Would you rather?

Would you rather eat poop or die? It was the quintessential question in a game we played as kids to pass the time. Given the choice between two things that totally suck, which one would you pick?

Would You Rather rarely involved a choice between great joys. “Live in a sprawling mansion or have a private jet?” might come up now and then, but it never provoked the same thought as a choice between two detestable fates.

It turns out that Would You Rather was actually good preparation for life, and especially for being your own boss. You probably already know which things give you happiness and which don’t. But in order to be successful, you need a more finely calibrated ranking system.

We spend a lot of time doing things that suck—despite all our varied preferences and love of our jobs, nobody ever gets to spend all their time having fun—so you should know which kinds of miserable are your favourite. You probably played an intuitive game of Would You Rather when you decided to go into business, and keeping the game going can help make you successful.

Would You Rather is a smart tool to help partners split up the tasks that are left on the table after everyone claims ownership of the things they love and excel at. “Would you rather clean the men’s toilets or file the WSIB paperwork?” isn’t quite eat poop or die, but it’s close.

You might be surprised at how differently you and the people you work with would rate what you hate. Being able to choose a preference on these tasks can minimize resentment in the early days when it’s all hands on deck for everything, and you’re not yet living the glamorous life you imagined as a startup founder.

That knowledge can also help inform your hiring and outsourcing decisions. In my first business, I knew which things I loved doing and which I didn’t want to do. But I couldn’t hire someone to do everything I despised, and I couldn’t decide which were best to outsource. So I just kept doing too many things myself, which was probably why I eventually closed the business. Had I focused on questions like, “Would you rather do your own bookkeeping or respond to inquiries yourself?” I could have made the necessary decisions, and would have been happier and more successful.

Or I might have still quit to do some other sometimes-abhorrent thing. Because if it feels like being an entrepreneur isn’t working out for you, it’s probably not that you aren’t cut out for it, and more likely because you haven’t figured out which brand of total suckage you can live with.

Too many of us have forgotten Would You Rather. It’s easy, as a business owner, to focus on the tasks we love and pay little attention to those we loathe. But figuring out how you feel about the latter can make a world of difference to your happiness, sense of fulfillment, team dynamics, and ultimately, to your business success.

Originally published in Our London on July 20, 2017.