The middle stretch of a journey is when the exciting moment of idea conception gives way to the long, slow, trying slog to the finish line. The promise of a fresh start is behind you, and the end far, far away. Volatility feels like the only constant. Each high—Yes! Champagne! $$$!—seems to be met by a heart-breaking low—Ouch! Rough! What happened?!

It’s this part of the journey where investor, entrepreneur, and co-founder of 99U and Behance, Scott Belsky, has directed his new book, The Messy Middle. Belsky's insights are meant for people embarking on a creative project, whether they are founders, entrepreneurs, designers, or artists. The Messy Middle is a guidebook for navigating the time when you start to lose hope and become overwhelmed with self doubt.

Belsky, now Adobe’s Chief Product Officer, sat down with 99U to discuss what we misjudge about the middle part of a journey, the two most important characteristics for building something, and to share his lessons from The Messy Middle.

***

Q. You’ve written The Messy Middle to focus on the wildly misunderstood part of a journey. What do we overlook about the middle? 

A. Typical headlines and the gravitational pull by all of the press around the starts and the finishes frustrate me. I feel like those are shallow, pithy ways of describing the journey, heavily edited for egos and sound bites, and don’t adequately reflect any of the provocative and sometimes controversial, or at least counterintuitive and conflicting insights that happen around the middle. 

What you need to think about in the middle of a journey is that sometimes the right playbook at the very start is the absolutely wrong playbook for the middle, and yet may become right again a little later on, and then wrong again. Leadership is about crafting instincts while understanding context and having some muscle memory around what you’re experiencing in the middle, and how to navigate it.

The muscle memory can come from your own experiences or those of others. Oftentimes, what I found in my own journey is that hearing a point of view of someone else, if I was careful not to just follow it because they found that it was useful, but rather just consider it as one data point, that wisdom is very helpful to me. I wanted to chronicle the essential insights for enduring the low points and optimizing the high points of that great volatility that happens in the middle.

The Messy Middle is a guidebook for navigating the time when you start to lose hope and become overwhelmed with self doubt.

Q. The book looks at two key characteristics—endurance and optimization—to steer through the volatile middle miles of a journey. How and where can we apply these characteristics to what we’re building? 

A. Let’s get into the psychology of it for the moment. At the low points, you start to make decisions out of fear. You become overwhelmed by the self-doubt, the anonymity, the ambiguity, and the uncertainty of the moment. In such conditions we are more liable to make the wrong decision. Also, that’s where teams disband, where people lose hope. That’s where we add complication to our products because we can’t spend the time to find the right solution, so we just throw crap in there to try to solve it with complexity. It’s really where a lot of great new ventures and new projects within big companies start to unravel.

Then at high points, we start to make decisions out of ego and we actually start to believe, often falsely, that we are at a high point because of the things we did as opposed to good luck or good timing, or the work of others that may have been out of our control. It’s important to recognize that we’re liable to start making bad decisions at the high points as well.

In the volatility of the journey, whether you’re at a low or a high, you are in a spotlight of seduction to go down the wrong path. What keeps you grounded is being empathetic with what the customer is suffering from, and focused on doing what’s right for the team.

Image courtesy of Scott Belsky.

Q. In one chapter you write about how teams tend to A/B Test products, but they don’t often A/B test processes. Why is it so important to A/B test the latter?

A. I think that we don’t feel like we have the luxury of testing and optimizing anything that works in the middle of the journey. If you have a Tuesday morning meeting and it just works, you don’t ever think well, maybe we should cancel and see what happens. But one thing I found across some of the most productive and admired teams, is that they were tinkering with the practices that were working. This makes perfect sense if you think about the world of A/B testing and the fact that you optimize the most important parts of the product. Optimizing process is important. If you believe that founders, entrepreneurs, leaders ultimately win because of how they manage, then how could you not allocate some energy, even when it’s scarce, to improving the things that you’re most proud of?

Image courtesy of Scott Belsky.

Q. You also write about hiring for initiative over experience. Why? And how does one spot “initiative” in a potential hire?

A. When we started Behance, we didn’t have any money or connections really in the tech world. We had no choice but to hire people that didn’t have a lot of experience but had tremendous amounts of interest and initiative. What I learned from that is, while it takes maybe longer to build things, what you lose with having lack of experience in your team, you make up for, and then some, with initiative.

I find that people who have a history of taking initiative and things that are interesting to them continue to do so. Initiative is the best indicator of future initiative. And then when you start to become more successful or you start to have venture capital, you become a resume snob and you say, “Oh, well now I’m going to hire the most experienced people.” Oftentimes, what you’ll find is you hire experienced people who think within the box of what they’re experts in and are less open to ideas and alternative approaches because their ignorance in this case – or their knowledge in this case – has become a weight on their willingness to be open-minded. It’s important to remember as you’re building your team to continue hiring for initiative, even if you want to balance it out with a little experience at some point.

https://www.instagram.com/p/BjlWwSKFURh/?hl=en&taken-by=scottbelsky

Q. In another chapter you talk about how to allocate resources across the duration of the journey, in particular when it comes to negotiating with people. What is your negotiation philosophy?

A. If you’re buying a house, you obviously want to get the best price. But when you’re negotiating a partnership or a package for someone you’re hiring, it is the start of a relationship, and the last thing you want to do is get the better of them. What you ultimately want is to both feel like you got the right end that both people can feel really good about it.

My strategy is that I’m going to put out what I think you should be getting in your package and why, and let’s focus the conversation on what I might be missing or what you might be missing.

It’s about being straightforward and knowing that we started the relationship in a point where, two years from now, you don’t look back and say, “I got screwed.” But actually, look back and be like, “Wow. I was treated right and that’s the way I’m going to treat others,” because that’s self-perpetuating and that builds culture.

Image courtesy of Scott Belsky.

Q. Of all the lessons in The Messy Middle, which one do you feel that you’ve grappled with the most?

A. In the final mile, for example, I talk about how the final mile is a different sport altogether and how you’d need a different set of mentors and a different set of coaches, if you will, because, despite all the confidence and skills you gained over a journey, before some finish line of sorts, you suddenly believe that you’re not ready.

In fact, it’s actually an entirely different set of factors that need to be considered in the final mile of a project. There were many times during my own entrepreneurial journey building Behance where I didn’t listen to outside people enough. I felt lonely at times during the journey and chalked that up to what it’s like to be the head of something and to have that burden on your shoulders.

What I’ve since learned from other entrepreneurs is that it’s really good to have people you go to for specific things. I don’t think the right way to do it is to have an advisory board or to rely just on your formal board, which is a mistake that I made. The people that were most helpful to me weren’t necessarily the right people to be on my board. Certain people are helpful for specific things, and you don’t want to necessarily be limited to just a few people who are there for everything.

Scott Belsky is the author of The Messy Middle and the bestselling book Making Ideas Happen. Watch his 2018 99U Conference talk and read an excerpt from The Messy Middle.