Non-obvious traits of opportunistic opportunities

As part of my practice to spot opportunity, I’ve been verbalizing this daily morning question:

“What opportunity can I leverage on today that will have the most impact for the least work?”

During the day, I would put on that hat of an opportunistic trickster, and try to find things that might give that degree of leverage.

What exactly do I look for? How do I know an opportunity is one by just looking?

Here’s a few non-obvious traits I look for:

• Not originating from routine: I try to look for them in places or platforms where I don’t frequent. That means for example, not Twitter, not Facebook. If it’s on my routine platforms, it could be coming from an account I don’t follow, or is a random encounter that didn’t come from my usual bubble. E.g. I recently tried to post stuff in Reddit groups that I don’t usually comment in, like r/IMadeThis. Or how I don’t usually post about my 5am club in Indie Hackers, but a random comment about it I left in someone’s post got picked by a moderator and he nudged me to share more in a post on IH, which resonated and ended up getting a whole bunch of new members!

• Potential for virality or scale: All things being equal, sending a random DM to one person has less possibility for scale or amplification than say a tweet. Or one cold email versus a blog post. This is where social media platforms plays well. Of course, outliers to the rule exists. If the person has a massive following for example, than it might be more well worth the DM than a tweet. Paraphrasing a good question I saw recently: Would you rather take $100k now, or a 30min coffee with Elon Musk? Sure, $100k now is almost a no-brainer, but it can be earned. If I’m optimising for opportunity, a coffee with one of the most electrifying entrepreneurs of our time is in fact the no-brainer.

• Inspiration is perishable, act immediately: This is a bit harder to describe. It’s just a feeling. Call it inspiration, a light bulb moment, gut instinct, or just a “Hmmm!” It’s a I-don’t-know-what-but-I’m-gonna-just-go-for-it moment. It’s like hunting prey and having that primordial sense of where they are, how they will behave. Same with opportunistic opportunities. This takes practice to be able to catch that, for sure. All along I’ve learned to not trust such whispers in my head, leaning instead on rational judgement and logic. But that’s not how it works in a stochastic world. And that’s really what this practice of spotting opportunity is all about – to develop more keenness of hearing for such whispers of random luck.

What else did I miss?