Career Oscillations

When we make plans, we think with consistency, regularity, and uniformity as stand-ins for discipline, discernment, and judgment. “I’m going to do this everyday,” or, “My approach is this,” or “I’m going to reach this milestone.” This is helpful in that it helps us get things done. The career ladder is one representation of this; “I want to be a director by 30, a VP by 32,” and so on.

Career ladders and linear hierarchies are now an outdated concept (during the age of multi-hyphenates, when unconventional career paths are now conventional) , but I’m not sure that we’ve found a replacement yet. I want to propose one: 

Career oscillations involve knowing when to basically flip to the opposite of whatever you’re doing, in order to explore something new and eventually allow a breakthrough to emerge.

It’s knowing when to apply pressure and when to ease up. 

When to say yes, when to say no.

When to start small, and when to bet big.

Here are three examples specifically related to careers:

Oscillate between competence and creativity

In the Business of Expertise, David C. Baker emphasizes the importance of competence if you want to make an impact. He asks, “Who will remember what you were doing 20 years ago at that point, looking back on your life? It’ll be the people that you worked with. It’ll be your boss. It’ll be the people that you were the boss to…. The main point I’m trying to make first is that you’re going to impact the world around you by just being competent and doing your job.”

After you’ve developed a base level of competence, and found your comfort and confidence with it—perhaps through working a job or in a field through three or four years—you can then set your sights outside of that field, taking the expertise that matters and leaving unwanted expertise behind.

Baker writes, “That process of creation is about understanding yourself and then defining a competence on top of that, and the building process never stops. Every time you enter a new room, all sorts of new doors appear that you didn’t even know existed until you got into the room.” 

In other words, it’s an oscillation; you keep moving back and forth between competence and creativity, developing skills and then taking them with you to find new areas to apply them.

Oscillate between roles, company types, and team sizes

If you’re working at a startup, maybe it’s time to join a Fortune 500 corporation. If you’re working on the client side, maybe you should join an agency. If you’re working to learn, maybe it’s time to earn. If you work at a very structured environment, try a chaotic one. If you’ve been managing people and stuck in meetings all day, maybe it’s time to get back into the swing of craft and find or create a staff, lead, or principal IC role. (HashiCorp’s CEO became an individual contributor!)

Or, if you’ve got a year’s worth of cash sitting in the bank, just take a sabbatical for a few months. Take on a big project, or a few small ones, that combine your personal and professional interests, and see where it takes you; the additions to your resume or portfolio could start a self-fulfilling prophecy and enable you to find new areas to explore your career. (You could write a book, for example!)

It’s in these transitions that you’ll learn a ton. You’ll develop your judgment and discernment. In roles where you stick with one project for a couple of years, you’ll gain depth of expertise and patience; in roles where you switch every couple of weeks or months, you’ll develop your breadth of experience and muscle for adaptation.

Oscillate between acceptable and excellent

Without a doubt, making something that is the best in its category—to a specific group of people—is a reliable way to create a competitive advantage. The problem is, it can be tempting to aim at excellence too early. Quality and excellence quickly compound and feed each other, creating a standard that’s way too high for anyone—even you!—to meet. It’s the perfect breeding ground for a creative block.

Most of the time, if you’re starting out on a project, it’s best to just aim to make the first few versions of it acceptable. Show people these versions and see how they react or respond. 

Once you’ve settled on a specific direction, and picked one version to improve on, it’s time make it excellent. Focus your time, energy, and willpower on making it the best possible work. Obsess over the details. This sounds difficult, but it shouldn’t feel like a slog; at this point, you should have the resources and people working with you to support your efforts.

I oscillated when I wrote my book; I independently published the first version in November 2020. It was acceptable, and I was proud of it, but I also saw it was only achieving a fraction of its creative potential. In early 2021, I signed with a publisher, which introduced me to a whole new world; I worked with an editor (Rachel Jepsen), a tech CEO (Joshua Levy), and the rest of the team at Holloway, to expand and revise the book. Even simply having people to bounce ideas around with, or to believe in the book, was a relief for me as a first-time author. Not to mention the reading experience is incredible now—but that’s another post for another time.

When in doubt, oscillate

Career oscillation is the new career ladder. This approach means accepting that progress is not linear, and that opportunity is everywhere. The best teams and companies will appreciate career oscillations and become more flexible with how they retain their people. 

You can also dial up or down the extremity of a career oscillation depending on your appetite for risk and chaos. Some people may choose to swing dynamically to opposites (e.g., I quit my job to start my dream business with a year’s worth of savings), but others may choose to swing lightly (e.g., I started a new project outside of my current expertise at my day job). 

It’s important that, again, this doesn’t feel overwhelming or scary; choose the oscillation you’re comfortable with, then ride it out.

A career oscillation may feel unrealistic at first, but it’s really not; the discomfort will enable you to realize how much of yourself you haven’t tapped into yet, and what questions you need to find answers to in order to start realizing your career potential.

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