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The Messy Middle Summary

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

They say that the beginning is always the hardest.

Scott Belsky begs to differ: true, starting things may be difficult, finishing them full of twists and turns; but the real problems come once you get to the middle.

The Messy Middle.

Who Should Read “The Messy Middle”? And Why?

OK, so you’ve started a project or a company, and everything was going fine for a while.

And then the first problem came; you successfully managed to tackle it, but you barely found the time to take a deep breath when another setback struck.

If the paragraph above sounds familiar, then The Messy Middle is the book for you.

And you can be sure that the three-phase process Belsky advocates in it (endure-optimize-finish and repeat) works every time!

Not only because it has helped Belsky become a millionaire, but also because The Messy Middle is based on insightful interviews with many of today’s leading entrepreneurs.

So, if you are trying to implement a big idea and you need a fresh insight – or simply motivation to get through the challenges of implementation – read this book and follow Belsky’s no-nonsense advice.

Suddenly, the unpredictable will look much less random.

As Seth Godin says: “The Messy Middle will help you see that you have more control than you dare to admit, and the ability to make a difference if you care enough.”

About Scott Belsky

Scott BelskyScott Belsky is an American entrepreneur, early-stage investor, and bestselling author.

After graduating from Cornell University and receiving an MBA from Harvard Business School, Belsky got a job at Goldman Sachs.

However, after a while he quit his job at the investment bank and left Wall Street altogether, using the $18.000 he had managed to save to start his own company.

The company would grow to become the largest online portfolio platform, Behance. In 2012, seven years after he had cofounded it, Belsky sold Behance to Adobe, where he was offered a job as a VP of Products, Mobile and Community.

Four years later, Belsky left Adobe and joined Benchmark Capital, where he is still a Venture Partner. He is also a Board Member at Cheddar Inc.

Belsky is also an early investor and advisor at successful companies such as Uber, Pinterest, sweetgreen, and Periscope.

The Messy Middle is his second book; we also have the summary of his first one, Making Ideas Happen.

“The Messy Middle PDF Summary”

“It’s not about the start and the finish,” writes Scott Belsky, “it’s about the journey in between.”

Well, consider The Messy Middle your roadmap: as you know full well, you can only get to your final destination if you have one.

Now, we don’t need to tell you that roadmaps are pretty detailed, and filled with many names and labels, icons and numbers.

So is The Messy Middle.

Nominally broken into three large sections (Endure, Optimize, and The Final Mile) the book lists hundreds and hundreds of lessons.

We’ve tried to list some of them in the Key Lessons section.

However, for the purposes of our summary – due to the space limitations – we opted to select the best ones in each section and analyzed each of them in detail.

The Inevitability of the Messy Middle

In retrospect, Apple, Microsoft, Twitter and Facebook were always going to succeed, right?

You can’t even imagine people like Steve Jobs or Bill Gates going to investors and being turned down by them with the ideas they had.

And you certainly think that if you had known Mark Zuckerberg or Evan Williams when they started their companies, you would have been a millionaire by now; because, well, why wouldn’t you invest in social media sites such as Twitter and Facebook?

And yet – at one point during their development, all of these projects seemed all but doomed to fail.

Don’t believe us?

Have you ever watched the HBO series Silicon Valley?

Well, Bill Gates says that that series is your best chance at understanding how the Silicon Valley works. In other words, no matter how good your idea is, you’ll encounter quite a few problems before you stop working for it, and it starts working for you.

Or read, for example, Nick Bilton’s Hatching Twitter.

Its short summary: one of the most successful social networking services in history was born accidentally, managed poorly and became successful by mistake.

And that’s rarely the story.

Usually, the second part looks a bit differently: many companies fail because they are incapable of swimming out of the inevitable Messy Middle.

When in it, everything is so tumultuous that it basically looks like hell – or a telenovela!

Either way, we’re not meant to experience so many ups and downs in life, so nobody would blame you for calling it quits after two or three of the latter.

Did we say nobody?

Well, Scott Belsky would.

Because that’s the first lesson he wants to share with you.

To paraphrase him using the words of a Nobel Prize winner: “If you’re going through hell, keep going.”

Endure: Short-Circuit Your Reward System

Scott Belsky founded Behance at the end of 2005, and for many years the company was struggling to make sense even to its own employees.

During this period – Behance’s Messy Middle – Belsky lost all appetite: he could only maintain it by taking anti-nausea pills.

And yet – he needed to endure.

One of the first things he did?

He hacked the company’s reward system.

You see, the main problem with big projects – whether writing a novel or building a profitable company – is that the real result comes only after years of effort.

And we are not biologically built to wait for rewards for such long periods of time.


Because up until recently – as late as the XVII century – the average life expectancy was about 25 years of age.

“For early humanity,” notes Belsky, “the prospect of spending five or ten years working toward an eventual outcome, however great it might be, was just not rational.”

Your nausea, tiredness, and lack of will – that’s just your body telling you that you may die soon and that you haven’t experienced anything before that.

Belsky’s conclusion:

Our addiction to short-term validation is so engrained that trying to defy it is hopeless. Accept this fact. While many people paint an incredible long-term vision for their teams, the prospect of long-term rewards is insufficient for long-term motivation.
It is virtuous to aspire to these goals, but a noble venture is not exempt from the need to feel incremental progress and be rewarded for it. Rather than fight the need for short-term rewards, you must hack your reward system to provide them.

For example, when Behance was founded, Google auto-corrected the search query to “enhance.”

When it finally stopped, Belsky organized a party – a kind of reward.

