When One Career Isn’t Enough

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Karen Deans is an artist, illustrator and designer. Her online Portfolio shows some of her work, ranging from colorful posters to clever postcards, from fine art to business logos, magazine covers and book illustrations.

And Karen is also a writer.  Among other projects, she is the author of children’s books, like the charming “Swing Sisters,”which tells the true story of African-American orphans back in segregated Mississippi, who traveled the globe as the first all-girl swing band.

I recall years ago, when it appeared that multi-talented Karen often struggled to pick one career path, trying to decide whether she should be an artist, or a writer? Or maybe a full-time Mom?

Now, Karen says, she wakes up early every morning, excited to plunge into a packed and varied workday. Her children are grown, which has brought her new flexibility. But much of her joy and energy seem to come from the awareness that she doesn’t have to choose just one career. She is intensely pursuing her writing career, but she also is building on her successes as an artist.

Karen has embraced the fact that, for her, two demanding careers are better than one.

A lot of people have more than one job

As a coach, I’ve noticed that a growing number of people are choosing to pursue more than one career at a time. For many money is the driver, like the young journalist who makes rent by moonlighting as a bartender. But others yearn for additional fulfillment or adventure, like the lawyer who has a side gig as a photographer, and the accountant who spends weekends working as a personal chef.

It’s increasingly common to combine a fulltime job in one field with a side hustle in another. A part-time job on the side can be rewarding, and not only for the extra cash. Your second job can help you build new skills, expand your network and reduce the risk as you move tentatively in a new direction. And if your day job is starting to feel dull, an entrepreneurial sideline can bring you the excitement of new challenges.

 Multiple careers can help manage risks

Karen, who lives in Bethesda, Maryland, is succeeding on a course that can be trickier than simply taking on a second job. She is managing what is sometimes called a “portfolio career,“and has curated a healthy collection of varied jobs and projects. Her work is roughly divided into two paths: writing for children, and being a graphic designer and illustrator.

Event program cover by Karen Deans

Karen told me, “I love both career endeavors. They are challenging in different ways, but ultimately the practice of each gives me great joy.”But freelance projects can be risky, and some are more uncertain than others. “The writing for children isn’t a for-hire project. It is, in some ways, speculative. Even with two picture books under my belt, every next book idea I pursue is up against big odds of ever seeing the light of day.”

“On the other side of the coin is my contract design and illustration work. I pursued this path after realizing that the book industry is not going to generate enough regular income or work to put all my eggs in that basket,”she said. So, Karen went back to school to hone her digital arts skills, mastering several Adobe programs.

“I’m about to receive my Associates Degree in Graphic Design. I’m like a poster child for the happy adult learner. Now I have all of these new skills at my disposal, and they are very marketable. And I really enjoy this work, too, which is a bonus,”Karen said.

With a full portfolio you must prioritize

I’ve heard clients say that having two careers can make it easier to manage time and set priorities, because it forces you to get rid of low reward items on your calendar or “to-do”list. I asked Karen how, with so many projects going on, she manages her time.

“I am generally a very organized person,”she said. “but when you are juggling many projects, prioritizing can still be a challenge. Like today. I have accepted a job designing a client’s website. I don’t really have the time to do that, given my other commitments. But I have the need, as it will generate income that otherwise wouldn’t be there. So I make a decision. I say: Okay, you will not be doing such-and-such next weekend. Instead, you will be working on this website.”

Karen carefully maps out a schedule of her tasks a week ahead, breaking her work calendar into defined blocks. “I’m always thinking several steps ahead to prioritize anything that is deadline-related. Unfortunately, for me, my book projects get pushed back because they are still in the proposal stage, and have not crossed over into contract stage, which provides deadlines. That’s when the writing will be pushed forward, and I will have to reshuffle my work priorities.”

A mixed portfolio can raise your profile and expand your network

Having two careers can translate into a wider circle of contacts, resulting in more exposure and longer client lists for both pursuits. Karen said, “I got one of my biggest graphic design jobs from someone I know in my children’s book circle. It seems completely unrelated, but then it isn’t. The more people you know, who know what you can do for them, the better. It’s a broadening of your network beyond the specialty that people know you for.”

Skills built in one field can stimulate creativity and help build expertise in another.

Projects in one type of career can give you a deeper skill set and better perspective about your work in another. “My writing comes in handy for my design work,”Karen said. “I have been doing layout work for magazines. While technically I am not serving in the capacity as editor, I often am like a third eye for the editor, and will alert the editor to language that might not work given the audience.”

And when things are going particularly well in one pursuit, the energy, different ideas and optimism can spill over to your other calling, where progress feels slower. “When I get discouraged, in either direction, because the work isn’t there, I always know I can turn to the other gig, not only to be productive, but also to come at it fresh and build something new in that direction.”Karen said.

Test the waters before you plunge

Like Karen, I love having a range of clients and projects. Working for myself this way brings me variety, opportunities to learn new skills, and interaction with a diverse circle of people. But I knew that even a full slate of contract work probably wouldn’t bring the benefits and relative security of working for a company. So I didn’t launch my portfolio career until I had a safety net, including retirement plans and a supportive spouse.

If you’re intrigued by the flexibility and adventure of a portfolio career, I urge you to plan ahead, finding ways you like to manage your clients, and lining up your resources. And instead of just quitting your day job, consider starting with a side hustle. It needn’t be an actual job. You can test whether you enjoy this kind of juggling by taking on several kinds of freelance projects.

Subscribe to Bev’s podcast “Jazzed About Work” at Apple Podcasts or Google Play.

Beverly Jones, an alum of Ohio University, is a former lawyer and Fortune 500 executive, an executive and transitions coach, and a leadership consultant with a broad and varied practice. Her column appears at Clearways Consulting LLC. Republshed with permission. For archives and additional content, visit the Clearways Consulting website.