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17. The messy middle

Guidelines, bad actors, cinema
people sitting down near table with assorted laptop computers
The small team is an aligned team. Image by Martin Meyer on Unsplash

Robert Frost’s poem ‘The Road Not Taken’ is famously misinterpreted. While many take it to be about making the right choice, it’s actually about post-rationalising our decisions. I was reminded of this when reading Scott Belsky’s business-book-meets-memoir The Messy Middle. Belsky ran the design-portfolio startup Behance for 7 years before selling it to design software giant Adobe in 2012. While his book includes stories from other entrepreneurial companies that Belsky has been involved in— ranging from Adobe to Twitter-acquired video streaming platform Periscope to hyper-feedback focused venture firm Benchmark—it’s primarily a story of the ups-and-downs of running a startup. Belsky was all too aware that startup stories—not unlike that road not taken—get abbreviated into a highlights real of inevitability, whereas the lived experience is far more murky. His book slows down that time, and even points to others who were just as committed founders but just didn’t have the same luck.

Two stories resonated with me. The first was Belsky’s challenge to founders to know when they have to tell staff and funders difficult news, rather than merely burying it (don’t hide the layoffs, explain why they’re important). The second was a plea that leaders remember to more generally do the hard-but-right thing even if there is noise from others to hold off (be it getting rid of a toxic person in leadership just before a funding round, or cutting a feature that has some fans but ultimately won’t serve the business’s main goal). Belsky has an acronym that he uses when talking about this to mentees: DYFJ. What it spells out in full: Do Your Fucking Job.

This month in digital government and design


  • I saw the film Everything Everywhere All At Once (EEAAO) not once but twice at the cinema. From memory this is the first time that I’ve done this. The film holds up on a second viewing, and I agree with the buzz of it being the most original sci-fi film since the Matrix. Part of this may be because of how much is going on thematically: loss of faith, ADHD… Walter Chaw interviews EEAAO writer-directors “The Daniels” (Daniel Kwan and Daniel Scheinert) and unpacks these themes and more.

  • I also saw Top Gun: Maverick this week: it’s the rare sequel that improves on the story. For those that can’t remember much about the original (it did come out 35 years ago), treat yourself to a scene from the 1994 film “Sleep With Me” where Quentin Tarantino gives a memorable (if not Navy-sanctioned) explanation of its themes:

  • Do you play games like Animal Crossing? Some researchers define these as ‘cozy games’ and explain why they’re important.

  • Remember Metafilter? The Web 1.0-era social network is still going, thanks to great community systems.

  • NZ soap Shortland Street turns 30 this year. Journalist Russell Brown points out that it was groundbreaking in terms of representation:

  • And finally, cultural differences via detective shows

Until next time,