You’ve no doubt heard someone — maybe me or Seth or other tributes to failure — encourage you to fail fast and fail often if you want to be a successful changemaker or entrepreneur. Fear of failure keeps so many people from actually starting the projects that’ll lead to them succeeding. It ends up being a kind of self-fulfilling prophecy.

It’s become more obvious to me that that counsel also covers making bad decisions. It’s not just that you have to embrace making a good decision and having the failure come up in the execution, but, rather, you have to be prepared to make bad decisions in the first place.

Here’s the bottom-line: if you’re not making bad decisions, you’re not making enough decisions.

Part of the changemaking journey is learning to make decisions with incomplete information, time, and resources. What it takes practice to see is that, most of the time, more of those items actually don’t help the decision get made. Usually, more information, time, and resources make it harder to make the decisions that need to be made.

There’s a big gap between the inputs — information, time, and resources — to your decision-making process and the output of that process. More experienced entrepreneurs jump that gap quicker and usually with better success, and, in the times when they make bad decisions, they know how to tuck and roll and keep their eyes forward.

What many of us fail to think about is that, as your business or project gains momentum, you’ll have to make more decisions precisely because its scope and visibility grows. If you haven’t worked your way through learning to make good decisions and recovering from bad ones when your business is young, it’s going to be much, much harder to make those decisions when people are watching and the decisions have a bigger impact.

At the same time that you’re disadvantaged by experience, perspective, and resources, you’re blessed by having a safer sandbox to make bad decisions. Would you rather make a bad decision when there are three people involved who know or when there are 300,000?

As much as we may not like it, we’re hard-wired to learn more from mistakes than we are from successes. A corollary to that is that we only learn to become successful by failing. Hence the “fail fast, fail often” thing.

Just in case this is all too theoretical, I’ll make it clear that you’ll:

  • Hire the wrong teammate and then have to let them go
  • Start using the wrong tech solutions over and over again as you learn which ones actually work
  • Ally with the wrong partner and get burned
  • Market a product, service, or event that no one (or almost no one) buys
  • Talk to a big name and look like a fool
  • Give a talk that doesn’t land
  • Create what feels like 99 pieces of crap for 1 masterpiece
  • Pay the wrong amount for taxes and have a bright, sunny, and cheerful mid-April day go dark very quickly
  • Start a nine-month campaign and find out three months into it that it’s the wrong campaign
  • [Insert whatever consequence of a bad decision that most stings you]

It’s not a rosy picture, I know, but I’d rather tell you the whole truth rather than just the pretty sides. Through my years of advising people, I’ve learned that the uglier truths that aren’t being shared cause more suffering and inaction because it’s so easy for people to assume that the inconvenient truths that are challenging them are doing so just because they’re inadequate or stupid. It’s not just you.

I’m obviously not encouraging you to willfully make bad decisions, nor am I encouraging you to not endeavor to get better at it. It just so happens that to get better at it, you have to be prepared to make some bad decisions.

A significant upshot to this that embracing the fact that you’ll make bad decisions will make it easier to decide early and often, which in turn will limit your decision fatigue significantly.

In the end, it can be hard to tell what’s a “bad” decision and what’s a “good” decision. In one slice of time or one perspective, things appear one way. In a later slice of time or different perspective, they appear a different way. “Never count a man happy until the end of his days,” the Greeks used to say, and the same truth applies here.

Think about a decision you’re stalled on right now. Do you need more inputs or do you just need to jump the gap already? Get real and get it done.

Charlie Gilkey is an author, business advisor, and podcaster who teaches people how to start finishing what matters most. Click here to get more tools that’ll help you be a productive, flourishing co-creator of a better tomorrow.

Originally published at


  • Charlie Gilkey

    Author, Speaker, Business Strategist, Coach

    Charlie Gilkey helps people start finish the stuff that matters. He's the founder of Productive Flourishing, author of the forthcoming Start Finishing and The Small Business Lifecycle, and host of the Productive Flourishing podcast. Prior to starting Productive Flourishing, Charlie was a Joint Force Military Logistics Coordinator while simultaneously pursuing a PhD in Philosophy. He lives with his wife, Angela, in Portland, Oregon.