How to design a portfolio career that works: These Renaissance women show how it’s done 

Gabriela Flax spent the first part of her career working in tech as a product manager. And while every day was different and varied, there were aspects of it that were causing her burnout.

“I’ve always really enjoyed the product marketing aspect of my work,” she says. “I really like talking to end-users about ‘Hey, this is how this thing helps you’ and how to articulate that.” However, she wasn’t able to work on it as much as she would have liked.

At the same time, Flax was in her 20s, living in London, and had stopped drinking alcohol. She began posting her journey in social media, talking about bars and places that were non-alcohol related.

Flax recalls, “The more and more I did that, I started having brands reaching out to me saying, Hey, we’d love to partner with you. We have this event coming up—would you come and speak about what it’s like living in London in your 20s and not drinking?”

By weekends and nights, Flax was organizing events and creating a lot of user-generated content for brands. She was able to exercise her creative muscle and passion for marketing, all while getting paid for it. Eventually, she left her tech job to pursue what is now commonly known as a portfolio career: where individuals make a living from multiple projects and streams of income. Today, she continues to do events and marketing for non-alcoholic beverage brands, alongside her career-coaching business, Pivot School.

Making money through multiple means is not a new thing. But in a landscape where side-hustles, gig work, and freelance contracts have become the norm and at times necessary, Flax’s career trajectory is becoming more and more common.

A solution to burnout

Flax pursued a portfolio career because she felt burned out in her full-time tech job. The same can be said for Anna MacKenzie, who had the same feeling about being a founder. After spending a career in beauty and tech, MacKenzie cofounded a successful, award-winning podcast and events business. But as a “multi-passionate generalist,” MacKenzie eventually felt burned out.

“When you’re a founder, you have to pour absolutely everything into a brand and business,” she says. “I really felt this desire to do multiple things. The reason that I pivoted into a portfolio career, which I didn’t have the language for at the time, was that I was looking for something that was halfway between being an employee and being a founder.”

A portfolio career, MacKenzie explains, allows her to maintain the freedom and flexibility and control of her earning potential. However, unlike being a founder, it didn’t require “the responsibility of building a brand, building a business, and having contractors or a team.”

Today, MacKenzie’s work setup spans advising early-stage beauty startups on how to get into major retailers like Sephora, mentoring, and selling digital products that guide people in building these types of careers. She also does fractional work for tech companies, which is when a high-level professional provides their expertise to a company and joins a team on a temporary, contract, or project basis. This is slightly different than a consultant, who typically plays more of an advisory role and isn’t often embedded in a team.

But as Fast Company covered in a previous story about this trend, pursuing it can have the trappings of hustle culture. Rice University management professor Scott Sonenshein said that self-employed portfolio careerists can have trouble setting boundaries when it comes to workload. He explained, “You might feel like you always need to be working because there’s more incremental money to be earned for taking on additional gigs, as opposed to what you might be doing if you were working full-time for a traditional employer.”

Being able to maintain a sense of control

For Tracie Sponenberg, preventing burnout is about being intentional with her schedule and work environment.

The former HR executive coach, keynote speaker, and consultant is having what she calls “one of the busiest months of her life.” Yet she feels nowhere close to burning out. For a few days, she can take a trip to South Carolina and work while overlooking the ocean. Things like that, she explains, “really help.”

Like Flax, Sponenberg experienced burnout during her corporate career (in Sponenberg’s case, in the aftermath of the pandemic). But since she’s been on her own, she’s been able to stay away from it. The decision to do this work, she explains, “and whether I succeed or fail is on me.” That sense of control, Sponenberg says, is what makes that feel like “huge relief” rather than a heavy burden.

For Flax, that sense of control has been extremely crucial to sustaining a portfolio career. She is aware that what hers looks like right now can change and evolve in the future.

“I think that’s the fun part,” she says. “If one piece works today, because you’re the one who is in charge of it, you also have the capacity to turn that part of the engine off.” If there are certain activities that no longer resonate, she explains, “I don’t have to ask permission for someone to stop doing that.”

