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April 11, 2024

On Portfolio Careers

For years, I thought my career was all wrong. Not because it was immoral. And not because it was going poorly, either. 

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For years, I thought my career was all wrong. 

Not because it was immoral.

And not because it was going poorly, either. 

I saw my self-care business, Inner Workout, support so many people during the height of the pandemic.

Through it, I certified three cohorts of people in a practice I developed. We launched a product with a Kickstarter, and it was over 200% funded. I was in talks about a book deal! 

Amid what most people would call success, I spent most of the sessions with my coach convinced something was off in my career. 

Sure, I was a business owner. 

But as soon as anyone complemented my “success” as a business owner, I compulsively told them about my work as a facilitator and consultant with Google and with FranklinCovey.

I called it adding context back then. I wanted people to know how I made full-time self-employment work. 

Transparency is important to me, but, if I’m honest, this disclosure wasn’t just about transparency. 

I was squirming within a construct that no longer fit me. 

Even though those contracts working in and with Fortune 500 companies didn’t change the fact that I was fully self-employed, it felt like I was cheating at business ownership. 

It was an involuntary rebellion against the Core Career Teaching. You pick something, and that something is supposed to provide your primary identity and source of income.

I tried to fold myself into that model. I convinced myself that the other things going on in my career were lily pads meant to transition me into my final form as only a business owner before they drifted into the distance. 

Those extra engagements were less transitory than lily pads. Sturdier too. As it turns out, I enjoy having a multi-faceted career. 

Correction: I enjoy it once I stop telling myself it’s wrong. 

Somewhere along the way, I picked up the term portfolio career. Charles Handy gave us that sweet exhalation of a concept in the 90s.

I call it an exhale because I used to have a mini existential crisis before introducing myself to new colleagues. 

What do I actually do?  I’d ask myself. And how do I explain it before my hyperventilation causes me to pass out or my externalized confusion causes the other person’s eyes to glaze over—or both! 

Now I say something like: I have a portfolio career exploring how people experience well-being and fulfillment in all aspects of their life. 

If they’re curious, they ask me to say more. If not, the conversation keeps rolling. 

This concept gave me a renewed sense of career confidence. 

Maybe it’ll do the same for you. 

What is a portfolio career?

The basic tenet of a portfolio career is that you have multiple roles or jobs at any given time. 

Sometimes you’re applying the same skillset in different contexts. Think of a psychologist who has a private practice, teaches a college class each semester, and is an advisor for a mental health startup. 

Journalist Taylor Lorenz, for example, is a tech columnist for the Wall Street Journal while also hosting a video podcast, Power User, with Vox Media.

Or maybe you’re more like me, using a variety of skills in different environments. In my career, I use my gifts as a writer, facilitator, operator, speaker, and coach. I’ve used these skills with high school students and corporate executives in libraries and Zoom rooms and conference centers alike.

There’s a lot of overlap in my skillsets, but that’s not a prerequisite for a portfolio career. 

You might be a fine art photographer who also codes software or a bookkeeper who bakes bespoke birthday cakes. (Ok, I got a little carried away with the alliteration there.)

But you get my point. There are as many ways to approach portfolio careers as there are people brave enough to embrace them and all their benefits.

What are the benefits of a portfolio career?

If a traditional career is a prix fixe menu, a portfolio career is a buffet. You get to fill up your career plate with the things you love while going easy on the tasks that make your stomach turn. 

Portfolio careers offer flexibility 

I should’ve added an asterisk here. Only well-managed portfolio careers offer autonomy. You set your own pace and standards. Choose when you work, what you work on, and who you work with.

You’d be hard-pressed to find me in a meeting before 10 am because my brain’s at its best in the mornings, and I try to reserve that time for myself. Throughout the year, I recalibrate my commitments to create the space I need in my work or personal life. 

Others use their portfolio career flexibility to volunteer at their kids’ extracurricular activities or build a travel schedule around Comic Cons.

Portfolio careers diversify your income

Two of the organizations I work with have done layoffs in the past year. I have friends who are months into job searches, and I hear small business owners quietly wonder if their business is going to make it another year. 

Portfolio careers don’t make you immune to economic conditions, but it’s harder for the well to dry up when it’s drawing from multiple sources. 

Portfolio careers keep things interesting

Fun fact: I sought out an ADHD diagnosis when I realized I’d built a portfolio career as an inadvertent coping mechanism. The novelty is necessary. Who can do the same thing day in and day out? Not me. I never made it over two years in a corporate setting. 

