Notes on “The Messy Middle”
“We celebrate starts and finishes, but rarely discuss the messy journey in between, where odds are defied and great teams and products are ultimately made.”
As someone who is navigating the ups and downs for the growth function of a startup, Scott Belsky’s “The Messy Middle” was like music to my ears. The insights and stories are memorable and digestible, but illuminating enough to keep me thinking for some time afterward. Below are the tactics and ideas that resonated the most with me:
1 — Endure
This section discusses the inevitable hardships of any bold project and how others worked through them.
1.1 — Leading Through The Anguish and The Unknown
- Short-circuit your reward system. 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. Make the most of the period in your journey when you must create your own rewards out of necessity. Milestones that are directly correlated with progress are more effective motivators than anything else.
- Don’t seek positive feedback or celebrate fake wins at the expense of hard truths. Fake wins are the reward equivalent of cocaine: They will artificially inflate morale but then take you down, perhaps lower than where you started. 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. 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.
- Be the steward of perspective. Your perspective during the most difficult times will help your team defy their own self-doubt. When distractions and drama arise, acknowledge them, and then re-contextualize them so that the suffering pales in comparison to the broader opportunity before you. Remind your team why you’re all there. They signed up to work with you because they believe in your vision and want to make something extraordinary. Your story has more gravity than you realize. 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 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.
- Do your fucking job. Avoiding conflict and hesitating before you disappoint others is not a weakness, it is having a conscience. Relationships matter, and the cost of upheaval in any relationship or team culture is very real. But just as a common cold can become full-blown pneumonia if left unchecked, infections in a team grow when not addressed. Your job is to detect infection, determine whether it is viral, and nip it in the bud if it is.
1.2 — Strengthening Your Resolve
- The only “sustainable competitive advantage” in business itself is self-awareness. Self-awareness is about preserving sound judgment and keeping relatable and realistic. However big your project or ambition, your journey is nothing more than a sequence of decisions: You’re probably many decisions away from success, but always one decision away from failure. Clarity matters. 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.
- Nobody remembers, or is inspired by, anything that fits in. Don’t succumb to society’s gravitational force toward what is common and familiar. One of the worst tendencies of the messy middle is pulling wildly fresh insights back toward the mean of normalcy. Don’t let this happen to you. While society wants you to conform, it needs you to break the mold to help us see differently and make life better for the rest of us.
- Take a dose of placebo and suspend your disbelief in yourself. You don’t know what you’re capable of. Whether it is navigating your career, starting a new business, or overcoming an illness, giving yourself a placebo of sorts that suspends your doubt is one of the greatest factors in making progress.
- To create what will be, you must remove yourself from the constant concern for what already is. As you encounter challenges in your own career, compartmentalize each drama individually and remind yourself on the horrible days that tomorrow will be better. Compartmentalizing doesn’t mean burying or denying the emotional toll; it means facing one challenge at a time and using each one to provide more perspective for dealing with others. To move forward, unbounded by the anxieties and insecurities of the moment, you must apply controls to the energy you spend assuring yourself that all is OK.
- Prompt clarity with questions. The perfect question is the 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.
1.3 — Embracing The Long Game
- Playing the long game requires moves that don’t map to traditional measures of productivity. 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. Instead, you’re content being in the muck and gain satisfaction from learning something new, not just ticking off-to-do items. Rather than seeking a positive outcome, you’re exploring all options to satiate your own interests. Playing the long game is a test of your fortitude, your ability to persevere, and just how genuine your interests are.
- 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. Their competitive advantage is available to any team, big or small, that is patient enough to stay focused, stick together, and move forward.
- Just stay alive long enough to become an expert. You and your team need to understand when expertise is an advantage and when it is a disadvantage. This all boils down to the industry norms you’re calling into question and whether or not key dynamics have turned such norms upside down. Rather than believe you can just “do it better” than your incumbents, anchor your thesis on what you believe everyone else is wrong about. More importantly, your team must value the benefits from sticking together long enough to ramp up expertise, gain velocity, and allow a long-term thesis to play out.
