Created with Sketch.

What to do when you can’t make a decision

Above all else, my client work always comes back to battling indecision. Business success is about making good decisions swiftly. You’ve got to be the most certain guy in the room.

Beginner entrepreneurs just procrastinate (fix that here) but seasoned pros get held up when they find themselves in a decision double bind.

It looks like this: “I have to make a decision before I move forward, but I can’t make a decision until I move forward!” 

Today’s post is designed to help you achieve two things. First, to identify when and where this double bind is occurring in your life/business. Second, to bust the paradox apart and get you moving despite feeling stuck.

The hard part about indecisiveness is that it feels so damn real. In my average week, I’ll hear at least ten separate instances where a client presents compelling reasoning for “waiting and seeing” or “watching this play out”.


A business partnership has fallen apart and a decision needs to be made about what new business/career to embark on next. Of course, that decision can’t be made until the old/broken business is totally wound up. So no action is taken.

A new website is almost ready to be launched and a decision needs to be made about which marketing strategy (at least three are on the table) to wholeheartedly embark on. Of course, that decision can’t be made until the new site is up. So no action is taken.

A startup founder is torn between seeking out more investment capital or strengthening the companies B2B sales channels to generate cash. Of course, that decision can’t really be made until a whole bunch of projects are ready. So no action is taken.

Are these scenarios starting to feel familiar? Do they serve as metaphors for the paralysis of indecision you’ve found yourself in?

To diagnose yourself with “entrepreneurial next-step indecision paradox” (I’m still working on the name) all you need to do is spot the pattern.

Where are you feeling like you’re at an important, strategic fork in the road right now? Are you stuck there waiting for something else to happen or progress? Perhaps something that will paradoxically occur only if you journey down one of the forked paths before you?

If the answer to any of those questions is “Yes”, then you’re in the double bind. Good news! The solution to the paradox is so painfully obvious you’ll punch yourself once you *get* it.

Just go down both paths

In almost every conceivable example where an entrepreneur is stuck at a strategic cross roads, progress will require massive learning either way. Option A? The first thing you’ll have to do is reach out to people, connect, learn the rules of the game etc. Option B? Same thing, albeit in a different area.

Let’s take the example of the startup founder. She’s torn between raising another round of capital or pursuing the (yet to be closed) B2B sales leads that could result in that precious bootstrap capital.

Say she magically decides to commit wholeheartedly to the first option? She’ll have to learn about raising a second series. She’ll have to reach out to investors – a lot of early stage gentle networking will be involved. She’ll have to schmooze existing investors. These are just a few examples of the dozens of things she’ll have to do!

Or if she commits to option B? She’ll have to start early stage networking with B2B sales channel partners. She’ll have to start polishing the value proposition and pitch. Cold calling. And the list goes on.

Everything I listed above represents actions that can be taken that continue the momentum down the fork in the road… without actually cutting off the other path.

This is the cinch: It’s time to throw out the fork-in-the-road metaphor. It isn’t serving you as an entrepreneur because it doesn’t make any sense. 

Newsflash: You’re living in an infinite plane of possibility.

All that “progress” means is traveling from one place to another. At any point you can find new directions to go in – changing course by a degree or two or even turning around. There is no fork in the road.

Entrepreneurs get totally paralyzed when they convince themselves that their dichotomy  is real. When you start to believe that you have to make a decision and that doing so will shut off the other possibilities.

A lot of folks stress the latin root of the word “decision” which is the same as “incision”. It’s all about cutting things off, essentially. And yes, there are times when you have to wield a knife – hiring and firing are examples that come to mind.

However, the vast majority of your entrepreneurial angst comes from the pressure you create when you tell yourself you must make a decision… when you simply don’t have to.

By adopting a philosophy of exploring both forks in the road (for a good while longer than most people think is possible), you’ll learn more about the decision you thought you had to make. You’ll discover further forks, shortcuts and loops. You’ll start to realize the decision didn’t really matter, or perhaps matters more than you realized but isn’t nearly so urgent.

