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 whole story and that there may be lessons to harvest or things to celebrate that are worth revisiting. It also reminds us of the importance of having and reviewing artifacts.

Third, the Journey Mapping exercise encourages you to take your somewhat structured set of sticky notes and create meaningful art out of it. For example, these were the sticky notes that I created for my 2020 (using Sticky Studio):

and this was my artistic rendition:

This part of the exercise almost always gets short shrift. We often treat art as optional — nice, but not necessary. Doing this end-of-year ritual with my colleagues the past four years has helped me realize that this is a mistake, not just with Journey Mapping, but with many of my exercises. Practically speaking, when you create something that’s beautiful, you’re more likely to look at it again. More importantly, the act of creation leads to an understanding that’s far deeper and more meaningful than a set of sticky notes can convey.

You can get a taste of what I mean by looking at the art that some of my colleagues created:

Everybody chose to tell their story differently, from emphasizing specific themes (e.g. needing space, “re-“ words) to capturing a larger metaphor (e.g. tree, river). My colleague, Catherine Madden, organized her year into five categories and wove her story into the tapestry on the right — you can read more about her story and process here. Seeing what people created and listening to their stories were incredibly moving. I will remember those stories in a way that I don’t think would have been possible if they had simply told them or shared their sticky notes. Moreover, I don’t know that they would have told the stories the way they did if they had not had the chance to create this art.

My 2020

The personal backdrop for my 2020 was — like everyone’s — all about the pandemic. I was incredibly fortunate to be healthy and safe and not to lose anyone to COVID-19. So many people were not that lucky. The numbers are staggering — 2.2 million deaths worldwide so far, 450,000 in the U.S alone. (For comparison, 400,000 Americans died in World War II.) What made it all the more heartbreaking — especially for someone whose purpose is to help society collaborate more effectively — was how divided and misaligned we were in these trying times.

I was way luckier than most, but pandemic life was still hard. I spent the spring simply trying to cope. Like many people, one mechanism I tried was growing plants. I found a wilted mint sprig in the back of my refrigerator, which I rooted in water for several weeks, then transferred to a pot. I observed and documented the process every day, occasionally sharing what I saw on Instagram. My partner, amused by the loving care I was showing my plant, named it, “Mo.” I was awed by how resilient my mint was, and I was also surprised how gratifying this simple, regular practice of paying attention to Mo Mint felt.

Resilience. Paying attention. These became recurring themes both personally and professionally. I went into 2020 hoping that I could spend 30 percent of my time on coaching and training individual collaboration practitioners. I felt that this would be the best path to maximizing my impact, and it’s also where I felt the most energy and joy. A third of the way into the year, as the lockdowns were starting, it was clear that I wasn’t getting enough traction to hit that number.

I also went into 2020 adamant that I would only take on organizational clients willing to try my muscle-building approach to addressing their challenges. Convincing clients to do this has always been difficult, but my yield in the first half of 2020 was even lower than what it usually was. In an interesting twist, both the pandemic and the racial unrest created demand around collaboration practitioners who could help with remote work and equity work. However, most of the prospects who came my way were more interested in quick fixes than the kind of deep work that real change requires.

Grappling with those two things in concert was hard enough. Doing so during a pandemic was even harder. Paying attention and focusing on resilience made all the difference in the world.

The previous year, I had started to experiment with video as a way to better communicate my frameworks and practices, and I had more ideas and partially written scripts than time to produce them. Several conversations I had been having with colleagues inspired me to revisit one of these videos, Acting Strategically, which I published in April.

The response was universally positive, with many people asking me, “What would it look like for me or my organization to do this?” This led me to dust off some workouts I had developed over the years and start piloting them with colleagues and friends. The pilots performed well, and I loved doing them. I started preparing an “official” offering for late 2020, when something unexpected happened. Focusing on strategy was helping prospective organizational clients understand my workout approach in a way that had failed to click otherwise. Even when it was clear that they needed to focus on areas other than strategy, because they were better primed for this approach, they were more open to using workouts to address other aspects of collaboration.

