I hadn’t read The Odyssey in years. I don’t think I’d opened it since school, back when I was mostly trying to keep track of all the characters and adventures and wondering why everyone made such a big deal out of it.

Watching the movie brought all of that back. The story was familiar, but this time something completely different stood out to me.

Odysseus spends twenty years trying to get home. Between the Trojan War and everything that happens on the journey after, his entire focus is getting back to Ithaca. What I hadn’t really thought about before is that while he was trying to get home, Ithaca kept moving. The people changed, the relationships changed, the kingdom itself changed. The problems waiting for him weren’t the ones he’d left behind. He wasn’t coming home to the same place at all.

That stayed with me long after the credits rolled, because businesses do exactly the same thing.

“We Already Tried That”

One of the most common things I hear from business owners is some version of “we already tried that.” Whenever I hear it, I usually ask a follow-up question. When? Three years ago? Five years ago? Before you hired your current leadership team, before your revenue doubled, before interest rates changed, before AI became part of everyday business?

The answer changes everything, because sometimes we’re making decisions based on a business that doesn’t exist anymore.

I’ve seen owners reject a pricing strategy because it didn’t work years ago, without accounting for the fact that years ago they had different clients, different costs, different competitors, sometimes an entirely different service offering. I’ve also seen companies hold on to approval processes that made perfect sense back when there were five employees. Now there are fifty, and nothing gets approved without the owner. The team is frustrated that decisions take too long, the owner thinks the team isn’t ready, the team thinks the owner won’t let go. The process was built for five people, and nobody ever updated it for fifty.

The opposite version happens too. Sometimes owners keep treating a long-time customer like they’re still the biggest account in the business, long after the business has outgrown them, and the relationship has stayed frozen because nobody stopped to ask whether it still made sense.

Updating the Picture in Your Head

One of the responsibilities of running a company is updating the picture in your head. The business you started isn’t the business you’re running today. The market isn’t the same, your team isn’t the same, your customers aren’t the same, and hopefully you’re not the same either.

That doesn’t mean every past decision was wrong. Some of them will still hold up. Others were right for a season that’s already over, and there’s a real difference between the two. The problem is treating both categories the same way, refusing to revisit either one just because revisiting feels like admitting the original decision was a mistake.

Where to Start

1. Pull up your last five “we already tried that” moments and write down when each one actually happened. If most of them predate a real shift in your business, that’s your list to revisit first.
2. Look at every approval that has to go through you personally. Ask which ones exist because the business is genuinely still small enough to need them, and which ones exist because nobody’s gotten around to changing them.
3. Pick one long-standing client relationship and be honest about whether the terms, the pricing, or the attention it gets still match what the account is actually worth to you today.
4. Set a recurring check, once or twice a year, to revisit pricing, processes, and top accounts on purpose, instead of waiting for something to break first.

Cafecito Takeaway

Odysseus didn’t fail because he made bad decisions along the way. He failed to plan for how long he’d been gone. He kept picturing the Ithaca he left, not the one that had kept moving without him for twenty years, and that gap between the picture in his head and the reality waiting for him is where a lot of the trouble started.

You don’t need a twenty-year absence to end up in the same spot. A few years of running the business day to day, heads down, is enough for your own version of Ithaca to shift without you noticing. The client base changes. The team changes. The cost of doing business changes. And the decisions you made for the business that used to exist quietly keep running the one you’re actually in now.

This week, ask yourself one question: what decision am I defending simply because it worked in the past? Then go find out if you’re still the same king coming home to the same kingdom, or if it’s time to see the place as it actually is now.