I could never do that


Hi Reader!

Three and a half years ago, when I left my role at Google, I could not tell you what I enjoyed doing. My job was my identity, and I had no idea what building my own business would do for me.

Entrepreneurship is such an interesting experience. No one tells you how many hours you'll spend teaching yourself things you used to have a team for. No one tells you how rewarding making something work will feel.

About every six months, I still question whether I've made the right decision. I hang out in this headspace for about a week, and then I remember that while the work is hard and the structure is different, I feel much more engaged, alive, and aware of what I want and need.

Some of that awareness came from my clients. You cannot spend three years sitting with people at the messy crossroads of big changes, asking them what they actually want, without eventually having to answer the question yourself.

For the past year, I've been going to art school.

Most weeknights I commute to NYC, and my free time at home is absorbed by drawing and, more recently, painting. For so long, I avoided pursuing art as impractical or an "I could never do that." Turns out I can. I have, and I continue to.

By giving myself permission to follow this path, I'm transported outside of time, fully present and having more fun than I think is reasonable. I've been fortunate to find an incredible mentor who, in a recent conversation about creating, reminded me, "This is real work too."

I'm convinced that what you are looking for is often chasing you too, if you stop trying so hard to outrun it. Whatever your version of “I could never do that” is - I hope you let it catch you.

Reflections:

What is your version of "I could never do that"?

What have you been calling impractical that might just be scary?

What areas of your life could feel more alive?

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The Monthly Compass

Your Monthly Compass is for leaders ready to grow with intention. Once a month, you'll receive practical tools, and reflections to help you build stronger relationships, navigate change, and find a path forward that's wholly your own.

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