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


The volatility of this tug-of-war is hard to stomach. You must pay less attention to the day-to-day incremental advances and more on achieving an overall positive slope. And that’s entirely determined by how you navigate the messy middle. The middle of the journey is all about enduring the valleys and optimizing the peaks.

The Rabbit Hole is written by Blas Moros. To support, sign up for the newsletter, become a patron, and/or join The Latticework. Original Design by Thilo Konzok.

Key Takeaways

  1. 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. Rather than fight the need for short-term rewards, you must hack your reward system to provide them. As you craft your team’s culture, lower the bar for how you define a “win.” Celebrate anything you can, from gaining a new customer to solving a particularly vexing problem. 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.
    1. Give your team the gratification of seeing their progress rather than just moving on. At Behance, we had “Done Walls” that were decorated with a collage of completed project plans, checklists, and sketches that literally surrounded us with the sensation of progress. And whenever I’m presenting a forward vision presentation to my team, I try to start with a few slides recapping what the team has already accomplished. Progress is the best motivator of future progress, but it must be merchandised sufficiently so that people feel it. While
  2. It’s dangerous to celebrate accolades or circumstances that are not linked with productivity, like getting “press” that you paid for or winning awards that are not representative of your impact.
  3. For strong companies, financing is a tactic. For weak companies, financing is a goal.
  4. Society has a grand immune system designed to suppress new ideas. To keep the water running and sustain life’s other necessities, society’s natural resistance to ingenuity surfaces in the form of doubt, cynicism, and pressure to conform. It takes tremendous endurance to survive such resistance.
  5. As a leader, you can’t always provide answers. And you shouldn’t, as the correct solution may still be premature. But what you can do is always add energy. This ability to turn negative conversations into positive ones is a trait I’ve always admired.
  6. A friend who worked for Google cofounder and CEO Larry Page told me that when teams presented product and business goals to Larry, he would often reply, “What would it take to achieve 100x of what you’re proposing?”
  7. When you feel lost in ambiguity, ask a different question. The perfect question is a key to clarity. It unlocks truth and opens minds.
  8. Playing the long game requires moves that don’t map to traditional measures of productivity.
  9. 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.
  10. The easy path will only take you to a crowded place. Be wary of the path of least resistance. It may look compelling in the short term but often proves less differentiating and defensible in the long term. Shortcuts tend to be less gratifying over time. The long game is the most difficult one to play and the most bountiful one to win.
    1. The best way for a start-up to “disrupt” an industry is to be a thesis-driven outsider—someone who hasn’t been jaded by the industry but has a strong opinion for what should change. You then just have to stay alive long enough to become an expert so you can compete with the different skills and practices you bring.
  11. Across so many teams I’ve worked with, I’ve marveled at just how quickly an idea takes hold when someone proactively does the underlying work no one else clearly owned. There is rarely a scarcity of process or ideas but there is often a scarcity of people willing to work outside the lines. Those who take initiative to contribute when it wasn’t their job become the leadership team of the newest stuff.
    1. 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.
  12. James Murphy, the founder and front man of LCD Soundsystem, said it well: “The best way to complain is to make things.”
  13. Pinterest’s Ben Silberman describes this process as “always reflecting backward and incorporating forward.” As he explains it, “I actually think you learn a lot more from your successes [than your mistakes]. There are a million reasons why something can fail, but usually very few reasons why something can work. When you want to learn to be a great runner—do you study slow people or fast people? I think taking time to understand why things succeed—whether they are your successes or others—is time well spent . . . you learn the most from things that go really well by asking why. Those are the things you want to understand and do more of.”
  14. Great teams are more than the assembly of great people. On the contrary, great teams are ultimately grown, not gathered.
  15. You can always get more resources, but resourcefulness is a competitive advantage. Resources become depleted. Resourcefulness does not.
  16. Hiring
    1. Past initiative is the best indicator of future initiative. Look beyond the formal résumé and ask candidates about their interests and what they have done to pursue them. It doesn’t matter what the interests are—bonsai cultivation, writing poetry, whatever! Instead, gauge whether the candidate has a history of being proactive in advancing their interests.
  17. Hire people who have endured adversity.
  18. Your second conversation with a potential hire should feel a lot more interesting than your first. First impressions count for a lot, but if you can’t continually build on that energy, the relationship isn’t likely to have legs beyond the initial spark. I call this kind of fire-starting ability aligned dynamism, which is when ideas vary but energy levels and a value for the mission align; this is the source of the embers that will keep burning long after the initial flint.
  19. Be frugal with everything except your bed, your chair, your space, and your team.
  20. Not only does a strong culture tolerate some necessary ruckus, it gains its edge from it. People disagree and fight for their beliefs only when they are engaged enough to care.
  21. Perhaps one of the most important unspoken roles of a leader through the messy middle of a project is that of internal marketer. For all the emphasis around obsessing over your customers and your public brand and message, there is surprisingly little focus on the internal brand and message.
  22. Present your ideas, don’t promote them.
  23. When it comes to speed and efficiency, the greatest risk is taking a shortcut in the one area that distinguishes you the most.
  24. Simplicity / Design
    1. Simple is sticky. It is very hard to make a product—or any customer experience—simple. It is even harder to keep it simple. The more obvious and intuitive a product is, the harder it is to optimize it without adding complication.
    2. Great products don’t stay simple by not evolving; they stay simple by continually improving their core value while removing features and paring back aspects that aren’t central to the core.
