I failed more than once before I finally stopped taking action just to prove myself right. I realized it late: I wasn’t investing my time to understand and improve. I was investing it to win. Real learning from mistakes takes more than repetition — it takes attention.
I believed experience would automatically make me wiser — that I would never repeat the same mistakes twice. I was wrong. I never corrected my ideas, so experience wasn’t teaching me anything; it was simply presenting reality to me, over and over, waiting to see if I’d finally notice. Whether I learned from it depended entirely on whether I was actually observing it.
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Learning from Mistakes While Circumstances Change
Looking back at my own decisions, I saw something uncomfortable. Circumstances kept changing. People kept changing. But my thinking often stayed exactly the same. I carried the same assumptions from one situation into the next, without ever taking the specific nature of that new situation seriously — the nature of the idea, the market, and the people involved.
The problem was never any single decision. It was how I perceived reality before I’d even made it. Every decision started with an assumption, and those assumptions rarely came from experience — they came from my own private theory of how things worked.
The Failure of an Unexamined Assumption
One of my ventures depended heavily on outsourced, skilled labor — the kind of team you cannot rebuild overnight. When the COVID-19 disruption hit, it introduced circumstances I had never imagined having to plan for. I had assumed, somewhere underneath everything, that money could resolve any obstacle.
That assumption turned out to be wrong: most of the team left and never returned, family responsibilities pulling them home in ways no salary could compete with. Looking back, I no longer see that as a simple business failure. I see it as the failure of one specific assumption I never knew I was carrying.
The Assumption Correction Cycle
I eventually understood that my mistakes weren’t repeating themselves — my thinking was. For the first time, I became aware of my own regret without becoming consumed by it. That awareness interrupted the automatic loop and kept me from falling into it again.
In our previous inquiry on what turns knowledge into skill, we explored how structured inquiry creates reliable data. When we look at repeated failure, the same discipline applies through a deliberate correction cycle:
- Unexpected Outcome: Reality provides friction or rejection instead of the expected result.
- Reflection: Pausing rather than reacting emotionally to the setback.
- Identify the Assumption: Isolating the unspoken belief that guided the action.
- Correct the Assumption: Aligning the mental model with what reality actually demonstrated.
- New Action: Executing with refined perception rather than repeated conviction.
Instead of asking “why did this happen again?” I started asking, “what assumption was I repeating?” That question changed everything. It moved my attention away from the outcome and toward the process that had produced it. I was studying patterns now, instead of simply generating new business ideas and hoping they would land differently.
I started correcting assumptions before turning ideas into plans. The mistake itself became less important than the thinking underneath it. Awareness must precede change — you cannot fix what you haven’t first noticed you are doing.
When we understand why we repeat the same mistakes, we realize that reality never argues — it simply produces outcomes until our assumptions change.
That left me with a harder question than any I’d asked so far: if I already know what to do, why don’t I do it? This, in the end, is what learning from mistakes actually looks like — not repeating them, but learning from mistakes deliberately, one assumption at a time.
— Kartikeya
Inquiry in Silence. Yoga in Practice.