By late summer, I found myself doing workouts with several organizational clients. It was gratifying and generative, but it was also taking my energy away from my individual practitioner offerings. I was conflicted, but I ultimately decided to go with where the demand was taking me and to hold off on my individual offerings indefinitely.

Looking Forward and Backward and Forward Again

Doing the Journey Mapping this past December had one more interesting twist. A few years earlier, Catherine Madden had suggested doing the exercise as a way of looking forward, not just looking back. At the beginning of 2020, I decided to try her suggestion, drawing what I imagined my professional curve might look like at the end of 2020. Here’s what I drew:

It was fascinating to compare this with how my year actually went. I had imagined a choppy beginning with a gradual upward trend, and I wasn’t completely wrong. However, the choppiness ended up being twice as long with an overall downward trajectory, there was never any “big” win, and while my year did end on an higher note, it wasn’t as high as I had hoped.

Still, as with all scenario work, the goal wasn’t prediction, it was to prepare for possibilities. Because I had imagined that my year would be choppy initially, I was mentally and emotionally prepared when that turned out to be true. I had also adjusted my strategic goals accordingly, so even though they ended up being off, they were not as off as they probably would have been otherwise. Finally, because I had written it all down, I had something to look at and reflect on at the end of the year.

I am determined to do this exercise again for 2021, but it’s already February. I’m about two months behind where I usually am in terms of planning, and I find myself more unmoored than I’ve been since starting this Faster Than 20 experiment seven years ago. I’m trying to be compassionate with myself. Last year was not normal, and while there are some positive signs, we’re not out of the woods yet, and there’s still a lot of uncertainty moving forward. I’m still excited about providing workouts, coaching, and community for collaboration practitioners. I have a set of clients I’m currently supporting, I have some ideas of what I want to offer individual practitioners later this year, and I will undoubtedly continue to experiment. Beyond that, I just don’t know.

What I do know is that rituals, community, and time to reflect matter. I am always grateful for my peers and our end-of-year gathering, but I feel especially so now. I hope many of you find Journey Mapping valuable as well.

Do the Work

It’s been one month since a white police officer in Minneapolis murdered George Floyd, a 46-year old Black father of five. I’ve found the subsequent response remarkable for its intensity, unprecedented diversity, and impact. While I’m moved by how many people and organizations seem genuinely compelled to act, I’m also vexed by some of the rhetoric around what “doing something” actually means.

Woke theatre aside, I get that it’s hard to know what to do or how. I can see how easy it is to be overwhelmed by the enormity of wanting to eradicate 400 years of structural and cultural racism or by the fear of doing or saying the “wrong” thing. Fortunately, there are a lot of resources out there, and folks have been circulating them with abandon. While many resonate with both my personal and professional experience, I’ve found several to be questionable or worse, and I can’t help feeling like most of this resource sharing misses the point. You can’t just work your way through a listicle and solve racism.

This work is hard, but maybe not in the way most of us think it is. The muscles required to create a more equitable society are the same ones needed to be skilled collaboration practitioners, and they can only be developed through practice and repetition. The key is to focus on the right things and to do them over and over again. The devil, of course, is in the details, and I want to riff on those here.

But first, I want to tell two stories. The first is about data, narratives, and human psychology.

According to the Mapping Police Violence database, 91 people have been killed by police in the 38 days since George Floyd’s murder. Nineteen of them (21 percent) were Black, a slight decrease from the overall percentage over the past eight years (25 percent). Thirty-two of the 91 killed were white.

I read all of the news items documenting each of these 51 killings (not counting the 40 victims of other or unreported race). The vast majority of the victims were armed. Many were violent criminals — rapists, murderers. Several of the deaths were the result of shootouts, and some cops died as a result. A few cases of both Black and white victims raised my eyebrows, but there was nothing that felt as clearly wrong and overtly racist as George Floyd’s murder.

