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When working with technology & innovation, we’re frequently faced with decisions to take on an idea and develop it into a viable product, feature or solution. I recently came across this concept of Freerolling that really resonated!

A freeroll in poker is when a player is guaranteed to at least split the pot while having a chance to win the whole thing, i.e. the potential downside is very limited. Even if you do not win it all, you walk away losing little to nothing at all.

Quite a useful mental model for dealing with decisions where we effectively have “nothing to lose”. When it’s a freeroll situation, we can make the decision to move in quickly and spend the time instead to make sure we make the best moves. There will always be some small cost to the decision to move in. But we’re really talking about outsized potential gains relative to limited loss exposure, which should be our trigger to move… and move fast!

It may sound almost too obvious. But in reality, so many of us approach such decisions expecting zero downside. And the size of the potential upside, coupled with some fear of failure or “wasted effort”, often mask such freerolling opportunities, lead to inaction and eventually loss of an opportunity that was always one-sided in our favor!

Free lunches could be hiding in plain sight. Can we find them?

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