When I was 19, I gave up a hard-fought place in Law school to study literature - letting go of a supposedly lucrative career so I could read (pretty darn amazing) books.
Several years ago I left a stable, decently-paid, respectable government role to work for a then-startup which nobody had heard of.
Both times, I had peers reach out to me to say they felt stuck and wished they could do the same, but thought it was too risky to shift from their current path. Today, I coach people who want to do something, but are worried the outcome won’t be as they imagine, and hence opt to stay where they are.
In some ways I'm fortunate, because I can't help being restless without growth and some discomfort.
But I also understand it deeply. Almost a decade ago, I held myself back from leaving a safety net and familiar culture at work. That’s 2-3 years I can’t get back.
I continue to struggle with dreaming too small, and having a fairly conservative approach to leverage and investments. I still don't want to fail big (of course!).
What's next?
What often surprises me is how often see risk and failure in black-and-white terms. We see our options as absolutes: A, B, or C. Or we see an existing system, and limit our actions to current protocol.
We often think the opposite of risk is safety.
This safety is an illusion. Staying still can also be risky.
This isn't encouragement to quit your job or leave something just because you're unhappy. But it is a call to recognize that we have more influence over possibilities than we realize.
Risk is reality. It’s also typically variable, and often manageable.
Here are 4 practical ways I’m trying to improve my relationship with risk and failure - and expand possibilities:
1. Due diligence - how do you know that you know enough?
Don’t take risks for the sake of it.
Whatever you want to do, make it concrete. What are the steps involved? What are the actual risks?
Figure out what matters and who the stakeholders are, if any.
Figure out who has done it before, and learn from them. Reach out and talk to strangers if need be. Get enough data points to get some areas of convergence.
2. De-risk
Now that you’ve done your due diligence, how might you reduce the risk?
Can you control a situation within certain parameters, so that it’s more manageable?
Can you run little experiments to test out things you’re not sure of?
If things don’t work out, do you have a back up plan? Do you need one?
3. Build confidence in your ability to deal with risk
None of us operate with 100% certainty. What is your threshold, and how much are you willing to push that each time?
If you’re not ready for bigger risks, that’s OK. Just start with small things to get yourself comfortable.
Also - figure out how much, and what kind of risk you’re ok with. Career risk, relationship risks, financial risks, physical risks etc etc. They’re all different.
4. Faster feedback loops
Regret is inevitable. But we want to minimise it. Due diligence helps. Those little tests help.
We also don’t want to get stuck in the sunk cost fallacy - move on, once you’ve decided something isn’t working. Don’t waste more time or energy.
Does this make sense for you? I genuinely want to know!
Reach out anytime.
P.S. Of course literature is not just reading books lah. It’s like looking at history or current sociopolitical contexts through multiple perspectives, rather than the false objectivity of non-fiction. And these days it’s almost brain-training for focus.
𝗛𝗶! 𝗜'𝗺 𝗟𝗶𝗻. 👋
𝗜 𝗵𝗲𝗹𝗽 𝗽𝗲𝗼𝗽𝗹𝗲 𝗱𝗲𝗳𝗶𝗻𝗲 𝗮𝗻𝗱 𝗽𝘂𝗿𝘀𝘂𝗲 𝘄𝗼𝗿𝗸 𝘁𝗵𝗲𝘆 𝗹𝗼𝘃𝗲, 𝘄𝗶𝘁𝗵𝗼𝘂𝘁 𝗹𝗼𝘀𝗶𝗻𝗴 𝘁𝗵𝗲𝗺𝘀𝗲𝗹𝘃𝗲𝘀.
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