The Messy Middle: Finding Your Way Through the Hardest and Most Crucial Part of Any Bold Venture

by Scott Belsky

Just a quick reminder: Shorter emails get faster response times. Fewer words go further (and are listened to more intently). Standing meetings (where your knees get weak) prioritize the point. The less preamble, the more focused your team will be on your message. Most attention spans don’t even make it to the end. Start with your point; don’t end with it.

while winnowing down your inbox gives you a strong feeling of progress, it’s just that—a feeling. Because unread message counts do not obey the golden rule of progress bars: Thou shalt not move backward. Instead, your unread message count is always a moving target. While you attend to it, you have the false sensation of advancing toward a goal, but the moment you look away, the target shifts farther into the distance as more messages roll in,”

“by dint of technology, it’s easy to see our progress when we’re doing relatively meaningless short-term tasks, while it’s quite difficult to see our progress when we’re engaged in the long-term, creative projects that will ultimately have the most impact on our lives.”

Keeping the ship moving, and breaking ice at the bow, is a painful responsibility, but the person who does it is the person who transforms big organizations. Be the person who asks the persistent, and often annoying, questions. Don’t try to get everyone to agree. Instead, put people on the spot to share their objections. When there is ambiguity about the next step, call it out. Ambiguity kills great ideas, and great leaders kill ambiguity.

Ultimately, you want a team that values conflict as a means to make bolder decisions and take the required risks for a more exciting end. Disagreement is great, so long as the team shares conviction when a decision is made.

“A good team does a lot of friendly front stabbing instead of backstabbing. Issues are resolved by knowing what they are.”

Be curious about competitors’ moves, but don’t emulate them. Instead, look at what your competitors do, and ask yourself a series of questions: “Are their strategy and goals the same as mine?” If their strategy and beliefs are different, and you still have conviction in your own, then you shouldn’t be distracted. Stay the course. Google launched in 1998 as the twenty-first search engine after other search engines like Alta Vista and Yahoo, but they took very few pages from others’ books because their strategy was unique and required entirely different tactics. Rather than simply index the web, Google was organizing the web in a way that improved the quality of search results over time. Google wanted to give you one great result first rather than a list of all the results. This alternative approach made all the difference. But if your competitor’s strategy and goals are the same as your own, then you need to ask yourself another question: “Is their tactic better?” If so, you should consider taking the same tactic yourself. In 2016 and 2017, Instagram infamously copied Snapchat’s tactics over and over again. Both apps were playing in the same field, and Instagram used what Snapchat learned to get ahead of it in its own game. Instagram implemented Snapchat’s “stories” and augmented-reality features, like facial overlays, because these tactics were directly aligned with its strategy: to host the media friends share with one another. Instagram was getting ideas from Snapchat, b...

If you have conviction in your own ideas and approach, then you should be the most competitive with yourself. Your past personal best—your most productive week, your most efficient sprint, your best-executed event—is what you need to beat. Competing with your past is the purest and surest way to make faster progress without compromising your vision. The greatest successes are the aggregate of persistent optimizations of personal bests.

“What distinguishes great founders is not their adherence to some vision, but their humility in the face of the truth.”

The greatest thinkers I admire anchor their ideas around a central truth—often one they believe is unique and unrealized by others. Whether it is a thesis for a new product or a future world they can envision and believe in wholeheartedly, it’s that vision that drives them. But when something or someone challenges their mental model of the truth, they embrace the new questions rather than look the other way. Rather than confront the tough questions defensively, they get insanely curious about what they might be missing. Rather than ask leading questions, buoyed by hope that their assumptions remain true, they switch into learning mode and open their mind to a possible new truth—a new anchor that could change everything.

Be open, humble, and eager to learn that you’re wrong—before someone else does.

Miraculous things are possible when you allow yourself to pursue an idea slowly. Like fine wine, the longer you can leave the grapes on the vine—and the wine in the bottle—the more complex the flavors become.

Time adds a value to creative work that cannot be replicated any other way.

To give bold ideas a chance, sometimes you need to act first and then adjust them as necessary.

