The curious technique successful people use to ‘connect the dots’

At Stanford University’s graduation ceremony in June 2005, Steve Jobs delivered an unforgettable Commencement address to graduating students.

In his speech, he shared a story about how seemingly-unconnected experiences ended up being critical to realizing his accomplishments, even though he didn’t know it at the time. His inspiring address is worth listening to in its entirety, but one lesson in particular caught my attention:

“Again, you can’t connect the dots looking forward; you can only connect them looking backward. So you have to trust that the dots will somehow connect in your future. You have to trust in something — your gut, destiny, life, karma, whatever. This approach has never let me down, and it has made all the difference in my life.”
– Steve Jobs

As I considered this, I realized that for some accomplishments in life, the “dots” are handed to us; such as graduating college: “pass this list of courses to earn your degree.” While these accomplishments are still difficult, it’s easier for us to trust that our dots will connect to achieve an end goal.

More often, however, we aren’t handed a well-defined curriculum to follow – especially for our personal goals. Instead, it’s up to us to discover the dots, leaving us wondering whether they’ll eventually connect and lead us to a successful outcome.

This practice of “finding the dots” is full of uncertainty, which can quickly turn into stress, anxiety, or complete loss of motivation. In other words, it’s difficult to trust that what you’re doing will eventually get you to where you want to be.

So I asked myself: How can I increase my trust that my “dots” will connect? What can I do to help me stay motivated to reach my goals successfully?

Answering this took a great deal of introspection, but in the end I narrowed it down to just one answer – a simple, practicable skill that reduces uncertainty for anyone looking to “connect the dots” to achieve their goals.

To understand better, let’s take a look at the true story of my good friend Mike, who recently “connected his dots” to build his self-confidence and tackle a goal that many of us consider, but rarely act on: a career change.

Mike’s Journey

For the last five years, Mike has been working hard as a property manager, but has struggled to find joy in an industry he’s not very passionate about.
He knew he wanted to get out of real estate, but didn’t have any ideas as to which direction to take his career.

One day, during his daily routine, Mike realized he could automate a set of repetitive document processes, saving himself a lot of manual effort and letting him focus on more interesting things. Unfortunately, with his company being fairly old-school, he knew it was unlikely that he would get his manager’s buy-in to make this happen on the company’s dime.

Never being one to take no for an answer (especially when it comes to stodgy management), Mike kicked off a personal side project to look into software development and try automating things on his own.

Leveraging the boundless resources of the internet to learn about this new skill, his hobby project gradually turned into something more. He found himself thinking about it during the workday, doing research on the weekends, talking to friends about it, and discovering new fields that he’d never even heard of, such as microcontroller programming. Dot by dot, his hobby was turning into a passion.

Mike’s research was largely undirected – for example, while solving one coding problem, he would come across another interesting sub-problem and do a deep dive into that. He installed Linux, followed various coding tutorials, and skimmed through technology textbooks. Eventually, after a few months, his scattershot “research” began to coalesce into understanding, and he realized it might be possible to turn his hobby into a career change.

As Mike was working through his next “dot”, he suddenly had a serendipitous “Ah-ha!” moment that immediately connected his dots – and fortunately, he thought to send me a text message when it happened, which inspired me to write this post:

“It’s crazy, I’ve been grinding for nine months and spinning my wheels, but something’s happened just in the last month. I’m finally past fighting the tools. Things that seemed alien are now becoming second nature…it’s like all the stuff I’ve read and didn’t understand at the time is coalescing all at once. It’s overwhelming in a good way…I’ll be ready for the bootcamp no problem after this.”
– Text message from Mike

This “Ah-ha!” moment gave Mike renewed self-confidence, excitement, and increased trust that he’ll be able to connect the dots in his future – and make his career change a reality.

Mike knows his work is only just beginning – he’s planning on kicking real estate to the curb and embarking on his software career with a coding bootcamp – but his next steps are very clear, and his confidence in his ability to succeed is at an all-time high.

Building Your Trust

Mike’s dots suddenly connected in his “Ah-ha!” moment and gave him the self-confidence to transform his hobby into a career move. Let’s think back to the lesson in Steve Jobs’ Commencement address: “You have to trust in something — your gut, destiny, life, karma, whatever.”

What was the source of Mike’s trust? How did he stay motivated to accomplish his goals, not knowing how his dots would connect?

Reflecting on Mike’s story and examining my own “Ah ha!” moments throughout life, I realized there’s one thing we can ALL trust in to lead us to a successful outcome: our own curiosity.

Every dot that Mike found; every step that he took led in a single direction: learn more about software development. In “finding the dots,” he was motivated by his own curiosity – uncertainty wasn’t even a factor. Eventually, with his”Ah-ha!” moment, his accomplishment became real.

After understanding that curiosity is the key, I examined Steve’s speech more closely and realized he touched on this idea earlier in his story: “[M]uch of what I stumbled into by following my curiosity and intuition turned out to be priceless later on.”

I wish I could find some way to contact Steve and explain: you don’t have to trust in your gut, or destiny, or karma to know that your dots will connect – you just have to trust in the power of your own curiosity, and the trust becomes implicit.

The Invisible Rope

Photo by Matej Vittek

I like to think of curiosity as an invisible rope that pulls us forward through compelling challenges, much like a water skier being pulled by a tow rope. Our fascination motivates us to solve interesting problems, and we can navigate the churn of uncertainty without fear of failure.

Eventually, curiosity will lead us to a conclusion – perhaps a better understanding, certainty of our next step, or even a decision to change direction entirely. In constantly pursuing things in life that fascinate us, we can use curiosity as our momentum.

In short, by trusting that our curiosity will lead us to that “Ah ha!” moment, we can discard the uncertainty that accompanies “finding the dots” and instead follow our curiosity to achieve a successful outcome. There’s no fear when our fascination guides us.

So what does this mean? How can we make practical use of this truth?

Cultivate Your Curiosity

Take a moment to consider what you’re curious about. What sort of problems captivate your attention? What fascinates you? Now ask yourself: when was the last time you invested effort to exercise your curiosity?

If it’s been a while for you, that’s ok. When I find myself demotivated or struggling to make progress (which is especially persistent right now, during the COVID pandemic), I try to find some aspect of the problem that I can be curious about. That spark alone is usually enough to renew my interest in “finding the dots,” and I can build momentum from there.

Consider your current challenges and find something within them to be curious about. Follow your curiosity for as long as it takes to have that “Ah-ha!” moment that inevitably happens. Trust – believe – that curiosity will help you connect the dots in your future, and you’ll realize your goals faster than seems real!

What’s one problem/challenge you’re facing right now, and can you find something within it to be curious about? Please share your thoughts, in the comments below; I’d love to chat about it!

See you in February!

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