Olly Headey

May 9, 2024

What Ifs

I’ve been solving some fun small problems for a little while. I’ve enjoyed it, but lately I’ve been feeling like I need a fun BIG problem to solve. Something big enough to need another like-minded soul (or two) to work with, but not flying cars big IYKWIM. 

The thing is, before you even get started on solving the big enough thing, you first have to solve the problem of discovering the big enough thing! Inception level two before you’ve even begun. 

I’ve found it all to easy to wrack one’s brain thinking in detail about problems to solve in underserved areas, with a big enough TAM, that you happen to be particularly interested in, as well as having deep enough knowledge about. It’s exhausting and there’s a certain futility in all of it. No wonder so many people never get further than this stage in business!

In his wonderful On Writing memoir, Stephen King wrote, “A strong enough situation renders the whole question of a plot moot. The most interesting situations can usually be expressed as a What If question”. 

“What if vampires invaded a small New England village?”, for example (Salem's Lot), or "What if a novelist has an accident and is rescued by a deranged fan?" (Misery).

I think the same applies for business ventures. You don’t need to work everything out up front (plot) if you have a strong What If situation:

“What if you could instantly play any song ever recorded?” 

“What if you could book rooms with locals rather than hotels?”

“What if your company finances were calculated and reported automatically?”

Starting with a strong What If is so much simpler, and far more fun. It frees you up to be more creative. So, if you’re thinking of starting a new venture, rather than grinding your mind trying to find specific gaps in the crowds of the Wellness or PropTech sectors, start by dreaming up some big and compelling What Ifs instead.

Sometimes dreams do come true.

About Olly Headey

Journal of Olly Headey. Co-founder of FreeAgent. 37signals alumni. Photographer.
More at headey.net.