Not every loss comes from making the wrong choice. | Wisdom for Your Weekend


I'm Good with Either One

June 13, 2026

Dear Reader,

Greetings from Parkwood Studios in the sun-drenched hills of West Virginia -

Have you had an ice cream cone recently? What's your favorite flavor?

Like me, do you love the cone, or is it just a vessel for the frozen treat?

I love wisdom. But I also love the last stage of eating an ice cream cone. That part when all that remains is the crunch cone and the melty, gooey ice cream that remains inside it.

With that, I invite you to dive into this week's fresh serving of wisdom. We'll explore the intracacies of making choices, as well as the consequences of how to respond when life makes certain choices for us. And yes, there's ice cream along the way.


I’m Good with Either One

It was a Thursday afternoon. Around four o’clock. Twelve chairs. Ten men. Four women. Plus my business partner, our art director and me. All packed into a 14-by-18-foot conference room. It was stuffy. Uncomfortable. Honestly, it was hot as Hades.

Have you ever tried to get a group of people to agree on something?

Maybe it was where to go for dinner. What to buy a family member for Christmas. Or where to go for summer vacation.

Whatever the decision, you probably remember the feeling. Everyone wants to move forward. Yet somehow, nobody does.

Many years ago, I found myself in a room full of that feeling.

This wasn’t our first meeting.

Or our second.

Or our third.

For months, my team and I had been helping an organization develop a new brand. We had presented concepts. Refined concepts. Revisited concepts. Created entirely new concepts.

And still, we were meeting.

That afternoon, the conference room walls were covered with storyboards depicting about a dozen strong possibilities.

Different logos, different tag lines, different color options. Each concept representing a different future.

Yet somehow, the room itself felt tired. A few people sat with folded arms. One man stared silently at a legal pad. Another rubbed his forehead as though concentration alone might produce a breakthrough. Three people stood against the wall because there weren’t enough chairs.

Most were nicely attired in suits and ties. They looked like capable people who had simply run out of momentum. We had all been there before. And somehow, after months of discussion, we still weren’t moving.

I made what I thought was a reasonable suggestion.

“What if a smaller group took the lead from here?”

The response came not in words, but in body language. Blank stares. Eyes dropping toward the conference table. A few slow head shakes, sideways. It was the kind of silence that says more than words.

I remember looking around the room and thinking:

We are never going to solve this by talking about branding.

That’s when Ellen’s Ice Cream came to mind.

Just down the street from our office sat Ellen’s Ice Cream.

If you grew up in Charleston, you probably know it. The ice cream is made onsite with fresh, local ingredients. Ellen's is the kind of place where people willingly stand in line while debating flavors.

  • Espresso Oreo.
  • Raspberry Walnut.
  • Almond Grove.

And an incredible vanilla bean with tiny black flecks throughout.

I looked around the room.

“I think we need a break.”

That got their attention.

“Let’s all walk down to Ellen’s.”

A few smiles appeared.

Then I made an offer: “I’ll buy everyone an ice cream cone under one condition.”

Now I had the room.

“You all must agree on one flavor.”

A few chuckles. A few raised eyebrows.
​

Then I added one more condition.

“It can’t be vanilla.”

That got a bigger laugh.

My business partner looked at me as if I had finally lost my mind. This was a big, valuable client, after all.

For the first time all afternoon, the room seemed awake.

Then the chairman of the client's committee stood.

He thanked me for the offer of ice cream in the polished, professional tone executives often use.

Then he explained that the committee would take the concepts back to their office and return on Monday with their top five choices.

The room nodded.

The meeting ended.

And I’ve thought about that room ever since. Not because of branding. And not because of ice cream.

To be honest, I still don’t know exactly why a room full of capable people found it so difficult to move forward.

There may have been dynamics I couldn’t see. Maybe there were concerns left unspoken. Or maybe the group was simply too large. I don’t know.

What I do know is this:

There was nothing wrong with vanilla.

In fact, Ellen’s vanilla bean was terrific. Had I stopped by on my own, I might have ordered it.

Vanilla wasn’t the problem. The problem was what it represented: the safest place for a room full of opinions to meet.

And maybe that’s why this story has stayed with me.

Because I’ve seen versions of that room ever since.

In committees, volunteer groups, churches. Even in families. Sometimes even in my own life.

We tell ourselves we’re waiting for clarity … for certainty. Waiting for one more conversation or another meeting. Believing we need to read one more online review.

Sometimes that’s wise. But sometimes we’re simply stuck.

Meanwhile, the possibilities wait patiently on the wall.

Waiting for someone to choose. Waiting for someone to move. Or for someone to say, “I’m good with either one.”

What stays with me all these years later isn’t the logo. It isn’t the committee. Not even the ice cream.

It’s the image of a room full of capable people standing within reach of several promising futures and finding it remarkably difficult to move toward any of them.

Have you ever been in a room like that?

I have.

More than once.

And I’ve learned that not every loss comes from making the wrong choice.

Some losses come from never truly making one at all.


Continue the Conversation

Wisdom Revisited with Wellness Entrepreneur Kate Reed

One of my favorite things about creating both this newsletter and The Main Thing Podcast is discovering unexpected connections between them.

This week's essay is about a room full of people who couldn't move forward. This week's podcast is about one woman who couldn't move as fast.

Three years ago, wellness entrepreneur Kate Reed joined me on The Main Thing Podcast with a simple piece of wisdom:

"Slow down."

When she returned recently, her wisdom had evolved. Now she says:

"Slow down... and soften."

In this deeply personal conversation, Kate shares what it was like to leave the security of a steady career to become a full-time entrepreneur. She also opens up about how a traumatic concussion forced her to slow down in ways she never would have chosen—and how that difficult season became an unexpected teacher of healing, boundaries, self-care, and grace.

If today's essay resonated with you, I think you'll find Kate's story just as meaningful.

🎧 Prefer listening? The audio version is available on our website, plus Spotify, Apple Podcasts and everywhere podcasts are found.


Wise Word of the Week

Yield (verb)

Pronounced: | yēld |

Meaning:

To willingly make room for another person, another perspective or another possibility; cease to argue about; produce or provide a result or gain.

Origin:

Olde English g(i)eldan - of Germanic origin, pertaining to “pay or repay”

When we yield, we are often taking the first step in moving forward.

As you enjoy the weekend and enter into the week ahead, mindfully seek an opportunity to yield. See if it unlocks some momentum for you or your group.


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One Last Thing ...

Will you help me shape what's next? One of the great privileges of creating The Main Thing Podcast and The Wisdom Newsletter is getting to learn alongside this community.

A few weeks ago, we launched a short listener and reader survey to help us thoughtfully shape what's next.

If you've already taken the survey, thank you. Your thoughtful responses are already influencing our conversations and future plans.

If you haven't had the chance yet, I'd be grateful for your help. It takes about 7 minutes to complete, and your feedback will help us create more of what serves you best. As a thank-you, you'll also have the option to enter a drawing for one of two $50 Bookshop.org gift cards from our curated wisdom collection.

​
​Looking forward-

~Skip


Skip Lineberg

Host - The Main Thing Podcast

"Your 9-Minute Dose of Wisdom"

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Hi! I'm Skip Lineberg, a podcaster and writer.

My aim is to help people get a little better at life. Interviewing the wisest people I know, I distill and share their wisdom with you by way of a podcast and this companion newsletter. I invite you to subscribe and get 2 free editions per month.

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