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

Highlights from Kindle

  • In Zen, the Buddha says you cannot travel the path until you have become the path yourself.
  • Until the tech industry becomes more representative of the people it’s trying to serve, these problems will persist—and our products will be worse off because of it.
  • Short-circuit your reward system.
  • One of the greatest motivators is a sign of progress.
  • It is hard to summon a sense of hope and self-worth when you’re on your own. So you squeeze out any semblance of progress you can find, and then you celebrate
  • Breaking through anonymity is a game of endurance, so you have to hack your reward system so that the absent short-term rewards you typically rely on, like revenue or new customer goals, are replaced by something else.
  • physiologically, we’re hardwired to have a strong preference for actions, decisions, and projects likely to yield quick wins, because delayed gratification causes anxiety and discomfort.
  • 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.
  • Milestones that are directly correlated with progress are more effective motivators than anything else.
  • While important to celebrate and manufacture wins early on, make sure they’re not fake wins.
  • If you keep searching for something positive, you’ll find it—but often at the expense of more important truths.
  • In hindsight, seeking positive feedback was toxic, because it was giving us the impression we were on the right track.
  • Actively seek out the negative trends as well as the positive, as your longevity over time will be determined by your awareness of weaknesses as much as your strengths.
  • three methods for assigning meaning to hard truths: State the facts clearly and honestly—Don’t; If you caused it, explain how such a bad thing could occur—What; Explain why taking the action is essential to the larger mission and how important that mission is.
  • You cannot win unless you know how you’re most likely to lose.
  • Funding shouldn’t be celebrated. If anything, raising money should make you nervous:For strong companies, financing is a tactic. For weak companies, financing is a goal.
  • What should you celebrate? Progress and impact.
  • “A leader that embraces uncertainty would be open to experiment with different ideas and let others experiment, too, rather than claiming to know the correct answer all the time.”
  • Whereas a leader who is behaving in harmony with the uncertain nature of a situation would be judged as fair and competent even if sometimes the outcomes are unsatisfactory due to bad luck.”
  • Suffering is inevitable, but by expecting it, you can manage your expectations and those of your team.
  • By avoiding conflict, we don’t smooth out the rough edges of our ideas and plans.
  • 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.
  • 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.
  • When you’re articulating a vision and set of assumptions with such passion and confidence, reality starts to bend your way.
  • your reality-distortion field shows people hope when they can’t see it for themselves.
  • 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 process of self-discovery.
  • By participating, everyone feels more in control of their destiny.
  • “When you have so much conviction that you’re doing the right thing, you see such a challenge as part of the process rather than a road block.
  • We wavered only on how we were going to get there but not the endpoint.”
  • When distractions and drama arise, acknowledge them, and then recontextualize them so that the suffering pales in comparison to the broader opportunity before you. Remind your team why you’re all there.
  • Your job is to help your team make sense of the strategy—what they’re seeing, doing, and working toward. You are the steward of your team’s perspective, and there is always a way forward so long as you explain it.
  • Leave every conversation with energy. Your job is to be an energy giver rather than taker.
  • 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.
  • 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.
  • It starts with building your own relationships with people in different teams across your organization and proactively serving as an ambassador, connecting the right people to expedite solutions.
  • It’s more important to be collaborative than to be correct.
  • Fight corporate obesity by gathering the right people in a room and depoliticizing process as much as you can.
  • During great moments, we are liable to have an inflated sense of self. We believe we are right more often than we actually are.
  • Similarly, in difficult periods when we are struggling to find the motivation and direction to move forward, we can become less aware.
  • Self-awareness starts with the realization that when you’re at a peak or in a valley, you’re not your greatest self.
  • We are not necessarily the cause of the situation, but we are the cause of how we see it.
  • Self-awareness means understanding your own feelings enough to recognize what bothers you.
  • Self-awareness means being permeable.
  • Those who are able to openly absorb and selectively integrate what they hear consistently outperform those who are impermeable to suggestion.
  • seek feedback proactively.
  • If you acknowledge your behavior when it happens, and then investigate what is driving it, you will become more open to the right insights from others.
  • Self-awareness comes from chronicling your patterns.
  • effort to understand how your own mind works is the only path to reliable self-awareness during times of stress.
  • Understanding the sources of your own negative tendencies also helps you make sense of others’ behavior.
  • “Knowing your own darkness is the best method for dealing with the darkness of other people.” Being in touch with your own flaws helps you support others with their flaws. Discussing your flaws invites others to do the same.
  • Without empathy for others’ problems, ideas become less viable solutions.
  • The trick is to integrate humility in your life.
  • Attribute your wins to those around you, and be the first to take responsibility for losses.
  • Ultimately, self-awareness is about preserving sound judgment and keeping relatable and realistic.
