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Between Meetings & Meals — Episode 014

Failure usually looks worse in your head than it does in real life

Between Meetings & Meals — Episode 014

Missed last week.

Apparently, I was too busy breaking apps, chasing ideas, and repainting ceilings.

But I’m back.
A little late.
Which honestly fits this episode perfectly.

The Pour

I think one of the underrated parts of getting into wine is how many bad experiences you have before you start figuring out what you actually like.

Bad bottles.
Overpriced bottles.
Bottles you thought would be amazing that just… aren’t.

Even opening wine was something new at one point.

Not because it’s hard, but because there are apparently a hundred different wine openers, all designed by someone who thinks they’ve reinvented the wheel.

At one point, we had a fancier wine opener we were trying to use, and Anisa somehow pushed the cork into the bottle instead of pulling it out.

Which immediately created a mini eruption of wine that shot upward.

We laughed, cleaned it up, figured out how to get the cork back out, and moved on with our night.

It wasn’t until the next morning that one of the kids walked into the kitchen and asked why there were red stains on the ceiling.

That’s when we realized the wine eruption had reached a little higher than we thought.

And honestly, that kind of feels like this whole process sometimes.

You mess something up.
You laugh about it.
You figure it out.
You get a little better.

And occasionally you repaint the ceiling.


The Table

A lot of cooking is failure too.

I think social media makes cooking look very linear. Like once you “know how,” every meal comes out perfect.

That has not been my experience at all.

I’ve undercooked steaks.
Overcooked steaks.
Pulled them too early.
Left them on too long.

Sometimes you spend all this time getting excited for dinner and then end up with meat that’s tougher, rarer, or more burnt than you wanted.

And it’s frustrating.

But over time, those misses start becoming reps.

You start learning the feel of things.
The timing.
The temperature.
When to trust yourself and when to leave it alone.

Not every meal is amazing.

But the more reps you get, the easier it becomes to replicate the great ones.

That’s true in the kitchen, but honestly it’s true in almost everything else too.


The Edge

I’ve been thinking a lot about failure lately because I feel like I’m in a season where I’m trying a lot of new things.

And when you try a lot of new things, failure shows up constantly.

I worked really hard building Waypoint. I packed so much into it because I genuinely thought it could help people. There were so many moments where I felt excited about where it was headed, and then right behind that excitement came another problem.

Architecture issues.
UX/UI problems.
Features breaking.
Things not working the way I imagined they would.

Even now, some of the feedback I get, or sometimes the lack of feedback, can feel like failure.

But I’m realizing that what’s really happening is pressure testing.

You’re finding the weak points.

The same thing happened this week with another app I’ve been building specifically for economic development and business retention.

I was excited to launch it during Coffee & Connect. The idea was simple: streamline workflows in the office, create an easy QR check-in system for events, and eventually build a rewards system for attendees.

I had spent the entire week building it.

Late nights. Early mornings. Constant tweaking.

I got to the office early the day of the event feeling excited because I thought everything was finally ready.

Then the app broke.

The event page that had been showing correctly every day suddenly disappeared because part of the system automatically archived it once the event date arrived.

So I spent the morning scrambling trying to get it visible again.

Finally got it back up.

We got to the event, put out the QR code, and immediately hit two more issues.

The first person never got their login email.

The second person got the email… but the login link was broken.

And in about thirty seconds, all the excitement I had built up came crashing down.

But honestly, after the initial frustration, I just laughed.

Because this is kind of the deal.

You try something.
It breaks.
You fix it.
You try again.

That’s the process.


The Lesson

I think the thing I’m trying to teach myself right now is not to beat myself up so much.

Failure feels personal sometimes, especially when you care deeply about what you’re building.

But most of the time, failure is just reps.

It’s feedback.
It’s pressure testing.
It’s the process of getting better in public.

And I think that’s something I’m trying really hard to model for my kids too.

Not perfection.
Not always getting it right.

Just the willingness to keep trying things even when there’s a chance they won’t work.

Because that’s really the only way growth happens.

Even when it’s frustrating.
Even when it’s embarrassing.
Even when there’s red wine on the ceiling.

The reps are the point.

Honestly, even this blog became part of that lesson this week.

I got so deep into building apps and experimenting with new projects that I completely missed posting last week.

Then Monday came around, which was the “deadline” I had built up in my own head, and I missed that too.

And I spent way more time than I should have beating myself up over it.

But here I am.

Dusting myself off and posting on a Tuesday.

Which honestly feels pretty on brand for this episode.

Read the original on Substack

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