Somewhere Between Resistance and Momentum

What happens when the roadblocks pile up and you can’t tell if it’s a stop sign, a signal to merge, a motion to pull onto the shoulder and rest, or to change your vehicle entirely.

I’m trying something a little different this week and starting with what’s been inspiring me lately. Here’s a quote I’ve had stuck to my computer for the past 8 days:

Fear doesn’t stop death, it stops life. 💥

And here’s a song that’s been getting me out of my office chair and dancing like the happy little nut that I am: Jackie Wilson’s “Higher & Higher.”
(BONUS: think about these lyrics in terms of SELF LOVE! Wow …woohoo!!)

Have you danced recently? Drop a comment—where were you and how did you feel?
I was just in Spain for a good friend’s wedding and the bride & groom planned two full nights of dance parties. One of them was under the stars, surrounded by olive trees while a giant disco ball created sparkly visual effects on the leaves. I felt liberated and FREE. 🪩💃✨

🎧 Prefer to listen? Here’s the audio version of this article. 😃

As humans, we are meaning-making machines. As an optimistic human (hi!), every roadblock becomes a curious new challenge. A question for the Universe. A chance to reflect: Is this a sign? And if so, of what exactly? I trust we always can rise above it—but the how can sometimes take a minute.

As an entrepreneurial optimistic human, the questions go a little deeper:
Should we invent something that’s never existed before? Should we build a ladder to go over, a tunnel to go under, a raft to float around, or a chisel to go straight through this wall—and should we sell that chisel while we’re at it?

And as a risk-averse, entrepreneurial optimistic human? Well… things can get confusing. And exhausting. Fast. 😅

Still, I’d always rather be on the court playing than in the stands spectating. Which means the roadblocks are inevitable.

So the question becomes: What do you do when they (the roadblocks) show up? And more importantly—how do you show up?

Do you fear-dump all over the situation? (I’ve done that recently—sorry Sam, lol.) Do you brush it off with false ease? Do you over-inflate something small into something insurmountable? Or do you try to look at it honestly and ask: Is this worth the time and energy to work around? Or is this the moment we pivot toward where we’re, perhaps, actually meant to go?

As someone who has made a life of building things that didn’t exist before, I like high-barrier-to-entry spaces. They thin the herd. Most people would rather romanticize an idea than actually do the physical, mental, and emotional work of bringing it to life.

Back in the day (like this photo circa ~2015): fueled by whisky and ambition. I didn’t always know what I was doing — but I knew I had to keep showing up.

But if you’re one of the brave ones—someone who’s realized the whole point of being alive is to try, to experiment, to live into the fullest version of what draws you forward, even if the what changes often or not —then you know the only real path is through.

With the new business Sam and I have been building since December 2024, we’ve hit plenty of blocks—especially lately. Sometimes we immediately see a way through. Sometimes we need to step back, take a beat, and reconnect with why we’re even doing this.

Recently, we hit one of those moments. A big one. I looked at her across our zoom screens and said: “Let’s treat this next week like a vacation from the biz. You’ve got a ton going on. I’ve got a mountain of other things. Let’s lift the pressure, let our brains rest, and come back to it in a week.”

It was a gift to be able to do that.

When we reconnected, the conversation was honest and spacious: Do we want to keep going? What could we do differently that would feel more fun, aligned, and sustainable?

These are good questions and it’s easy to get lost in them! The trick is to not stay lost. Because if you linger too long in the questions—circling the hard thing without ever re-engaging—you might find you’ve left the court entirely and taken a seat in the luxury box, watching your own halftime show.

So, when I find myself lingering too long in the pause, here’s the final question I ask:

What—if anything—will I regret if I don’t take another step forward?

Bingo.
That’s usually the one that cracks something open.

Real-time optimism. Still navigating. Still working to consciously choose joy and laugh at myself — even when I find myself massively confused in the messy middle.

Because while I’m not afraid of failure, I am afraid of regret. If I know I’ll regret not trying, then I know I’ve got more in the tank. If the answer is nothing, then maybe it’s time for a pivot.

Here’s one more little truth I’ve learned: When I want to return to something I’ve set down for a while, the fastest way back in sometimes is to identify, then detach from the outcome, and then keep it removed for a moment until I feel that I’ve plugged my whole self back into the mission again and the excitement and joy are flowing.

Usually, it’s the largeness of the end goal that can create the fear-to-restart barrier; selling the company, publishing the book, putting oneself or a product out into the world and having it succeed. The expectation we can put on a project or ourselves can makes the reentry point feel too enormous. For me, if I strip all that away and the answer to this question is yes, “Am I picking this back up because it feels good, fun, and true to who I am in this moment?” I can usually begin again.

Take this Substack as an example. Sometime last year I told myself, “Gosh I’d really like to keep this going but only if it turns into something with X number of paid subscribers.” Well, that’s the period in time I’d stalled out before I could even open my laptop and putz around with a new piece. That kind of attachment to the outcome does not foster genuine community building or playing with various forms of self-expression—that’s just pure pressure.

So I asked myself: “If I do the work to write, edit, record, and promote these pieces and I never make a dime— would that be worth it?” The answer was a whole-body Yes. I don’t think that would have been true at other points in my life — which is kinda cool. It signals to me that I’ve changed, yet again.

The value for me here now is the JOY of getting to engage honestly — with myself, with you, with the craft. It’s in meeting myself in the written (and now audio!) form. And the delight of seeing, after a post goes live, that someone out there opened it. Sat with it. Perhaps even felt something.

I often wonder how many of you are out here also navigating life with consciousness, curiosity, and an appetite for truth (a word with an ever-growing importance in it’s definition). I like to think it’s a lot.

Who knows where this will go or if this — or if anything we create will ever reach the particular size or stages we might be able to see in our minds eye? I sure don’t. But I do know that I love creating. And I love writing. I am truly enjoying documenting the in-between. I’m also deeply grateful for the connection to you that this space is already creating.

So… if you’re looking for an onramp to reengage with something that’s calling you, maybe detaching from the outcome or asking different questions can help. Maybe something else will. Either way, I’m excited to see where this all goes — for all of us!

Do you have a Substack—or a creative practice—you’re showing up for, even if no one’s clapping yet? If yes, drop it in the comments & tell us a little about it. Maybe we can support each other, grow together, and share what’s resonating.

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Your turn:

When you hit a boulder in your path, what helps you decide? Are there questions you ask yourself—or your people—that help you find the spark to push forward or the peace to pause?

💬 I’d love to hear. Drop your go-to reset question in the comments—or just leave an emoji that captures where you are right now.

📝 And if you know someone else navigating a stuck moment, feel free to share this with them too.

✨ We’re all somewhere between pause and drive. I’m so glad (and deeply touched!) that you’re here.