I’m sure a lot of us have common misconceptions about successful entrepreneurs and their companies. It’s easy to look at people who’ve ‘made it’ and think that their journey has been all plain sailing. Scott Belsky is such an entrepreneur, having founded Behance, a platform for creative professionals to show off their work, which eventually got acquired by Adobe. In “The Messy Middle”, Belsky eradicates any illusions about the process of creating – whether it’s a business or a product – being painless. He writes about the different stages of a startup lifecycle: the start, the middle and the finish. Belsky makes the point that “it’s not about the start and finish, it’s about the journey in between.”

Fig. 1 – Scott Belsky, Navigating The Messy Middle – Taken from: https://medium.com/positiveslope/navigating-the-messy-middle-7ca6fff11966

At the start, there’s “pure joy” to begin with. That is before reality kicks in and things hit bottom. Belsky describes the finish as “final mile of journey and the recovery time between one project and the next”, the point where you can allow yourself to take a break and make a change. I, however, specifically bought the book because I was intrigued to read Belsky’s thoughts about the ‘messy middle’. Belsky writes about this period, as a collection of peaks – ‘optimising’ – and valleys – ‘enduring’. It’s this period which benefits from volatility. Volatility being positioned as a good thing might sound counterintuitive to some, but Belsky argues that “volatility is good for velocity”:

“The faster you move, the better your chances of learning and momentum to soar above the competition.”

Scott Belsky, The Messy Middle

To achieve this level of velocity, Belsky encourages conducting experiments, and lots of them. Running these experiments means that you’ll be both enduring the lows and optimising everything that works. In “The Messy Middle”, Belsky shares a ton of lessons learned and tips, particularly in relation to those stages of your company or product that are dominated by enduring and optimising. Allow me to give you a quick shopping list of those points by Belsky which resonated with me most:

• Avoid validation in the form of false positives –  To objectively observe the performance of your new creation or product, put yourself in others’ shoes. Belsky refers to points made by Ben Horowitz about telling the truth in this respect (see Fig. 1 below).
• Celebrate progress and impact – Especially at the early stages, celebrate anything you can. Whilst you should avoid ‘fake wins’, celebrating quick wins and progress milestones is important.
• Master the art of parallel processing – This involves being able to focus on a specific problem whilst also churning through the omnipresent anxiety and uncertainty involved in building things.
• Friction unlocks the full potential of working together – Hardship brings your teams together and equips you to endure for the long haul.
• Do Your Fucking Job (‘DYFJ’) – Leading a team through enduring times requires many “rip off the Band-Aid” moments. Nobody wants to inflict pain on their team, but quick and controlled pain is better than a drawn out infection. This also implies checking your ego at the door, instead concentrating on what needs to be done.
• Self awareness as the only sustainable competitive advantage in business – Your sense of self is likely to shift when you’re at a peak or in a valley (see Fig. 2 below).
• Break the long game down into chapters – Belsky recounts the approach by Ben Silbermann, CEO of Pinterest, who breaks up every period of his company into chapters, each with a beginning, goal, reflection period, and reward. Chapters help break down the long timescale it takes to build something extraordinary. I like to think of them as strategic milestones, each time getting one step closer to achieving the vision for the business.
• Do the work regardless of whose work it is – Everyone has an opinion, but few are willing to do something about it – especially if it falls outside their formal job description. Belsky describes his marvel at just how quickly an idea takes hold when someone proactively does the underlying work no one else clearly owned. He goes on to talk about how hiring for people with excitement about the idea, ability to contribute right away and the potential to learn is key when assembling a team.
• Never stop crafting the “first mile” of your product’s experience – Whether you’re building a product, creating art, or writing a book, you need to remember that your customers make sweeping judgments in their first experience interacting with your creation – especially in the first 30 seconds. Belsky call this the “first mile”, and he argues that it’s important to prime your audience to the point where they know three things: 1. Why they’re there (2) What they can accomplish and (3) What to do next.
• Identify and prioritise efforts with disproportionate impact – Belsky shares a nice prioritisation method by Jeffrey Kalmikoff, which Jeffrey uses to help choose where to focus his energy: look at each item on the table and assign a 3 for very important tasks that would make a huge impact on strategy and revenue, a 2 for something with less significance, and a 1 for something inconsequential.
• Stress-test your opinions with radical truthfulness – “Sound judgment, achieved through aggressive truth seeking, is your most differentiating and deterministic trait. It’s all about being honest.” This is one of the founding principles behind Bridgewater, the leading hedge funded founded by Ray Dalio. One of the most fundamental principles driving behaviour at Bridgewater is the notion of “Know what you don’t know, and what to do about it.”

Main learning point: In “The Messy Middle”, Belsky has written a book that I expect to be coming back to over the coming years; it’s a great reminder of the realities involved in creating things and contains a lot of valuable lessons learned as well as practical tips.

Fig. 1 – Ben Horowitz – Three methods for assigning meaning to hard truths, taken from https://a16z.com/2017/07/27/how-to-tell-the-truth/:

• State the facts clearly and honestly.
• If you caused it, explain how such a bad thing could occur.
• Explain why taking the action is essential to the larger mission and how important that mission is.

Fig. 2 – Self awareness, by Scott Belksy – Taken from “The Messy Middle”, pp. 54-56:

• Self awareness starts with the realisation that when you’re at a peak or in a valley, you’re not your greatest self.
• Self awareness means understanding your own feelings enough to recognise what bothers you.
• Self awareness means being permeable.
• Self awareness comes from chronicling your patterns.
• Self awareness means dispelling your sense of superiority and the myths that people believe about you.

Related links for further learning:

1. https://www.themessymiddle.com/
2. https://a16z.com/2017/07/27/how-to-tell-the-truth/
3. https://www.adamgrant.net/
4. https://www.mindtheproduct.com/2017/07/enter-matrix-lean-prioritisation/
5. https://ryanholiday.net/stop-examine-reconsider/
6. https://blackboxofpm.com/ruthless-prioritization-e4256e3520a9
7. https://www.lifehack.org/articles/productivity/how-to-learn-what-you-dont-know.html
8. https://en.m.wikipedia.org/wiki/Stroop_effect