It’s entirely possible to teach without doing or making mistakes. We memorise formulas, regurgitate recipes, and recite entire piano melodies.

Yet the lessons that we carry around today are the most painful ones.

It turns out that once we know the answer, we stop asking. We stop wondering about the colours, the materials, the process and the uses in a different situation. How does this relate to that?

Free-range teaching is the act of giving questions, to show possibilities and to sit with the tension of knowing the answers.

“If the cafe doesn’t succeed in 6 months, what will do about it?”
“What about the people who don’t read the instruction?”
“What are the pros and cons of grandma adopting crypto-currency?”

As we go about helping others level up, we have the option to decide if it is a lesson is worth understanding. If it’s worth the struggle before something clicks.

It might be convenient to give the answer but when a new complex problem shows up, then don’t expect someone to out-perform google.

The alternative is an inconvenient way of teaching, free-range.

If Marco Polo were to be brought back to life, he might be out of a job knowing that Google has mapped out the world. It would be impossible to make a living with his passion for exploring and uncovering new continent.

Similarly, the switchboard operator, bowling alley pinsetter and the beloved milkman would be devastated to know that they would be out of a job too.

And what if we go back in time?

Supposedly if we brought our passion for coding, photography and F1 racing to the days of being a cavemen. These passions could not have existed, let alone saving us from the sabertooth tiger.

So, where did passion come from?

My guess is that the reason it’s our passion project isn’t that we were born to do it. It’s just that you thought it was going to work. And your real passion is to do something that works.

It works to afford your rice and beans, the respect from the people you look up to and forward motion in alignment to your utmost potential. And more importantly so, to stretch you in a way that feels like you’re dancing at the edge of failure.

Passion is perhaps a line weaving through of all the things that we want. A solution that works.

Steve Jobs might have broken a lot of hearts but it not his fault.

The other day, I went for a meeting in a big building. As I approached, the guard opened the door and greeted me. I asked for direction. Then I went up to meet the head of this big company. Now, the guy who is upstairs had a way bigger paycheque than the guard. But he was a little cranky and a bit bitter.

The interactions with the guard were some of the best interactions I’ve had all day. He was positive. He’s open for connecting. He wanted to solve problems. So, the next day, I baked some cookies and handed it to him. He was stunned and surprised.

It turned out that he loves pottery, but pottery is not the only thing he loves. He also loves people, engaging with people, solving problems and bringing kindness. He’s just not selling pottery for a living.

The point is this. Just because your passion doesn’t make you money, it doesn’t mean that you need to sell your soul to the devil. There are many in-between. Find a job that pays the bills. Clock in, do your best and clock out. A tuition teacher, a barista, a nanny or even a guard.

Don’t think that you’re not allowed to pursue your fascination with colours and textures, or your fascinations with music and theatre. You have the time in between the job. Don’t let go of this incredibly fierce self-accountability for you to recognise that you’re in control of all of those things.

Good news. It turns out that if you add some time between your gut reaction and eating that ice-cream. You might make a different decision.

And the science is out. It takes 90 seconds for emotion or urges to pass. We can use this before checking social media, making purchases and screaming at someone. The list goes on.

Here’s the tricky part. If you add any thoughts to the emotion, it can linger on and becomes a mood.

Every time an urge comes about, start a 5 minutes countdown timer. And instead of adding fuel with our thoughts, just let it be.

And yes, I’m being conservative with 5 minutes. Because if it’s worth to eat that ice-cream, it’s worth it to wait 5 minutes.

When I was 23 years old, I decided to be a wedding planner. I entered meetings explaining the detailed process of how I design weddings. The meetings were long.

And one day, my wedding shoot got featured in an international publication. After which, I realised the conversation changes. I was no longer asked about my design process. Couples trusted me to plan the most important day of their life.

So when I started an animation studio, I did something different. I went to the most well-known companies and offered to make their animation at cost. And after enough portfolio, the long-winded meeting got shortened into a sentence.

It became, “I’ve made animations for Scoot, DHL and UOB.”

I took out all the risk. And the story became a free leverage asset. The conversation shifts from ‘can I trust you’ to ‘how can you solve my problem?’

Perhaps, you can leave the story to fate. Or you can work diligently to earn it. If the work is important enough, it might be worth building the story.

Fear runs deep in our genes. The discipline master walking around tapping a thick bamboo cane on his feet. Or the manager doing his rounds, inspecting the work that you do. It doesn’t take long for us to get our act together in the presence of fear.

Anger could also be fuel to pull all-nighters, build companies and amass wealth. The founder of Reddit, Alexis Ohanian was told by Yahoo that his company’s traffic was “a rounding error”. He framed it up, hang it on the wall and looked at it all day.

As Jim Denthmer pointed out that there are not one, not two but five things that can motivate us. And they are all equally powerful. They are fear, extrinsic rewards (money/status), intrinsic reward (meaning/purpose), play and love.

It’s entirely possible. Some of the very top professional are trafficking in play. The deal makers negotiating contracts. The athletes playing sports. The coders writing algorithm. They are able to out-learn, out-work and out-last everyone because it’s fun to them, and work to you.

Perhaps if your fuel is hindering you from where you want to go, it’s time to look inside and choose a different kind.

(HT podcast interview on The Knowledge Project)

There are many reasons why we do things. Our jobs, our exercises and even our meals. And within each, there are layers upon layers of reasons.

Perhaps the job was about money, but it might also be for friendships or a place to feel useful.

Perhaps cooking our meal was about health and deliciousness, but it might actually be a semi-distracted environment for your child to reveal the truth about their day.

As we get stuck, getting caught in a cycle, it could be a good time to start a dialogue with ourselves. Why do we do the things we do?

And as we get to the core of it, we start to uncover these motivations. It could be about guilt, shame and fear. It could be about perks, status and jealousy. It could be about fun, learning and joy.

It worth noting here that any piece of wisdom that anyone gives, about what you need or what you want, it’s going to sound like nonsense to you. I think fundamentally we just have to find it for ourself, so the important part is not the answer, it’s the question.

We just have to sit there and dig with the question. Unpacking the layer of reasons and finding the motivations behind each one of them. Differentiating between necessity and fuel, fear and longing.

Perhaps then, we can piece it back together, rearrange it with our priorities. But this time, consciously.

Maybe just maybe, when we can find enough, we are able to get unstuck and do the next thing, and the next thing. Slowly, we can shift from something we ‘have to’ do, to something we ‘get to’ do.

Like all important things, it starts with a pen and paper, staring into mid-space and asking why.

(Thanks Chiara Cokieng for teasing out this article.)