It’s not the work that wears most founders down. You’re built for hard work. If running through walls was a job… well… I guess it is. And this is that job. And look at that, you’re good at it.
No, you have super human resilience to hard work and pain.
What gets you, is the constant, never ending, relentless, walking up the slightest of inclines with the stiffest of headwinds that is decision making.
Everything is a decision and they all fall on you and so much of it is something you’re solving for the very first time.
You nodding your head yet or are you too tired for even that?
Yeah, I get it.
And maybe we can help. First, it helps to work with good number and a partner who has seen inside the numbers and decisions of a lot of businesses just like yours or at least close enough. Someone who can provide context, examples, projections, historical numbers, or even just an ear to listen to you talk it out.
But second, I have seen the same things trip up and drag down operators for YEARS.
Here are three mistakes that when fixed, I believe would help every operator make better decisions and make the process a little lighter for them.
Mistake #1: The Goal is… Everything.
Here’s a common scenario. You find a point in your business holding you back and look into solutions to solve it. As soon as you start the research - for a solution to one specific problem - you expand the goal of that solution to everything that could be a problem.
Take software for example. You start shopping for a basic tool like a CRM just so you can keep better track of contact information and resurface cold leads. But once you start looking at all the features and options, suddenly the solution needs to address all of them optimally.
These problems were not at the top of your list nor are they major bottlenecks for your success. But here you are making them a factor in the decision.

Easiest way to improve decision making is go in with a narrow set of goals and priorities. Then ruthlessly eliminate options that don’t serve that end NO MATTER HOW COOL THEY OTHERWISE MIGHT BE.
And if you do feel like there are just too many unknowns to say what the priority should be, either a) hold off until you know more, or b) prioritize flexibility and whatever gives you more options.
Mistake #2: Making your gut CEO.
Now I know. It’s often said, and I think often right, that your gut reaction is usually the right one. After all, our “gut reaction” is the aggregate of thousands and thousands of data points crunched by what is still to date the most impressive computational machine on the planet - your brain.
But here are two places to be careful.
Entrepreneurs tend to be optimistic people. You have to be. Which can mean you see what you want to see. Your “gut” is looking for things that support your prior beliefs or assumptions and point to it all working out. Which creates some big blind spots for risk.
While you’re optimistic, you’ve seen some shit. Your gut wants to avoid anxiety so it looks for things that make you feel better about scary things… but it also wants to avoid actual pain caused by mistakes. And you’ve made some mistakes. And it remembers all those kicks to the tender bits MUCH more clearly than that time it was just ok. Even more than the time it was great. Operators have a much wider range of emotional outcomes and unfortunately that means some low lows. Your gut is trying to protect you and sometimes that means steering you away from things with risk.

Both of these are good things, or I should say PRODUCTIVE things in a lot of situations. But they need to be managed. So yes, listen to your gut. Maybe don’t let it drive.
Mistake #3: Right vs Wrong
A lot of fear around decisions usually comes from believing that there is a “right” and “wrong” option or worse yet, a good or a bad one.
You think it is binary and you need to pick the right outcome.
In reality, you’re deciding between two (or more) buckets of potential options. What I call Outcome Profiles.
Here’s what I mean.
The height of the bars (y axis) is how often something happens. Where it lands on the x axis is the outcome. Far to the left, very negative, center is neutral, right is positive.
Instead of thinking will this outcome yield A or B outcomes, think about it as will this yield A or B range of outcomes.
The top one is something pretty normally distributed. Most common outcomes are neutral with the frequency declining as it approaches the extremes. A big win is possible, but unlikely. As is a big loss.
The middle is an option where there are a bunch of bad outcomes, a few ‘meh’ ones, and then some really good ones. Classic risk/reward.
And the last one has one really bad scenario that is not only possible, but likely, and then a few good options if it works.

In golf you have situations where you’ll be looking at the green and deciding where to hit the ball (assuming you have ANY control on that to begin with). You would assume, well just hit it at the pin - that’s the goal. But what if in between the pin and you is a pond and on the other side is out of bounds. If you hit it short, trouble. Hit it long, also trouble. It has to be perfect. Risk, reward.
If you hit it to the right of the pin though, you eliminate the highest possible outcome of putting it in the hole (highly unlikely) but you also make every mistake something you can easily survive.
You’ll hear golfers say, “if you miss, you want to be (right/left/long/short).”
That’s making decisions based on scenarios rather than a binary set of assumed outcomes.
Make a call and be prepared to fix it later
You’ll never get them all right. The most successful founders I’ve seen have a habit of making decisions with confidence. But not confidence that they’re right, confidence that if they’re wrong they’ll fix it later.
They’re not successful because they avoid mistakes. They’re successful because they take chances and then fix whatever didn’t work.
Best of luck out there.
