⛰ The Map is not the Terrain.

The folly of believing that the first will help you conquer the second.

🎧 The Soundtrack

Listen to this while reading:

✨ The Wonderings

When distance is more illuminating than the details:

This is an essay mostly about startups. But also about any difficult endeavour where you’ve been charting a map in your mind for months, maybe even years.

Eventually, you come to a point where you say to yourself: “I have the map. Now I may commence”. It’s also easy to look at the map, marked in milestones: come up with an idea, assemble a team, build a product, tell people about it, get them to pay for it, grow it - and say, “now that I’ve mapped it, I am prepared to go do it.”

That’s probably the single biggest folly of first time founders. The reason people say that startups are impossibly hard to explain unless you've done them is one reason:

The map is not the terrain.

The map shows you space, the markers, the milestones. It knows nothing of friction and grit and perseverance. Of setbacks. Of doubt.

Maps are exercises in intellectual bravado. Encouraging you to say: Look at what I know! Look at my cleverness in figuring this all out. Fooling you into false security.

Maps are business plans. The Terrain is the arena in which things are built.

The Terrain is where everything gets real. Where you decide if this journey is really the one that you want to be on. Where after the first arduous climb and devastating descent you have to dig deep and figure out if you're in it for the long run. There is no shame in turning back or stopping. But nor is there much time to idle and deliberate.

Teams are forged on terrain. Culture matters not because a map looks hard. Or that it’s long and winding. Culture matters because when each of you individually is focused on putting one step in front of the other, trying to get through this impossibly stretch, culture is what binds you. It's what give you assurance that you have a teammate with you without casting a glance behind.

I never understood terrain when I first started thinking about leaving my corporate job. At big companies, there is no terrain to speak of. The jungle has been cleared, the land flattened by bulldozers. That isn't to say there aren't challenges, but they're wars fought on grand battlefields with ample resources, not stealth expeditions on the most meagre of rations.

So how does one prepare for the Terrain?

🗺 First, arm yourself with a sketch of a Map. This is your insight and your mission and your Big Vision. This map will not be step-by-step Google Maps instructions but rather your guide, especially the middle years when you feel most stuck - can’t turn back and afraid to push on. This Map should mark destination not distance. You shouldn’t stall before you set out to try to fill in details you don’t know. You can’t know, won’t know, the details until you come upon them.

✏️ Second - as you do traverse the Terrain, fill in the Map as you go. These are your experiments, your findings, your metrics. What worked, what didn’t to get you to this point. So that if you need to go back a bit and try something new, it doesn’t feel bleak and daunting but rather just another approach to test and try out.

🏃🏻‍♀️ Lastly, if there is training to be done before you set out or in the early miles, then learn to be nimble. On being perceptive. On taking in and responding to the data around you quickly and decisively. On training your team on doing the same. Setting up one week sprints with bold experiments tethered to clear goals and metrics.

Fractions of degrees pointed in the right direction in the early steps will compound to miles and miles saved and will hasten you to your destination.

But a Map won’t help you with that. Because the second you step foot on the Terrain you’ll immediately feel disorientated. The pungent smells, the biting wind, the rocky inclines, the peaty, boggy soil.

The quick sprints will settle you into a rhythm until it becomes second nature. So that by the time the early energy starts to fade, muscle memory kick in. And that’s what ultimately will power your mission in the middle and longer stretch.

The map is not the terrain. I tell myself this every morning when I consult my Map - my mission there to point my ambition towards each day. I take pride and solace in the miles we’ve already covered. In what we have learned. In the team we have recruited along the way.

But my gaze always settled on the Goal. Off in the ever-shifting distance. It’s there that I keep in my mind as my North Star as I set off on the day’s expedition. Will direction, with resolve, with purpose.

🔮 The Curiosities

Ode to Dirt

Written and by Sharon Olds

Dear dirt, I am sorry I slighted you,
I thought that you were only the background
for the leading characters—the plants
and animals and human animals.
It’s as if I had loved only the stars
and not the sky which gave them space
in which to shine.  Subtle, various,
sensitive, you are the skin of our terrain,
you’re our democracy.  When I understood
I had never honored you as a living
equal, I was ashamed of myself,
as if I had not recognized
a character who looked so different from me,
but now I can see us all, made of the
same basic materials—
cousins of that first exploding from nothing—
in our intricate equation together.  O dirt,
help us find ways to serve your life,
you who have brought us forth, and fed us,
and who at the end will take us in
and rotate with us, and wobble, and orbit.

🗺 Point Two Designs Maps

The daughter of parents that for 30 years built and grew a travel company from the ground up, I’ve been surrounded by maps all my life. They hold a fascination for me that few other things do. Put a map in front of me and you’ll have to excuse me from fruitful conversation for some minutes. I came across these gorgeous prints years ago. I love how they sit at the intersection of art and science - accurate geographic markers set to striking colors.

🌳 Forest app

One of the hardest parts of day-to-day building is the constant context switching from dealing with minutiae of a release to the high level strategic work. This app is deceptively simple in its premise - “plant a tree” for a set period of focus time - usually right around the 25min of a “pomodoro”. If you touch your phone or go away from the screen, the tree dies. Successfully focus for that period of time and you’ve planted a tree. Sufficiently motivating for me and a great way to quickly “get into flow”, especially with its background soundtracks.