Do things uncomfortably differently

I had erroneously spent much of my life doing "all the right things"...study hard, be in competitive sports and leadership activities, go to an Ivy League university, work hard at my job, get promoted...the list goes on. But after 2 decades of doing that, I realized that all this only leads to above average results. 

The epiphany came to me that if I wanted to see outsized results, my approach was all wrong and had to change. Doing things the way tried and true ways are totally fine if you want those expected results of a financially stable life. And that's totally fine for those whose desire is exactly that. 

For me, I've always dreamed of doing things that attain outsized results. It stands to logic that my original approach was never going to yield outsized results. As such, I decided to go do things differently...uncomfortably differently. This means taking more risks by treading in paths that are not well trodden. For me, it meant that continuing to climb the corporate ladder was no longer the path I wanted to follow as that path is definitely a follower's path.

So, I decided to be a startup founder. I believed that I had grown a thick enough skin over the years to take a gamble on myself. I wanted to try my hand at taking on more risk by starting a company rather than working comfortably in an established one for the opportunity to get that outsized financial success.

But I fell into a trap of my own making: I started to follow the playbook of all the things a startup founder needed to do to be successful. Again, I believe this playbook, while well-intended, ultimately also leads to above-average results but not amazing results. And investors (which includes me investing in myself!) really care a lot about outsized results, not just above-average results.

Hence, I have to constantly remind myself to avoid the standard ways of failing, so as to significantly increase the odds of outsized success. Yes, I might experience outsized failure, but as the saying goes, "no pain, no gain!". 

In the recent past, I felt like I had gone into a dark and lonely place in my startup journey. In a chatty world of social media, everyone is touting all the great things they are doing for their startup, to puff up their chest to gain customer and investor confidence. It is hard to confide in anyone when the going gets rough, and to just be raw with your fears and emotions. You don't want to unnerve your cofounder, worry your investors, or rattle your staff team. Where does a startup founder go for any form of genuine support?

After a few days of moping around at home and a good cry, I finally realized that the new risk I needed to take on is one of a willingness to share emotional vulnerability so as to get that outsized impact of catharsis support. I decided to share my worries with a few startup founders who are on a similar journey with me. I didn't get advice from them, just a listening ear. And that alone was helpful. 

While conceptually, the idea of being willing to take on risks for outsized outcome makes sense, I can only say that executing on that concept is a lot harder than it sounds because it takes quite a bit of courage but it definitely pays off in spades.