Engineering a form of stability

Like any entrepreneurial venture, pursuing a this kind of employment does come with risks.

For MacKenzie, this was familiar territory as a founder. But when she decided to pivot into a portfolio career, she landed a lucrative contract, thanks to her extensive network that she’d built during her corporate career and previous business. Because of that, she was able to take her time to experiment and explore with what she wanted to do next. Having that kind of financial security without the stability of a full-time job is something that MacKenzie continues to prioritize.

“To this day, I’ve always had one reliable income stream. Whether that’s a client or a product, I know we’ll bring in enough revenue to cover my life,” she says.

Having this structure in place can also help prevent individuals from putting themselves in a position where they’re constantly selling, which can be a recipe for burnout. While Flax asserts that no contract roles are perfectly safe, being a freelancer where you’re having to pitch your services every single day is quite different from being a contractor with two fractional jobs who do a little bit of writing on the side.

What it takes to succeed

For some, this can also be a temporary arrangement. It can also be a way to build a career around a lifestyle change. MacKenzie believes that it’s a structure that new parents can benefit from, especially for those who are highly skilled.

“There’s an inherent flexibility in terms of how you design and structure your career,” she says. She also believes that it’s a strategic way for people to scale their careers outside of just client work.

But it’s not an arrangement that is suitable for everyone, at least for the long term. Flax says that she has seen many different archetypes try out portfolio careers. And in that time, she’s seen those with similar personality types and motivations both thrive and struggle.

The willingness to improve your risk tolerance

One of the key things that she believes will be crucial is one’s appetite for risk. You need to be someone who “finds the process of instability as something that they can gamify [and] conquer,” Flax explains. When people tell her that they want to pursue this path, she encourages them go ahead only if “not doing so will eat away at you.”

In many instances, this also requires you to put yourself out there, network, and build your personal brand. “If that’s not a line of activity that you’re willing to go down, it’s not impossible, but it’s going to make it harder,” she says.

If you don’t have a high tolerance for risk but still want to go down this path, Flax says, “you’ve got to want to strengthen that muscle.” And that can start when you’re still in your corporate job. Maybe you volunteer for a project that has the potential to fail big. Or perhaps you look for micro examples in your personal life where you can get more exposure to risks.

Alternatively, you can just take the jump and see how you react. Flax suggests, however, having a backup plan you can return to if you do decide that it isn’t for you.

Self-awareness and sustainability

Ultimately, maintaining a portfolio career for the long term requires a good sense of self-awareness.

Sponenberg, for example, knows what she’s good at (and what’s she’s not). When she started her business, she knew that cold calling and traditional business development wasn’t her forte. “What I do know how to do is help people and be really useful and offer advice,” she explains. And due to her multi-decade HR career in manufacturing and distribution, companies came to her for help. So she worked hard to be the go-to person for them anytime they had a people issue.

Flax also says that understanding your working style and tailoring your portfolio career around that is also important. This type of structure, she says is “great for people who are multi-hyphenates, who have so different interests and want to exercise those different parts. But be very conscious if context switching is going to cause you whiplash,” she says.

Flax recommends that at the start, you should be very conscious about how many components you introduce. This way, “you don’t feel overwhelmed by the ecosystem that you’ve built yourself,” she explains. “It can have two pieces to it that scratch very different parts of your brain,” she says. “It doesn’t need to look like a web.”

Accepting that it’s not for everyone

And if it turns out that it’s not something you’re able (or want) to sustain, Flax asserts that there’s no shame in going back to a nine-to-five.

“It is so okay to have a corporate job that pays your bills that you enjoy, ” she says. “I think there’s a bit of an anti-corporate or anti nine-to-five or anti-traditional work rhetoric that’s going on right now, largely driven by the freelance portfolio career self-employment world. It is not for everyone, and that is so okay.”

“It is one of the many ways to think about work. It is not the only way. My personal opinion is that yes, we are moving more towards a decentralized type of work. Having a portfolio career may, in the long term or the medium term, serve you well in that way. But I don’t think in our lifetime, there’s a reality in which no one has a corporate job anymore.”

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