We’ve all heard about the power of positive thinking. And I’m pretty certain that somebody has encouraged you to “look on the bright side” when something isn’t going the way you’d like.
But have you ever considered the power of negative thinking? By which I do not mean being hopelessly pessimistic. Maybe there’s some value in that, but what I’m referring to is a simple not-so-positive question that has the power to significantly improve your approach to risk-taking and decision-making.
“What’s the worst thing that could happen?”
I ask that question all the time whenever I’m trying to make a decision about what to do with my business. A lot of times it’s the first question I ask when I’m considering a new idea. Let’s say, for example, that I’m writing a script for a new training video, and I’m trying to decide if I should include a particular joke. My worst-case scenario could range anywhere from “people don’t think it’s funny” to “people find it offensive or controversial.” If the answer seems to be the former, I’m more inclined to include it in the final draft; if the latter, I’m probably going to cut it out or rewrite it.
Imagining worst-case scenarios is equally beneficial for bigger decisions. Let’s pretend you’re considering buying an expensive piece of equipment for your business. The worst thing that can happen is probably that it doesn’t improve your business as much as you think it will, and that you’ve basically thrown away your money. So then the question becomes, “If this ends up being a mistake, is it one that I can handle? Or does it have the potential to ruin me?” How you answer that question is absolutely going to influence what you decide to do.
This process, by the way, is the reason that I have not yet gone parachuting, because the worst thing that can happen is that I’ll die, and up until now I’ve made the decision that whatever pleasure I might experience from jumping out of a plane isn’t worth that risk. But who knows? The risk of dying in a parachuting accident is fairly small, and maybe someday my kids will want to do it and ask me to join them when I’m older and closer to being dead anyway. So if that happens, I may reconsider the risk of dying against the value of participating in a unique experience with my children.
The point I’m trying to make is that thinking negatively – imagining the things that could go wrong, and then really running those scenarios through – can be a very important part of making reasonable, intelligent decisions. When I was considering getting into stand-up comedy, I wasn’t sure I’d be any good. So I went to an open mic and watched 20 comedians do their 5-minute sets. Three of those people got zero laughs, and I walked away thinking, “If I try this, the worst thing that can happen is that I’ll be tied for worst with people who’ve been doing this longer than I have.” That ended up being all the encouragement I needed to give it a shot myself a week later (where I was comfortably in the bottom half but not the worst performer, by the way), and that decision has ultimately led me to a career that has taken care of me and my family for the past two decades.
So the next time you’re trying to decide whether to ask someone to dinner or invest in a new marketing strategy, I hope you’ll spend some amount of time thinking deeply about everything that might go wrong. It could end up making all the difference.