  • The more aware you are of yourself and your surroundings, the more data you have to inform your decisions, and the more competitive you will be.\
  • what you gain in relatability by latching onto an existing model, you lose in free-range innovation.
  • resisting the urge to fit in.
  • When front-running the future, the trick is to aspire for a small audience that loves your product rather than aim to please the masses.
  • One of the worst tendencies of the messy middle is pulling wildly fresh insights back toward the mean of normalcy.
  • Learn to say ‘fuck you’ to the world once in a while.” Do your thing.
  • progress is vision paired with initiative.
  • big part of overcoming doubt is suspending your disbelief.
  • what determines whether you succeed or fail is grit, a special blend of passion and perseverance directed at accomplishing long-term goals.
  • Grit is having stamina.
  • Grit is living life like it’s a marathon, not a sprint,”
  • The trick is to separate the hardship from what you’re learning.
  • “strong opinions, weakly held.”
  • Paradoxically, the busier you are at any moment in time, the better your decisions may be because of the greater perspective you have.
  • Storms have the habit of feeling like their own little worlds, even though they’re just weather patterns and they move on.
  • TAKE NOTE OF YOUR “INSECURITY WORK”
  • insecurity work—stuff that you do that has no intended outcome, does not move the ball forward in any way, and is quick enough that you can do it unconsciously multiple times a day.
  • Insecurity work puts you at ease, but it doesn’t actually get anything done.
  • Once you’ve identified your insecurity work, establish some guidelines and rituals for yourself.
  • Whenever I meet with a team that lacks clarity or feels stuck, their breakthrough often comes from a new question or problem to solve rather than a better answer to the original question.
  • 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.
  • When you feel lost in ambiguity, as a different question. A question informs the answer more than we realize.
  • Avoid questions that already include a possible answer to avoid biasing the discussion. If a question is accusatory, it will trigger defensiveness. A rhetorical question won’t get alternative answers. A yes or no question won’t spark discussion beyond its answer.
  • When you’re building something new, focus on asking the right questions instead of having the right answers.
  • Leading a reset happens in six phases: feeling anger, removing yourself, dissecting the situation, acknowledging your role, drafting your narrative, and then getting back in the game.
  • Curiosity is the fuel you need to play the long game.
  • When you’re genuinely curious about something, you’re less likely to measure productivity in traditional ways
  • Patience doesn’t mean tolerating inaction or slower progress: It means allowing alternative forms of measuring the impact of action.
  • However you decide to hack the structure of your team to allow for a long-term execution of strategy, you must hold on to the key elements of your vision.
  • (attribution has a way of finding its way over time).
  • When you see something wrong, take the initiative to fix it.
  • “The best way to complain is to make things.”
  • When you find yourself frustrated or critical, channel that energy into persistent creation.
  • “always reflecting backward and incorporating forward.”
  • On the contrary, great teams are ultimately grown, not gathered.
  • Resourcefulness > Resources
  • Initiative > Experience
  • Instead, gauge whether the candidate has a history of being proactive in advancing their interests.
  • Initiative comes from obsession.
  • While expertise qualifies you, obsession mobilizes you in a way that runs circles around the experts.
  • Diversity drives differentiation.
  • Traits such as courage, a tolerance for ambiguity, self-reliance, and an urge to prove oneself are more powerful drivers of performance than a couple more years holding a particular job title.
  • Grafting talent is just as important as recruiting talent.
  • Grafting talent is about empathy, integration, psychological safety, and real-time communication.
  • “psychological safety,” which refers to “a shared belief that the team is safe for interpersonal risk taking,”
  • as a leader on your team, a certain percentage of your energy should be devoted to mentoring others.
  • The best reason to fire people who are not performing well is to keep your best people.
  • comfort also breeds complacency.
  • The more voluntary suffering you build into your life, the less involuntary suffering will affect your life.”
  • The best teams are more credit sharing than credit seeking;
  • As the leader, you need to carefully balance the need for structure with the need to accommodate the autonomy and idiosyncrasies of your team.
  • Process is how we force alignment when it doesn’t happen naturally.
  • Your challenge is to lead an efficient team that is fully aligned with as little process as possible.
  • “Powerful enough for professionals, accessible enough for everyone”
  • Ideas are misunderstood unless they can be visualized.
  • Thus, to capture your audience’s attention, you should always couple abstract descriptions with concrete images or physical representations of your idea—as these visual aids appeal to and satisfy our most primal neurological instincts.
  • Present your ideas, don’t promote them.
  • Whether you are sharing an idea with colleagues or pitching an idea to investors, be less polished and more real.
  • Delegate, entrust, debrief, and repeat.
  • No one ever did anything awesome or great because they were told to.
  • Telling people what to do is the opposite of responsibility …. The danger is people are “doing” their jobs, not “thinking” them.
  • The more collaborative your team, the more important it is to know who is responsible for what.
  • making sure that everyone is aligned on how their role within the company matters.
