to look like,” and he drew a classic, straight, upwardly directed line, denoting a clear, singular, linear career path. 

“But this,” he said,”is mine.” And with that he drew this:

My first instinct was to play the product marketer and construct appropriate messaging to spackle the cracks in between Jim’s many occupational interludes, to construct a narrative thread that would somehow make all of his myriad experiences and passions make perfect business sense.

But I couldn’t – more like I wouldn’t.

It dawned on me: Why should he have to gloss over some of his most meaningful, formative chapters in life in order to be an attractive hire? And, if the smooth, uncracked version is what gets him a job, is that even a role that he necessarily wants or that can fulfill him?

Of course, sometimes we need to simply pay the rent and hold jobs that sustain that need. Conventionally these roles have been the ones that take up 100% of our work time, and sometimes more than that. But should they?

I had the immense pleasure of interviewing “human Venn diagram,” Harvard senior lecturer, entrepreneur, performer, wife, mother, and author or The Portfolio Life Christina Wallace on this very subject. And her advice on risk-proofing your life for fulfillment by diversifying your portfolio of career activities really spoke to me.

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Premium Members: For inspiration on how (and why!) to set up your portfolio life, tune into our “In the Trenches” podcast conversation with Optionality Advisory Committee member, Harvard Senior Lecturer, “Human Venn Diagram,” and author of The Portfolio Life Christina Wallace January 19.

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Reading Christina’s book, I felt as though a weight had been lifted. A lifetime side hustler, I’ve held whole careers in the shadows, coming out, so to speak, only during transitional periods in-between full-time roles, to share–maybe confess–my predilection for opportunities other than moving my employer’s business up and to the right. I know I’m not alone, hiding my creativity, non-profit-generating superpowers, desire to travel, pregnancies, until they were undeniably conspicuous. In some cases there was no forcing function and I kept these parts of my Venn diagram to myself, leading to deep suffering.

But why should we hide whole parts of ourselves from the work we do, or want to do? Why should we hide the rich experiences that make our skills, our work, unique? 

Rather than obsess about how to pad, or spackle, or rework, our resumes, maybe our time would be better spent refocusing and refining our personal Venn diagrams. This has become my pursuit.

Here’s to the polymaths, the multi-hyphenates, the keepers of scraps of paper, and to imperfect, authentically drawn, squiggly lines.