Planning is the Cousin of Procrastination

"Mediocre founders spend a lot of time talking about grand plans, but they never make a decision."

Steve Jobs introduced the first iPhone in 2007, in what is now considered a legendary demo of a legendary product. Jobs spoke extensively about keyboards. Most phones at the time had physical keyboards — flat plastic keyboards that took up the bottom half of the phone, below a little screen. Jobs slammed this design:

“(These phones) all have these keyboards that are there whether you need them or not. And they all have these control buttons that are fixed in plastic, and are the same for every application … well, every application wants a slightly different user interface, a slightly optimised set of buttons just for it. And what happens if you think of a great idea six months from now — you can’t add a button to these things — they’re already shipped! So what do you do?”

He argued that the solution was a software keyboard, displayed on a large touchscreen, and adapted to every application on the phone. Ken Kocienda led the design and engineering of the iPhone keyboard. He wrote about his experience at Apple in Creative Selection, which provides a rare insider’s account of Apple. In it, he explains that getting the keyboard right was central to the iPhone’s success because it was the primary mode of interaction with the device. If the keyboard had been a bust, it might have sunk the iPhone, as bad handwriting recognition sank the Newton before it.

Designing and building the keyboard was a major challenge and it took years to get right. The book gives a great account, but one of the parts that surprised me was the team’s planning process, or lack thereof:

Planning is the cousin of procrastination

Planning feels productive because you map out where you think your product will lead and the best way to get there. The problem with this approach is that you're not getting feedback along the way. You can't figure out if it's the right path on the whiteboard alone. It's easy to plan and feel productive about it, but action is all that matters.

That's not to say that planning is bad, but rather that it's easy to overdo and easy to underdo. Just the right amount of planning is an art form. Enough to give you a clear direction. Not so much that get you lost in the weeds and use it as an excuse not to put in the real work. Most people have the tendency to over-plan, so a useful heuristic is to always plan less than you're comfortable with and get to acting.

Sam Altman, CEO of OpenAI and former president of Y Combinator, says:

[Y]ou have to be decisive. Indecisiveness is a startup killer. Mediocre founders spend a lot of time talking about grand plans, but they never make a decision. They’re talking about you know I could do this thing, or I could do that other thing, and they’re going back and forth and they never act. And what you actually need is this bias towards action.

Cedric Chin has written about this idea previously. He highlights a passage from The Year Without Pants¹, where veteran product manager Scott Berkun talks about a major bet he had to make with his team at Automattic:

"All that analysis just keeps you on the sidelines. Often you're better off flipping a coin and moving in any clear direction. Once you start moving, you get new data regardless of where you're trying to go. And the new data makes the next decision and the next better than staying on the sidelines desperately trying to predict the future without that time machine."

Brian Armstrong, the founder and CEO of Coinbase, makes a similar point. In his interview with investor Patrick O’Shaughnessy, Armstrong says:

“It doesn't even matter what you do as long as you do something, because that's my other favourite quote, is “action produces information.” So at a certain point, you got to stop pontificating about this stuff and just try something, anything. You're going to be embarrassed by the V1 until you go out there and you create. That's part of the product development process, is just dramatically scaling back kind of the ambition and the feature set and everything to rapidly iterate and prototype these things, but go do anything. The first thing you try is almost guaranteed not to work. So don't give up, just go try the next thing, and the next thing, and the next thing. That's the only way that new products and companies ever get created in the world. You got to put a lot of shots on goal to get one to eventually work.”

The value of action isn’t just the information it produces, but the additional benefits of moving quickly. Decisions in the real world are often time-sensitive — the sooner you act, the more value you realise from having acted. Often, it’s the fastest product — not the best product — that wins.

Action starts small

Like most things, action starts small. Sam Altman, again:

“The best founders work on things that seem small but they move really quickly. Every time you talk to the best founders they’ve gotten new things done. In fact, this is the one thing that we learned best predicts a success of founders in YC. If every time we talk to a team they’ve gotten new things done, that’s the best predictor we have that a company will be successful”

Keep the time gap between the ideas you have and the actions you take as small as possible. Next time you have a great thought about what you should do, take action. It doesn't have to be big, it can just be something. The movement is important.

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The iPhone we have in our pockets today is pretty damn phenomenal, but it didn't start out that way. It started out as a shitty prototype that didn't have 3G, only worked on one cellular network, and had a screen that cracked all the time.

But the iPhone team continued to act. They built prototypes and tested ideas. They sought out feedback when it was painful to hear. They acted and iterated and fed new information into their decisions. It’s why there are 1.2 billion iPhone users in the world today. Action wins.

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What I’m Reading

Good and Bad Procrastination (Paul Graham) 

An old (2005) piece from PG. It poses an important but difficult to answer question - "What's the best thing you could be working on, and why aren't you?"

How We Build the Future (Kevin Kelly)

"Over the long term, the future is decided by optimists." This is not a world we have fewer problems. This is a world we have as many, if not more problems, but those problems themselves are opportunities. It is much, much harder to create a future that we would like to live in- unless we can imagine it first."

Confront Reality (Aaron Swartz) 

Very relevant to today’s piece. 

“Chris Macleod calls this “epiphany addiction”: “Each time they feel like they’ve stumbled on some life-changing discovery, feel energized for a bit without going on to achieve any real world changes, and then return to their default of feeling lonely and unsatisfied with their life. They always end up back at the drawing board of trying to think their way out of their problem, and it’s not long before they come up with the latest pseudo earth-shattering insight.” Don’t let that happen to you. Go out and test yourself today: pick a task just hard enough that you might fail, and try to succeed at it. Reality is painful — it’s so much easier to keep doing stuff you know you’re good at or else to pick something so hard there’s no point at which it’s obvious you’re failing — but it’s impossible to get better without confronting it.“

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Social cover image courtesy of Linus Lee.

1. The book gives a behind-the-scenes look at the company behind WordPress.com - Automattic - which powers over 1.4 billion websites on the web.