BLOG: Wrestling With Doubt

When people say it’s lonely at the top, what they really mean is: ‘it’s hard taking decisions’.

When the book stops with you, there’s nobody else to give your ideas the thumbs up. How are you supposed to know they’re right? Maintaining confidence in your own business decisions is a complex issue.

While we need to believe in our company more than anyone else, we also need to realise when our ideas are terrible and try to nip them in the bud. Day to day, I often find myself hammering out conflicting points of view in my brain: will this succeed or won’t it? Should I do this – should I do that? Is this a good idea – does it stink? It drives me crazy. These battles underpin a complex dilemma that every business leader has to confront every single day – am I doing the right thing?

Indecision is completely understandable in a changing environment, but it can also be unsettling for investors, customers or employees. Visible indecision may even result in people quickly losing confidence in us. It might be on a much larger scale, but you only have to look at the 2012 US fiscal cliff negotiations to see where uncertainty can lead you. The US Senate’s inability to decide on the future budget drove money markets in a spin, press in a lather and incomprehension all round.

The trouble is that decisions never go away, and even once you’ve make one it’s just replaced by another. Take employing a new member of staff – you have to weigh up whether the business can afford the cost; if the business can grow without the increased capacity; or if the finance should instead be invested in new products?
Eventually it becomes ingrained, I guess. I’ve reached a stage where I’m second guessing decisions all the time in light of what the alternatives might be. Where it gets complicated is when Plan B isn’t enough and you start thinking about Plan C too. It can get plain silly, as by the time you’re contemplating a Plan D your faith in Plan A has all but evaporated. Not only do your own opinions start conflicting but even your own good ideas!

Do I think too much? Well perhaps, but I was always very keen not to mess up. I found it really frustrating that there was often no way of knowing the answer before it was too late. I wound up treating all significant business decisions as risks that I wanted to avoid or minimise. But I had to learn that business is like life, if you don’t take any risks you’ll miss out on the experiences that make it all interesting. For a company to live you need to take risks.

All of this worrying about decisions wasn’t just causing stress and indecision, it was eating up all of my time. I spent too long considering the views of my advisers and trusted friends. Eventually, I realised I had to listen to myself, I had to start trusting my own judgment. This alone did not address the self-doubt and I had to almost start a mantra in my brain so that I could ease my mind without forever mulling the ‘what if’s’. For me, this strategy was as simple as accepting that at times I would make the wrong decision and that it was okay to do so. While that may sound simplistic it was also liberating.

Even, with all the thinking I dedicated to running my business, not every decision was correct. Nor are they now, but developing that approach to keep the mind at peace was essential in gaining the self-belief necessary to run a business. This stopped me from being my harshest critic and allowed me to focus on the important work, and even occasionally get things right!


The flagship product of mobile data experts Overlay, The Context Engine, enables devices to intelligently monitor their own behaviour. This intriguing tech gained them international acclaim in 2012 and led to a successful buy-out bid from Inmobi.

Illustrated By Aaron Miller

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