The Messy Middle – Scott Belsky

The Messy Middle – by Scott Belsky
Date read: 10/20/18. Recommendation: 9/10.

More than a business book, and that’s what I loved about it. It’s a book about embracing the long game and leading through ambiguity–whether you’re a founder, entrepreneur, or artist, you’ll find relevance. Belsky details the endurance it takes to bring an idea to life. It’s not always as pretty as the beginning or end, but the middle is worthy of equal attention since it’s where most of the journey takes place. As a product manager, I found the book to be particularly insightful for my daily work and career. The next time I’m asked for a great product book, I’ll be recommending this. But again, the beauty of this book is that it’s relevant for anyone who’s building something from nothing. Those who are leading others (or themselves) through uncertainty will benefit greatly from it. Far from a generic business book with the same recycled ideas, it’s original, practical, profound, and one of the best books I’ve read all year.

See my notes below or Amazon for details and reviews.

My Notes:

You cannot travel the path until you’ve become the path. Embracing the middle is the only way through.

-“The truth about telling the truth is that it does not come easy for anyone. It’s not natural or organic. The natural thing to do is tell people what they want to hear. That makes everybody feel good…at least for the moment. Telling the truth, on the other hand, is hard work and requires skill.” Ben Horowitz

-“There is no better measure of your values than how you spend your time.” SB, accounting of how you spend your minutes is hard truth of your values.

-Routines backfire when you do them without thinking. Throw a wrench in every now and then to see if it feels liberating and is no longer relevant/effective.

-Sometimes you guard your time too closely. Fluidity/flexibility to adapt is important, or else you won’t reach full potential. Need to create and preserve some margin of downtime in your day to accommodate opportunities. 

-You deserve this and you are enough. There’s a part of all of us that fights our own progress. Overcome these insecurities and doubts.

-"You are not your org chart, your department budget, or your title. Don’t let success at a company prevent you from pursuing scary and wonderful new opportunities to build.” Hunter Walk

-“You need to do your fucking job.” What Belsky would tell himself before going into a tough meeting, negotiation, or firing someone.

-“Playing the long game requires moves that don’t map to traditional measures of productivity.” SB

-“Curiosity is the fuel you need to play the long game.” SB 

-Resourcefulness is a competitive advantage. “Resources become depleted. Resourcefulness does not.” SB

-80% on boulders, 20% on pebbles.

Lead your team:
-Teams need to be reminded of where they are and progress they’ve made. Call out landmarks you pass and the terrain ahead.

-When discussing your teams efforts so far, weave in stories and leverage the perspective that excites you the most.

-Your perspective during trying times will help your team overcome moments of self-doubt.

-Not all meetings end with a solution, quit seeking a false sense of closure. Instead actively lead through a process of self-discovery.

-Unresolved conversations are draining. If you can’t provide closure, add energy, turn negative into positive. 

-“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.” SB

-Don’t aggressively market yourself, celebrate the people on your team and empower great makers. “Ego is rust. So much value and potential are destroyed in its slow decay.” SB

-Pick your fights and don’t deprive others of their own process. Sometimes the best way to instigate change is to plant questions as seeds and let them take root so you can avoid immediate reactions. 

-“For extraordinary outcomes, seek conviction in your work and build teams that value conviction over consensus.” SB

-Hesitation breeds incrementalism.

-Most effective way to communicate a vision is to declare it, rather than blunting blow with a comforting narrative that makes it sound less drastic.

-Progress is only possible once a decision is made. Can always backtrack and adjust as you learn along the way. Keep moving!

-Make your mind up quickly and go with the option that feels most right at first (don’t survey every available option). Otherwise you’ll waste time and energy searching for alternatives that may only be mildly more beneficial.

-Self-awareness is the greatest competitive advantage for a leader.

-Your sense of self shifts when you’re at a peak or in a valley. 

-Effort to understand how your mind works is only path to reliable self-awareness during intensity/stress.

-“You cannot win unless you know how you’re most likely to lose.” SB

-“Knowing when to ignore your experience is the true sign of experience.” -John Maeda

-Avoid temptation to describe what you’re building in context of what already exists (i.e. “It’s Airbnb for X”). 

-When you feel overwhelmed, remember the vision. Compartmentalize your ideas, look ahead, worry less about day-to-day concerns. 

-When you feel lost in ambiguity, ask a different question. i.e. Not “why aren’t people signing up?” but “what kinds of people would benefit most?”

-When you’re building something new, focus on asking the right questions instead of having the right answers. 

Defy prescribed roles:
-Directing blame and expressing disappointment take more energy than tackling whatever you’re criticizing. Take the initiative, even if it falls outside of your job description.

