Beware the Business Quicksand: Lessons from a Serial Mistake-Maker

Previously, I talked about chasing shiny objects. Let’s assume you chase one and dive right in.

It will eventually happen, so how do you prepare before getting stuck in business quicksand?

Picture this: You're the Denver Broncos, and you've just shelled out a king's ransom for Russell Wilson. Oops. Suddenly, you're stuck with a quarterback about as mobile as a statue and a contract harder to escape than Alcatraz (Jack Nicholson). Eventually, you can get out of it, but at a massive cost.

Or how about those officer workers turned wannabe farmers? One minute they're dreaming of idyllic country life; the next, they're drowning in goat and chicken poop and wondering how the hell to operate a tractor. They have more stuff than a hoarder's garage sale and no clue what to do with it all.

Here's the kicker: we humans are masters of self-deception. We fall in love with an idea and suddenly see the world through rose-colored glasses. We're so busy planning how to spend our millions that we don't notice the gaping holes in our business plan. We haven’t had a quarterback in ten years, now we have the change to get Super Bowl winning QB Russell Wilson! Without noticing that he might be past his prime.

And let's be real—businesses are just as guilty. They're like kids in a candy store, grabbing at every shiny new idea without thinking if it's actually good for them. Our businesses all have these scars, and dead cap hits—that idea that we loved but never really panned out—blaming the market, not ourselves.

So what's the secret sauce? Start small. Test the waters before you dive in. It's like dating—you don't propose on the first date (unless you're in Vegas, but that's another story). Try things out, see if they work, and only commit if they show promise. Rinse and repeat.

Consider how easy it is to walk it back.

If things don’t work, how easily can you get out of it, and what are the costs—time, legal, financial, emotional, and long-term damage to the business?

Remember, it's better to have a crappy little side hustle you can ditch quickly than a massive money pit you're attached to like a ball and chain. Nobody wants to end up with a warehouse full of bedazzled fidget spinners and a mountain of debt. (Yes, that's a real thing that happened. Look it up.)

Instead of dreaming about how you will spend all the money from your great idea, dream about how the idea might not be great after all, and think about all the ways you can get out of it if it doesn’t work. How can you test the idea for the least possible cost and the lowest amount of damage?

I am writing this because I have made these mistakes. Wasting too much money on the wrong thing and having it take literally years to unwind. Those were costly lesions, and honestly, I am not sure I would have learned them had I not made the mistakes,

Now, I test small and let the market confirm before going to the next level. That slows things down, which some people can’t handle, but it gives you the priceless option of walking away relatively unharmed.

Take a step back the next time you're about to go all-in on your "revolutionary" idea for artisanal, hand-crafted botanical salve. Ask yourself: "Am I prepared to throw all this in the dumpster if it doesn’t work out?" That question alone is sometimes enough to set you straight. We can all handle throwing away (or donating) a box, but twenty pallets worth—that’s a different story.

Ask yourself: “If this doesn’t work, how long will it take to recover financially? Will this take precious cashflow away from my core business, stunting that in the process?”

Does pursuing this path mean turning down all future opportunities for a while? If so, is this the best opportunity?

Russell Wilson, homestead dreams, and savior products. Don't get stuck, folks. Keep your options open, your investments smart, and your exit strategies handy. That way, when opportunity knocks, you're not too busy trying to offload a truckload of unsold merchandise to answer the door.

Diego

Listen to the long version of this letter on Carrot Cashflow.

In case you didn't know, I write several short posts like this each week on Instagram - check them out @diegofooter.