You don’t need a dopamine-dysregulated brain like mine to want a portfolio career. Maybe you love strategizing but loathe execution. Or you’d rather listen to Baby Shark on repeat than work with only one client or within a single industry. 

Portfolio careers are like standing on a BOSU ball. When approached with intention, they provide just enough instability to keep you fully engaged.

And when portfolio careers aren’t approached with intention, well, let’s get into it...

What are the drawbacks of a portfolio career?

Your portfolio career is up to you

Saying yes to a portfolio career means sending the idea of a set career path off with an air kiss and a wave. There’s no rubric of core competencies that will put you in the running for a promotion. Your growth and development are entirely up to you. You create the structure. You build the opportunities. It’s as liberating as it is overwhelming. 

On the best days, you feel possibility coursing through your system. On the worst days, you’ll have said yes to far too many things that still somehow aren’t paying you enough money. You’ll miss the steady rhythm of bi-weekly direct deposits and clearly defined growth trajectories. 

Portfolio careers can burn you out 

The concept of well-being plays a large role in my portfolio career. In my book, Inner Workout, I talk about the origins of the term burnout, and I dedicated a whole season of the Inner Warmup podcast to the concept. 

People think that finding fulfilling work is the antidote to burnout. After all, don’t we get burned out because of the external pressure—the deadlines, the miscommunication, the unreasonable expectations? 

Not always. When you’re more invested in your work, you’re more susceptible to burnout. That intrinsic motivation tempts you to push your limits. 

If you’re serious about having a portfolio career for the long term, learn how to do it sustainably.

Portfolio careers are harder to brand

One of my earliest business ventures was in the brand strategy space. Back then, I bought into the advice of having a niche. “Just be known for one thing,” they said. “And the opportunities will flow to you.” 

It feels like we’re playing a game of telephone, and the simplest message wins. People understand what you do, how to work with you, and for what opportunities they should recommend you. 

When you have a portfolio career, you’re adding a layer of complexity to the telephone game. This isn’t a career-ender. It just means something—like an aspect of what you do or the clientele you work with—might get lost in translation. 

Here are a few ways to deal: 

Connect the dots.

I picked this one up from Michelle Pellizzon Lipsitz. She encouraged me to find a core question I’m trying to answer through my work. 

My core question is, “How can we experience well-being and fulfillment in our work and lives?” Everything I do, from building an app that helps people find more time for self-care to helping leaders be better coaches to making paper as a form of emotional processing, is a way to answer that question. 

When I’m talking about my work to other people, I share this unifying statement: I help people get closer to what they really want in their lives, careers, and businesses. It’s more active, and it’s in plain English. Unless you’re taking a philosophy class, fulfillment doesn’t come up on a daily basis. But I hear people talk about what they want all the time. 

Mallory Contois, a startup veteran with a portfolio career of her own, suggests you define a thesis for your portfolio career the same way a venture capitalist defines a thesis for their fund.  

A thesis is a unifying statement with a point-of-view. What do you believe, and how does that belief impact your career choices?

Mallory offers this template for building a portfolio career thesis:

I spend my time focusing on things that ____, because I believe _____ and I want to create ______ impact.

Talk about what you do often

Once you’ve connected the dots for yourself, it’s time to share that perspective with others. People who choose portfolio careers need to talk about what they do—a lot. Find yourself at the border of what you fear is annoying, and then talk about it a little more. (I need to take my own advice here.

Talking about what you do doesn’t necessarily mean talking about yourself. Share client results. Add commentary to a news story. Offer an anecdote. 

Example: If you just spoke at an event, talk about the question someone asked you during the Q + A, how you answered then, and how you’d answer now that you’ve given it more thought. Now people remember that you’re a speaker without you having to design a graphic in Canva to remind them. 

Don’t let anyone’s lack of understanding limit you

Portfolio careers are only getting more popular, but there are still plenty of people who can’t—or choose not to—understand multi-faceted careers. There’s nothing wrong with you. To use tech terminology, you’re an early adopter. Other folks will come around, but it’ll take a bit for them to wrap their brains around these unfamiliar career configurations. 

I’m six years into my portfolio career. It’s surprised me, delighted me, and, yes, at times disappointed me. But I couldn’t imagine approaching my career any other way.

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