Recently I’ve been looking back on the last 10-years of my life and reflect on where I am. Predictably, I’m left looking as much at what I didn’t do as much as what I did.

Regret is a powerful force that I know plagues most of us. Worse yet, it is difficult for us to predict it in the moment that a choice comes to us. So when we’re thinking, should I shouldn’t I, it is very easy to keep putting things off, until it becomes, I didn’t.

In the last 2-years, I have 2 major regrets that continuing to plague me. They are both so bad, that they even undermine my confidence in my ability to execute in the future. My regrets come from a single common place, lack of action. Looking back now, it is impossible to predict whether-or-not failure would have occurred. Instead, I’m left with “failure by default,” which is not a great place to be.

One of my mantras this year I’ve stolen from Nike, it is the iconic, “Just Do It.” I know this sounds silly, but for someone prone to over-analysis to the point of paralysis, it is a good reminder. It is good to remember that it is better to do something and fail than to do nothing at all.

It comes down to is that over-analysis begets fear. These many times come in the form of what is statements.

What if …

  • No one will buy what I have to sell?
  • I look stupid?
  • I can’t do this?
  • The product grows beyond my means to support it?
  • People won’t pay for it?

Here’s the thing, there will always be questions, but the best way to answer fear, in this case, isn’t to give up. Instead answer the questions honestly or understand that these questions can be distractions.

Sure, some of these questions, like “Will people pay for something like this?” are important ones to answer up front, but don’t assume you know the answer. Instead, find some people who you’re thinking would be your customers and talk to them. Ask them what sort of problems they’re having and find out if what you’re looking to do will solve those. If so, ask, “how much would it be worth to you to have this taken care of for you?”

The idea is that we fear what we don’t know. Fear also causes us to draw our own conclusions. Not based on reality, but based on our own understanding and prior experience. It is easy to let this fear tell us it is right and that it knows what will happen. The reality of the matter is, you need to buckle down and do the work. Answer the question by doing, not assuming.

If you find that nobody will buy what you’re looking to sell, then use those conversations to find what they would buy. These types of actions, when taken, can bring confidence and ease the fear. Ultimately they can provide the knowledge needed to make something happen.

The key, though, is that you need to decide what that next action is to move you forward and “just do it.” You won’t always get the result you hoped for, but sometimes you’ll actually end up with a better end result. No matter what it is, I’m sure it will be better than the alternative, which is a future full of, “what if I had done it?”

That is definitely one definition of hell for me.

I know I no longer want to live with those type of questions and I hope you wouldn’t either.

So I ask you, what is one thing that you’ve been putting off because of fear? And what is one thing you can do right now to move it forward?

I’m a father, traveler, and web developer @Automattic. In the wee hours, I’m also working on new projects like 1 on 1 Questions.