Addicted to Figuring Things Out

When I left New Orleans in June of 2023, I had no idea what this journey would look like or how long it would last. I had a few weddings and events planned in different places, so I structured my first few months of travel around those. Beyond that, everything has pretty much unfolded month by month.

So nearly two years into this nomadic life, you’d think I’d be pretty good at surrendering to uncertainty. And sometimes, I am. But the truth is, my need for control and relentless urge to "figure it all out" still shows up with a vengeance.

You see, this way of living is the antithesis of how I used to operate. Since childhood, I was encouraged to map out my next steps—where to go to college, what to study, what will come after that. I vividly remember struggling to define my ‘passion’ for my college essay, sifting through hobbies and interests, wondering if guitar was meant to be my life’s purpose.

Later, when I started working in New Orleans, I found great pleasure in figuring things out. Solving problems and strategizing for the future were what made my job fun and exciting. I used to smile and say, “Everything is figure-out-able.”

So when I launched into this period of uncertainty, I was committing to loosening my grip on the illusion of control. To sitting with the unknown and somehow training myself to be okay with it, maybe even one day to enjoy it.

Like anything, our awareness ebbs and flows. Fast forward to two weeks ago, when I arrived at my Airbnb in Southern California. I was excited to be in such a beautiful place, but also feeling the fatigue of constant travel. This was technically the last place I had booked, (other than a vipassana meditation course right after it) and so almost immediately, the "what’s next?" voice swooped in. Without realizing it, I handed the microphone to this voice and let it run the show.

I frantically searched for housing, even toured an apartment in Santa Barbara, and grilled everyone I knew about LA’s neighborhoods. Suddenly, it wasn’t just about exploring; it was a mad dash to find an apartment when, in reality, I don’t even know where I want to live yet. My attention shifted entirely from the present to an imagined future, leaving me feeling restless, anxious, and overwhelmed by the pressure to have it all figured out. It was a full-blown "what am I doing with my life?" moment, and it didn’t feel good.

Then, with some assistance, I recognized what was really happening: I was in resistance. I was saying "no" to my journey, triggering a self-made spiral of control-seeking and suffering. It took a day or two for this awareness to settle in, but as I softened and said "yes" to what is, my need for certainty dissolved entirely. Externally, nothing had changed, but internally, everything had shifted.

In a classic case of ego takeover, I had handed over the microphone and stopped allowing everything to be what it is. As soon as I returned to the present moment, the magic reappeared. I found myself appreciating what was around me, sleeping like a baby, swelling with gratitude, meeting amazing new people, immersed in conversations that felt aligned, deep, and exciting, and noticing the abundance and beauty that surrounded me the whole time. Most notably, I felt calm and happy inside.

All of a sudden, I am not only okay with not knowing where I’ll go after here, but I’m grateful that I don’t have it figured out. What might I be making room for in my life when I don’t fill it with plans just to quiet my ego’s desire to have it all mapped out?

This doesn’t just apply to living nomadically. Pause for a moment and think about your own life. Is every moment packed with work, chores, social obligations, and things you feel like you should be doing? Do you ever leave space for the unexpected?

When we over-schedule and over-plan our lives, we crowd out the space for magic to occur— for aligned opportunities to come along when we can actually say yes to them, for spontaneous adventures that make us feel like we’re alive.

As a recovering addict of "figuring things out," relapses like this are to be expected. The pull toward certainty is strong, and satisfying it can feel good—at first. But the truth we all can agree on is that there’s no such thing as certainty anyway! We do an excellent job convincing ourselves otherwise, and we make ourselves crazy trying to attain it, but no matter how meticulously we plan, everything can change in an instant. When we stop kidding ourselves and get honest about the fact that certainty is an illusion, we open ourselves to a deeper sense of peace, a richer experience of the present, and the magic of possibilities we never could have planned for.

I forgot this a couple of weeks ago, and I’ll probably forget again. When I do, I’ll return to the present moment, notice the resistance, loosen my grip— and reacquaint myself with exactly where I am.

If you want to explore this type of work more deeply, join me for a 75-minute experiential group workshop where you'll dive into your own inner work in a safe, facilitated space on Wednesday, April 9th at 4pm PST// 7pm ET. Come as you are.