I’ve always been fascinated by the idea of designing your life. It’s one of those things that seems so simple in theory but can feel impossible in practice. There are entire books dedicated to the topic—Bill Burnett and Dave Evans’ Designing Your Life and Tim Ferriss’ The 4-Hour Workweek are two of my favorites. I read them while developing a special topics course called Foundations for Your Future.
Teaching that course was eye-opening. I had students coming to my office hours, but they weren’t asking about assignments or exams. They wanted to know about my life. How did I get here? How did I make career decisions? What did my path look like? The truth is, it wasn’t a straight line.
Many of my students came from families where their parents had stayed in the same jobs for decades or ran a business, and the idea of crafting an intentional life centered around happiness was foreign to them. They were taught that you pick a career, stick with it, and that’s that. But what if that career doesn’t make you happy? What if you grow and change?
I’ve changed careers a lot. I’ve done it in pursuit of happiness and a constant thirst for knowledge. Burnett and Evans talk about how curiosity is one of the most important mindsets in life design. To make good decisions, we have to access our feelings and gut reactions to alternatives. We also have to be okay with testing things out. One of the core ideas in life design is prototyping—trying small experiments, gathering data, and then adjusting course. And sometimes, that means letting go of things that no longer serve us.
I can’t tell you how many miserable people I’ve spoken with who want a more fulfilling life but feel stuck. They’ve spent years building a career and don’t want to “waste” the time they’ve invested. I get it. I’ve built and sold multiple businesses. My first company, a coffee and tea business, had my whole heart and soul in it. Selling it was painful. But it was the right decision for where I was in my life. It’s easy to dream of doing it all, but that’s not real. The next best thing? Finding someone as passionate about your vision as you are and letting them carry it forward.
Designing your life isn’t about finding the perfect path—it’s about creating a life that aligns with what matters most to you, even as that evolves over time. As Bill Burnett says, “A well-designed life is a life that is generative—it is constantly creative, productive, changing, evolving, and there is always the possibility of surprise.”
So go ahead, get curious, prototype your next move, and embrace the surprises along the way.
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