Skip to Content

Alex Hillman

better coworking, better business, and better communities

Twitter Instagram

Search this Site

Type in terms like retention, culture, or tummling and press enter to search.

If you can’t find what you’re looking for by searching, don’t give up! Shoot me a message on Twitter, I might be able to point you to a post about the thing you’re looking for.

On Risk Taking

2 minute read
by Alex Hillman

Risk taking means different things to different people.

To an entrepreneur, it may mean betting it all on a big idea. To an artist, it may mean sharing or inciting an emotion. To many working class americans, it may be leaving a job that’s anywhere from “okay” to “god-awful” in pursuit of something better.

But I think that if you dissect successfully (read: healthy) risky behavior, it comes down to an either innate or learned ability to trust yourself.

And I’m not talking about skydiving, swimming with sharks, doing drugs, or having unprotected sex – that’s not risky, it’s dangerous.

Most day to day risk is really about understanding (or a lack of it)

“See what is possible in what you don’t yet understand, share what is possible in what you see differently.” – Hilary Austin

I have this quote in my sparkfile from a TEDx event I spoke at many years ago. I’d forgotten about it, but seeing it again recently put it in a new light.

If I think about the risk-takers I admire, they spoke out or acted on something they saw differently than others, and invited others into that conversation.

Taking that step requires a large degree of trusting themselves.

I think back to when I first met Chris Messina and Tara Hunt – these two people were operating on a completely different set of frequencies from the ones that my employer-at-the time was.

On one hand, the way they were thinking, talking, and acting was different from the environment that I actively wanted to remove myself from. On the other hand, and more importantly, that they validated my feelings that what I was thinking could be realized in the form of words and actions.

I went from being alone in my craziness to realizing that I could trust myself to be right. And that’s when I started to open my mouth and bring words into action, even when it seemed risky – because I learned to trust myself, and I understood that somebody else could be having the same experience I was having before I’d met Chris and Tara.

If they unlocked me, who could I unlock, simply by trusting that I wasn’t alone?

Risk taking is a polarizing activity no matter how you slice it. But when you lead risk taking with trust, rather than disillusionment  or false hopes & expectations, amazing possibilities lie on the other side.

What are you doing to help people learn to trust themselves rather than operate on disillusionment and false hopes & expectations?

This will help make sure you can find the most useful resources. I respect your privacy & email. Absolutely no spam, and I won't ever share your data. Pinky promise! 🤞

Hey, thanks for reading!

Alex Hillman I am always thinking about the intersection of people, relationships, trust and business. I founded Indy Hall in 2006, making us one of oldest fully independent coworking communities in the world. This site is packed with the lessons and examples I’ve learned along the way. You can find me on Twitter, too! 🐦 Say hi.