Windows of Opportunity: A Fleeting Chance at the Impossible

In the summer of 1964, a young engineer at NASA named Gary Flandro was assigned a seemingly mundane task: to study ways of exploring the outer gas giants of our solar system.

These planets didn’t get as much attention as our near neighbors, and remained largely unknown.

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As he researched the possibilities, Flandro made a stunning discovery: according to his calculations, the planets Jupiter, Saturn, Uranus, and Neptune seemed to enter an extremely rare alignment once every 176 years.

This alignment meant that a spacecraft launched from Earth in a precise window of time could “slingshot” from one planet to the next using each planet’s gravity. This would allow the trip to be made in just 10 years, instead of the 40 years it would otherwise take.

The next alignment would occur in 1977, just 13 years away.

NASA got straight to work, and used Flandro’s discovery to launch the Voyager program. The Voyager 1 and Voyager 2 spacecraft left Earth at just the right moment to kick off the greatest tour of planetary discovery in history.

The twin Voyager spacecraft charted Jupiter’s complex cloud forms, winds and storm systems and discovered volcanic activity on its moon Io. They studied Saturn’s rings and found enigmatic braids, kinks, and spokes. Its flyby of Neptune uncovered three rings and six previously unknown moons, a planetary magnetic field and complex, widely distributed auroras.

Author Stephen J. Pyne summarized this profound legacy: “Voyager did things no one predicted, found scenes no one expected, and promises to outlive its inventors. Like a great painting or an abiding institution, it has acquired an existence of its own, a destiny beyond the grasp of its handlers.”

43 years after launch, the Voyager spaceprobes continue to transmit useful data as they explore interstellar space, where no man-made object has ever traveled. Their discoveries also laid the groundwork for future missions to use the “gravity-assist” method, including the Galileo mission to Jupiter, Cassini mission to Saturn, and New Horizons, which visited Pluto in 2015.

A Modern Space Adventure

I first heard this story from Eric Anderson, the Founder of Space Adventures. His company kickstarted the space tourism industry in 2001 when it sent the first private citizen to the International Space Station (ISS) aboard a Russian Soyuz rocket.

In November 2019 I found myself in Seattle, and asked Eric to meet me for lunch after first connecting online. We met at an upscale Japanese restaurant on the top floor of his headquarters building in downtown Bellevue. The view from the restaurant windows soared out over the incredible fall colors and waterways of the Pacific northwest.

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We spent lunch talking about our shared interests – productivity, software, entrepreneurship, and space. I was reminded of my youthful obsession with space, waiting impatiently for the next issue of Popular Science magazine to arrive and explain the next stage of ISS construction with colorful diagrams.

As we parted ways, Eric sent me a video of a talk he had given recently at the Getting Things Done Summit in Amsterdam. He’d spoken for the first time publicly on a concept he’d learned from decades working in space tourism, astrodynamics, and space mission design: Windows of Opportunity.

I believe that Windows of Opportunity represent the most important step forward in our understanding of goal-setting since the SMART framework was introduced in 1981. I highly recommend you take the time to watch the 22-minute recording of his presentation:

A Window of Opportunity, according to Eric, is “A rare set of circumstances and a brief moment of time in which an otherwise impossible outcome is potentially achievable.”

Flandro recognized such a Window of Opportunity in 1964, and took hold of it. He recognized that not all moments are created equal. That the chance to take advantage of such a rare planetary alignment justified changing NASA’s priorities dramatically. By jumping at that chance, he helped accelerate decades of discoveries which continue to this day.

Eric discovered the importance of Windows of Opportunity through his own business ventures.

The year was 1999, and Eric had a little problem: he had founded a space tourism company, but had no viable way of getting people into space. NASA refused to let the space shuttle be used for commercial flights. It began to dawn on Eric that the sophisticated private space launch vehicles being developed at the time might not be ready for years (they’re just starting to become available today, more than 20 years later).

The ISS was just coming online in a golden age of international cooperation. The U.S. and Russia were collaborating with 15 other nations in a global effort to get every component in place. There were more nations committed to space exploration than ever before.

Eric saw his Window of Opportunity.

He approached the Russian Space Command and asked them a daring question: what would it take (and cost) to get a private citizen into space? Their initial response was laughter and dismissal. No one had ever asked such a question.

But Eric persisted, traveling to Russia in person multiple times to show his seriousness. Finally, they conceded it was possible. But he first had to fulfill a long list of requirements, medical checks, training, and waivers, not to mention an exorbitant cost. It was clear they didn’t really expect him to go through with it.

But Eric was unstoppable in his determination. It took several years of intense effort, but in 2001 Space Adventures launched the first space tourist, Dennis Tito, into orbit for 8 days aboard the ISS.

