Building Conviction

Note to future self…

Lately I’ve been thinking quite a bit about how do we or how should we build conviction around making major decisions in our lives? In my case, I am specifically referring to how do you build conviction around pursuing an idea or vision that’s extremely risky?

Should you try to muster up a ton of courage to just believe in your vision no matter what and keep plowing? Or should you have an emergent strategy where you follow leads until something seems to work? I don’t believe that there’s a right answer to this question. Instead, I believe that the optimal strategy lies somewhere in between (surprise surprise).

STOP: I actually started to write this post two weeks ago and kept a draft of it (the two paragraphs above) in my notes because I didn’t have a thesis around this topic to write a full post but now I do and here it’s. Ok, now back to my stream of thoughts.

So I watched this interview with Kevin Systrom (Co-Founder of Instagram) and one comment he made realize that I might have found a simple framework for thinking about building conviction.

Kevin mentioned how he’s quite negative when it comes to evaluating his own ideas and that his wife suggested that this might be the reason why he has been able to do so well in life. Kevin argued that maybe that’s the case because he would stress his idea a lot trying to find something wrong with it. He argues that if you do that and you can’t prove to yourself that you’re wrong, then there’s only option left and that is that you’re right.

Now I absolutely love this idea of being your toughest critic and stress testing your own idea for a couple of reasons. First, it’s simple. Second, it’s proactive as opposed to reactive. By proactively stress testing your ideas/believes before you put them out there in the world you save yourself a lot of time and the rejections that you will face otherwise.

This framework is obviously not a silver bullet for having bullet-proof conviction. There’s always the probability that you will overlook something important when it comes to stress testing your idea. However, by stress testing your idea thoroughly you will cover 90-95% of the factors that might severely affect your plans. In theory it should also eliminate the biggest risk factors and anything that you forget to consider will be probably be second or third order factors.


Ok so what’s a concrete way of thinking about building conviction. If you’re thinking about a startup idea this is a good place to start:

  1. What are the key reasons why this might not work? List them.
  2. Why hasn’t this idea worked before? Why will it work now?
  3. Do people really need this? Will people struggle in life or with their business if this didn’t exist
  4. Can you monetize this at scale?…

Alternatively, write a two-column list and title the left column risks and right column solutions. On the left-hand site write down all the answers to question #1. Then go over each of the risks on the left and try to find a solution. Write that solution on the corresponding row on the right column. Repeat until you have a solution for every risk.

That’s it for now. I am going to go stress test my own thoughts. I will keep you posted on how it goes. Also remember this:

Always be your toughest critic.

Now back to work…