  • When people know where their small part fits in the whole, they recognize how indispensable their work is. They feel more accountable.
  • Great management is this delegate, entrust, and debrief cycle on repeat.
  • Start with your point; don’t end with it.
  • Ambiguity kills great ideas, and great leaders kill ambiguity.
  • your job as a leader of change is to challenge peace as a default.
  • Create an environment where people can withstand a fight and engage in friction as it arises.
  • OBSERVE AND LEARN, DON’T EMULATE
  • Ease of engagement and quick return to one’s ego are two tried-and-true tenets of any successful social product, regardless of its purpose.
  • Be curious about competitors’ moves, but don’t emulate them.
  • Although you should follow them closely, don’t become defined by your opponents.
  • Stay tuned but not governed by what’s going on around you.
  • Competing with your past is the purest and surest way to make faster progress without compromising your vision.
  • Disbelieving your own ideas diminishes your creative energy and sets you up to fail.
  • 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.
  • Facebook’s infamous “move fast and break things” mantra, which graces everything from posters to coasters around Facebook’s campus, establishes a mind-set in technology and start-ups that the best path forward is always the fastest one, even when it’s reckless.
  • Note: It matters how speed is achieved. By cutting corners or expediting processes.
  • Speed through the generic stuff, but take the time you need to perfect the few things that you’re most proud of. Remember that customers don’t engage with functionality. They engage with experiences. They are moved not by features but rather by their experience of using your product. Moving a mile a minute is great, so long as you slow down when you’re crafting something that will ultimately become your competitive advantage.
  • Oftentimes, the best way to proceed is by charging ahead without too much reliance on the processes developed to maintain the status quo.
  • Conviction > Consensus
  • Conscious trade-offs are a competitive advantage when the result is dedicating more focus and energy to what you’re best at.
  • 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.
  • For the sake of your own focus and ability to make great product decisions, reduce and add to your product in parallel.
  • The flaw with pursuing and preserving many options is that doing so stunts your progress in any particular direction. When your energy is split, so is your speed and focus, and the resources around you are harder to tap when your narrative is too broad.
  • Instead of one fifteen-second elevator pitch to a potential investor, you muddle your story with a hybrid.
  • the greatest cost of trying to sustain multiple initiatives is having too little thrust behind one goal.
  • I fell victim to the allure of optionality in the first few years of Behance. While our mission “to organize and empower the creative world” supported all our initiatives, in reality we were splitting our energy across too many things.
  • The struggle to extinguish great ideas and possibilities for the benefit of a central goal is common in the literary world. In fact, there’s even a common phrase for it: “Kill your darlings.”
  • “there were actually three different Walts: the dreamer, the realist, and the spoiler.
  • You trade decisiveness for certainty, even if it means compromising productivity and your team’s engagement in the process.
  • “As organizations get larger,” he explained, “there seems to be a tendency to use the heavy-weight Type 1 decision-making process on most decisions, including many Type 2 decisions. The end result of this is slowness, unthoughtful risk aversion, failure to experiment sufficiently, and consequently diminished invention.
  • In order to disrupt an industry, our instinct is to be different. But the best way to capture the share of an existing industry is to be familiar. The most widely adopted products and services accommodate new customers with recognizable patterns instead of “retraining” users with something entirely new.
  • Use human existence and muscle memory to your advantage by leveraging existing patterns whenever possible.
  • The only time you should force new behaviors or terminology is when they enable a unique and important value in your product.
  • 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.
  • If you can’t help yourself and must search for ways to improve, at least learn to scrutinize a system rather than its parts. When
  • Effective design is invisible.
  • You need to prime your audience to the point where they know three things: Why they’re there What they can accomplish What to do next
  • lazy-vain-selfish principle is true for all kinds of product experiences, online and offline. In the first 30 seconds, your visitors are lazy in the sense that they have no extra time to invest in something they don’t know. They are vain in that they want to look good from the get-go when they engage with your product or service. And they’re selfish in that despite the big-picture potential and purpose of what your product stands for, they want to know how it will immediately benefit them.
  • Do > Show > Explain
  • When it comes to the adoption of new products and ways of working, novelty often precedes utility. As you’re building new products and experiences for customers, consider how they will be novel before they prove useful.
  • 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.
  • A leader’s job is to constantly reiterate the mission and the steps required to achieve it.
  • If you don’t support inbred innovation, your team’s indifference to the future of their own creation will halt its evolution.
  • passion for an idea doesn’t always correlate with the need for it.
  • We focused too much on ourselves, our interests, and our intuition rather than testing the broader market. Note: Tipitap
  • Even though we found a bunch of other people like us, our interests were not a proxy for everyone else.” Note: Tipitap
  • The consequence of starting a project out of sheer passion is making decisions without considering those you’re serving. Empathy for those suffering the problem must come before your passion for the solution.
