Overthinking and Underthinking

Feeling frustrated that you're not coming up with any answers to the big career change questions? When it feels like trying to squeeze water from a stone, here's the antidote.

Career change clarity often feels like two steps forward, one step back. When you're excited about an idea and then you find out it will take more than you expected to get there, it can feel like sliding way backwards. But you're actually still going forward.

When Kaitlyn Casso worked in marketing, she found a passion for photography when she took that on as part of her role. Later, after spending a year looking for a new marketing job to no avail, she felt she was trying to force a career to work that she no longer wanted. She decided to take a chance on her new passion and now she's an independent brand photographer (and much happier!). The dots in her story connect in a way she couldn't have predicted, but she says sometimes we have to be patient with letting the answers come to us over time - they aren't instant.

Have you ever set arbitrarily ambitious goals for yourself, then felt like a failure when you didn't meet them? High achievers tend to make things really hard for themselves, and be tough on themselves for not measuring up to their own standards. Why is that?! We've become suspicious of things feeling too easy, but sometimes the answer isn't doing more, it's doing less. 

In her 30s, Vanessa Awong decided she'd had enough in her finance career and decided to become a doctor while also starting a family. "Let's just say yes and figure out the rest as we go," she told herself, and that started her new path. With four years of commuting out of town, it wasn't an easy road. She's an M.D. now and has thrown some creative projects and consulting into the mix, because why not? 

"How do I get from here to there?" is the million dollar career change question. Sometimes you can get there in one big leap, but lots of career changes happen by strategically hopping between a series of lily pads. Here's how to know if you can make a shift in 1 move or if you need to lily pad hop, and real life examples of what hopping looks like.

Alejandra Molina is co-founding a language learning app, currently focusing on medical Spanish during the pandemic. She doesn't have a tech background, but believes in figuring things out with a willingness to learn, to find inspiring mentors, to see value in all of your previous experience, to put imperfect ideas out there and get feedback. "Take everything calmly," she says, noting a venture capitalist's advice that each VC would give different feedback based on their own backgrounds. It's a good reminder that when everybody and their uncle has an opinion on our professional goals, we have to be careful about who we listen to because everyone's opinion is based on their own backgrounds.

Overthinking is a thing, but so is underthinking. We dwell on some career change questions to the point of overthinking, and we skip over the useful questions by underthinking. If you find yourself drawing a blank, here's how to know which it is and what to do instead.

Claire Simeone is a marine veterinarian and 2018 TED Fellow who started her own conservation-focused company, Sea Change Health. She has carved her own way through her field by following subtle clues. In our chat she describes how she learned to listen to those sparks: by separating her self worth from her career, and by separating fear-based anxiety from anxiety provoked by deep misalignment between our careers and who we really are. 

As a coach I tend to hear similar themes in the fears and objections potential career changers have. We can take those thoughts as signals that we are weak and inferior, but they're often actually just behavioral economics at play. Here are 5 ways the difficulties of career change can be explained by behavioral economics. It's not you, it's your brain.