The sweater incident

(Watch this on Youtube)

I need to tell you something I kept from my wife for four years.

Andrea bought me this SmartWool sweater hoodie for my birthday a while back. Really nice. Like, really nice. The kind of thing I would never buy for myself because I'm the guy who buys clothes at Target and calls it a day. She made sure I knew how much it cost. (She did not need to remind me twice.)

So the first time I wore it, I noticed those little tags on the inside — right at the waist, kind of scratchy, super annoying. And there was even a dotted line with a little scissors icon. Like, cut here. Clear instructions.

So I grabbed my pocket knife off the shelf in my closet.

You already know where this is going.

I cut through the tag. And then I cut right through the sweater.

I just stood there staring at this hole in a sweater that probably cost two hundred dollars, and my brain immediately went to: Andrea is going to kill me. We're done. This is how it ends. Not infidelity, not finances — a pocket knife and a SmartWool hoodie.

So I did what any rational adult would do. I hung it back up in the closet and panicked quietly.

After a few days of low-grade dread, I remembered that our friend Grace is a talented seamstress. So I called her up and said — and I'm not proud of this — "I need to tell you something, and you cannot tell Andrea."

Grace took the sweater. Fixed it. Did such a good job that unless you were inches away staring at it, you'd never know. I wore that sweater for years. Got my money's worth. Well — Andrea's money's worth.

About four years later, I was feeling brave. I asked Andrea, "Hey, you know that SmartWool sweater you got me? Do you think I've gotten our money's worth out of it by now?"

She said yeah, I wore it all the time. Then she asked why I was asking.

"Funny story..."

I watched her eyes go wide. Her jaw dropped. She couldn't believe I'd done it. She couldn't believe I'd sworn Grace to secrecy. And she couldn't believe she'd never noticed.

And guess who didn't get in trouble?

Here's why I'm telling you this. (Besides the fact that it's genuinely funny and I grabbed that sweater again this week and it all came rushing back.)

For four years, I was convinced that telling Andrea the truth would be catastrophic. That she'd be furious. That it would be this huge thing.

Would she have been upset? Yeah, probably. Gutted, even. Would we have gotten over it? Of course. But I never actually asked myself the question: what's the worst that could happen?

I just assumed the worst and acted accordingly. For four years.

I do this in business too. Or I used to.

The first time I launched my mastermind, I almost didn't.

I was at the tail end of an in-person event I'd hosted. Business owners from all over the country, all over the world. It was the last morning. Everyone was getting ready to wrap up and head home. And I had this idea — this mastermind I'd been building in my head for months — that I knew I should pitch to the room.

And I chickened out.

Too many questions. Would people even be interested? Was the price too high? Was I the right person to lead this? I decided I wasn't going to mention it. I'd just close out the event and figure it out later.

As I was wrapping up, somebody raised their hand.

"Hey — we know you can't host events like this every month. We're spread out all over the place. But we want to know what's next. How do we stay connected? How do we keep pushing each other?"

My stomach dropped. In the best way.

I very hesitantly started describing what the mastermind would look like. I was making it up as I went, honestly, because ten minutes earlier I'd decided not to do this. When someone asked how much it would cost, I gave them the number the way you tell someone you backed into their car — sheepishly, bracing for impact.

One guy stood up, pulled out his wallet, grabbed his credit card, and chucked it at me. "Sign me up. Take all my money."

Seven more people stood up right behind him.

I stood there realizing that every lie I'd been telling myself — they won't want this, it's too expensive, who am I to lead this — was just the sweater story all over again. I'd assumed the worst without ever asking the question.

What's the worst that could happen?

Someone says no. Someone says it's not for them. That's it. That's the whole thing. And you get over it. The same way Andrea and I would've gotten over a hole in a sweater.

That moment launched the first official mastermind group I ever led. And it changed everything about how I do business — not because of a strategy or a framework, but because I finally stopped hiding in the closet with the thing I broke, hoping nobody would notice.

Speaking of which — mastermind applications are officially open.

I'm building the next group right now. Small. Intentional. Business owners who are done making every decision alone and want people around them who will push, challenge, and call them out (in the best way).

This round I'm offering a six-month option for those who aren't ready to commit for a full year — and yes, the six-month includes an in-person meetup.

Applications close in three weeks. Twelve seats. If you've been sitting on something — you just read a whole newsletter about what that costs you.

If you want to see what it looks like, hear from people who've been through it, and watch the video — head to mastermind.ryankoral.com.

And if you're not ready, that's okay. But do me a favor — next time you're holding back on something, ask yourself the question: what's the worst that could happen?

It's almost never as bad as the story you're telling yourself.

To taking the shot, Ryan

P.S. I still wear that sweater. Grace did incredible work.

P.P.S. Seriously — three weeks. Twelve seats. Don't be the one hiding in the closet with the thing they broke. mastermind.ryankoral.com