The Many Faces of Career Reinvention

You might feel like a lobster changing shells, a butterfly still stuck in cocoon state, maybe Madonna or Taylor (depending on who reigns pop in your heart) breaking up with one part of yourself and searching for the style, soul and grit of your next album.

Hello, reinvention.

You might not even be able to articulate it, all you know is that you're a bit lost and waiting for a sign. You can tell you're not "done". You can feel that there is something else waiting for you out there.

It probably feels that way because there's not just one way a career change happens. There isn't a roadmap, a clear set of rules.

There's not even one kind of career change, though they always seem to get lumped in together. I've tried to lump them in together, but the challenges, feelings, and examples of people who've been there, done that—they defy lumping.

For creative careers, change is not only a constant in the work that you do, but in how you approach your career. There are new mediums, new perspectives, new tools and mediums being invented and realized all the time.

A career change starts to look less like a career change as we've traditionally come to know them—hard pivots and 180s—and more like iterative steps on the path to a portfolio and body of work tied to intent and philosophy rather than role or even skill.

I want to talk about the rainbow of career changes that exist, and dive into some examples, challenges and advantages beyond the oft-highlighted, big grand career change we recognize most. Because any kind of change, just because you want it, is reason enough to go and get it.

There is the shadow career change, common for a lot of creative careers, where sometimes one or more day jobs are necessary to sustain a life until the work pays off and turns a side hustle or hobby into a career.

Stephen King often had two jobs while he wrote on the side. Whoopi Goldberg was a licensed beautician and worked as a morgue beautician before she became famous as an actress and comedian. Phil Knight, founder of Nike, worked for years as an accountant before his side hustle, selling shoes, blew up big.

Challenges: The challenge here is not burning out or giving up before you get there. In order to sustain yourself mentally, emotionally and financially, you may not have put a lot of effort into moving up in a traditional career setting, choosing instead to take jobs that allow you the time and energy to be creative outside of it. You may find yourself in a dance between wanting financial security and creative independence and that can feel like a hard choice to make when your peers seem to be getting ahead and an uncertain future awaits you.

Your advantage? I call this one a shadow career change because it's not an internal career change, and that in itself takes away a lot of the uncertainty common to career changes. These people often know exactly what they want to do, and the kind of success they're looking for is often the "make it big" or continue in obscurity kind. This kind of career change happens with time, effort and maybe a bit of luck, when the type of work they're doing is well received enough to swap or take the place of a day job. The advantage is focus: you're not exploring or unsure. You're probably spending your energy wisely and you're not wasting time.

Career changes happen for people who are already successful too; they're not just a way to escape a bleak situation.

Vera Wang has had many successful careers. As a teenager, she was a world-class figure skater. After her Olympic dreams were shattered when she failed to make the US team, she went to a liberal arts college and worked in retail before becoming the youngest ever editor at Vogue, without any journalism or fashion training. Then, she became design director at Ralph Lauren, yet still without any formal fashion or design training. And do I have to tell the rest of the story? You know Vera Wang best for her bridal business, and she even recently reinvented herself as a Gen Z fashion influencer...in her 70s.

Challenges: With this kind of career change, you may be doubtful. You may spend even longer than other career changers to make the pivot and the choice, not because you're risking more financially, but because you're risking safety and the net of knowing what you're good at and having others recognize it too. You may even stay too long. You may have lost your internal compass, listening to others who you respect for cues on what you should do next. You may be hearing voices of people saying that you shouldn't risk a good thing, and besides, you've made a name for yourself. Do you really want to start over?

Your advantage? You have safety, security and a network, and this network can be transferable to your next career too. You're also experienced and maybe even a leader in your field; that means you probably have a bank of soft skills as well as a mind for strategy, two super important things for "late bloomers" who, instead of banking on specialized skills that can take years and years to build up, may instead find their success through leadership and soft skills, and the ability to get things done, influence people, and if your dream career is entrepreneurial in nature, hire and grow a team. Oh yeah, and chances are, you have money too, more money than the you at 21 did. Money can't buy happiness, but it sure can buy resources, people, time and independence.

There's the iterative career changer, someone who moves into or builds a tangential or expanded career rather than make an entire 180. These are the stealth career changers.

Walt Disney was working for a newspaper as an animator when he was fired because he "lacked creativity". He then went on to found a company synonymous with imagination and innovation; Disney's engineers are even called "Imagineers". While the scale of this career change blew up because we all know Disney, being fired was a catalyst for Disney to build a company that took his love of animation (aka what he was being paid for) and build a new context for it: by starting his own company. He didn't technically change his passion or his vision; he just expanded it by thinking outside the box of his role (animator) and into an entire field (animation).

Most people's career changes fit into this category, even if they're not building Disney-esque companies. They don't even realize that change, through the course of their career (aka what a "career change" technically is), is what's happening, every time they try a slightly different role, every time they're promoted upwards or sideways too.

Maybe they're in the same field (or maybe not).

Challenges: Because this kind of career change doesn't necessarily feel like one (even though it can still include major risk-taking)—it could just feel like doing what you've done before, but bigger and better. That means it may be easy to slip into a mismatched career simply because it's in your periphery. You may be so used to trying different things that rather than take the time to be proactive and really consider where you want to go next, it may feel like you're making the easy choice. So, are you expanding because you want to or because you feel like you have to? Is this the career change you want? What else is there? Be careful not to get stuck in permanent career purgatory, where your game of telephone has led to a good career but not your best, most fulfilled one—just don't confuse "best" with "perfect". Best will be just as hard and challenging as anything else.

Your advantage? You have insider knowledge and experience, and you're not starting from scratch like 180 career changers might. You can take low-risk leaps to test your career assumptions and not burn out as much as you might from working multiple day jobs to sustain yourself or starting over in an entirely new context. You may also benefit from job security because you're not stuck doing one very specific thing over a long period of time, or because you've expanded your definition of your own career on your own terms as an entrepreneur. And these are all really amazing advantages, if you're headed the right way.

Then there's hybrids, people like Julia Childs, who had a successful shadow career as an advertising copywriter, people like Gabrielle Chanel, who had a day (er, night) job singing at clubs, then built a successful business selling hats and iterated from being a hat designer to clothes, perfume and her now-global empire, carried on long after her 1971 death.

There's people who defy categorization altogether, where the line between a career change and a side project is too fuzzy and there is no beginning nor end, just layers.

There's "late" bloomers, people who defy conventional standards, that dictate or enforce a period of exploration and trial and error while we're young, but that somewhere along the way, we are meant to stop learning and changing. (But does it really count as a career change if your career is nonexistent, if you're 22 and fresh out of school?)

Maybe let's just call it a series of reinventions, as we all try to keep up with the tide of change in the world, in our chosen industries and most importantly, with ourselves.