Comparison

I’ve always thought of myself as a very confident person. I see confidence as a part of who I am. It goes very far, to the point that when in doubt, I don’t recognise myself in my actions and I get into all sorts of out-of-character behaviours.

For years I was convinced it took confidence to be an entrepreneur. Then I met a few highly successful self-made millionaire foudners, with multiple successful exits behind them, totally insecure. Insecurity being almost their caracter trait.

So clealry, confidence is not a necessity. It is just my thing. However there is something else, far more important, that is in fact needed: saying no to comparisons. Doubt is not the enemy of the founder; comparison is.

You are driven by your heart. You are driven by your talent. And you are driven by your instinct. And when you start to question and look at what people are doing to the left of you, or to the right of you, you are gonna lose that clarity of thought. Listen to the information. In the end it has to come from who you are. Own your decision… And own who you are but without apology. —Anna Wintour, Editor-in-Chief of Vogue

I love this quote from Anna Wintour. She captured the essence so brilliantly. When you want to achieve something, you simply can’t allow yourself the luxury to look at what others are doing. It might sound counter-intuitive, especially when we are expected to benchmark, measure, and prove. She explains it so well.

The reason why you shouldn’t be looking at what others are doing is related to what I wrote in the Introduction : because as a founder you are in pursuit of meaningful experiences. And an experience is meaningful only if you can apprehend it as your own, as resulting from your heart/talent/instinct. Only then can the journey mean something to you.

In pursuing meaningful experiences, others are useful to the extent to which they inspire you, not as a benchmark. This nuance is very important. And it plays a key role in setting goals, because you can’t have a dream-come-true moment when you are fighting for goals and dreams other then your own.


In a start-up, there are challenging times when it is difficult to keep the eye on the prize. For me, there is a particular type of moment that challenges my confidence. It’s when I am working on a big an important goal, and I’ve identified all sorts of strategies to put in place to increase my chances of getting what I am after, and I’ve done them all, and now there is nothing more to be done and I know I just have to wait. I’m not very good at waiting, and that is when I get into the “If only I had <something the founder next to me has>, if would be easier for me” and “Maybe I should be pursuing a different goal instead, like <the one that the foudner next to me is pursuing>” mindset.

It takes a huge amount of discipline for me, when I have to endure waiting, not to start looking at what others are doing. I’ve seen other founders triggered by other types of situations (faliures, dissapointments, conflicts).

Get curious about what triggers you to compare. That’s when Anna Wintour’s quote will come handy as a reminder of the why what others are doing doesn’t matter.

Normalizing comparison

Market positioning of your product is the main reason that makes it difficult to just stop looking at what others are doing.

You have a natural interest to place your product in a market segment not well covered by the competition. So, you have to look.

You are also accountable to investors, who are operating on a different frequency then you are. Investors are constantly trying to answer the question “Will this work?” while the founders are trying to answer the question “How to make this work?”.

It is easy to slip into comparisons.

The questions I ask myself as a sort of sanity check are:

  • Is my inquiry into what others are doing limited to market strategy and informing the investors, or am I trying to reassure myself that I am good enough?
  • What boundaries and habits do I need to put in place so that I can focus on looking inward rather than looking at what others are doing and still navigate investor talks and marketing work?

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jamie@example.com
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