-“There is rarely a scarcity of process or ideas but there is often a scarcity of people willing to work outside the lines.” SB

-“You’re either a cog in the system or a designer of better systems…challenge every system you find yourself confined by.” SB

-Asking for permission to do what you know needs to be done will yield hesitation at best, rejection at worst.

Prioritize your team:
-“I have met many founders who obsess over product and steamroll their team. Most of them have failed. Team comes first.” SB

-If you want to execute well over time or make great products, prioritize your team over your goals and tend to your team before your product.

-Hire people seeking a journey rather than a particular outcome.

-Closing the confidence gap of new hires is more important than closing skills gap. Building confidence is important if you want to unleash someone’s potential. 

-Maturity and perspective > age and accolades.

-Best reason to fire people who aren’t performing is to keep your best people.

-Salary bands: subconsciously biased by age, years of experience, gender, and other characteristics that don’t correlate with indispensability. 

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

-Greatest thinkers anchor ideas around a central truth they believe is unique and unrealized by others, but embrace questions when someone challenges them…they don’t look the other way.

-Poor leaders are too worried about being loved. The best founders have conviction in their ideas and aren’t hedging by spreading resources thinly across too many ideas. 

-Hold on to the openness, humility, and brashness you had in the begging.

-Speed through the generic stuff, but take time to perfect the things you’re most proud of. This is what differentiates your product, so it deserves a disproportionate investment of resources.

-Uniqueness of your product needs to be baked in, not sprinkled in at the end. Otherwise it’s likely to taste bland.

-Customers don’t engage with functionality, they engage with experiences. Make it more human friendly and accommodating to natural human tendencies.

-Competitive advantage is as much about what you choose to let go and not be, as it is about what you focus on. 

-One feature in, one feature out. Keeps you focused on simplicity.

-Having to explain your product, least effective way to engage new users.

-Empathy for your customers and humility in your market are powerful filters. Focus on these before you fall in love with your solution.

-Greatest brands developed by playing at far end of the spectrum and not trying to be everything to everyone. “Playing to the middle makes you weak.” Don’t give up your edge to appeal to broader audience.

-Engage emotionally as you create, but detach yourself when you’re evaluating.

-Every product or service in your life either helps you spend or save time. Best products remove a daily friction.

-Don’t be too different, familiarity drives utilization. Train customers on something new only when it’s core to what differentiates your product. Helps reduce cognitive friction.

-Big part of innovation is saying ‘you know what I’m really sick of?’ What frustrates you likely frustrates many others.

-True innovators value art up front and compete against incumbents through stuff that doesn’t intuitively scale. Give your customers something precious, uniquely personal, emotional, and seemingly scarce that cannot be easily scaled, automated, or commoditized. Preserving the art in your business gives it a soul that people can connect with. 

-At the beginning, must run manual experiments, spend endless amount of time with customers, and tinker until you find something special.

The Product Lifecycle:

  1. Customers flock to a simple product.


  3. Product gets complicated.

  4. Customers flock to another simple product.

The First Mile:
-Fewer options, shorter copy, simpler steps.

-Need to prime your audience to know, 1) Why they’re there, 2) What they can accomplish, 3) What to do next.

-30% of your energy should be allocated here. Top of funnel for new users, deserves to be well thought out. 

-Remember, people are lazy, vain, and selfish. You have 30 seconds to engage and address each concern.

-Best hook is doing things proactively for customer. Once you help them feel successful and proud, will engage more deeply and take time to learn and unlock the greater potential of what you’ve created. 

Measuring Success:
-Always ask “what is the real goal here?” Answer is rarely as measurable as you may think.

-Avoid too many measures, the more numbers you’re tracking, the less attention you pay to any of them.

-Boil your business down to one or two core metrics.

-Prefer, a referral network for independent professionals, uses a single metric, “number of working pairs.” Allows them to focus on what matters instead of getting caught in surface measures like revenue or downloads.

-Iconic and breakthrough product insight are not the result of trying to improve a metric. Square’s iconic UX requiring everyone to sign using a finger instead of bypassing small transactions.

-“For strong companies, financing is a tactic. For weak companies, financing is a goal.” SB

-Is the team attempting to defy a likely outcome or make it happen in a better way? Invest in the latter. Uses forces already in play.

“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?’” Tim Ferriss

Desire to Learn:
-Warren Buffett spends 80% of each day reading. When asked about keys to success, Buffett pointed to a stack of books on his desk and said, “Read five hundred pages like this every day. That’s how knowledge works. It builds up, like compound interest. All of you can do it, but I guarantee not many of you will do it.”

-Annual letters to investors, Buffett is self-reflective and self-deprecating. Admits when he struggles to understand something or has made dumb decisions. Remarkably open to changing his mind. All because of his persistent desire to learn.