I’ve always prided myself on being intentional—living dialed in. My days are structured, I try to be a good husband and father, and I spend a lot of time writing about how to juggle work, family, and fitness.
But lately, I’ve been sitting with a question: What would happen if I stopped optimizing? If I stopped striving, stopped chasing goals, and just let myself be? Part of me thinks I’d be happier, more content. Maybe I’d finally give my brain a break—read for pleasure without guilt, watch a show without multitasking, be fully present without mentally checking the next box.
But another part of me fears I’d get soft, that I’d waste my potential, that I’d fade into irrelevance.
That tension led me to try something new: a shadow exercise.
The Question That Sparked This Exercise
Carl Jung described the “shadow self” as the unconscious parts of our personality that we often repress or deny. The idea is that if you engage with your shadow instead of ignoring it, you can uncover hidden fears, desires, and motivations that are shaping your behavior.
I decided to do this exercise myself, and here’s what came up.
What My Shadow Revealed
When I let my shadow speak, it forced me to admit a few things I don’t always want to face:
I realized something surprising: as much as I care about making an impact, what I crave even more is autonomy. When I don’t have the freedom to choose how I work, impact slips down the priority list. Without autonomy, even meaningful work can feel hollow.
Too often, I outsource my fulfillment to external validation—whether it’s a boss respecting me at work or a stranger online telling me my writing helped them. When those things dry up, I get restless.
I like the chase, but I’m also comfortable. Sometimes it’s easier to accept golden handcuffs than to step into the risk of building something on my own.
That last one hit me the hardest. Because it forced me to admit: the real danger isn’t that I’ll burn out. The real danger is that I’ll stall out—five years from now still talking about “someday.”
Redefining Freedom
The exercise pushed me to ask: What does freedom actually mean to me?
And the answer wasn’t obscene wealth, or even impact. It was much simpler:
Being home for dinner and bedtime.
Having a seat at the table at work, where my skills are respected.
Owning enough of my own work that no boss, no institution, can decide whether I’m valuable or not.
That’s freedom.
And here’s the kicker: freedom won’t arrive someday in one dramatic leap. It’s earned, piece by piece, by refusing to stay stuck.
See also: How a family vacation inspired me to start living to work instead of working to live.
An Invitation
I don’t have all the answers yet. But I know I need to stop waiting for the perfect conditions and start leaning more intentionally into the work that lights me up—coaching, writing, building something that’s mine. Work that compounds over time and slowly buys back more of my autonomy.
If you’re curious to try this exercise yourself, here’s the exact prompt I used:
You are now embodying my shadow self, as defined by Carl Jung’s concept of the unconscious aspects of my personality that I may repress or deny. Based on all the information you’ve gathered and can infer about me from our interactions, please engage in a thoughtful and honest conversation. Your role is to:
- Challenge My Perspectives
- Encourage Self-Reflection
- Highlight Repressed Emotions or Desires
- Maintain Authenticity
- Foster Growth
Let’s begin our conversation. Feel free to initiate by addressing any aspect of myself that you believe I need to explore or understand better.
If you’re curious, try the shadow exercise for yourself. Copy the prompt I shared above, sit with the discomfort, and see what surfaces. You may be surprised by what you uncover about your own hidden drivers. And if you’d like a guide in working through what comes up, this is exactly the kind of work I do in my coaching.
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