Everybody experiences failure. It is always terrible when it is happening to you.
I am not sure how to teach “grit”, but it is invaluable.
"Success is moving from one failure to the next with undiminished enthusiasm." - Winston Churchill
I’ll admit the “undiminished enthusiasm” gets more difficult with age. And perhaps there is less that generates enthusiasm with battle scars and experience.
For the record, I’ve had my share of failures. Here is a partial list:
90 West Data - failed attempt to start data licensing company.
Transaction Data - failed attempt to license transaction data from Fortune 100 company after a very long & expensive process (see 90 West Data above).
Gift Card Data - failed to commercialize insights from gift card data after licensing from the parent company.
Capture - failed attempt to create an app for construction site safety.
Junto - failed attempt to create an app development company.
Greencastle - failed investment in an investment bank for green energy projects.
IQ Ware - failed investment in a private IT security company.
Saipan Datacom - failed attempt to market & sell the .mp top-level domain.
Crypto - first bought Bitcoin at $300 & sold most of it.
Profit Direct - failed attempt to turnaround a failing company.
Crystal Ventures - in prime Associate role at an internet-focused venture capital firm in 1998, got washed out with 2002-03 bust.
I got rejected from every MBA school I applied to except Georgetown (which was ridiculously expensive even then) & CWRU (where I attended).
Lockheed Martin - this was my first job out of undergrad; I was (am) a terrible accountant & terrible at managing bureaucracy.
Without a ton of specifics, I was cut from various hockey teams as a kid, I’ve applied for many jobs that I didn’t get; I’ve gotten terrible grades in classes I liked; I’ve been unsuccessful in selling various services/products; I’ve lost out on potentially big deals; I’ve gotten passed over for promotions.
Perhaps these are not all outright failures. Some were OK, but maybe not as good as they could have been. Some (maybe) have led to good things that I otherwise would have missed1.
The main takeaway is that I learned something & got a little better from each experience. Here are a few takeaways:
You’ve got to be trying new things to be failing at those things.
If you aren’t failing, you aren’t pushing yourself enough.
Forgive yourself. It is not the end of the world.
Have confidence in yourself. I tend to think someone else is better than me or has already thought of my idea, or perhaps a mindset along the lines of “if I know about it we must be late in the cycle”.
Optimism is a superpower.
The most frustrating situation is when you fail because you make the same mistake you’ve made in the past. Learn from those failures & mistakes. Avoid repeating past errors. A little self-reflection helps in this practice.
When a friend fails, be a friend and reach out.
I’m not sure I have grit as much as an irrational amount of confidence.
Failure is tough. It is difficult to watch your kids fail and struggle. But it builds the resilience needed to get through life.
"The Story of the Chinese Farmer" by Alan Watts