The lengthy distance between where you are and where you wish to be—with all of its difficulties—is there for a reason, and the ups and downs feed each other in valuable ways. In Zen, the Buddha says you cannot travel the path until you have become the path yourself. Only by embracing the middle will you find your way through.
The easiest route to take is to glide in the direction of wherever fate pushes. But living at the mercy of circumstance makes you a passive participant in your own story. Without a fight against fate (aka the status quo), you’ll never venture beyond the expected. You can stretch your potential only by enduring the volatility of the journey, by getting curious about the bumps, and by optimizing every aspect of your product, team, and self.
The insights ahead will equip you for the middle-journey turbulence. They will also remind you that you’re not alone. But we need to face the mess head-on and learn how to endure and mine the volatility. Exploring the trenches of lost hope, uncertainty, and exhaustion help make such conditions more familiar—and therefore bearable, maybe even manageable.
Short-circuit your reward system.
One of the greatest motivators is a sign of progress. Hardship is easier to tolerate when your work is being recognized (either through external validation or financial rewards), but long journeys don’t show progress in the traditional sense. When you have no customers, no audience, and nobody knows or cares to know about what you’re making, the greatest motivators have to be manufactured.
Don’t seek positive feedback or celebrate fake wins at the expense of hard truths.
What should you celebrate? Progress and impact. As your team takes action and works their way down the list of things to do, it is often hard for them to feel the granularity of their progress and you need to compensate. Celebrate the moments when aggressive deadlines are met or beaten. Pop champagne when the work you’ve done makes a real impact. Even if it’s just a few customers that make use of a new product or feature, these are the real milestones you want to celebrate.
Accept the burden of processing uncertainty.
No matter what your creative endeavor is, uncertainty will be lingering around every corner. There is simply no way around uncertainty and the angst it will cause for you and your team. Strive to continually process it rather than let it cripple you, to accept the burden without surrendering your attention.
Fight resistance with a commitment to suffering.
Despite whatever hacks and strategies you employ, you will get burned repeatedly. Society’s immune system is powerful and indiscriminate. Suffering is inevitable, but by expecting it, you can manage your expectations and those of your team. You can build a culture that is as much about the experience building the product together as it is about the product itself. By doing so, at least you’re in your own little world suffering among friends! As you hire people to join you, you can evaluate not only their skills and interests but also their tolerance and commitment to enduring the fight against the self-doubt and gut-wrenching hardships that real life and society will throw at you.
Friction brings us closer.
Groups help us manage life’s frictions, and the challenges we face bring groups together. Rather than circumventing or burying it, use the frictions you encounter to learn how to cooperate and build your team’s capacity to handle adversity. Whatever you do, don’t fear tension and confrontation. Passivity arrests your development as a team. The fights bring you a level deeper, they force you to cover more surface area of opinion so you can ultimately discover the best solution. And, often times, we desperately need the clarity that crisis provides. As the early Roman emperor Marcus Aurelius once quipped, “The impediment to action advances action. What stands in the way becomes the way.” Indeed, the frictions we encounter help us find a better way so long as we face them.
Be the steward of perspective.
Teams need to be reminded where they are and what progress they are making. As a leader, you are your team’s window. You need to call out and describe the landmarks that you pass along the way, constantly reinforce the terrain you have already covered, and prepare folks for the map ahead.
Likewise, it is your responsibility to steward perspectives when you’re not even sure the conversation will end in a solution. Some of the best conversations are ones that are not trying to answer a “yes or no” question. In such conversations, instead of prompting closure, your goal should be to lead your team through a process of self-discovery.
Leave every conversation with energy.
Your team needs energy transfusions, especially in the middle miles when circumstances feel dire and there is no end in sight. Acknowledge the trials and uncertainty you’re facing, followed by reiterating your plan of how to climb out, what you’re aiming to achieve, reminding your team why you’ve come together to do that, and then add your own enthusiasm and confidence. In the final moments of every meeting and communication, you need to reiterate purpose and leave people with the energy to achieve it.
If you don’t like the way government is being run, cross party lines.
If an organization doesn’t let politics and burdensome processes get in the way, then size becomes an advantage. If not, well . . . big companies become couch potatoes while the future of their industry passes them by. Of course, this all comes down to the leaders themselves and whether or not a culture supports people stepping out of their traditional roles. Fight corporate obesity by gathering the right people in a room and depoliticizing process as much as you can.
Prompt clarity with questions.
Whether you’re an author suffering from writer’s block or a start-up team struggling to satisfy its customers, the solution is to change the question you’re asking. If the original question plaguing you is “Why aren’t people signing up for our product?” maybe the better question is “What kinds of people would benefit most from our product?” When you feel lost in ambiguity, ask a different question.
The perfect question is a key to clarity. It unlocks truth and opens minds. It is distilled by having empathy for your customers’ struggles and ignoring sunk costs and past assumptions to get at the root of a problem. When you’re building something new, focus on asking the right questions instead of having the right answers.
Strategy is nourished by patience.
To foster patience for yourself and those you lead, pick a speed that will get you there, and then pace yourself. Celebrate persistence over time as much as the occasional short-term wins you have along the way. Craft a culture in your project or team that values adherence to a vision and continual progress more than traditional measures of productivity. Establish a structure that allows teams to pursue long-term projects beyond the gravity of day-to-day operations. And remember just how rare it is to stick to a strategy over the long term. This competitive advantage is available to any team, big or small, that is patient enough to stay focused, stick together, and move forward.
Do the work regardless of whose work it is.
A shared trait among entrepreneurs and innovators within big companies is defying prescribed roles. The future is drafted by people doing work they don’t have to do. You need to be one of those people—and hire them, too. There is too much wondering and talking, and too little doing. So don’t talk: do. Care indiscriminately. If you’re willing to actually do the work, you’ll have more influence than those who simply do their jobs.
You are not your work.
When you’re finished, your fate and your work’s fate diverge, but your identity belongs to you. And you are not your work. Your work, or your art, is something you’ve made. It can fail, be sold, or be left behind, but it can’t be you. A successful final mile requires letting go of what you made and returning to who you are, your values, and your curiosities that are kindling for whatever comes next.
To be done is to die.
The messy middle miles that you endure and optimize your way through don’t get any easier and never repeat themselves, because they are the moat between vision and reality. The messy middle is a life’s work, and when anyone crosses the finish line and pushes an extraordinary creation out to the world, we all benefit. In this sense, we’re all in this together, learning the hard way, and sharing the insights garnered from our own journeys to help us all maximize our middles so that more great ideas see the light of day. The future is created by those who endured and optimized through the messy middle to create it. For you and for the rest of us, stick with it.