- 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.
2 — Optimize
This section is all about capitalizing on your strengths and improving every aspect of your team, product, and self.
2.1 — Optimizing Your Team
Building, Hiring, and Firing
- Resourcefulness > Resources. Resources come and go, but resourcefulness is a muscle that kicks in throughout the lifecycle of any business. Without it, capital cannot be used efficiently. Focus on building your team’s resourcefulness.
- Initiative > Experience. As you assemble your team, look for people with excitement about the idea, the ability to contribute right away, and the potential to learn. What your team lacks in experience they can make up for with initiative. Initiative comes from obsession. The more infatuated you are with something, the more likely you are to know (or want to find out) more about it. The greatest disruptions of industries are facilitated by relative outsiders, obsessed with the industry, who find a way to survive long enough to become an expert and then leverage new techniques to change the game. While expertise qualifies you, obsession mobilizes you in a way that runs circles around the experts.
- Diversity drives differentiation. The shortcut to differentiation of thought is diversity in the form of different personalities, genders, ethnicities, nationalities, backgrounds, and kinds of education and experience represented at the table to extend the surface area of possible solutions for every problem you face. When you become more accustomed to working with people far younger or older than you, come from different places, speak with different accents, your mind and hiring practices become more open to the possibilities.
- Hire people who have endured adversity. 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. As you build your team, seek people who have endured adversity. Ask prospective team members about their most defining challenges. Life matures you a lot faster than time, and a lot of life can happen in a very short amount of time.
- Seek people with whom discussions evolve by a step function. Build a team of people dynamic enough to make every conservation a step function that is more interesting than the one before it, and smart enough to make the complicated simple and accessible to everyone.
- If you avoid folks who are polarizing, you avoid bold outcomes. If you find ways to accept and empathize with difficult people, your culture will become more tolerant and your product will have more edge. As you’re building or investing in teams, don’t try to keep the chemistry too clean. Teach your team to value conflict and develop a tolerance for passionate and respectful disagreement.
- Grafting talent is just as important as recruiting talent. Setting up new talent to succeed is an active process that doesn’t happen on its own. Grafting talent is about empathy, integration, psychological safety, and real-time communication. It’s about identifying with their experience, shining the spotlight on their strengths, and becoming a thought partner, coach, and advocate for them.
- Foster apprenticeship. As a leader on your team, a certain percentage of your energy should be devoted to mentoring others. Apprenticeships are mutually beneficial, as you’ll prepare emerging leaders on your team to take more senior roles while developing a culture of constant learning and teaching. Make apprenticeship an expectation.
- A steady state is unsustainable, keep people moving. Your challenge is to develop a healthy rhythm to keep your team in a constant state of motion. If you don’t shake up life every now and then, life will shake it up for you. Too much calm exacerbates any disruption, so building up your and your team’s tolerance for change is a positive long-term strategy for increasing tenacity.
Culture, Tools, and Space
- Culture is created through the stories your team tells. As the founder of a project or a team, take stories seriously and inject yourself into them. Stories are what you make of them, so take some poetic justice and mine every experience for the little gems characteristic of your team, the moments that made an impact. Culture is a naturally occurring phenomenon and simply needs to be nourished, inclusive, and celebrated. The stories in the early days lay the foundation for your culture forever.
- The products you use to create impact the products you create. Consider the tools you use and your internal documents as crucial to your team’s DNA. These factors will either harm or enrich your team and the products you produce. Internal systems are the first things you neglect when you’re busy, which means they are a competitive advantage if you can value and enrich them over time. You need to allocate time for optimizing the tools your team uses, your internal communications, and the environment in which you create. If you don’t, the products you create will suffer.
- Attribute the right amount of credit to the right people. Be meritorious by assigning credit truthfully. As you recognize people who work for you, assign credit as you would influence. Ultimately, you want the people who really did the work to get rewarded and have more influence next time around. While you may think assigning credit is about rewards, it’s really about assigning influence for future decisions.
