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

by Scott Belsky

Society is remarkably hypocritical. We shun things before we celebrate them. We chastise students who drop out of college to pursue a fascination that cannot be taught in school, and then we celebrate them when they become dropout-cum-wunderkinds like Jobs, Zuckerberg, or Gates.

when you’re bearing the brunt of naysayers, it’s normally a good sign. When everyone thinks you’re crazy, you’re either cr...

“Believing you can accomplish what others can’t is basically the ultimate strength and biggest weakness of entrepreneurs.”

Indeed, you must learn to hear the constructive criticism but consider doubt from pragmatists as a positive signal.

The more you toil over different perspectives, the more you remember what you learn.

Finally, don’t value what others do or advise you to do more than the most unique convictions you have for your vision.

Don’t blindly optimize, keep auditing your measures.

Because of our love of and dependence on metrics, we can easily forget which goal they’re actually measuring.

“Sometimes, the thing that matters doesn’t make it easy for you to measure it. The easiest path is to find a stand-in for what you care about and measure that instead. For example, websites don’t actually care about how many minutes someone spends on the site, they care about transactions or ad sales or making content that moves people to take action.

Stand-ins are seductive because they are easy to measure, and they are dangerous because we get obsessed with them instead of being obsessed with what they represent.

Seth suggests a good litmus test for your measures is to ask the question, “If you had to choose between increasing the stand-in stat or increasing the thing you actually care about, which would you invest in?”

Don’t let artificial measures abstrac...

reiterate for yourself and your team the real impact you desire to make, not just the...

Always ask “What is the real goal here?” The answer is nearly never as me...

Avoid too many measures, because the more numbers you’re tracking, the less attentio...

Are we investing our time in the most important things? . . . Simple back-of-the-envelope calculations will help you prioritize features according to their return on investment, making sure the outcomes are the highest possible over a given period of time.”

Data is only as good as its source, and doesn’t replace intuition.

We love data. It answers questions. But the definitive nature of data means you must use it with caution. When presented with a statistic that has broad implications, your first question should be about its integrity.

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.

people are prevented from achieving their best performance by emotional interference.

It is something he thinks can be overcome through systematic practice.

getting to the truth through “thoughtful disagreement.” That’s why employees are encouraged to challenge each other repeatedly and without reservation.

“Know what you don’t know, and what to do about it.”

Understand that the ability to deal with not knowing is far more powerful than knowing.

Constantly worry about what you are missing.

Successful people ask for the criticism of others and consider its merit.

Dalio’s underlying value for self-awareness above all else.

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.

“Knowing when to ignore your experience is a true sign of experience,” observed my mentor John Maeda.

“If you’re immersed in a context, you can’t even see it.” The cost of expertise is familiarity and becoming biased against new ways of doing

One of the best ways to maintain (and reclaim) the benefits of naivety is to surround yourself with different people.

The science of business is scaling; the art of business is the things that don’t.

Most industry pundits, investors, and incumbents overlook art until it impacts the bottom line and becomes a true source of differentiation.

don’t optimize the art out of your business.

Your true blind spot is how you appear to others.

It is impossible to know how you come across to others. People see you through a very personal lens made up of their own experiences, insecurities, fears, and aspirations, just as you see others.

What you agree to do, do right.

Active commitments are investments of time, energy, and resources in areas you willingly choose to love and pursue.

If you’re founding a new company or building a dream team, you’ll commit yourself to countless emails and meetings to recruit talent.

You’ll take midnight calls if it means closing the right candidate for a role on your team, and you’ll send sneaky emails un...

But when you commit to doing something that doesn’t align with your interests, you’ve taken on a passive commitment. Perhaps you’re maintaining an old product or keeping a difficult customer because you cannot summon the courage to say no.

realistically, it’s never clear how valuable an opportunity will ultimately be. After all, blind dates are a waste of time until you meet “the one.” And introductions in business are no different.

Something that doesn’t distract you from everything else in your life is unlikely to ever get sufficient attention from others, never mind the attention it deserves from you.

Distraction is a form of natural selection.

Build a network that amplifies signal.

The more accomplished you become, the more noise you are exposed to. “Noise” has become a commonly used reference for the incessant banter, marketing messages, and regurgitation of stuff you already know. Noise tends to flow into your in-box and life but does nothing for you.

“Signal” is the stuff you hear and learn from others that impacts you: the right question, feedback, or intro...

High-signal people don’t want to discuss what’s popular; they want to discuss what’s not, or why what’s popular is wrong.

There is no better measure of your values than how you spend your time.