The perfect plan is a recipe for failure

The world is too complicated to predict. It makes no sense to sit in your office designing the perfect plan. You’ll never get it right. I have been guilty of waiting too long and working too hard on a plan. By the time I was ready to execute, my plan was no longer relevant.

Experimentation trumps perfection

As I have said before, my inner perfectionist is one the biggest blockers to my success. It wants everything lined up perfectly with a clear and proven path. It is a major effort for me to overcome this. One thing I try to do is reframe my actions as an experiment. An experiment is successful if helps me understand a problem space better. It doesn’t have to make me money, make me look good, or solve a problem. It gives me results that help me home in on something I am trying to achieve, even if I don’t achieve it this round.

In The Upside of Down, Megan McArdle observes “there is no way to know whether something works until you put it out there and see how your target audience reacts.” Jim Collins encourages us to fire bullets before cannon balls. – ie try something small and see how it works – don’t waste all your gun powder on a big attempt that might miss.

In this light, I try to take a scientific method type of approach to projects. Will this project help me get closer to my long-term goal? Have I defined the question I’m trying to answer? What is the hypothesis I am trying to prove? Then, I get to experiment with projects! Success is no longer having the big win. It is uncovering learnings that help me understand my problem space better.

Planning is still important

If I’m lucky enough to get my inner perfectionist on my side, I typically over correct. I skip the problem definition and hypothesis. I jump right into testing. The catch is that I don’t put the effort in to identifying what I’m testing. Who knows what the results of my test show. I certainly don’t.

Steve Blank, in his book, The Four Steps to the Epiphany, applies this well to new companies. In it’s essence, he encourages us not to scale until we’ve fully understood the problem we’re solving and have confirmed that we can solve it. Many of us want to scale too quickly, be it in our personal lives or business.

Many of our modern thinkers (Blank is one, Rob Fitzpatrick and Marty Cagan are others) warn us about jumping in too fast. All of them tell us to identify the problem first. Here’s something that’s eye opening about our take on all of this. In the Kindle edition of Cagan’s classic book on Product Management, Inspired, he lists out 10 steps to assess a new opportunity. Note that in this screenshot, the Kindle app is telling me that only steps 5-10 are frequently highlighted. Most people did not highlight steps 1-4, even though, as Cagan continues on the very next page, “The hardest question to answer is usually the first… the value proposition.” If the people who get paid to plan for the future skip the early steps, how likely are the rest of us going to fall into that same trap?

Of course, this isn’t limited to product managers. We are all guilty. Here’s what Susan A. Ambrose and her team say about it in their book, How Learning Works. “Lack of planning is consistent with a body of research that shows that students tend to spend too little time planning.” They go on to point out that experts start slower and finish faster because they spend “proportionately much more time than novices planning their approach.”

How to prepare your brain to fail

Finally, we have our egos to contend with. Personally, I want to get a W on the board as soon as possible. Stepping back for a second, that analogy came a little too easy. Even with my work and focused attention, I’m still thinking about wins and losses. Even with all the work I’ve done, while I’m writing this blog post on this very topic, I still have unconscious biases that treat experiments as wins or losses. It is hard to adopt a fail-fast methodology if you don’t have a lot of failure in your life. By the way, this is the opposite of a humble brag. As I’ve written about before, if you’re not making mistakes, you’re making a mistake. It’s hard to grow without failure. In fact, if we define ourselves by our short-term successes, we can box ourselves into a corner of stagnation.

Of the people in my life who fail fast and grow fast, all of them have had massive failures in their past. They are also, to a person, some of the most successful I know. Interestingly, they all have larger, more present egos than me. They are also passionately focused on the long game. Short term failures roll off their backs. Both John Medina in Brain Rules and Megan McArdle call this out. Fail fast, have a short period of analysis, then get right back in the game with another attempt. Wait too long and you lose momentum, jump in immediately and you won’t capture the learning.

Hey Future John

Fearing failure and identifying your overall failure or success with any one project means you’re stuck in the short game. Accepting failure, analyzing your results, and trying again is just a step in the process of the long game. Stay in the long game!

Thanks to Christopher Windus for the photo of the rusted-out car.