It was in 2005 when Steve Jobs delivered his now famous Stanford commencement speech. He told three simple stories of passion and courage. These stories still live on and are retold today.

While ‘Stay Hungry, Stay Foolish’ was the most memorable phrase, perhaps the most enduring idea was on connecting the dots. It was about trusting your gut and following through even when the future looks cloudy. It was about how serendipity makes everything clear.

It’s a seductive idea. After all, foresight doesn’t see as clearly as hindsight. If that’s the case, it makes little sense to plan for the future. Perhaps that’s why we have well-intentioned advice on how we should chase our passion. Even if evidence and analysis suggest we should do otherwise.

Robert Greene calls jumping in without a strategy ‘tactical hell’. You’re forced to fight battle after battle, reacting to the needs and demands that pop up around you. There’s no long-term plan that charts where you’re headed. As it stands, serendipity seems to be a great teacher but a terrible leader.

The Dangers Of Serendipity

Using hindsight to justify actions made in the past can often be dangerous. It’s clear in the ubiquitous example of tech college dropouts who went on to build their own companies. If Bill Gates, Steve Jobs and Mark Zuckerberg did it, who’s to say that you can’t?

It’s a classic case of survivorship bias. For every single big name that made it, there are thousands who didn’t. Those who failed to connect the dots are unheard of while the stories of the same few names get repeated in popular culture. We make judgments about what we should do based on the people who survived, totally ignoring all the guidance from the people who failed.

These were the people who had astronomical talent and a fair serving of good luck — they were the ones who made it despite their situation and not instead of it. It’s possible that you do the same, but unlikely. Counting on serendipity to succeed is far from a wise decision. Hope is not a method.

Charting The Course

Having a strategy means that there’s a long-term goal you’re heading towards.

You know what you want, and understand that there are certain steps you need to take. You build habits and put into place support systems that help you stay the course when times get tough. You get the necessary resources, education and training you need.

For those who aspire to be doctors, you head to medical school. For those looking for a career in law, you go to law school. For those who want to build a tech company, you go to college and then drop out — or so says the script provided by popular culture. But the point is that you continue learning so you can be better than you originally were.

That’s not to say that you need a full script for the next 5 years. You need only a general direction that you can take. So long as you’re headed the right way, there’s little to worry about. You just need to make course corrections along the way.

When Steve Jobs dropped out of Reed College, he left without a solid plan. He was given the unusual opportunity of dropping into classes at Reed College even though he wasn’t paying tuition. A course in calligraphy imprinted in him the importance of beautiful typography, which later became a defining feature in the Macintosh, and then in all computers.

Tim Ferris doesn’t make five-year plans. Instead, he treats his life as six-month projects and two-week experiments of various types. He then takes the most attractive window of opportunity that pops up. At a point in time, he finally managed to convince himself to take a four-week vacation from his work in order to regain his sanity. That break turned into an 18-month trip, which provided the basis for his book, the 4-Hour Work Week.

Piercing The Fog Of War

Some people manage to stumble into success. But more often, it’s the result of a long-term plan, albeit improvised.

Alexander Fleming accidentally discovered penicillin in 1928 after mistakenly leaving a Petri dish uncovered during one of his studies. However, his work had long begun before that. He was already studying the effects of antiseptics in World War I, theorising that antiseptics was killing more lives than it was saving due to improper application. Fleming had long developed the skill and knowledge to make astute deductions from his observations through his work. He would not have made that serendipitous discovery otherwise.

Indeed, more could have been done if Fleming had focused on winning his academic peers over. Fleming was never able to personally interest or convince a chemist skilled enough to further refine and mass produce penicillin. Penicillin was commonly adopted only 12 years later for medicinal use with the arrival of World War II. He contributed a great deal to humanity but would have done far more with a few simple adjustments.

These achievements were not a mere leap of faith. They were a result of years of bridge-building. While those who achieve great things may recount their journeys modestly, oftentimes their course is guided by timeless principles that we would all do well to abide by.

What Lies Around The Corner?

It’s difficult to predict exactly what happens. No matter how we plan, we inevitably run into brick walls. In such cases, the ancient philosophy of Stoicism proves instructive, calling for the practising of virtue during times of difficulty. These are the times where you develop the fortitude and character necessary to turn trials into triumphs.

But beyond being a good teacher, there seems to be little reason for wanting to run into brick walls. They are part of the journey, but never the destination. In this regard, having a solid strategy detailing the whats, whys and hows of what you’re after really matters. Jumping headfirst in the undisciplined approach of more is not the best way of chasing after your goal.

It’s alright to trust that the dots will connect. Just make sure to line them up first.

Take Care Of Strategy, And Serendipity Will Take Care Of You


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