1 milestone down. 15641 to go.

Optimize: Learn How to Be an A/B Tester

Now, the problem with having many ups and downs is not only our biological incapability to endure them easily; it’s also the effect this has on our thought processes.

It’s only natural that when you have an idea which eventually doesn’t amount to anything, you are crippled by self-doubt and lack of confidence; and you don’t even want to find out whether the next one will work.

The opposite is also true: when something works, your ego starts working against you.

“The number-one killer of start-ups,” writes Bo Peabody, “is when entrepreneurs confuse ‘being lucky’ with ‘being smart.’ You must possess the humility to distinguish one from the other.”

Belsky can do you one better: it’s not only about humility and about self-awareness – but it’s also about implementing a good process which can help you distinguish between what’s smart and what’s merely lucky, between what’s good and what’s bad.

It’s called A/B testing and just about everybody – from Google to the smallest startup – does it.

You want to change the color of a button on your site?

Test it and compare the results with the current state of affairs!

If the color change brings new customers – then do it; if it doesn’t – then it’s probably the wrong decision.

It’s that simple!

And it applies to everything:

A/B testing isn’t just for digital buttons—you can use it to advance all areas of your life, from A/B testing your daily habits to how your team functions. A team might change how and when they meet, or an individual may try using a new tool for a week. If it works, the change is made permanent. If it makes things worse, you simply revert to the previous version.
The best optimizers are always trying to figure out why something works.

The Final Mile: Always Repeat, Never Finish

And now the most interesting part.

Eventually, if all goes well, you’ll make it: you’ll emerge victorious from the Messy Middle and reach the final mile.

Scott Belsky’s suggestion: it’s time to go back now!

Wait… what?

But isn’t the very idea of enduring and optimizing getting out of the Messy Middle? Why would I ever want to go back and ruin my life all over again?

Well, because, that’s the price you pay if you want to be successful. “The paradox of making progress,” writes Belsky, “is that it moves us past the early period when we’re the most willing to make the bold moves that actually accelerate progress.

Take Facebook for example!

If you ever get a chance to walk around its headquarters, you’ll notice many posters and laptop stickers saying the same thing: “This journey is 1 percent finished.”

And there’s probably no need to remind you that the only two websites more visited than Facebook are Google and YouTube.

However, Facebook keeps evolving because it always tries to sustain the “we’re still just getting started” mentality.

You want an example of a company which instead of sustaining this mentality attempted to sustain its final product.


That’s right: you’re either a Facebook always in the early innings or a Myspace which believes a single touchdown brings the victory.

It’s always a long season, and then another one, and then another one.

After all, nobody said it was going to be easy.

Key Lessons from “The Messy Middle”

1.      First, You Need to Endure
2.      Then, You Need to Optimize
3.      Finally, You Need to Repeat

First, You Need to Endure

The Messy Middle part of your journey – be it a large project or a large company – is always the most difficult one.

However, if you want your journey to be successful, then you must endure it.

Start by short-circuiting your reward system: ascribe milestones, so that you have many goals and rewards instead of one.

Embrace the uncertainty and take a dose of OBECALP to suspend your disbelief in others (read the word backward if you want to know what we mean by it).

Reset if that’s the only way forward.

And do the work regardless of whose work it is.

Then, You Need to Optimize

IF you want to endure – hire endurers; foster apprenticeship and keep your employees moving.

Be an A/B tester: you don’t know if something works until you compare it to something else. That goes for everything: whether your product, your team or yourself.

Accommodate free radicals: usually, they are the ones who move things forward.

Simplify. Iterate.

Question core assumptions.

Finally, You Need to Repeat

And when you get to the finish line – turn around and go back.

Always stay in the early innings, because continuing to learn is the elixir of life.

And because, well, to be done is to die: “for those who love what they do… the creative pursuit never ends. Creativity is never finished:”

The messy middle miles that you endure and optimize your way through don’t get any easier and never repeat themselves, because they are the moat between vision and reality. The messy middle is a life’s work, and when anyone crosses the finish line and pushes an extraordinary creation out to the world, we all benefit.

Like this summary? We’d like to invite you to download our free 12 min app for more amazing summaries and audiobooks.

“The Messy Middle Quotes”

One of the greatest motivators is a sign of progress. Click To Tweet Don’t seek positive feedback or celebrate fake wins at the expense of hard truths. Click To Tweet To create what will be, you must remove yourself from the constant concern for what already is. Click To Tweet Be frugal with everything except your bed, your chair, your space, and your team. Click To Tweet A lot of big problems don’t get solved because we can solve small problems faster. Click To Tweet

Our Critical Review

Joe Gebbia, co-founder and Chief Product Officer at Airbnb, provides us with one of the best descriptions of The Messy Middle you’ll find anywhere:

“Starting a new venture is like jumping off a cliff and sewing a parachute on the way down. This book is the parachute.”

Of course, Gebbia is not the only one with this opinion.

“Having been through the ups and downs of the Messy Middle many times,” writes Tony Fadell, the inventor of the iPod, “it’s critical to understand the challenges ahead.”

And then he goes on: “This insightful book empowers you to approach them head-on. Belsky’s powerful toolkit, based on hard-earned experiences, is an essential guide to building a compelling product, revolutionizing an organization or growing your leadership abilities.”

It’s difficult to add anything new without echoing Gebbia and Fadell.

Then again, who could blame you for taking their words at face value?

After all, they’ve gone through the Messy Middle quite a few times. And emerged – as millionaires!

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