The point here is that you’ll learn far more than simply blindly committing to one strategy and “eliminating” the other because you have told yourself you have to. You still might make a decision to cut off one avenue or option, but when you do you’ll have better reasons for doing so.

When you use this strategy, big decisions will always appear blindingly obvious.

The real point here is that if your decision isn’t stupidly obvious it’s an indication that you need to keep marching down both paths for a while longer. Keep paying attention. Keep assessing. Keep learning until something that isn’t already obvious clicks and suddenly is.

The simple truth is that action is the solution to strategic-indecisive-angst. Call it Lean, Agile or just being intelligent but testing things out for a while in a few directions is always going to work out better than blindly plunging down one path just because you want to come across as decisive.

Yes/No poll question: Have you ever hesitated way longer than you should on a big business decision?  Tell us in the comments.


+ Add Comment
  1. Breaking away from the pervasive idea that there is “one right answer” is a challenge. As someone working to get out of its paralyzing grip, to try experiments in which I allow myself to fail and learn, I appreciate this post. Thanks so much for articulating what I am just beginning to observe. It accelerated my learning and renewed my resolve.

  2. I really enjoy your articles. I don’t always agree, but you certainly make me open my mind to new possibilities. In this case, I see a recipe for burnout. Trying to pursue two completely different business strategies simultaneously will take more time and effort than many human beings have to give. In addition, I think the lack of focus will water down the effectiveness of the strategies and make it more difficult to determine which one deserves eventual commitment.

    You bring a great perspective to the “forks in the road” and “The One And Only True Correct Answer For All Time” ideas. The real world isn’t that black and white and you have done a great job shifting perspective to consider alternate ways of pursing the options available.

  3. I hesitated way too long on deciding to finally leave the safety and comfort of a corporate job and go out on my own. I got to the point of being totally burnt out and feeling uninspired and lacking in confidence. It took me way longer to get back that feeling of confidence and excitement than if I had made the decision earlier.

    It was much like how people approach having kids- I kept feeling like, “I’m not ready quite yet. I just need a little more money, a little more knowledge, etc, etc.” Excuses, like you said. Possibly valid excuses, maybe, but still excuses.

    Finally I heard a quote that really rang true with me: “You’re never ready, it’s just your turn.” Thinking about it that way finally pushed me over the edge to make the decision and start pursuing my entrepreneurial goals while still in the safe confines of a job. Like you said, I was able to choose both things for a while and get the confidence I needed to take the leap.

  4. Hey Peter,

    Insightful post here. I’m going to agree and disagree. You can certainly take both forks in the road in almost all cases…but eventually you’ll find that you’re going to have to choose ONE sooner or later.

    The real question is, how do you know when you’re ready to take that one path?

    The problem is, as to how Beau alluded too, sometimes you CAN’T.

    (Even though I feel that most times it’s pretty obvious, but that’s a discussion for another time!)

    1. Hey Daryl,

      I think we do actually agree – the point of this article is that in most cases entrepreneurs can explore both paths until what to do next becomes very obvious. That’s the moment when you’ve got to decide.

  5. I’d like to add a somewhat functional point of view. If you are not able or willing to decide between alternatives it apparantly pays off (consious or sub-consious) to not decide. The moment the pain of not deciding is high enough, you will make the decision. Asking yourself “what could be the benefit for me to keep this problem instead of solving it” can lead to to the real reasons why you are not deciding.

    1. Hey Marc, you’re right on about the pain threshold – it’s something I’ve talked about in a tone of posts. The question you pose is basically a more eloquent way of saying what it took me 1000 words to articulate ! Thanks for contributing 🙂

  6. Yes. And it like what Daryl says here about eventually choosing one of the other. And sometimes we even end up choosing or un-choosing unconsciously through self sabotage… this really sucks!

Leave a Comment

Outsource your battle for Focus and Productivity

Commit Action’s Executive Aide service helps business owners become the highest leverage version of themselves possible.

Visit Peter’s other business