I’m currently re-reading The Art of the Good Life: Clear Thinking for Business and a Better Life by Rolf Dobelli. It’s a great book. I’ve been struck by how relevant many of the arguments from Chapter 6 “The Negative Art of the Good Life” are to technical leadership and decision making.

The context of writing this post is relevant as I’m currently embarking on front end development leadership of a major new product.

Upsides and downsides

The chapter begins by discussing the concept of “upsides and downsides” as they relate to flying a plane or investing in the stock market. What resonated with me was the tendency for people to be seduced by upsides while underestimating the impact of likely downsides when making investments - either in the stock market or, more commonly in my life, in trending technologies that promise great returns for a team. As he explains - and as you’d hope, this is not the case with aircraft pilots who will focus their attention on the potential downsides before embarking on a flight - the upside gets almost no attention.

Before and during a flight I focus almost exclusively on the potential downside and how to avoid it. The upside, on the other hand, gets very little of my attention. The majesty of the snowy Alps, the gorgeous cloud formations, the way my sandwich tastes at this dizzying height - all that will come. As long as I keep the downside at bay the upside will take care of itself

This resonated strongly with me from the perspective of making technical decisions that will have an impact on the team, users and organisation over the medium- to long-term. Adopting TypeScript is one such decision but there are many others that technical leads must make - and I believe giving sufficient focus to the potential downsides will guide us well.

As a front end technical lead, some downsides I’m particularly conscious of are anything that might:

  • negatively impact developer productivity in the short- medium- and long-term
  • impair the ability for the user interface to work for everyone, both now and in the future when people are accessing it in ways that are inconceivable to me right now
  • put the organisation on the wrong side of expected standards and legal duties (whether these relate to accessibility regulations, GDPR or anything else)
  • dependencies and complexity that might create problems for ongoing maintenance and future changes
  • be difficult to recruit for in future

These are the things that matter to me - and they should. A major failure of any will significantly impact a team’s ability to deliver value. Taking the time to actively consider the potential downsides will help avoid decisions that you’ll regret later.

Play conservatively

Similarly, Dobelli then explains how investor Charles Ellis recommends amateur tennis players play conservatively with a focus on not making mistakes since they - unlike the pros that can place virtually every shot wherever they choose - lose games through their mistakes.

They smash the ball into the net. They aim too long, too high, at the wrong area of the court. Professional tennis is an entirely different game to the amateur variety: pros win points, amateurs lose points.

This reminds me of projects where we are all (if we’re honest) dealing with the same uncertainty about the effect of our actions as an amateur tennis player. Yet all too often teams seem to have inflated expectations for the upsides of a given tool only to end up in a trough of disillusionment at which point they try to seek out the newer technology that will solve all their problems. There are aspects here of an end-of-history illusion, i.e. this library is the one - but that’s another blog post in itself.

You can’t say with certainty what will make your team more effective in the short- medium- and long-term - but you can be reasonably concrete about the problems you want to avoid, and use these as a lens through which you review candidate technologies.

Avoid the downside

And this brings me to the point: I honestly feel like the biggest wins are achieved by giving adequate weight to avoiding the downsides in our decision making.

A good part of the good life is steering clear of stupidity, foolishness and trends instead of striving for ultimate bliss. It’s not what you add that enriches your life - it’s what you omit.