"Everyday is one less day" - Tom Ford

On Doubt and Optimism for Entrepreneurs

When I was a 35 year old CEO, I knew everything. Now I’m a 58 year old CEO and there’s rafts of things I don’t know.
- Howard Diamond

If you have attended an event where entrepreneurs are bound to be lurking, you will undoubtedly notice they are the most optimistic people ever. It’s their job to be right? They have to exude confidence in what they are doing because they are always selling, even when they aren’t.

However what you probably might not know and rarely see are the moments when the most confident and even the most successful entrepreneurs doubt themselves. The reason you don’t see it often is because they are masters at hiding it. In fact, I doubt myself quite often but you wouldn’t notice it because I never show it. I’ll explain in moment how I deal with doubt and uncertainty.

It’s an unwritten rule that entrepreneurs should always show that they are certain about what they are doing. Unfortunately doubt and uncertainty could be seen as a weakness and if customers, employees or investors sense that the entrepreneur is not in control it could lead to disaster (or so us entrepreneurs think).

I think that doubt should be seen as an asset to entrepreneurs and can be leveraged as such. Every entrepreneur should have a core group of people around him that he trusts to share his doubts with, who can often add valuable advice and perspective. However if you don’t have that core group yet or don’t want to bother them with every case of self doubt, here is how I often deal with doubt internally.

1. Dealing with Fear & Worst Case Scenario

I think most entrepreneurs’ doubt stems from the fear of failure. Am I good enough? Will this work? What happens if it doesn’t work? We all ask ourselves these questions, it’s only natural. At some point you need to get comfortable in dealing with fear and the best way to do this is to understand your worst case scenario. I have already experienced my worst case scenario before and I would be comfortable experiencing it again – therefore the only way for me is forward!

2. Knowing What You Don’t Know

I often find that I only doubt something because I am uncertain about a specific area of expertise or how something works. I will then spend time figuring out what I need to know and educate myself, thanks to Google University. If I am unable to educate myself sufficiently I will then seek out someone who can assist. Over time I have become more aware of what I don’t know and have realised that it’s impossible for me to know everything and always have the right answers – and I have become comfortable with that.

3. Play Devils Advocate

When I am in doubt I like to play devil’s advocate in order to asses the reason for doubt. Often attacking issues from different perspectives can add clarity. It’s not an easy task because you have to be honest with yourself and it will take time for you to become better at it. It’s definitely a skill worth teaching yourself.

4. Forget the Hype & Don’t Take Things Too Seriously

I know this isn’t easy but sometimes you need to realise that you can’t control everything. Don’t take everything too seriously. Let things go and let the world figure it out for you, which can often work out better. Remove yourself from the environment that is causing you to doubt yourself and go do what makes you happy. You can always come back to it later but constantly fretting over something will only cause you to stress more which isn’t conducive to solving your problems.

In closing, don’t be afraid to doubt yourself. I think there is something wrong if you don’t experience doubt every now and again. I’m not saying you shouldn’t be certain about things, I’m just saying don’t be afraid to doubt yourself. Once you become more comfortable with doubt, it will be easier for you to be more optimistic as you will be more confident and secure in yourself as an entrepreneur.


  1. Jason Adriaan · March 19, 2012

    Entrepreneurs are these really mystical creatures in society that have the audacity to go against everything the people around them believe is possible.
    With this we often find ourselves alone, a one man army against an endless stream of problems topped with pessimism. This can be daunting for normal people, and this is why normal people do not become entrepreneurs.

    So what I do to stay sane is simple, I stay focussed on tangible goals and follow rigid steps in order to accomplish them, I ignore destructive negativism and try to stay positive through surrounding myself by like minded people.

    Your family, and friends are very rarely people to confide in with the day to day of business, because they all would rather you have get a job and they are far too emotionally involved to give you objective advice.

    Finally I listen to tons of great music, lock myself in a dark room and work my ass off.