Hi. I’m Shannon, and I’m an intellectualizer. 

(Cue chorus of fellow overthinkers: “Hi, Shannon!”)

Intellectualizing is my superpower and my crutch. It’s a pro-social, productive coping mechanism, but it’s still a coping mechanism. It means that I’m good at breaking things down and understanding them, but when a problem or situation is so complex and multivariate as to defy these efforts or not have a “right” answer—which, like, is life—then I have a hard time tolerating the ambiguity. Intellectualizing has benefited me a lot, but it’s also kept me stuck at times, because you know what’s easier than doing something about your problem? Reading another book about your problem. 

The more we dwell on possibilities, the more paths forward we uncover, the more complex and encumbered those paths appear, and the murkier the choice of path becomes. It’s a paradoxical phenomenon where the pursuit of clarity leads to more confusion.

Raise your hand if you relate! 

It’s really only in the last 5 years or so that I’ve come to terms with a truth that I now remind myself of weekly:

There are a lot of blog posts and interviews and TED-like Talks on this exact subject, so please give it a google and see what other resources you find. But I wanted to talk about this subject here because I think it’s relatable to those who identify as creatives, both professionally and in our leisure time. 

It’s too easy to put off a creative project or endeavor with the intention of being as prepared as possible before getting started, and of course you need something to go on if you’re starting from absolute scratch. But pretty often, you don’t actually need more and more and even more hypothetical, speculative information. There’s a limit. Then, you need to take a step, see what happens, and absorb actual, experiential information so you can continue to take the next step. You will learn so much more about what is or isn’t possible, how you do or don’t feel, what you actually want or not after taking a step than you will from a book or a podcast or a night of existential dread spent staring at the ceiling. 

Below, I’ve got 3 tips for taking that action in the face of uncertainty. But also if you’re ready to act now, here’s the TL;DR takeaway of everything: 

Say the thing. Try the thing. Ask the question. Make the pitch. Get involved. 

…now think a little more. (But only a little.) 

Repeat.

Or try one of these:

Think like a scientist

This one might be the most obvious. Try to design your path forward with clear moments of testing with room for iteration, quite literally like you’re exploring the hypotheses of an experiment. You’ll relieve the pressure of getting to the right answer right away and trick yourself that you’re still in your info-gathering comfort zone! 

Baby steps? Try microsteps. 

Do your next steps look like this?

1. Create a business plan

2. ?????

3. Profit 

Woof. I will definitely listen to another Diary of a CEO rather than do step one. 

But what are the microsteps of step one? Maybe they’re something like: 

1. Purchase a business plan template from Gumroad 

2. Use ChatGPT to create a rough draft following the template

3. Edit and personalize the rough draft 

4. Email it to Uncle Carl and get his feedback on the draft 

5. Decide whether Uncle Carl’s feedback is actually useful or if all of it boils down to “Add more blockchain!”

6. Etc. 

Before you know it, you’ve taken a lot of action, and you’ve clarified things along the way!

What’s the best that can happen?

It only makes sense when you’re planning things out to brainstorm worst-case scenarios so we can prepare to thwart or combat them. But rarely do we also ask ourselves “What’s the best that can happen?” Because that’s a possibility you have to prepare for, too. This question is often transformational, not just because it opens new avenues to explore, but also because it can be extremely motivating! When you begin contemplating all the good that potentially lies ahead, you’ll want to get there faster. 

Over to you…

The next time you find yourself in analysis paralysis, remember: clarity is a destination. You can’t get there by thinking. You have to walk.

What’re your strategies for shaking yourself out of overthinking? Let us know in the comments!

For more…

Follow us on LinkedIn and on Instagram. Stay tuned to our Substack space for new community features and ways to meet your fellow subscribers.

And let us know if you’d like to go deeper with us to talk about you and creativity. We do:

• 1:1 coaching and mentorship

• Team workshops and consulting for marketing and leadership

• Speaking and appearances on podcasts and at events

Say hi anytime.

Kumbaya,Shannon & Kevan