Building the Plane as We Fly It: A Founder Pivot (and the View from Up Here)

The projects and challenges we undertake as entrepreneurs are sheer madness. I say that kindly. If you remove your own perspective and step back, they look very different from the perspective of an outsider. As Entrepreneurs, we generally don’t stop to think. To ask ourselves; “Am I thinking too big? Is this build realistic?”

We’re sitting here tinkering, inventing, launching, scaling… while the rest of the world is going “he’s doing WHAT?” (or too often… “is she out of her mind?”). My own partner often comments; “I watch you heading off into that back room and trust that you’re just making it happen, even though I don’t know what, I know you’re trying to build the world.”

That reverent disbelief; the raised eyebrows, the concerned looks. That’s the stuff of Entrepreneur gumption, because we’re not really concerned about doubt. Or at least we’re not allowing it to sit in the driver’s seat. Doubt, and overcoming it, leads us to who we are. And where we are – in the pilot’s seat.

We are those dreamers. The slightly (or very much) unrealistic. We’re determined to build beyond what’s in front of us and reach further than we know how to. We are the ones building the plane as we fly it.

I love this analogy. It first entered my brainspace when I was sitting backstage at Planet Hollywood in Las Vegas during the Scorpions residency. Another unlikely project; reaching debatably too far into the realm of “how the f*** am I going to make a docfilm happen?” The analogy came from my dear friend Rob Hammersmith, drummer of the one and only hit rock band Skid Row. Whom I was interviewing for the documentary series I was directing. The analogy came up during the interview, in reference to the calculated trajectory of a band navigating new social media and marketing trends in an upended industry. Tough space to be in. You can watch that interview here, if you feel so inclined.

But that statement “building the plane as we fly it” struck deep. It was not only personally relevant to the docfilm project at hand - but pretty much the way I live my life. Thinking big, yes. But also flying precipitously close to Danger Zone, never quite sure if I can stay afloat through this particular flight path.

But that… THAT is precisely the stuff that makes up the world of an entrepreneur. And that’s what I’d like to preface the rest of this blog upon. We are all in this because we pathologically (yup) and systematically strive to achieve - when we’re not even sure what the final outcome looks like.

So with that, I’m here to share a founder pivot. I built this platform with the express intent of sharing snippets of life as a small business owner. When I was asked to build educational material, I allowed that mission to veer – to a world of lessons, guidance and content. Content that, if I can be completely honest, started to feel icky. Everywhere I go these days, you will meet The Business Coach. They’re lurking at every networking corner; circling sharks, ready to spring on the helpless, hapless business owner. They’re ready to fix and format, authoritate and impose. They have a prepackaged six-step method to solve life in general. All I need to do is sign up for a free conference and then spend six figures on their program, committing once a week to worship of the systems of a false idol. They’re the used-car salesmen of the business world and… well… I feel like I slipped dangerously close to that scope of existence.

But let’s acknowledge and move on. I’ll take a moment to placate my ego here by reminding myself that not a cent was made; no system was monetized and I steered very mindfully away from anything that felt like becoming a circling shark. But still… it was not where I wanted to be. No, nope, never, not a chance, no way, uh-uh. (also... oops.)

At the same time, I was quietly a part of another project. Fossick Travel. It was that almost-secret passion project running in the background, one I rarely shared. But it was quietly amassing a significant following, despite the neglect. One singular ‘aha’ moment in late 2025 led to the development of a new product for that platform. And, well, once I started to lay out the ideas, the concept took hold and built itself. I was nothing but the conduit to a very cool new creative travel system. With the potential to sit at a crossroads of helping both sides of the tourism duality; guests looking for new experiences, and destinations seeking ways to secure more involved guests. It felt like a solid solution to a lot of problems - problems I’ve personally experienced in my time supporting many hospitality and tourism clients. So there, now it was personal.

That’s all I will reveal for now. The platform announcement deserves a day of its own. But it’s the foundation for the pivot I want to share with you.

I’m moving to a real-time share-fest of the life of a Startup Founder. Rather than stacking a pile of resources on the table or guru-ing or my way to supporting other entrepreneurs, I am going to simply share the journey as I build Fossick Travel. I’ll leave the lessons, the challenges, the wins and losses on the table for you to interpret (and learn from) as you see fit.

This won’t be about the vision, or the offers, or the admin or any sort of six-step process. But if you’ve ever looked at someone else’s polished launch and thought, How are they so far ahead? How TF did they manage that? …this is the remedy. It will talk about the to-do lists that never end. Decision fatigue. The constant context switching. The pressure to be the engine and the learning curve and the doer and the maker and the strategizer. I won’t whine, but I’ll place my hard-earned lessons alongside the moments of pure motivation, vision and uplift.

It might hit a little too close to home. If that’s you: Welcome. Just know that you’re not doing it wrong. You’re doing founder life and you are building a bloody solid plane as you fly it.

And the view from up here is spectacular.