I caught up with a friend Nick O’Brien yesterday. We’ve never met in person (I’m not quite sure how we met in the first place) but once every couple months we hop on Zoom for a couple hours and chat through startup & community ideas, new AI and tech we’ve been trying, etc with laser beam enthusiasm.

This time Nick said something that stuck out to me. We were talking about a series of a few dozen pop-up art events he’d put on in Wassau, WI with all sorts of incredible exhibits, live art, live glass blowing, drone video projection mapping, all part of a broader initiative to spur investment for creative art projects in the city. I was impressed.

I asked “how do you pull this stuff off? That sounds like an absurd undertaking for one person to manage and execute on” And before I could blink he said a line I won’t forget:

“All creatives love creating when there are no expectations. I love creating when the expectation is ‘this guy’s crazy, like there’s no way that this is going to happen’”

That really resonated with me. I hadn’t really externalized it before, but it felt so obviously true form my personal experience. I’m at my best when expectations are either null or impossible. The most pressure seems to come in the messy middle.

I think that’s part of why I love working on Saturdays. It just feels like so much more being accomplished because it’s the day with the least ‘work’ expectations. It’s also why I love building startups, because they are inherently ‘impossible’… until they’re not.

The Expectation vs. Creativity Arc

Thinking about it, the paradox of expectation shows up everywhere. When we first launched Uptrends, we had the most creativity and freedom when nobody was watching or when the challenge seemed absurdly difficult. We could pivot overnight, try crazy things, experiment.

But once we had investors and thousands of users? THAT’s when the real pressure hit. The messy middle. There were suddenly concrete expectations, people watching, the weight of awaited delivery. In the middle, creativity became constrained. Our progress slowed, and after a certain point of capitulation + nothing to lose, we pivoted, and suddenly again we were back in a world of renewed creativity.

I think this patterns happens often with startups: 

• Phase 1: The early days are purely creative energy with zero expectations (the ‘side project’ phase, you’re just doing it for fun)

• Phase 2: Then, the messy middle arrives when you've gained traction, then you have real expectations to meet. It becomes harder to find new creative energy

• Phase 3: After a certain threshold of expectation, you either break through or break down, through pivot or perseverance. Otherwise you die.

Hacks for Maintaining Creative Freedom

So naturally the question is — with this progression from none to some to impossible expectations, how does one maintain the creative freedom? I’ve found a few practice ways to maintain creativity

1. Carve out sacred creation time outside normal working hours, like those Saturday sessions where anything I create feels like a bonus, not an obligation

2. Build multiple projects simultaneously so when one feels high-pressure, I can shift to another with lower stakes

3. Create artificial constraints - limited time, resources, or tools can paradoxically increase freedom by reducing the pressure of infinite possibilities

4. Embrace crazy - sometimes just saying "this probably won't work" gives you permission to try anyway

5. Find accountability-free zones where you can experiment without immediate judgment - maybe it's a side project, a personal challenge, or just a different workspace (goin to coffee shops helps me)

6. Schedule "experimental time" specifically for wild & weird ideation with no expectation of producing anything usable

I think the founders who maintain their creative ~spark~ through growth seem to master this mental toggle - executing on expectations while preserving pockets of zero-expectation creativity.

In reality we all need to find our versions of that creative freedom. For Nick, it's those "impossible" community art projects. For me, it's Saturday work sessions and new startup ideas.

I'm convinced that protecting these zero-expectation zones isn't just good for mental health - it's essential for maintaining the creative spark that makes the difference between mediocrity and greatness.

So, keep embracing projects that make people say "this guy's crazy, there's no way that's going to happen." Because sometimes, that's exactly the expectation I need to thrive.

Peace,
Ramsey