Society tends to eventually celebrate what was, at first, shunned. Companies are no different. If you can withstand some tyranny, you’ll be rewarded for it. Oftentimes, the best way to proceed is by charging ahead without too much reliance on the processes developed to maintain the status quo.

Decisions based on consensus typically end up with an ordinary outcome because by seeking to please everyone, you boil your options down to their lowest common denominator: whatever option is most familiar to the most people and therefore gets the least protest and the fastest support.

You can consult groups, history, and common knowledge, but the tough decisions and crazy notions of future possibilities come from within.

All advice you receive is too generic to help you—you need to decide for yourself in your exact situation.

Hesitation breeds incrementalism—the tendency to make changes too muted, too slowly, and too late. You need to attack the hesitation and galvanize the troops to move forward without looking back.

Great teams implement change when it’s still uncomfortable to do so, ahead of the realized need. Don’t give those resistant to change false hope for things staying the same; when a decision is made, declare the implications and chop off the rearview mirror.

Successfully optimizing your product, whatever it may be, means making it both more powerful and more accessible. The key to striking this balance is grounding the decisions you make with simple convictions, the absolute simplest being Life is just time and how you use it.

Optimizing the product you’re making is ultimately about making it more human friendly and accommodating to natural human tendencies.

The pursuit of a great product requires discipline, endless iteration, and grounding your objectives with your customers’ struggles and psychology.

Productivity and performance are too often conflated. Instead, you need to decide what aspects of your team and product distinguish you most—and what you’re willing to be bad at. Your competitive advantage is a conscious admission and acceptance of your weaknesses as well as a recognition of your strengths; it’s as much about what you focus on as it is about what you choose to let go.

spectacular achievements are ultimately the result of doing something different exceptionally well.

“The question that I find most helpful to ask is, ‘if you had to keep 10 percent, which 10 percent would you keep, and if you had to, absolutely had to, cut 10 percent, which 10 percent would you cut?’

Experiments are important, and you need to try different paths to find the best one. But if an experiment fails to become part of your core strategy, it should be killed. Focused creativity is more important than more creativity.

If you don’t think your bold, against-all-odds project is awesome, make a change. And if some aspect of your product isn’t working, make the tough decisions to kill it. Without such honesty and decisiveness, your work (and career) will fail to progress. Once you admit something isn’t working and make the change, you’re liberated. You’re ready to consider solving an entirely different problem with your full mind and extending your energy long enough to make it happen.

Don’t be creative for the sake of it, despite the urge to do so. Popular terms and actions are popular for a reason. Adopt simple patterns, proven to be successful, whenever possible, and train your customers only when it’s a new behavior that is absolutely core to what differentiates your product. Familiarity drives utilization.

You can’t expect new customers to endure explanation. You can’t even expect customers to patiently watch as you show them how to use your product. Your best chance at engaging them is to do it for them—at least at first. Only after your customers feel successful will they engage deeply enough to tap the full potential of your offering.

Old assumptions don’t get questioned enough because we’re used to them, and new ideas get dismissed too quickly because they are foreign and challenge conventions. Engaging and empowering new talent is a reliable way to break old patterns. As the leader of a team with new and old talent, your challenge is to balance the need to incrementally optimize alongside the need to change and question everything. Knowing the tendency to be limited by a local maxima, challenge yourself to welcome disruptive forces when you find yourself defensive. Strong denial is a signal for a hard truth. Foster inbred innovations.

When pursuing a new idea or solution to a problem, run it through three filters: Empathy with a Need and Frustration: You have to understand the struggle of your users. Are you empathizing with customers who will benefit from your idea? What is their frustration and where is it coming from? Since you are often a customer of your own product, pay special attention to what frustrates you. As Jerry Seinfeld once explained in an interview with Harvard Business Review when he was asked where his best ideas come from, “It’s very important to know what you don’t like,” he explained. “A big part of innovation is saying, ‘You know what I’m really sick of?’ . . . ‘What am I really sick of?’ is where innovation begins.” What frustrates you likely frustrates many others. Humility with the Market: Humble yourself with the market dynamics around you. Is there another company in a much better position to serve your customer than you are? If so, what has prohibited them from doing so? What change in the market could immediately cripple your prospects? Passion for the Solution: The final filter for an idea is whether or not you are passionate about the solution. I recall a number of on-demand laundry start-ups that had a market opportunity but whose founders realized, a few years into the journey, that they didn’t really care about laundry. Just because you see a market need doesn’t mean you’re the one to solve it. If you’re not willing to spend day and night, year after year, solving the ...