  • Having empathy for your customers should come before falling in love with your solution. Likewise, the market dynamics around you should be understood before turning an idea into an active venture.
  • When pursuing a new idea or solution to a problem, run it through three filters:
    1. Empathy with a Need and Frustration: You have to understand the struggle of your users.
    2. 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?
    3. Passion for the Solution: The final filter for an idea is whether or not you are passionate about the solution.
  • Willing > Forgiving > Viral > Valuable > Profitable
  • Ranking customers by LTV (lifetime value) helps sales and customer service allocate resources. New product efforts are geared toward driving LTV, and the best customers are those with the highest LTV.
  • “For a consumer brand that you want a lot of people to know about, you need something recognizable, easy to talk about and share, and feels accessible,”
  • Best to market > First to market
  • A cool new product can be an indication of the next big thing—but it isn’t always the next big thing itself. You’re running a race to be the very first team to get it right, not the first to cross the finish line.
  • PR is very helpful when a company needs to explain itself. Otherwise, it just gets in the way, especially for early-stage teams. The best press comes when you’re ready for customers to judge your product, and tells the story of how your product came about.
  • When prioritizing tasks, focus your team on levers that have a disproportionate impact on your odds of surviving and succeeding.
  • Loewenstein outlines five curiosity triggers that alert people to information gaps. They consist of questions or riddles, unknown resolutions, violated expectations, access to information known by others, and reminders of something forgotten. The best advertisements, and most-clicked headlines, play on most if not all of these triggers.
  • “The [Caltech] researchers also found evidence for what they call ‘inverted-U’ behavior,” Eric Jaffe writes. “That’s the tendency of curiosity to be greatest at some mid-point between ignorance and wisdom—the peak of the inverted U.”
  • Ambiguous intrigue has a way of garnering interest better than any product description or list of features ever will. I call this force the “magic” of engagement.
  • It’s an illusion, concocted to enchant your prospective audience and break through their rational selves.
  • Playing to the middle makes you weak. You’ll never be an industry leader if you give up your edge to appeal to a broader audience.
  • Don’t compromise your specialty just to please your market—because if you do, it might not be there much longer.
  • Make a plan but don’t plan on sticking to it.
  • You need to be confident to be willing to change your plan. Being willing to change your mind means you are still permeable and willing to learn.
  • You make progress by planning, but you succeed by deviating.
  • Systems Thinking: choosing your projects based on the skills and relationships you will develop.”
  • Maximizers need to be assured that every purchase or decision was the best that could be made,”
  • A maximizer is the type of person who will spend an entire day schlepping around from shop to shop, searching for the best option for the best price, whereas satisficers “settle for something that is good enough and do not worry about the possibility that there might be something better,” he says.
  • Maximizers may feel like they have reached the right decision—but the satisficers often do so much quicker and end up being happier with the choices they’ve made.
  • “endowment effect.” This describes how we have an inclination to disproportionately value things because we own them.
  • advice should be sought, reconciled, but not necessarily followed.
  • The best advice doesn’t instruct—it provokes.
  • don’t value what others do or advise you to do more than the most unique convictions you have for your vision.
  • Your most precious resource is time, and the most important measure is how effectively it is used.
  • Data is only as good as its source, and doesn’t replace intuition.
  • Common sense and near-term metrics help you optimize your product incrementally and reliably—but iconic and breakthrough product insights are not the result of trying to improve a metric.
  • In contrast, great inflections are the result of instincts for what will serve your long-term goals; they’re about feeling, not thinking.
  • Build a culture that values alternative viewpoints rather than seeks and rewards those that support your own.
  • The cost of expertise is familiarity and becoming biased against new ways of doing it.
  • BE “REMARKABLY UNSCALABLE” AT THE START Note: One thing we did wrong in tipitap…. Started scaling things from word go. Made us spend lot on energy on unnecessary things.
  • The more credit you need, the less influence you’ll have.
  • Credit for one person depletes ownership by many.\
  • Nothing corrodes the potential of a team faster than a sense of superiority.
  • Opportunity is lost as soon as you devalue those around you and embellish your own capabilities.
  • Remove yourself to allow others’ ideas to take hold.
  • 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.
  • when you create something new you become, if only for a short period of time, numb to your surroundings. You zero in on the aftermath of your work.
  • Your primal need for validation takes hold and shifts your focus to who is seeing your work and what they’re saying about it.
  • “Keep making a ruckus.”
  • Preserve some patience to improve something that will last forever. By adding a brick instead of continually searching to create something new, your contributions may outlast your stay.
  • Finally, as you seek to make your own creations more institutional to withstand the test of time, turn yourself from the maker into a contributor.
  • You are not your work.
  • 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.
  • Realizing a deeply held conviction was wrong is a new lease on life. It means you’re still a student, still learning, and not done
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