Few questions create as much anxiety as "What is my purpose?". It's an important question, and to protect my sanity I try to limit the scope. I care the most about today. What is my purpose today? My long term purposes and goals don't change but my day to day actions will.

Over the last few years, my primary focus has been to do work that I feel helps people do better. This is difficult, and I still don't know the best ways to do this. There is a lot of trial and error. Trial and error has a downside that is rarely talked about: errors tend to get thrown out quickly without ceremony.

It is frustrating when work gets thrown out. It hurts. When work is thrown out, and it isn't clear what went wrong or why, that frustration grows into a demotivating pain. In the startup world, a culture exists to take risks, make little bets, and learn from small mistakes. It is less common to know how, though, and bad mistakes are made. When a mistake cannot be transformed into a story to be told, nobody can learn from it, and it is a bad mistake.

When work is thrown out before it even sees the light of day, a huge demoralizing blow is dealt. One of the most amazing social scientists in our day, Dan Ariely, conducted a series of studies to test exactly how demotivating it is when work is not acknowledged. He clearly showed the fastest way to destroy motivation is to discard work without acknowledgement. Even if the work was to ultimately be discarded, acknowledgment was key to maintaining motivation. People continue onward even after previous efforts were thrown out, as long as they were acknowledged first.

Work will always be discarded. What is missing is a space and culture to acknowledge that work. The key to maximize learning and maintaining motivation is acknowledgement. The best place to start this practice is before any work gets done. Starting before is necessary for the entire team to feel cohesive. I now have a method to ensure this gets done, simply and easily.

With the help of a single screenshot from a random blog post, and subsequent discussions with a friend, we came up with a simple list of questions that should be answered before doing any work. This ensures work won't be thrown out without understanding why. The questions are simple but sometimes finding the answers is hard. This difficulty is a good thing; without facing the difficulties early, they will manifest first as doubts and frustrations and then become failed projects.

Three Questions of Purpose

Why is this


What will we


How do we measure


It's very important to write the answers down. It makes it feasible (and perhaps trivial) to revisit the answers, which creates a moment of acknowledgement. There is significant value in revisiting these answers and not just at the end of the work cycle. In the midst of progress there are periods of waning confidence and momentum. When this happens it can be a huge boost to read again why this work is important. Similarly, if it seems the project may not succeed, looking at what is hoped to be learned can soften that blow. This is built-in acknowledgement.

The final question, "How do we measure success?", is very important because so often we assume we're right and we know better. Without determining and articulating the desired outcome it's far too easy to delude ourselves into thinking we succeeded.

There are failures and amazing lessons that surround us so we don't have to make the same mistakes ourselves. Dan Nguyen wrote an excellent report on why infinite scroll failed at Etsy. I'm curious what was so important about infinite scroll to justify the work. Equally, or perhaps more important, was the challenges in measuring success and failure after the fact. This is a recurring issue, as many A/B tests start without a clear definition of success. Something as shallow as better conversion may dilute the real lesson. This dissonance yielded a great whitepaper, "Most Winning A/B Test Results Are Illusory".

Don't test just to test; test a hypothesis. Determine and define what the best means, how you measure it and why it's important. Figure out, beforehand, how you can learn what "the best" really is (and conversely what is the worst). Most critically, decide all of this ahead of time. These three questions are a great first step:

  1. Why is this important?
  2. What do we hope to learn?
  3. How will we measure success?

Photo courtesy Flickr user Erik Drost