On Fitting Into Boxes When You Don’t Have To

I quit my last “real” job a few years ago.

On paper, it was great—a senior executive role at a tech startup, a fortune in stock options, a great team… but I knew something was missing. This was my 3rd job in as many years, so it wasn’t them, it was me—I couldn’t bear to spend 9+ hours a day every day on something that felt so… flat.

I quickly realized that the obvious “start my own tech startup” wasn’t the answer either, which led me on a long journey of self-introspection, studying, experimenting, and eventually realizing what I truly wanted to do in my life—what I had always wanted to do but kept denying: Art and design. Now I create large-scale minimalist art.

This journey also led me to write what I was learning, which led me to start this blog, which led me to realize that I want to give people what I wish I had when I quit my job: A playbook for how to go from a life that looks great on paper but lacks a sense of purpose and… aliveness, to a life they’re in love with. I built a program that only requires one hour a day to figure out what to do to be able to look back at your life at 90 and say, “I truly, fully lived.”

The biggest reason I couldn’t figure out what I wanted to do was that I was trying to fit into a preexisting box—but none of the preexisting boxes fit me.

I’m an artist. I’m a technologist. I’m a teacher. Turns out I don’t hate writing, as I falsely believed my entire life, so now I’m also a writer. There isn’t a box for all these things together.

I’m sure to some it may sound like I don’t know what I’m doing, yet I’ve never in my life been more sure.

We’re all complex humans with many facets, interests, and abilities, some of which we still don’t know about, because we have preconceived notions about ourselves and what’s possible for us that we never question. Trying to fit into socially approved boxes can make our lives feel… flat. Small. Meaningless.

I don’t know if my 90-year-old self will say I was happy, or successful, or impactful. But she will definitely say I did my best to live fully expressed. And I have the deep faith it will lead to all the above.

Are you trying to fit into a box that doesn’t fit you?

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