Structure and Communication
- When you have the right people, there are no rules for structure. So long as you have the right people aligned around the right objectives, be flexible. Observe, learn, and then adjust. Despite all the conventional wisdom out there, you’re allowed to change the rules. These tweaks could help you or hurt you, but you’ve got to take some risk to achieve an irregular outcome. Embrace best practices until you need to change them. Then break them.
- Process is the excretion of misalignment. Install process for your team, not for you. Spend more time on achieving alignment than imposing process. Audit your processes frequently and always try to cut them down.
- Merchandise to capture and keep your team’s attention. Be creative in how you merchandise tasks and progress to capture and keep your team’s attention. When you must implement a new process, give it some beauty. Loyalty to a new system comes from believing in it and being attracted to it. The design, nomenclature, virtual confetti that explodes from a completed task — these little touches can go a long ay in spurring utilization.
- A mock-up > Any other method of sharing your vision. Sharing a design, a series of samples, or a rough prototype quickly aligns people. Without it, much of a discussion is spent orienting a group around a concept and addressing basic questions and misunderstandings. Without a mock-up, people are trying to interpret something in the dark by feeling one edge at a time. A mock-up or prototype is worth countless meetings and debates. A mock-up turns the light on.
- 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. A little texture in the form of uncertainty and admission of the challenge is helpful for everyone. The right partners will see your challenges as potential rather than weaknesses, and your honesty will set the right tone for future collaboration and navigating the ups and downs of the journey together.
- Delegate, entrust, debrief, and repeat. As your project and team scale, get into a rhythm of distributing responsibilities to others, entrusting them enough to feel ownership, and then debriefing to increase the quality and efficiency of the execution. Great management is this delegate, entrust, and debrief cycle on repeat.
- Know how and when to say it. With so many options for how to communicate with your team, it can be easy to choose the path of least resistance rather than focusing on your objective and which type of communication will help you achieve it. We get in trouble when we choose to communicate the easy way versus the right way. As our channels for communication expand, we must endeavor to be more thoughtful about how and when we communicate.
- Nothing beats explicitness. Aspire to say it like it is. When you’re solving a problem. When you’re building a product. When you’re communicating your intention.
- There is power in brevity. Shorter emails get faster response times. Fewer words go further (and are listened to more intently). Standing meetings prioritize the point. The less preamble, the more focused your team will be on your message. Start with your point; don’t end with it.
Clearing The Path To Solutions
- Tackle “organizational debt.” When you’re unsure about something, whether it be an email or a comment made in a meeting, act on it or ask about it. Stuff that sits idle, misunderstood by you and likely by others as well, plagues progress. Handle something once, not many times.
- Break bureaucracy by piercing ambiguity with questions. 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.
- Creative block is the consequence of avoiding the truth. Extracting truth is a delicate balance of curiosity, restraint, and compartmentalizing hope. Take great care to ensure past assumptions and old truths never obstruct new discoveries. Be open, humble, and eager to learn that you’re wrong — before someone else does.
- Moving fast is great, so long as you slow down at every turn. 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.
- Value the merits of slow cooking. We can round out our work with a few slow-cooked projects — you just can’t forget what you’ve got on the stove. You must keep coming back to it, checking it every now and then, adding a dash of salt here, skimming off the foam here. Over the course of your life, these projects could become your greatest creations.
- “Ask for forgiveness, not permission.” 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.
2.2 — Optimizing Product
Simplifying and Iterating
- Make one subtraction for every addition. 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. Your intuition is sharper when your product is simpler. For the sake of your own focus and ability to make great product decisions, reduce and add to your product in parallel.
- If you don’t think it’s awesome, stop making it. 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.
- Beware of creativity that compromises familiarity. 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.
- Effective design is invisible. If design is important to your product or process, challenge yourself to look past the graphics and what’s new and shiny at the surface. Reduce elements — and any step requiring decisions — whenever you can. Fewer options, shorter copy, and simpler steps will always bring your product to a better place.
- Do > Show > Explain. 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.
- Novelty precedes utility. 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. Sometimes the initial reason to use a product, and get through the first mile, is to have fun.
