The Cost of “Someday”
A behind-the-scenes look at what happens when you stop deferring and start building.
Every organization has a “someday” list.
The rebrand that never quite gets prioritized. The content strategy that’s been “in the works” for three years. The bold idea that came up in a board meeting, got tabled for further discussion — and was never discussed again.
But what if the right time already came and went?
In this episode, Eric and Jonathan go behind the scenes on a project that almost didn’t happen: building Seymour Studios, a turnkey media space designed to make storytelling fast, simple, and accessible for the social impact community in Santa Cruz.
Eric pitched this same concept to another local organization months earlier. They stalled. Jonathan saw the potential, moved on it, and now the opportunities are already flowing in.
They cover:
➔ Why rigid strategic plans often kill the opportunities they’re meant to create.
➔ The hidden friction that stops good ideas from ever getting off the ground.
➔ How to screen opportunities without defaulting to “someday.”
➔ What it looks like to pursue the end goal relentlessly — while staying flexible on the journey.
➔ The early returns from building momentum instead of waiting for perfect conditions.
If you’ve ever felt stuck between vision and execution — or wondered why some organizations seem to move while others stay frozen — this conversation will challenge how you think about timing, risk, and the real cost of deferral.
Stop waiting. Start building.
Episode Highlights
[00:00] Introduction: The cost of “someday” and why opportunities rarely wait
[01:40] The pattern Eric has seen over 16 years of working with nonprofits
[03:05] How the studio idea came to be, and why another org passed
[04:38] Jonathan’s lightbulb moment: connecting the studio to a longstanding problem
[06:18] The hidden friction of media production (and why it kills creativity)
[08:00] Other flavors of “someday” — board approval, distractions, unclear ROI
[10:04] Leadership, culture, and organizations in motion
[14:05] Balancing opportunism with focus: how to avoid shiny object syndrome
[14:30] Relentless pursuit of the end goal vs. rigid journey planning
[17:30] Screening opportunities: the donor/supporter “look them in the face” test
[19:49] Early feedback from the community — and why people see themselves in it
[22:02] The future of content: accessible, human, less polished, more interesting
[23:27] The quantity play: why more stories > fewer perfect ones
[25:00] Challenge to listeners: shed the someday mentality in 2026
Notable Quotes
“We’re so focused on the journey — what step we’re making, when, how much it’s going to cost — that when you build that rigidity into your plan, you’re not ready to take those opportunities that would get you to your end goal more quickly.” — Jonathan Hicken [14:30]
“Clarity of purpose — a really clear crystallized version of a vision — is what allows you to pursue that so relentlessly. Because if that’s vague, you just can’t do it by definition.” — Eric Ressler [15:05]
“It’s not loosey-goosey. It’s one where I feel like I could look a donor or supporter in the face and say, ‘This is going to help us deliver impact more quickly.’” — Jonathan Hicken [17:50]
“That energy and that buzz is what creates capacity, what creates opportunity — not the other way around.” — Eric Ressler [10:45]
“Get your reps in. The next time someone pitches you a new idea, screen it against your vision, your end state, and your near-term goals. Build that muscle.” — Jonathan Hicken [25:43]
“More and more, we have to be better communicators in this space. How do we take those big scientific concepts that are esoteric, inaccessible, unequitable — and break them down into stories, into narratives, into conversations that are more accessible, more human.” — Eric Ressler [22:02]
P.S. — Feeling stuck between where you are and where you know you could be? Cosmic helps social impact orgs build trust through story-rich brands, compelling campaigns, and values-aligned strategy. Let’s talk about how to get moving: https://designbycosmic.com/