Navigating The Messy Middle

I’m excited and super-f’n-anxious to share a 5+ year obsession/project nearing the finish line (and now available for pre-order!). THE MESSY MIDDLE is a collection of insights for traversing the hardest and most crucial part of any bold creative project, new venture, or turnaround.

No matter what it is you’re trying to create or transform, the myth of a successful journey is that it starts with an idea, followed by a ton of hardship, and then a gradual and linear rise to the finish line. But no extraordinary journey is linear. In reality, the middle is extraordinarily volatile — a continuous sequence of ups and downs, flush with uncertainty and struggle.

The elusive “positive slope” is as good as it gets.

Every advance reveals a new shortcoming. Your job is to endure the lows and optimize the highs to achieve a positive slope within the jaggedness of the messy middle — so that, on average, every low is less low than the one before it, and every subsequent high is a little higher.

Endure the lows and optimize everything that works (product, team, process, self-hacks, etc…).

Quite simply, the book’s 130+ insights help you do three things:

  1. Endure the human-tendency-defying woes of the middle (your war with self-doubt, the roller coaster of incremental successes and failures, and bouts of the mundane amidst sheer anonymity — by strengthening your resolve, embracing the long-game, and short-circuiting your reward system to stay with it long enough to figure it out).
  2. Optimize the hell out of everything that works (constantly improving the way you hire, structure, and manage your team, relentlessly simplifying and iterating your product while staying anchored by your customers’ needs, and crafting your instincts to make better decisions and internalize what you’re learning while staying relatable).
  3. Not screw up “the final mile” of a successful project (once the finish line is in sight, the game changes and so do we…).

The book is broken down into three sections of insights (Endure, Optimize, & The Final Mile) culled from interviews of entrepreneurs, artists, writers, and executives about their middles, as well as many of my own experiences. The book includes gems from entrepreneurs and thinkers I admire like Joe Gebbia (Airbnb), Alexa Von Tobel (Learnvest), Anne Wojicki (23andMe), and Tim Ferriss (author), founders I have worked with from companies like Pinterest, Uber, Cheddar, Periscope, and sweetgreen, artists like James Victore, and mentors like Tony Fadell and John Maeda among many others, alongside research I conducted to help us better understand the messy middle.

The middle isn’t pretty, but it is illuminating and full of essential realizations. It’s time we start talking about it and find ways to mine its fruitful volatility.

I hope you’ll take a minute to pre-order THE MESSY MIDDLE at any of these fine establishments, and I hope it serves you well:

Amazon // Barnes & Noble // IndieBound // 800ceoRead // Hudson // BAM!

😬💥