So the other day I’m standing in front of my closet, wondering what shirt I’m going to wear that day. And for whatever reason I’m unable to make a decision. Intellectually I realize it’s really very silly. I’ve got like 5 or 6 perfectly good shirts to wear, yet I’m unable to commit to picking a shirt. It’s like that cliche where you can’t decide what restaurant to eat at.

This of course led into a train of thoughts and self-reflection…what is it that is preventing me from picking out a shirt? What kinds of things prevent me from making a decision? How does that relate to management? And what could I do about it?

Here are some of the reasons I could think of.

What if it’s the wrong choice?

If I’m sort of teetering back and forth between a comfortable-yet-plain tshirt, and a nicer button-down, it’s because I really want to wear the tshirt but I’m worried that something will happen and I’d wished I’d worn the button down instead. I’m worried I’m making the wrong choice.

Should we save that image in .jpg or .png format? Should we buy licenses for Sublime or Visual Studio? Should we build on Azure or AWS?

One way I’ve found to get past this one is to think about the cost of change. Let’s say we buy Visual Studio, then decide 4 months from now we really should have bought Sublime instead. What’s really the cost of change? To be honest, not much. Sure, some licensing fees and whatnot but it’s not like we have to rewrite the whole product from scratch. Just change it.

Even switching something heavyweight like from Linux to Windows is not necessarily as insurmountable as you might think. I’m certainly not saying it’s easy but it is completely feasible to decide to shift something fundamental and just plan and execute the change. If the change is going to pay itself back in the long run in gained productivity or TCO savings, then it’s completely reasonable and worth it to make the change.

So think about the decision in front of you, and think about what the consequences are if you make the wrong decision, or want to change it. In many cases the cost is not that high, or the decision is at least reversible, so let that be a confidence builder in just making a decision and giving it a try.

I need to have enough shirts for later.

This is an interesting thought that appeared in my head. I have a certain number of clean button down shirts, and I’m worried that if I “use one up”, then I’ll have one less button down shirt in case I need a button down shirt tomorrow.

I’m worried about committing a developer on a project because some other project might appear tomorrow and my bench is exhausted.

So first of all, while a “better” option might appear tomorrow the truth is that there is a perfectly good option right in front of you right now. Sure, there’s a probability of occurrence for some opportunity in the near future, but the probability of occurrence for the project right in front of your face is 100%. Guaranteed results, motion, revenue, right now gives you immediate gains, whereas waiting for what might happen, there’s that possibility that the result is zero.

Move forward now. Commit now. If there’s a way to make gains right now, as long as they are the right results and in the right direction, then take that opportunity and make those gains, even if they are small. Because you can always adjust tomorrow.

There’s too many choices.

This is the typical “analysis paralysis”. There’s almost too many shirts to pick from. Some of the differentiators are almost negligible. OK, I’ve decided to wear a polo, so do I wear the blue one or the black one?

Should we build this next project in Python or Ruby? Or .NET? Or Node? Or php? Or Java?

You know what? Maybe the differentiators don’t matter that much. Maybe it doesn’t really matter which shirt you pick. Maybe it doesn’t really matter that much whether your API backend is in Node or Python. If your technical team can do both, and both languages do everything you need them to, then maybe in the long run it doesn’t really matter. Just pick one and move forward.

Does anyone really care whether my polo is blue or black?

I’m paying more in lost opportunity trying to make a decision than if I’d just picked something and started making progress right away. I could already have some features and releases done instead of arguing about which language has better garbage collection or SDK support.

All these thoughts went through my head as I stood there in front of my closet. Meanwhile, like 20 minutes had passed and I hadn’t even picked out a shirt yet.