Freedom and anxiety // Two-sided values // Spiraling

December 15, 2021 · reading

I’ve spent the last few months in a sleep-shredding spiral of anxiety. It’s recently started getting better. Very recently. Like four days ago.

Here’s the idea that broke it, from The Entrepreneur’s Guide to Keeping your Shit Together📘 by Sherry Walling. :

The core values that most entrepreneurs share—freedom, ingenuity, adventure, and meaning—come with baggage. ** With **freedom comes a huge dose of anxiety.

With ingenuity comes opportunity for failure.

Those of us who handwrite the scripts of our lives create adventure, but we can also find ourselves in unknown, unpredictable, and unstable surroundings. 

Sunday was my low point.

But being the low point also means that it was simultaneously the turning point. 

You gotta hit the bottom to bounce.

Can one have so much freedom that it creates such a weight of responsibility that one is no longer free?

I think so.

And I think that finding a way to balance the freedom that an entrepreneur craves with the responsibility that is required to get that freedom is the key to staying healthy and sane as an entrepreneur.

I feel like I’ve now dug myself far enough out of the hole to once again see sunlight.

Because inside of this intense pressure is our final core value: the quest for meaning.

Sherry’s book helped me see that the anxiety isn’t because I’m failing; the anxiety is because I care. And because I’m throwing myself into the deep end, trying to figure out some stuff that I’ve never done before.

Which is better than just “okay.” It’s fantastic, because I want to be the sort of person who is willing to shoulder the ambiguity and discomfort of doing something I’m bad at in pursuit of something that matters.

There will be good days, and there will be lots of bad days. The question is whether or not you have the life that you want.

This little piece of reframing has made all the difference. I still feel the discomfort of navigating through the fog, but it’s not spiraling.

I’m no longer seeing these feelings as inherently bad, but as more of a natural side effect of following my values. It’s supposed to hurt. (Only a little bit, though.)

Keeping your core values—freedom, ingenuity, adventure, and meaning—in the forefront of your mind, even when you face failure, is one of the best tools you have to combat the challenges of the entrepreneur’s life.

I’m still on high alert, because there’s a laundry list of important stuff that I’ve got figure out how to succeed at. 

But the spiral has ended. 

And that was thanks to being shown the other side of each coin:

Freedom and anxiety.

Ingenuity and failure.

Adventure and instability.

Meaning and isolation.

So what now?

Right now, I’m focused on building the systems and habits to preserve this insight.

Because I have zero interest in finding myself back underground.

Know your personal demons as well as you can. Yes, think about them. Contemplate them. Let someone else in for a look, too. And then figure out how to get past them. 

📘 All of the above quotes are excerpted from The Entrepreneur’s Guide to Keeping your Shit Together by Sherry Walling.

(And to Sherry, if you happen to see this: Your book helped me out a lot. Thanks.)

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