It’s About the Journey — Not the Destination
Principles for Leading Software Teams: Part III
You would be forgiven if you read the title of this article and assumed it would be about personal improvement rather than leading software teams. It does sound a bit more like a Buddhist proverb than a leadership principle. As I’ve said before, my approach to managing a software team is a bit unorthodox. By now, hopefully you know what to expect from me, so let’s dig in on how I stumbled into this principle.
Many years back, my wife and I were building a new home. I had grand ideas for some beautiful landscaping. I spent a lot of time planning and getting things just right. In particular, we had two blue spruces planted in our side yard. I’ve always loved the look of a blue spruce. Within a year, they were dead. I was inclined to judge myself a failure, but that’s unfair. I didn’t know blue spruces needed dry roots. I didn’t know that particular part of the yard was so wet. What should I have done? Waited until I understood everything about gardening and everything about the nuances of my yard? No. Better to get started and learn along the way: embrace the journey.
The end of that story was that we acknowledged the fact that our side yard was practically a swamp and realized that the destination for that part of the yard wasn’t actually pine trees but rather a baldcypress and a weeping willow. Not only did they grow much better, but they actually helped make it less of a swamp.
Our lives are littered with examples of our inability to perfectly plan things out. Our natural and reasonable response when things don’t go according to plan is to just try harder. As I write that sentence, I’m reminded of Boxer, the horse in Orwell’s Animal Farm, who reacted to inadequacy with “I will work harder.” (Spoiler: it didn’t work out so great. He ended up on his way to the glue factory). Instead, why not just acknowledge reality, cut yourself some slack, and embrace the fact that we are unable to predict the future.
That said, there are additional reasons not to get too attached to what you believe to be the best destination. After all, just because something is hard doesn’t mean we shouldn’t try. In particular, as humans, our ego can get inextricably attached to the destination we imagine. On the journey, we will often (always?) learn things that should cause us to alter the destination; but if my ego is attached to it, I’m tempted to ignore those lessons. If I’m the expert entitled to choosing the destination, adjusting that destination must mean I’m not very good at my job. I’m sure we’ve all been around people that want to stand by their decisions in the face of evidence that it was the wrong decision. It’s human nature, but it’s bad for business.
Additionally, if you’re choosing the destination from a position of leadership as is so often the case, you’re likely not in the weeds sensing the data that might be causing the people that work for you to think the destination should be altered. For many leaders, that’s a difficult thing to hear. You’re unlikely to believe them, or maybe worse, you imagine they don’t believe in you as a leader. (This is actually touching on a very fundamental principle of leadership, but we’ll leave that for a later post).
Coming at it another way, destination thinking can be paralyzing. A big, ambitious goal can seem impossible to reach. In an effort to rise to the task, engineers will attempt to understand “all the things” and get stuck in analysis paralysis. That can lead to stress (and we know what that means). A favorite book of mine, Hannah Hurnard’s Hinds’ Feet on High Places, sums this up well. The protagonist Much-Afraid is overwhelmed at the prospect of the destination ahead of her. The Good Shepherd comforts her with:
Much-Afraid, don’t ever allow yourself to begin trying to picture what it will be like. Believe me, when you get to the places which you dread you will find that they are as different as possible from what you have imagined…
Good advice: stop worrying about that destination because it is likely to look a lot different by the time you get there. Just take the next step on the journey and enjoy discovering the destination.
Do you remember writing specs believing you had thought everything through only to discover when you actually started using the software that there were major usability problems or even functional gaps? Good thing you spent all that time up front thinking about it. The problem was you couldn’t adequately imagine the destination with the information you had at the time. When was the last time you ever saw a specification/waterfall project come in on time and under budget?
What if Amazon held onto their original destination? Likely, they would just be one of many failed book retailers from the dot com boom. Instead they were willing to “discover” that their destination (for now) was actually world class Infrastructure as a Service. Jeff Bezos has famously said that he has lost billions on failed experiments and that failure is necessary for survival. That’s someone that is willing to learn along the journey.
I would claim we can even find this principle in the spiritual world too. If that’s not your jam, skip ahead. Let’s consider a couple of passages from the Bible. James warns us against destination thinking and instead encourages us to preface all of our plans with, “If the Lord wills…”. In other words, feel free to make your plans, but don’t assume it’s going to work out the way you expect. Of course, James’s point is that our lives are fragile, not so much that we can’t effectively plan. Even so, I don’t think it’s a stretch to apply it here: have an attitude of flexibility in case things don’t work out the way you plan. In another passage, Jesus famously told us not to worry about tomorrow (the destination). This is in line with other admonitions in the Bible to lean on our faith for comfort rather than worrying, but again, it is absolutely in line with my earlier point about how a destination can paralyze us. Just worry about today. That’s plenty to keep us occupied. We’ll figure out tomorrow when tomorrow comes.
Never Even Talk About A Destination?
If I’m not careful, you might come away from this thinking that I’m making the case that the very concept of setting a destination is bad, but that would be a failure on my part. How do you even know what the first step of the journey is if you don’t have a destination? You won’t. There’s always going to be some first impression of what the destination is. That’s okay. In fact it’s even important. A good CEO can inspire great work by casting a vision. My point isn’t that you can’t set a destination, it’s that you should expect it to change along the journey. Doing so will make the journey much more enjoyable. In the words of Corrie ten Boom, author of The Hiding Place, “Hold everything in your hands loosely, otherwise it hurts when God [or in our case, the journey] pries your fingers open.”
What Does it Look Like to Embrace the Journey?
Engineers have historically been valued for their ability to anticipate all scenarios. Once I was lamenting to my manager that my wife (rightly) complained that I was too negative. His retort? “That’s what makes you a great engineer. You’re imagining all the things that could go wrong.” In other words, you can anticipate all things and therefore decide what the destination is. It was (and still is) a very common sentiment, so there’s some cultural heavy lifting to do. At my company, we have a lot of practices/applications in place to encourage journey thinking. Lest this post go on too long, I’ll cover those details in my next essay. In the meantime, please leave a comment below. I know there are a lot of people out there that disagree with this sentiment. Maybe you can convince me otherwise. After all, I’m happy to learn along this journey. ;)
Curious to Learn More?
Check out Principles for Leading Software Teams: A Guide for related articles and reference materials.
Postscripts
Ed Catmull sums this up well in Creativity, Inc. Discussing honesty and candor in chapter 5, he says, “And yet, candor could not be more crucial to our creative process. Why? Because early on, all of our movies suck.” They don’t know the destination. More generally, there’s a lot of great stuff in that chapter indirectly about psychological safety.
Nassim Nicholas Taleb goes so far as to label this in Antifragile: “the teleological fallacy”. It is “…the illusion that you know exactly where you are going, and that you knew exactly where you were going in the past, and that others have succeeded in the past by knowing where they were going.” In his chapter “History Written by the Losers” he lists a number of companies similar to Amazon that ended up making their name and fortune in a “destination” much different than what they had originally intended.
David Epstein in Range has a chapter titled “Flirting with Your Possible Selves” which is all about how our career is a journey and much better served by experimenting along the way.