This event marked the birth of the space tourism industry, and contributed to a new wave of attention and investment in space exploration. It helped reignite a new space race that fueled the rise of SpaceX, Virgin Galactic, Blue Origin, and the X-Prize today.

In his presentation, Eric asks the audience, “What’s the value of a shift in thinking like that? Opening up chances for millions of other people? That’s what these windows do when we grab them. They create new chances and new opportunities. They build.”

He then tells of how he began to look at his own life, and realized that “…nearly all the value [in my life] came in these definable, transformative moments…Moments of vision, perception, recognition, of actually seeing not only the opportunity, but what it meant to me at that time.”

The crucial thing to understand about Windows of Opportunity, he says, are that they end:

“You may have only moments to recognize it. You have to be able to clarify what it is, what it means to you, so quickly. You have to be ready to take action that you’ve thought about, that could be momentous, quickly. Distraction, hesitation, indecision – these will ruin your chances.”

Just 18 months after that first historic mission, the Columbia Space Shuttle was lost. Access to space was restricted, launches were cancelled, and the window that Eric had taken advantage of closed.

“We think these windows will go on forever, but they don’t. You have to be decisive, and grab it while you have it.”

Personal inflection points

Since being introduced to this idea, I’ve begun to realize that my own life has been powerfully shaped by Windows of Opportunity.

In 2007 I decided to apply for the Peace Corps, an overseas volunteer service program run by the U.S. government since the 1960s. I was living in South America at the time, and completing the application and interview process while overseas was incredibly challenging. The Peace Corps administration recommended I wait until I returned to the U.S. to complete my application, but I insisted on moving forward.

The 2008 financial crisis hit the next year. Applications to the Peace Corps soared and became much more competitive as young people sought to escape the collapsing economy. Luckily, my application was already in the queue and was approved shortly thereafter.

In the midst of the worst economic crisis of my generation, I was fortunate to spend two years serving in Ukraine learning a new language, acquiring new self-reliance skills, and gaining valuable teaching experience that would become the foundation for my career.

In mid-2013 I was taking my first tentative steps toward self-employment, looking for any chance to gain some exposure for my ideas. I received an email with a request for speakers for a local meetup that I occasionally attended, and decided to apply. I had no idea what I would speak about, but with the help of the organizer I developed a presentation on how to measure one’s productivity. It was a lot of unpaid work for the chance to speak for 15 minutes in front of a small group. A recording of my talk was posted online and received no more than a few hundred views, an apparent failure.

But a couple years later I got a message from David Allen, author of the mega-best-selling book Getting Things Done and my personal hero. He had seen my video, and invited me on his podcast to talk about it. That interview was my huge break, and became the jumping off point for dozens of other podcast interviews in the years since.

In 2015 I wrote a guest post on the Evernote blog, describing my views on how digital note-taking apps could be powerful tools to enhance people’s creative output. I thought that I was just scratching my own, obscure itch. But over the next year, I received a steady stream of messages from people wanting to know more.

I had discovered a window of opportunity: Evernote had ridden the explosive growth of the iPhone and grown to more than 200 million users worldwide. But few of those users knew how to properly set up and use such a powerful program. They were hungry for training in how to integrate digital notes into their work and lives. The product I created to address that need evolved over the years to become my flagship online course Building a Second Brain.

Each of these moments were inflection points for me. Windows of Opportunity that stayed open for mere weeks or months. Each of them required a heavy dose of luck, but luck wasn’t enough. I had to take decisive action – apply for a spot, deliver a presentation, write an article – to realize the potential of the moment.

Timing is paramount

The conventional way of setting personal goals was to ignore time as a factor completely.

Perhaps you were encouraged to think of a “Big Hairy Audacious Goal” – the most outrageous ambition you could imagine. Publish a book and sell 1 million copies! But such lofty goals always take place far off in a hazy future, providing no guidance for what we should do today, tomorrow, and next week.

Or maybe you were fortunate enough to discover the SMART framework, which had you set realistic, measurable goals with a deadline for completion. Perhaps this led you to set a more conservative goal: to self-publish your book by “the end of next year.”

But this due date is completely arbitrary. It doesn’t take into account the constantly shifting landscape of your career, business, or the economy. So that arbitrary deadline comes and goes. Like a high interest debt balance, your goals get “rolled over” year after year, adding to the burden of guilt you feel for not pursuing your dreams.

Windows of Opportunity is a revolutionary way to think about goal-setting, because it recognizes that there is now one factor that is decisive in your ability to reach your goals: timing. Timing has become even more important than vision, hard work, or planning. That “T” at the end of SMART, which stands for “Time-bound,” is no longer an afterthought tacked on at the end – it is the most important element of your goals.

As the world changes faster and faster, the timing of when to make a leap becomes ever more important. This principle is well-understood in the startup world, where launching your product a little too early or a little too late is often a death sentence. But now we are all startups-of-one, and it is quickly becoming just as important on the individual level that we get the timing right.