- Break incrementalism by questioning core assumptions. Engaging and empowering new talent is a reliable way to break old patterns. 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. If you don’t align your team with a mission they identify with, they can’t help evolve the product. Breakthroughs will germinate from within and, if nourished with enough flexibility, attention, and internal celebration, become actionable. If you don’t support inbred innovation, your team’s indifference to the future of their own creation will halt its evolution.
Anchoring To Your Customers
- Empathy and humility before passion. 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.
- Build your narrative before your product. As you embark on your next project, consider developing your narrative and building your brand first. 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?
- Hit the streets, there is no better way. Push yourself to go door-to-door, in whatever way that applies to you. Spend time sitting next to your customers to better understand their jobs or lives. Push yourself to ask more questions and spend more time building relationships. Connect with people you meet by looking for something to learn. By doing so, you’ll feel the granularity of your business, unearth invaluable realizations, and earn new customers, all the while building the relationships that make your creations more viable and sustainable.
- Resist the urge to play to the middle. The greatest brands were developed by playing at the far end of the spectrum and not trying to be everything to everyone. 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. As you manage your brand and contemplate your own evolution, hold on to what makes you distinctive. Don’t compromise your specialty just to please your market — because if you do, it might not be there much longer.
2.3 — Optimizing Yourself
Planning and Making Decisions
- 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. Business plans are a standard part of building a new venture, but they should be approached as a thought process, not a map. Adaptability and instincts make all the difference. You make progress by planning, but you succeed by deviating.
- Success fails to scale when we fail to focus. At some point in every career, lack of opportunity and options stops being the problem. Instead, you’re faced with a new challenge: when and how to say “no” and how many options and choices you really need to make a great decision. Most people fail to understand that their past success was likely the result of a more singular focus with fewer options. If you hope to scale your success further, you must choose more wisely and decline more opportunities.
- In almost all cases, best to ignore sunk costs. The real reason we cling to our original convictions is the energy, time, reputation, and money we invested in them. These resources are sunk costs the moment they are spent. Only by allowing yourself and your team to cut such investments loose can you empower people to change their minds when they should.
Crafting Business Instincts
- Mine contradictory advice and doubt to develop your own intuition. Whether the advice you receive is actionable or just outright negative, reconcile it to conceive your own approach. Always pair what you hear with a different viewpoint. Play contrarian and consider why a tactic worked for someone else but may fail for you. The more you toil over different perspectives, the more you remember what you learn.
- Don’t blindly optimize, keep auditing your measures. Measures become your anchors and will, for better or for worse, restrain your product and your thinking and determine your blind spots. Set them in the area you wish to explore and in which they can make the most impact with the least time, and keep evaluating their efficacy and alignment with your long-term goals.
- 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. In some ways, instincts precede awareness and help you make a decision months or years before that data proves it obvious.
- Stress-test your opinions with radical truthfulness. As you elevate your ideas as well as the opinions and insights of those around you, challenge yourself to give feedback and absorb as much of what is given back to you. 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. Build a culture that values alternative viewpoints rather than seeks and rewards those that support your own.
- The science of business is scaling; the art of business is the things that don’t. 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.
Sharpening Your Edge
- Your true blind spot is how you appear to others. You’ll never be perceived as you intend to be, so no matter how much control you think you have, stop being presumptuous. Don’t assume that the opinion you express are what people hear, or the way you project yourself is what people interpret. Instead, try to see yourself and your message through the lens of those around you. You’ll never achieve full resolution, but every bit of contrast helps.
- What you agree to do, do right. For what you agree to do, do right. When you stop nourishing something, let it go. Passive commitments, at best, dissipate into nothing and, at worst, lead to painful extractions and reputational damage. Everything you do should be an active commitment or nothing at all.
- Build a network that amplifies signal. As your network grows, so will the noise. The 6th-sense-like intuition that leaders get at the peak of their career is the result of developing a network and filter that fosters a high signal-to-noise ratio. By going deeper with those you consider most competent, you are amplifying the power of signal in your life.
