The blank page has never felt quite as empty as it does when there’s no one else in the room to laugh at that terrible first draft.

If you’ve spent any time in the comedy trenches, you know that the real magic of sketch writing isn’t the final performance; it’s the chaotic, collaborative electricity of the writer’s room. It’s in that beautifully humbling process where you throw out your innocent (arguably hilarious) sketch baby, and the room begins to fill with “what if” potential. What if you add this random character tick? What if they spoke like this? What if they encountered a…? The sketch starts taking real shape. The beats get better definition, and suddenly a collective spark turns a mess of ideas into something brilliant. Energy is bouncing everyone, building momentum, and there’s that shared high where everyone is making each other laugh. The sketch baby is now a full-blown awkward teen, and it’s ready for prom. (Look, it’s the analogy I’m going with right now. )

Lately, I’ve found myself deeply missing that specific rhythm – missing being in that kind of room – missing that energy.

How that ties into fundraising…

Every year, I try to channel my creative energy into organizing a fundraiser for the American Foundation for Suicide Prevention under our team, The Jay Walkers. We’ve pulled off successful, highly creative fundraising campaigns in the past, but trying to find a brand-new, engaging hook every single year is exhausting. That is precisely where a writer’s room saves you; it takes the burden of constant innovation off a single pair of shoulders.

When you’re flying solo, the creative fatigue is real.

The Weight of the Milestone

This year, the silence feels heavier than usual. We are marking the tenth anniversary of losing Jay, a milestone that carries a massive, quiet gravity. When you hit a decade, you want to build something that honors that span of time. You want an event that feels big enough, meaningful enough, and creative enough to match the weight of the memory – the weight of Jay’s memory.

But trying to find that initial momentum when everyone is exhausted – when even the people closest to the memory, including his family, are tapped out of energy – feels like a sudden gut punch. It’s a stark reminder of how isolating the solo lift of leadership can be, especially when the milestone means everything to you.

And I’m not going to lie, I sometimes look at what other teams are doing to drive their fundraising, and I think, “DAMN! That’s impressive!” while kicking myself because I can’t get a single idea off the ground. That comparison spiral is brutal. How do they get traction and I can’t even (fill in the blank)?

Which is why, in my attempt to drive momentum and make this year memorable, I over-corrected. I took a specific event idea and completely whiffed it (Google assures me “whiffed” is a word, so I’m keeping it). I obsessed over the outcome, while I let go of the actual planning. I completely dropped the ball when it came to providing actual, straightforward direction. The part of me who understands project management shook her head at the part of me who is that full-on idea fairy wanting to dump their idea baby at a friend’s house and have a party weekend in Vegas. (I know, I know, there are a lot of baby analogies happening today, but hey, in fairness, I think of ideas as infants who, when nurtured, can flourish and grow into something amazing.)

Long story short, I came up with a framework, but I didn’t provide a simple roadmap that got us to the final event, and the idea crashed and burned hard.

When a sketch doesn’t work, you toss the script and try something new. But when a fundraising event stalls out, the stakes feel entirely different. It doesn’t just feel like a bad draft; it feels like I’m letting Jay down. It feels like I am personally failing his memory, and that is a paralyzing weight to hold when you’re trying to be a team captain. It hurts my heart in a deep way.

Navigating the Solo Lift with Grace

But as the captain, the person calling the shots, I know part of the fix is I have to be a better leader, and I have to provide clear direction. I have to create that writer’s room – identify the right people to bounce ideas around.

And the truth is, there’s actually a different, potentially brilliant idea for a fundraiser on the horizon. (The “brilliant” part is not thanks to me at all but to the person who came up with the idea.) To make it work, I need to roll up my sleeves, be a more active participant, and ensure the people involved have the tools to succeed. I need to step up more and provide direction and remove barriers rather than expecting it’ll all work out.

I can’t hold my breath, cross my fingers, and think “it’ll all be fine if I just walk away.”

Because the truth is, life is incredibly loud for everyone right now. People have demanding jobs, family stuff, mental health struggles, or just plain burnout. In volunteer spaces, especially when I’m asking everyone to come back again and again, ideas quietly fade away when the logistics get too complicated.

And that’s okay.

The beauty of remembering the sketch room is remembering that collaboration requires a certain amount of grace (and a bit of humility). If someone shows up exhausted or off their game one week, everyone in the room has their backs until they find their footing next time. Organizing a fundraiser is no different.

Ten years after losing Jay, I know the folks who support the Jay Walkers, whether they donate a dollar (reminder, every donation makes a difference – no matter the size), sign up to walk, or share a post about the team or why supporting the cause matters, are all doing their best to make a difference.

Jay’s memory isn’t fragile, and it’s not dependent on me pulling off a single, flawless, over-complicated production (despite me really wanting to have achieved that for this anniversary).

Until then, I’ll work on how to be the director this project and team needs. And sure, the events might look a little simpler this year than what I initially envisioned (and hoped), and they may also look simpler than what we’ve done in the past (sorry, no disaster pieces), but the core goal remains untouched. We build what we can, with the hands we have, for a cause that desperately needs the light.

Want to keep up with this mess? Of course you do!

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