For a decade, I was on a set life path. Then I decided to change it all & start from scratch. This was hard. For many months, I was lost. Till I did Daniel Vassallo’s “Small Bets” course. It was one of the most transformative experiences of my life. Here is what was game-changing…
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Daniel shared many things that I agreed with & was already doing. I am NOT sharing any of those. I am sharing the 4 lessons that were hard. The ones that challenged my assumptions. They led to the most personal growth for me. Let’s dig in:
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1️⃣ CHANGE HOW I LOOK AT MY FAILURES
I have always taken my failures personally & tried to learn from them. While this has helped me improve, I now see that learning from failure is useful in the Predictable world & less so in the Stochastic world. Quick definitions:
(A) Predictable: Has a clear path to follow & a linear relation between effort and results. Ex: Exams, becoming a doctor-engineer (B) Stochastic: Decisions made by other human are consequential for outcomes. Lots of randomness & unpredictability. Ex: business, art, even non-profits.
In the Stochastic world outcomes are a mix of talent + effort + strategy + luck. It is impossible to untangle the role of each in the final result. When I would analyse my success I acknowledged the role of luck. But for my failures I only blamed myself.
As I understood the role of luck & uncertainty in the Stochastic world, I realised that it was possible I was over-analysing my failures. Sometimes things are just out of your control. The wise move then is to acknowledge that & move on instead of learning the wrong lessons.
An unexpected consequence of this: For the first time in my life, I have stopped beating myself over my failures. I have become kinder to my past self & there is a sense of acceptance. If this is all I took from Daniel’s course it would have been worth it. But I got a lot more…
2️⃣ STOP SEARCHING FOR MY ‘1 BIG’ IDEA
Throughout my sabbatical, I have been looking for my 1 Big Idea. The one I can pursue for a decade. But I now realise that great ideas are like love & inner peace: The more desperately you look, the less likely you are to find.
Also even for ideas I am excited about, it is impossible to tell if one of them is the big one. You just can’t make these predictions in the Stochastic world. That’s why even VCs, whose job is to bet on the future, invest in a portfolio of startups & not just 1 startup.
So I am going to use a different approach: - Try many small bets - These bets should be in domains where I have expertise & credibility - I should try these bets in parallel - Overtime, keep the ones that work and remove the ones that don’t The endgame is…
Either, I find a portfolio of bets that work & together give me success & meaning Or, one of those bets becomes huge & then I can decide if I want to focus exclusively on that. Overall approach: ✅ Start Small → Get early wins → Build from there ❌ Wait for 1 big idea
3️⃣ SEEK INSPIRATION BEYOND MYSELF
Most of my life I have come up with ideas by, reading-thinking-learning-ideating, mostly by myself. These are my defaults & they work well for me. But Daniel showed me the limitation of my approach. In fact several people have shared on this.
Paul Graham once explained that the best way to come up with ideas is to observe the world around you & not by just thinking. He quotes Richard Feynman: ”The imagination of nature is greater than the imagination of man”
Ben Casnocha shared that Opportunity = Person. “Every opportunity is attached to a person. Opportunities do not float like clouds in the sky. They’re attached to people. If you’re looking for an opportunity, you’re really looking for a person.”
Daniel’s examples & these quotes showed me my mistake. I was trying to come up with ideas & opportunities all on my own. I was not leveraging the world & people around me. I thought I was being original but I was just being sub-optimal. To change this I am doing 3 things:
(A) Have more chats: First with old relationships from offline world & now with new & purely online connections (B) Setup twitter to stay away from fights & politics & use it as an idea generation tool (C) Join communities of people on a similar journey Let’s dig into (C) more.
After months of being on my own Daniel’s community gave me a group I can: - ask questions of - share challenges & wins with - get feedback from & I have learnt a lot from seeing many peers try their small bets.
Not only has all this increased the quantity & quality of my ideas it has made the journey more fun. I have reconnected with old friends & made new ones. And now I have a system which regularly keeps surfacing inspiration & ideas for me to try. I plan to do a lot more of this.
4️⃣ INCREASE MY LUCK
For most of my life I have misunderstood luck. But the Stochastic world depends heavily on human decisions. And where there are human decisions there will be randomness & hence luck. So instead of dismissing luck I should work to increase it.
You increase your luck when opportunities come to you. This happens when you are: - Capable (you can deliver value) - Credible (people see you as capable) - Top of mind (people think of you when they think of this topic) For too long I ignored the last 2.
So that’s why I am now active on Twitter. I share where I have offline credibility & personal experience: - My lessons from building 321 Foundation - My journey to figure out my next phase - Stories of how startups build their Team-Culture-Product Slowly my luck is increasing.
Over the last few months, many past connections have reached out with opportunities. I already had credibility with them but I was not top of mind. As that changed, the opportunities increased. But what has surprised me even more is the opportunities from new connections.
These are people I have no offline relationships with. Yet they have reached out with ideas for collaboration that even a few months ago seemed impossible. All of these opportunities existed in the world. I just needed to increase my luck to catch them.
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Overall, this journey of starting from scratch has been liberating & hard. Daniel’s course has helped me navigate it better. My journey though, is still in its early stages. I intend to share my lessons & highlight as I go along. Hopefully, it will help other fellow-travellers.