End-of-Year Journey Mapping: How my 2020 Went and How 2021 Is Looking

Four years ago, I started organizing a small end-of-year gathering with other Bay Area collaboration practitioners to celebrate and make meaning of the year together. We would spend the first few hours of our session mapping how our individual years went using an exercise called Journey Mapping, then we would share our respective stories with each other and toast the end of the year with libations and snacks. It was a lovely ritual, and it became an annual tradition.

This past year, we couldn’t do a face-to-face gathering due to the pandemic, so we decided to do it remotely instead. Going remote had three wonderful benefits. We were able to divide it into two sessions, which netted us more time. We were able to invite more people, including folks who lived outside of the Bay Area. And, it was a good kick-in-the-pants for me to write up the exercise so that others could organize their own gatherings. (Several folks did, which made me incredibly happy.)

Journey Mapping is a quick way of visually telling the story of a project’s highs and lows over a bounded timeline. (Product managers may be familiar with customer journey mapping, which is similar in spirit, but different in practice.) You can do the exercise on your own, but it’s nicer in a group setting, even when everyone is doing it for themselves (as we do in our end-of-year ritual). It’s like working out with a buddy — you’re more likely to do it if others are doing it with you, and it’s a wonderful way to support each other and build community. When you do it as a group on a shared project, it serves as a fantastic tool for making meaning together and for discussing and developing shared narratives. I often use it as a ritual for teams to celebrate, mourn, learn, and transition.

How you do the exercise is not as important as simply making time to reflect regularly. The more you do it, the more you’ll understand how best to adjust it for your specific situation. That said, Journey Mapping has three attributes that I think are particularly powerful.

First, it contextualizes your work in your overall life. The toolkit specifically asks you to map highs and lows both professionally (or with a specific project) and personally. In a team setting, the tendency is to skip the personal brainstorming, especially when you have limited time. Sometimes, this is warranted. However, you lose a lot when you do this. Several years ago, I did this exercise with a startup’s leadership team, which was struggling mightily with interpersonal dynamics. Earlier that year, they had been running out of money, and they weren’t sure they would be able to raise another round of investments. Not surprisingly, that was a low point professionally for everyone. At the same time, one of the leaders had also been dealing with a family tragedy and the dissolution of a relationship. The rest of the team never knew about this and only found out about this through the Journey Mapping exercise. Learning about their teammate’s personal struggles many months after the fact caused them to re-examine how they viewed their behavior during that time, leading to greater empathy, a little regret, and ultimately forgiveness.

Second, the Journey Mapping exercise asks you to list the highs and lows from memory first, then to review your calendar, journal, and other artifacts and add anything you might have forgotten. This reminds you that what you might be feeling and remembering in the moment is rarely the