“So why do you make money?” My question is often met with a dismissive stare. As if the answer is so obvious, that the question isn’t even worth asking. It’s one of the first questions I ask during my coaching onboarding process. Yet scrappy founders, law firm partners and professional investors – who typically don’t struggle for words – find themselves befuddled. Then a light bulb goes off. “Optionality. Money gives me tons of options.” I’ve heard this answer enough to respond with a gentle dose of snark: > __“You know you can’t eat optionality.”__ ## The trouble with optionality To set the record straight, I believe that [collecting options (within reason]()) is an earnest life strategy. It drives sound career decisions like working at McKinsey, striving for that big promotion and getting a fancy MBA. Yet optionality can be an easy cop out when trying to discover what __you really want out of life.__ In the fantastic essay, [The Trouble with Optionality](), Harvard Business (_and Law_) professor Mihir Desai describes the slippery slope of unconstrained option collecting: > _The comfort of a high-paying job at a prestigious firm surrounded by smart people is simply too much to give up. When that happens,__the dreams that those options were meant to enable slowly recede into the background.__ For a few, those destinations are in fact their dreams come true—but for every one of those, there are ten entrepreneurs, artists, and restaurateurs that get trapped in those institutions._ How can we ensure that our __dreams don’t recede into the background?__ ## The 5 Whys Process Let’s turn to a problem-solving process from the famed [Toyota Production System](). According to Wikipedia, [The 5 Whys Process]() is an “iterative interrogative technique” used to: > _Explore the cause-and-effect relationships underlying a particular problem. The primary goal of the technique is to determine the root cause of a defect or problem by repeating the question “Why?” Each answer forms the basis of the next question._ Let’s take a sample automotive problem: __the car will not start.__ Here’s how one could apply the _Five Whys Process_ to identify the root cause: > ___Why?___ – The battery is dead. (First why) > > ___Why?___ – The alternator is not functioning. (Second why) > > ___Why?___ – The alternator belt has broken. (Third why) > > ___Why?___ – The alternator belt was well beyond its useful service life and not replaced. (Fourth why) > > ___Why?___ – The vehicle was not maintained according to the recommended service schedule. (Fifth why, a root cause) So what on earth does this have to do with optionality? ## $2,000 a month in passive income (Why?) One of the steps in [setting effective goals]() is understanding __The Why__ behind a particular goal. During a recent RadReads workshop, one attendee shared [a simple FIRE goal](): > Generate $2k/month in passive income for 2021 But as he applied __the 5 whys__ to this [passive income goal](), he was shocked by what it revealed: > ___Why?__ – I want to be free from working in the corporate world_ > > ___Why?__ – I want to pursue my own interests without the worry of obligation_ > > ___Why?__ – I want to be free_ > > ___Why?__ – I want to have more time to explore myself_ > > __ _Why? – I have not had enough time to understand who I am___ It turns out that his dream of __understanding who he was__ had been overpowered by the machinations of generating $2k/month of passive income. ## Start with why The 5 Whys are a powerful tool in the journey of uncomfortable introspection. There are countless examples on the Internet of this process working its magic. Curious about __why you want to own your own business__ : ![5-Whys-Problem-Solving](/images/blog/5-Whys-Problem-Solving1.png) (FWIW, there are way easier paths to spending more time with your kids than starting your own business.) Curious about __why you exercise__ : ![Blog post image](/images/blog/image.png) (For me, Crossfit was a vain attempt to [combat my mortality]().) ## So back to optionality So what’s the typical root cause driving my coachees’ pursuit of optionality: __I want my children to be happy.__ __What a beautiful and worthwhile motivating force.__ One that makes life worth living. So as you apply __the 5 whys__ to your biggest goals, please ensure that your “biggest dreams don’t recede into the background.”