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The Comfortable Choice

When organizations face a crossroads, they almost always have two options in front of them: the comfortable choice and the necessary one.

Every organization eventually faces a moment where the Comfortable Choice and the Necessary Choice are at odds.

When Organizations Face a Crossroads

When organizations face a crossroads, they almost always have two options in front of them: the comfortable choice and the necessary one.

The comfortable choice is familiar. It doesn’t ask much of anyone. It preserves relationships, avoids friction, pushes unity, and keeps the peace. People who advocate for it are easy to be around. They don’t push too hard or ask too many questions. They understand that some things are just the way they are.

The necessary choice is different. It requires looking honestly at what isn’t working and naming the problem – even when it breaks the comfort of silence. For real change, systems and accountability structures that outlast any one person’s tenure have to be built in. Uncomfortable questions about whether the organization is actually serving its members or just sustaining itself have to be asked, and answered.

The comfortable choice and the necessary choice are rarely the same choice.

Genuine Reform Work is not Glamorous

Anyone who has done genuine reform work inside an institution knows what it actually feels like. It’s showing up to meetings where your agenda items get skipped, asking questions that people would rather avoid, and documenting things that have never been written down. Nobody asked you to do this work, but institutions without memory are institutions without accountability. Somebody has to care about that. Nobody thanks you for it. But it’s the only kind of reform that actually sticks.

I’ve been thinking about how reform actually takes place: the people who most need it are often the people most resistant to it, and prefer to avoid conflict. Not because they’re bad people – most of them are kind, hard-working, and good people. But reform requires admitting that something wasn’t working, and that admission is genuinely hard. It’s easier to frame the person asking the questions as the problem than to answer the questions. What I’ve figured out is that when reform comes, conflict is inevitable. While being unified around a common purpose is a worthy goal for any organization, being unified about mediocrity is not.

Except for when I’m in the red suit, and the day I was married to my lovely bride, I’ve never been the most comfortable choice in any room. I came into this work reluctantly, because I believed the organization I care about deserved better than what it was getting. I still believe that. I’ve tried to demonstrate through my character, words, and actions – through the record I’ve built, the questions I’ve asked, and the lines I’ve refused to cross even when crossing them would have been easier.

Whether that’s enough is not my decision to make.

Think Carefully What You’re Actually Choosing

But if you’re part of an organization facing a crossroads – any organization, in any context – I’d ask you to think carefully about what you’re actually choosing when you choose comfort. Because the comfortable choice has a cost too. It’s just a cost that gets paid later, by the people the organization was supposed to serve.

The necessary choice is usually the one less often made, because it’s harder, and more likely to be criticized. But it’s also the choice that moves an organization from the way it’s always been to a new and Lord willing, a better path.


I wrote this because I believe it. Not because it’s comfortable to say, or because it’s likely to win me any popularity contests. If you’ve read this far, you probably believe it too. That’s enough for me.

—Craig

Craig Hamilton is a professional Christmas performer, Christmas ambassador and the creative mind behind Santa Craig Cringle. He writes about Claus professionalism, sustainability, and the evolving craft of Christmas and holiday portrayal.

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