    3. Forcing yourself to have a “one feature in, one feature out” guideline will help you develop your product with a bias toward simplicity. While simplicity benefits your newest customers and the majority of your current customers, it also benefits your own process to grow your product and solve problems as they arise.
    4. Beware of creativity that compromises familiarity.
    5. The only time you should force new behaviors or terminology is when they enable something better
    6. Effective design is invisible.
    7. Never stop crafting the “first mile” of your product’s experience.
      1. I’d argue that more than 30 percent of your energy should be allocated to the first mile of your product—even when you’re well into your journey. It’s the very top of your funnel for new users, and it therefore needs to be one of the most thought-out parts of your product, not an afterthought.
      2. Optimize the first 30 seconds for laziness, vanity, and selfishness.
      3. Your challenge is to create product experiences for two different mind-sets, one for your potential customers and one for your engaged customers. Initially, if you want your prospective customers to engage, think of them as lazy, vain, and selfish. Then for the customers who survive the first 30 seconds and actually come through the door, build a meaningful experience and relationship that lasts a lifetime.
      4. If you feel the need to explain how to use your product rather than empowering new customers to jump in and feel successful on their own, you’ve either failed to design a sufficient first-mile experience or your product is too complicated.
      5. The absolute best hook in the first mile of a user experience is doing things proactively for your customers. Once you help them feel successful and proud, your customers will engage more deeply and take the time to learn and unlock the greater potential of what you’ve created.
    8. As you’re building new products and experiences for customers, consider how they will be novel—even gamelike—before they prove useful.
    9. You need to prime your audience to the point where they know three things:
      1. Why they’re there
      2. What they can accomplish
      3. What to do next
    10. Empathy for those suffering the problem must come before your passion for the solution.
    11. But be sure to define the purpose of every feature in your product before determining its fate. Is it to strengthen engagement, appease a very small set of important customers, or get new customers in the door? Features with a different purpose require a different measure.
    12. Build your narrative before your product. - The narrative is not a description of what your product is or does, it is the story of how and why it must exist.
      1. Our narrative was that technology needed to empower creative people to make ideas happen. By uploading their portfolios, creatives could get more exposure and attribution for their work, resulting in more job opportunities. We called it “creative meritocracy,” the idea of creative people getting opportunity based on the quality of their work rather than what agency they worked with, where they went to school, or whom they happened to know.
  25. Ollie Johnstone and Frank Thomas, two of Walt Disney’s chief animators, once said of Walt Disney himself that “there were actually three different Walts: the dreamer, the realist, and the spoiler. You never knew which one was coming into your meeting.”
  26. Contrary to logic, you don’t want to attract all of your customers right away. You want your first cohort of willing customers to be quite small so that you can communicate directly and provide an incredibly high level of touch. At the start of your business, you want to iron out the kinks. As you expand, you want to do so slowly.
  27. Networks are served, not led
  28. The best advice doesn’t instruct—it provokes. The benefits of soliciting wisdom from others is indisputable, but the real value of advice comes from reconciling its contradictions.
  29. As someone who believes wholeheartedly that self-awareness is the greatest competitive advantage for a leader, I love the idea of developing tools and norms that promote it.
  30. The science of business is scaling; the art of business is the things that don’t.
  31. Relationships
    1. In the early days of Behance, I used to write personal emails to a handful of customers every day introducing myself, giving some suggestions for the portfolio they posted on Behance, and offering to answer any questions directly. Many of these exchanges became relationships that lasted years and yielded customer insights that we would have never garnered from a dashboard.
    2. Genuine relationships with and between our members was our competitive advantage against other technology companies like Squarespace and Wix that sought to commoditize websites and online portfolios.
    3. Our in-person events for five thousand people around the world would generate tens of thousands of social media posts, and the images would ultimately reach hundreds of thousands of people. But more important, these events prompted conversations and relationships that went far beyond our brand as a service and instead made it a lifestyle.
  32. In your work, try to find the things you love that nobody else cares about.
  33. There are two ways to build a network and source signal: growing surface area or going deep. In the beginning of your career, optimize for surface area. As you become more focused and a source of signal in your own right, you’ll want to shift from seeking surface area to going deep with a smaller group of people whom you respect. Rather than meeting as many people as possible, you’ll want to focus on the people you deem the most competent. You also need a margin to mine circumstantial opportunities and explore the unexpected.
  34. The busier and more ambitious we get, the more protective and intentional we become of our time—but sometimes it’s too much. Ambition shouldn’t override opportunity.
  35. Ego is rust. So much value and potential are destroyed in its slow decay. Achievement rarely ages well, unless you keep sanding it down.
  36. I was struck by the man’s sense of peace and happiness. His smile and mannerisms carried no weight to them—the man seemed so incredibly content with his world. So, that’s what it looks like to end on your own terms, I thought to myself. 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.
  37. One of my favorite sayings from ancient times is “Wealth is ultimately feeling like you got your full portion.” When I finish a project, I aspire to feel full. And when I lay dying, I hope to look back on what I would consider a full life.

What I got out of it

  1. Some valuable and deep insights on the building process and how to navigate through the "messy middle." Topics around leadership, design, simplicity, and doing things that don't scale will stick with me

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