When turning an idea into an active venture, you must seek empathy with your customers and humility in your market. Don’t let your passion drive you too far ahead of where your customer is. Empathy and humility act as powerful filters. The day you lose empathy is the day you lose.

Every creation needs a narrative. The narrative is the story of what you’re building in the context of why it matters. What inspired the idea? Why does it need to exist? What makes it relevant? How does it make the future better?

The narrative is not a description of what your product is or does, it is the story of how and why it must exist.

Developing a brand early on, even before the product, helps develop a powerful values-driven narrative akin to the company having its own voice. You will find, when you’re making certain decisions that impact the customer’s experience of your product, the brand will speak to you.

The narrative should always be framed in the context of life itself. How does your product empower people? Does it help people save time or make them forget time? How does it take natural human tendencies into account, like the desire to look good or make better (and fewer) decisions? And most important, what about your creation will eventually be taken for granted? There’s nothing more impressive than inventing what becomes obvious. The only way to create something that withstands the test of time and becomes a critical part of your customers’ lives is to understand the broader narrative around your product.

If you’re building a network, be humbled by the fact that you’re not in control and that the community doesn’t belong to you. Serve your network, promote transparency and meritocracy however you can, and then engage as a proud and committed steward.

I now look at nearly everything through the lens of a question: ‘Will I develop relationships and skills that will persist beyond this project and help me even if this project fails?’ That is really the hurdle for me saying yes to new options and opportunities.”

Value is best measured by the resources you’d be willing to spend to do it again, knowing all that you know now.

We love data. It answers questions. But the definitive nature of data means you must use it with caution. When presented with a statistic that has broad implications, your first question should be about its integrity. Where did it come from? What was the sample size, time range, and breakdown of people from whom the stat was captured? What is the context around the collection of the data? Only when you have interrogated your data sufficiently should you consider how to use it.

You don’t need to agree with what you hear, but you need to know what others think and candidly dissect why you agree or disagree.

Give your customers something precious, something that cannot be easily scaled, automated, or commoditized. The greatest innovations in an industry are strange and artlike before they become the new standard. Do things that your competitors and incumbents wouldn’t even think of doing for lack of financial reward. Only through these explorations will you discover the key differentiator—the art—that surprises customers and builds a remarkable product and brand.

In your work, try to find the things you love that nobody else cares about. Your gut fascinations are lead indicators of what may prove important over time. So many things in work and life can be scaled. But when you come across something that cannot, like art, relationships, or details, pay special attention. By preserving the art in your business, you give it a soul that people will connect with.

Everyone perceives you differently, so acknowledge the blind spot. In order to become aware of what you can’t see, attempt to determine how you’re coming across. For example, ask people, “If you were me right now, what would you be doing differently?” This question not only yields advice but also gives you a sense of how others view your position and actions.

To tap the full potential of your team, sometimes you have to let go of the reins and let people have their own creative process. Even if you think your first draft is perfect (unlikely), allow your colleagues to play with an idea without your presence. This fosters a sense of ownership and alignment that expedites execution. More often than not, great ideas grow out of good ideas—and it keeps the band together.

The most humbling part of creation is that you’re never truly done. A finish, it turns out, is an abstract mile marker that makes your long journey through life more digestible. Being aware of where you are in that cycle of creation and which way the wheel is turning is imperative to keeping the cogs turning. From every finish comes new possibility, so long as you lead it well and pass the baton on.

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.

It’s not just about moving on when you’re performing at the level you always wanted to be remembered for—the desire to “end on a high.” It’s about moving on when you feel fully satiated and can therefore allow yourself to pursue something different.