Exploring Opportunities: Overcoming Entrepreneur’s Block

This article explores entrepreneur’s block – the symptoms (feeling uncertain), the causes (entrepreneurial maturity), the challenges (exploring amidst uncertainty – aka the valley of death) and the cure (creating conviction).

The Symptoms: Feeling Uncertain

Many exploration stage entrepreneurs struggle with entrepreneur’s block: not doing their work, working half-heartedly, not getting things finished and constantly feeling frustrated with their progress as a result.

  • Can’t decide what to work on?
  • Too many options, but not enough time?
  • Always feels like there’s more important work you could be doing?
  • Overwhelmed into inaction?

Entrepreneur’s block is all about how you feel – you feel overwhelmed, you feel like there’s something better you could be working on, you don’t feel like doing certain work – and the action, or lack of action, you take as a result.

  • Not starting: it feels like you’ve too many things to work on and you don’t know where to start
  • Not finishing: when you do start on something, a better opportunity comes to mind, or you begin to notice all the reasons this might fail, so you stop working on it (leaving a lot of unfinished projects)
  • Spiraling: false starts and lack of progress leave you feeling overwhelmed and full of doubt – leading to greater indecision and deeper block: maybe I’m just not cut out to be an entrepreneur?

The Causes: Entrepreneurial Maturity

There are many causes for creative blocks, both external causes (e.g. financial pressures) and internal ones (fear of failure etc.) – self-actualizing creativity demands psychological security.

However, when it comes to entrepreneurship, I believe that the most common cause for being blocked is simply that you are becoming a better entrepreneur! 

You’ve become conscious of your own incompetence. Previously you could plough ahead in ignorance, sure that your idea would work (as you couldn’t see the risks) and sure how to do it (as you couldn’t see the alternatives). Now you’re able to see all the risks, all the alternative options – and it’s paralysing. 

The fundamental difference is lack of conviction: whereas previously you were certain of your path, now you’re not convinced by any of your options. 

Most entrepreneurs yearn to regain this conviction. How easy it would be to proceed if you could find that idea you’re certain would work…

However, the only way to get there is to realise that your current lack of conviction makes sense! You haven’t explored the options yet, conviction isn’t possible. Conviction was only possible previously due to your ignorance. Sure, it had it’s benefits – you weren’t feeling stuck like you are now – but ultimately it was the conviction of a fool. This naive conviction is no longer possible: you need to give up searching for it. Instead, you have to learn how to proceed without conviction…

A mature entrepreneur sees the risks and alternatives, but proceeds anyway. They have learned that conviction must be created.

The obstacle is the way: how can you choose what to work on and how can you motivate yourself to get that work done without conviction?

The Challenge: Exploring Amidst Uncertainty (aka walk through the valley of the shadow of death)

Proceeding without conviction is hard. I call it the valley of death. Ben Horwitz calls it the struggle. Uncertainty makes it hard to stride confidently in any direction – all options seem like bad ones. You don’t know if any of these ideas will work. They might not. You’re proceeding 100% on faith that you’ll find something; proceeding even when you’ve lost that faith that you’ll find something. 

But, proceed you must. There is no way to get conviction for an idea without creating that conviction.

The Cure: Create Conviction

  1. Realise that you have to go through it: you have to create conviction even when you don’t have it. You can’t find conviction. You will always be unsure if any idea makes sense: you have to just start doing it anyway. Starting something without complete conviction can be painful. It might look like it’s easy for everyone else, but that’s not true. 2 things make this more palatable:
    1. Accepting that starting without complete conviction has to be done: there is no easier path, there is no idea you will be 100% sure of in advance. This acceptance comes with experience (of trying to find an easier path)
    2. Accepting that there is nothing else you’d prefer to be doing: that you’re never going to be happy working on someone else’s idea. So you’re going to have to go through this pain at some point. This acceptance also comes with experience (of searching for other exciting options to work on)
  2. See the challenge for what it is: the balancing act of exploring amidst uncertainty. At the heart of the challenge is uncertainty. Should you keep exploring to find a better option? Or shouldn’t you commit to making progress in one direction? This balancing act of exploration vs. exploitation is particularly acute at this stage of idea exploration. There is so much that is unknown.
  3. Start somewhere: make a decision, make a commitment.
    1. Decision making amidst uncertainty – what to work on when there are a multitude of options, none of which seem clear – is a key skill as an entrepreneur. You need to begin developing it now.
    2. You might make the wrong call. That’s fine: it was the best call you could make with the information you had at the time. 
    3. Define a commitment: what will you get finished? No matter how strong the doubts, commit to getting to that point.
    4. Do something: build a product. Talk to customers. Start!
    5. Prepare to manage your doubts: have I missed a better option? Look at all the things that could go wrong with this business? 100% of the time, you can choose to sit around trying to think of a better idea… or, you can commit to just doing your current best idea and see where it takes you
    6. Prepare to manage other people’s doubts: other people will not understand this proceeding amidst uncertainty: to them, you either believe in an idea or you don’t. For better or worse, these people are not like you – learn to ignore them
  4. Go head on: you have to pass through this valley at some point, don’t wait to be dragged kicking and screaming. You know that you want to be an entrepreneur, you know that you are capable of doing it. Put in place whatever supports you need for yourself and go face the music.

You don’t start being an entrepreneur when you find a business idea. You start being an entrepreneur as soon as you start making uncertain decisions and commitments. So do that: start. Make a decision. Make a commitment. Even if it might turn out to be wrong.

When you’re feeling blocked, remember that you are already an entrepreneur. You’re already doing everything I’ve outlined above – you’ve just lost sight of this. Your challenge is to remember! To regain and retain that perspective. This is a process, and you’re right in the middle of it.

If you find yourself regularly struggling with entrepreneur’s block then let’s chat: perhaps working with a coach or an accountability group of other exploration stage entrepreneurs will help.