In the brief moment when a new industry is emerging, making a name for yourself in that industry is vastly easier than it will be once it matures. When a new social media platform starts gaining traction, there is momentarily a far greater chance you’ll be able to build a following before everyone else comes rushing in. When you join a young company that is starting to grow rapidly, you have a fleeting opportunity to take a major leadership role and grow along with it.

These are the kinds of chances that are constantly opening and closing before us.

As Eric puts it, “Think about the Windows of Opportunity that lie ahead. They’re open. All of us, in all of our domains, they’re swimming in front of us. We have to look up. We have to be willing to open our eyes and really see what’s there. Where are paradigms shifting?”

Windows of Opportunity are less about dreaming up fanciful visions completely divorced from reality, and more about staying as sensitive as possible to your environment. What’s changed, and how can you change to match it? What goal is unusually achievable right now, even if it’s not the original goal you set for yourself? What opportunities are you blind to because you’re too wedded to the current path?

To take advantage of them, we have to be opportunistic, a dirty word that we typically associate with thieves and scoundrels. But there is a positive way of being opportunistic: to follow the path of least resistance, to go around obstacles instead of through them, to concentrate your efforts on the greatest leverage points.

What is your Window?

Windows of Opportunity might seem unimpressive at first glance: the chance to meet someone who happens to be passing through town, the chance to speak in front of a group when the main speaker cancels last minute, or the chance to get exposure for your ideas when a publication is accepting submissions.

These moments might seem insignificant, but their impact is momentous. They are slight deviations in the trajectory of a rocket launch that will eventually determine whether you end up landing on the moon, settling Mars, or exploring the outer solar system. They are dramatic pivot points that permanently change the direction of your life.

When these moments arrive, it’s not time to start researching things, or making long-term plans, or getting a degree. It’s too late for detailed analysis or asking your friends what they think. You must act. You must create. You must find your voice and speak now.

Eric describes it this way: “The greatest risk of all, is that you don’t even see the window. That you don’t recognize it. You don’t see the opportunity. You don’t understand even if you see it, what it means to you. You don’t know what to do about it. Or you do, and you fail to act within the window…that opportunity’s gone forever. All the value that could have been created is lost.”

There is a common misconception that you will always have the opportunity to achieve any of your goals. That’s simply not true. Most goals don’t wait around until you can find the time. They are open only for a season, when the planets align just right, and then they are gone forever.

This may seem daunting, but there is a silver lining: there is always another window coming soon. The greatest opportunities come in peaks and valleys, feasts and famines, dry spells and downpours. You have to stay flexible and fluid, because the next window won’t look like the last one. You might start a blog instead of changing jobs. You might publish a website instead of a resume. You might start a community instead of creating a product.

To be open to the possibilities, you have to start with the possibility that you might end up exploring a different planet than you expect.

What most often gets in the way of people recognizing their Windows of Opportunity is some preconceived idea of “how things should go.” A series of assumptions that Step A should come first, followed by Step B, and then Step C, and so on.

But that isn’t how Windows of Opportunity work. The reason they are opportunities is that they are moments in which it is possible to cut the line. Something’s changed – a rule, a policy, a constraint, or a new technological capability. In that change there is a chance to skip steps. But it’s up to you to notice the implications of the changes that are constantly happening around you.

Windows of Opportunity have another interesting implication: they are unique to each person. It is always tempting to compare your goals to others as a measure of how ambitious or driven you are. But these windows are specific to each person’s path through the landscape of reality. What makes them opportunities is the way they fit your unique combination of skills, knowledge, and past experiences. Our paths may intersect at certain points, but your chance is almost never a chance for me.

In other words, Windows of Opportunity are about creating something that has the potential to be not just linear, and not even exponential, but singular – a fleeting chance at the otherwise impossible. These are goals that no one else – not one of the 7.6 billion other people out there – can accomplish. They lie at the intersection of knowledge, skills, and relationships that only you occupy. The goals you find there might not be impressive or even coherent for others, but they are the ones that will be most meaningful to you.

I’ll leave you with some final words from Eric Anderson on what it takes to achieve them: “You have to notice that chance. You have to recognize what it means to you. You have to get ready for it. You have to give yourself a chance to be there, to do something that could mean everything…A chance to save a life, or to turn one around. A chance to end a war, or stop one before it gets started. Your most effective action is one taken at that moment that gives you the best chance at an otherwise impossible, transformative event.”

As you start the new year, my question for you is: What is the Window of Opportunity opening before you at this very moment? What would you have to risk, to let go of, or to question to be able to leap through it?

Thank you to AbdulFattah Popoola, Yorgo Hoebeke, George R. Silverman, Sam Ismail, Choi Veer, and Karthi S for their feedback and suggestions on this post.

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