Why Most Goal Setting Fails (and the Exercise That Fixed It for Me)

Every January, we’re told to set goals. More goals. Bigger goals. Smarter goals.

And yet… most of us still feel weirdly unclear about what we actually want.

In this solo episode of Don’t Be a Jerk, I share a goal-setting exercise that completely reframed how I think about my life. It started with a single line from a friend that stopped me cold: “Most people set goals for their resume. You should be setting goals for your tombstone.” Then, I stumbled across a book called Creative Visualization by Shakti Gawain while I was on vacation, and it changed everything for me.

These ideas sent me down a rabbit hole of reflection, journaling, and some uncomfortable honesty about what I’ve been optimizing for (and what I haven’t).

In this episode, we talk about:

- Why traditional goal setting often leaves people feeling empty

- The difference between resume goals and life goals

- The five most common regrets people have at the end of their lives

- Why clarity about the end can change how you live right now

- And how a simple writing exercise helped me realign my priorities around love, family, work, and fulfillment

This is about designing a life you’d be proud to look back on. If you’ve ever felt successful but still slightly off, I think this one will resonate with you.