Have you ever been asked a question that seems straightforward, but you know there's a whole can of worms hiding under the lid?
It happens to leaders all the time.
Your boss asks, "Can you get me a report on profits?" A team member asks, "What's the policy on sick leave?"
Simple enough, right?
Except, as the subject matter expert, you recognize the multitude of follow-up questions layered beneath the ask. What information do they need? What are they trying to accomplish? What problem are they hoping to solve? What are they actually asking me?
This isn’t exclusive to business.
Your brother-in-law asks, “What are you up to on Saturday?” Your teenager asks, “Hypothetically speaking, if there was a party on Friday night…?”
Your brain automatically starts running The Suspicion Protocol. You know nothing is as simple as it seems.
So why then do we treat our own thoughts and actions with such unexamined acceptance?
What if, we approached our own desires with the same suspicion, but you know, called it curiosity.
I once asked a friend what her biggest dream was. “If you could do absolutely anything in the world,” I asked, “what would you do?”
You know what she said?
Sleep.
She wanted to take a month, go somewhere, turn off her phone, and sleep.
I think we can all relate to the sentiment. There's absolutely nothing wrong with wanting a break. But when that’s your response to ‘imagine anything’… consider my curiosity piqued!
I had so many questions. Was it sleep she wanted? Or was it to feel rested? Recharged? Inspired? Did she want peace? Freedom from responsibility? To feel valued and seen? Or was it simply the opportunity to spend a small sliver of her time selfishly, without somebody needing something from her?
Option D please: All of the above.
And that's kind of the point.
Over the past two weeks, we've been exploring the power of intellectual detachment, stepping back from the emotional connection, and inspecting the language we use in our day-to-day.
This week, I want to introduce one of my favourite methods for putting those ideas into practice:
The Five Whys.
It's a simple technique: get suspicious! Start with a thought, ask why, and continue compounding and questioning the answers until you've unearthed a root of the original statement.
Consider this:
I want to start my own business.
Why? Because I want to work for myself.
Why? Because I want freedom to make my own choices.
Why? Because I’m tired of asking permission to live in my life.
Why? Because I am an adult and I want the freedom to choose how I spend my time.
Why? Because I want to attend my kid’s afternoon recital, or go for a walk in the middle of the day, or work from Starbucks at 2:00 PM without feeling guilty. I want to feel like I'm actually living a life for me, instead of being held hostage.
Well, now we're getting somewhere.
I love this as a simple starting-point practice because it doesn’t act as an argument—we haven’t disproved the original statement—but we have opened the conversation up to exploration. It’s a tool to help you identify what is important to you, which then leads to the opportunity to consider all the variables.
You’ll hear me use the term informed decision a lot. So frequent, in fact, you’ll probably grow sick of it. But that’s what “why” does. It helps you make an informed decision.
Now, if I ask you what you want, is your answer still to start a business? Maybe. But now you have something else to consider: What does freedom actually look like in the life you're trying to create?
Let's Talk About Fuel
Remember our car analogy from last week?
If we're moving from point A to point B, our vehicle is the what, our goal is the destination, our why is the fuel. It's the catalyst behind the movement, the power behind the action.
Three dollars of gas might get us to the next station, but it isn't going to take us across the country.
Put diesel in a gas-powered car, and you're in for an expensive lesson.
What does the car need? It all depends.
A vehicle is relatively simple. We can identify its mechanical requirements, determine what it needs, and fill the tank accordingly.
Humans? Instructions not included. We're influenced by experiences, expectations, habits, emotions, beliefs, and a lifetime of programming. Two people can want exactly the same thing for entirely different reasons.
And sometimes, what we think we want is only the tip of the iceburg.
The Five Whys helps us investigate what we need, so we can understand what we’re actually trying to accomplish, and make more informed choices about what’s required to get us there.
Now, this doesn't mean we need to investigate every little thing.
If you fill your car at the same gas station every Tuesday because it's what works for you, fantastic. Carry on.
Our goal here is to create the capacity to examine our thinking when it's required, not to encourage endless self-analysis. You don’t have to deep-dive contemplate the act of brushing your teeth in the morning; unless brushing your teeth somehow contributes to you being late for work, which contributes to your stress, which contributes to your unhappiness, etc. etc. so on and so forth.
Your time and attention are valuable, too. This doesn’t need to be overwhelming.
We spend an awful lot of energy trying to make the right choices. Our confidence shakes because we’re looking at thought #1 and wondering whether we’re going to get it wrong.
But what if confidence didn't require certainty? What if confidence comes from understanding why something matters to us, considering our options, and being willing to take responsibility for what follows, because we value the potential outcome?
Take our aspiring business owner.
Understanding that she values freedom doesn't necessarily mean she shouldn't start a business. It means she has a bar to measure against as she builds, a comparison that will help her with her decisions along the way. A foundation that will allow her to pivot if she needs to. This is where the deeper why becomes extremely valuable.
The better we understand what matters to us, the more intentionally we can choose what we want to build our lives around.
And maybe that's where confidence begins. Desired outcomes move from right and wrong to ‘does this align with what matters to me?’ In understanding why we've made the choices we’ve made and being willing to stand behind them.