Episode 306
Getting Past Disappointment
Disappointment comes in all sizes. Sometimes it’s losing your AirPods somewhere in your apartment and having to fall back on an old wired pair. Sometimes it’s discovering that the IKEA cabinet system you carefully planned cannot coexist with geometry, physics, and an 82-inch basement ceiling—and suddenly not wanting to organize the basement at all.
Then there are the disappointments that change much bigger plans, and open the door to something else entirely. A layoff can make space for a new YouTube channel. A canceled Camino can become an RV trip through eastern Oregon, complete with fossil digging and the Painted Hills.
The disappointing thing doesn’t have to become secretly wonderful. But when one imagined outcome has started to feel like the only good outcome, remembering what actually matters can make other possibilities visible again.
What We Talk About
- 01:44 — The IKEA cabinet plan that seemed perfect until geometry and physics got involved
- 03:14 — When disappointment makes starting over feel so overwhelming that doing nothing becomes tempting
- 04:22 — Lowering the basement floor, raising a house, and other "reasonable" ways to preserve the IKEA plan
- 06:14 — How an idea can start to feel like the only solution
- 07:30 — Returning to what Shannon actually wants from the basement instead of how she expected to achieve it
- 08:38 — Shifting to the hope that something unexpectedly better might turn up
- 09:30 — A layoff, Hannah’s new YouTube channel, and disappointments that lead somewhere surprisingly good
- 11:10 — A potentially disappointing Polestar test drive, a wrong apartment floor plan, and the canceled Camino that became an eastern Oregon adventure
- 16:32 — Outsized disappointment as a clue that an idea of perfection may have been hiding in the plan
Key Takeaways
- Disappointment can feel especially intense when a particular outcome has quietly become the perfect ONLY desirable outcome.
- Once the preferred answer seems impossible, black-and-white thinking can make every other possibility look inadequate.
- Some disappointments require an immediate adjustment, while others leave a project sitting untouched until there is enough energy to reconsider it.
- A changed plan may lead to something unexpectedly wonderful, but it could also lead to another disappointment—the Polestar test drive could still go either way.
- The solution doesn’t have to be found before the feeling shifts; by the end, Shannon’s unresolved basement problem has become a fun puzzle again.
The Bottom Line
Disappointment might mean wired earbuds instead of AirPods, donating furniture because the floor plan was wrong, canceling a long-awaited trip, or having to rethink a carefully planned basement project. Sometimes the alternative is simply what has to happen, and sometimes it turns into an experience that would never have happened otherwise.
The realization isn’t that every disappointment is secretly a gift—it’s that an outsized reaction may point to a perfect outcome that had started to crowd out every other possibility. Janine still doesn’t know whether the Polestar will be a revelation or a huge disappointment, and Shannon still doesn’t know what will go in the basement, but the uncertainty feels less overwhelming by the end than it did at the beginning, and new ideas become possible.
Want More Like This?
Shannon and Janine look at how rigid expectations and standards can make life harder, and how greater flexibility can create space for other ways of doing things.
Wildfire smoke disrupted Shannon’s eastern Oregon RV trip, while Janine’s computer failed during an important project. They discuss how preparation and knowing what mattered helped them adapt when events did not go as planned.
Episode 177: How to Change Your Mind
Once we’ve committed to a particular outcome, it can be hard to step back when circumstances change. Shannon and Janine discuss commitment bias, perfectionism, and the value of considering alternatives—a good match for the broader question of what comes after a plan doesn’t work out.
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