- There is no better measure of your values than how you spend your time. Don’t feel loyal to routines — question their continued relevance and effectiveness. Some routines become outdated, and nearly all routines can be optimized if you take a moment to question them. Every now and then, break a routine and decide whether doing so was in any way liberating.
- Leave some margin to mine the circumstantial. Part of managing and auditing your time with great care is making the most of wherever you find yourself. When you’re seated next to a random person from an entirely different trade at dinner, try to learn about their specialty. 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.
- When you fail to disconnect, your imagination pays the price. Be aware of the cost of constant connection. To keep perspective and nourish your imagination, create windows of non-stimulation in your day, rituals for disconnection, and periods of time in your life where you get out of your element and allow for new questions and curiosities to take hold.
Staying Permeable and Relatable
- The more credit you need, the less influence you’ll have. When you find yourself hungry for credit at the moment, make a long-term investment instead. For your own potential if nothing more, take every chance to shine the spotlight on others.
- 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. Even if you think your first draft is perfect, allow your colleagues to play with an idea without 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.
- “Keep making a ruckus.” Questioning and prodding to uncover the truth is bound to irritate others. As a default, people want to avoid conflict, and it is always easier to confront long-term concerns later on. But being truthful requires a tolerance for disappointing others. It’s the only way to optimize. Seek the ruckus.
3 — The Final Mile
From every finish comes a new possibility, so long as you lead it well and pass the baton on.
Approaching The Finish Line
- The “final mile” is a different sport. In the final mile of any journey, the terrain changes. Psychologically, you’ll ponder the implications of finishing and likely have mixed feelings. You’ll start to question yourself and your motivations. You may feel inclined to turn inward and bear the new terrain on your own, but you can’t. The final mile is not meant to be traveled alone.
- Stay in the early innings. As you approach the later stages of your project, your challenge is to hold on to some of the openness, humility, and brashness you had in the beginning. Keep repositioning the ultimate goal to be as far away as you can see, and never forget that blind spots only grow as you succeed. In mind and in spirit, stay in the early innings.
- Don’t underestimate the value of adding a brick. 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. As you seek to make your own creations more institutional to withstand the test of time, turn yourself from the maker into a contributor. Set your predecessors up to succeed by empowering them to build upon what you’ve done.
Passing The Baton
- If you can’t end wonderfully, end gracefully. Much like the end of a book or a movie, how you end your project determines your chances for a sequel. Don’t let your anger, shame, or anxiety prevent you from ending gracefully. If you handle it well, failure is merely a step in the right direction.
- 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.
- Aspire to finish on your own terms. A great finish is on your own terms, and it starts with that fully satisfied feeling that you want to hold on to. If you can bifurcate your identity and emerging interests from your past accomplishments, you’re ready for a new chapter. Your legacy will never retire, but it is set on the note you leave it with.
Never Being Finished
- Continuing to learn is an elixir to life. Curiosity, self-scrutiny, and a willingness to change your conviction all share a common theme: the persistent desire to learn. Learning is an elixir of life, so drink it daily.
- You’re either part of the living or the dying. Whatever challenge you’re suffering from, you can use it to decide if you want to live less or live more. When you find yourself dwelling on the end of a journey, double down on the joys and curiosities of the day. Not only are they real, but they also offer a path to a richer life.
- We are so willing to trade time for money when we are young, and money for time as we age. If it’s something you just want to accomplish but don’t wish to remember doing, consider saying no. However, if it is an experience that you wish to remember, then spend the time enduring the friction to create memories you’ll never forget. Because the best parts of life have friction, and memories are all that we have.
- To be done is to die. The greatest end is a new beginning, and feeling done is your greatest obstacle. Your final mile needs to give rise to a new first-mile experience in which you, once again, start something because you can’t stop thinking about it, where you’re naive enough to embrace all possibilities, and when you’ve become empathetic for people suffering a problem that either fascinates or frustrates you. You’ll need to keep feeding your interests, stay permeable, and never assume that what worked before will work again.
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