Reading about these 51 deaths left me feeling depressed, but not outraged. As I dove more deeply into these incidents, I couldn’t help wondering how I would have felt about racialized police violence if I had not been exposed to countless stories like George Floyd’s over the years, if my only exposure to police violence were accounts like the 51 articles I read.

It was a troubling thought, because of all the numbers that I mentioned and stories that I shared, there’s only one that really matters: that 25 percent of people killed by police are Black. Why does that number matter? Because only 14 percent of Americans are Black, which means that Black people are disproportionately killed by police by a big margin. Even if George Floyd or Breonna Taylor or Philando Castile or any of the many Black women and men who were definitively unjustly killed by police over the years had never happened, that 25 percent number would still be a clear indication of a racial disparity that needs to be addressed.

Therein lies the essential challenge. No one has ever looked at a number and taken to the streets. There are lots of mental hoops required to make sense of that number, to trust its implications, and then to get outraged by it. We’re seeing this play out right now with the massive racial disparity of COVID-19 deaths, which is killing far more Black and Latinx people than police violence, yet hasn’t resulted in large-scale public outrage. In a perfect world, it shouldn’t take a shocking video of a Black man being callously suffocated to death by a smug white police officer for folks to recognize that the system is racist, but for most of us, that’s exactly what it took.

Except that’s not quite the whole story either. As visceral as George Floyd’s death was, it still wouldn’t have had the impact that it did without the massive amount of work and resources that the Movement for Black Lives has invested in organizing, mobilizing, and collectively aligning around a policy platform over the past eight years. Contrary to how it may appear on the surface, the Movement for Black Lives isn’t just a hashtag. It’s also not a single organization with a clear hierarchy of decision-making and leadership. It’s a network full of leaders, organizations, and activists, some more visible than others, but every one of them playing a critical role. That makes it harder to understand, talk about, or fund.

Human beings love simple, emotional narratives. We need to accept this about ourselves and leverage it to motivate change. But once we allow ourselves to be moved, we also have to be willing to let go of these simple, emotional narratives and dive more deeply into the messy and far less compelling nuts and bolts of the work. Real change takes lots of hard work, the kind that most people are completely uninterested in hearing about or doing.

The second story I want to tell is about basketball.

When your team has the ball and is trying to score, one of the easiest ways to help your teammates is to set a screen. This consists of positioning your body so that it serves as a kind of wall that prevents the defender from chasing your teammate. If the defender sees it coming, they can try to dance around the screen, but that split second of separation is often enough to give your teammate an advantage. If the defender doesn’t see it coming, then it results in a collision, which usually hurts them a lot more than it hurts you.

If you’re defending, and you see the other team set a screen, all you have to do is yell, “Left!” or “Right!” depending on where the screen is relative to your teammate. At best, your teammates can adjust and eliminate the offensive advantage. At worst, you save a teammate from a painful collision. It is a simple and effective intervention that doesn’t require any special athletic abilities. All it takes is attention and communication.

Still, it’s not intuitive. Many players — even experienced ones — have to be told to “call out the screens,” often by a frustrated teammate who has just been flattened by one.

I find this fascinating. Basketball is a hard sport to learn and play. I’ve played it my whole life, and I’m still mediocre at the shooting and dribbling part, which require physical acumen. But I’m great at calling out screens, which simply requires me to talk. Why is it so hard for others? Why isn’t this the first thing that people learn how to do?

It turns out that being an ally is a muscle, and that developing that muscle takes practice.

A few weeks ago, I was on a check-in call for a network of Black activists and allies. On the first part of the call, folks shared a number of inspiring stories about some of the amazing work happening on the ground in Minneapolis and other places around the U.S. Themes around being invisible and the importance of reclaiming one’s own agency and not replicating existing power dynamics came up over and over again.

Afterward, we broke out into small discussion groups. I was in a group with four other people, including a moderator. None of us knew each other, so the moderator called on people, one-by-one, to introduce themselves, and he inadvertently skipped me. I waited several moments for someone — anyone — to point this out, but nobody did, and the group started diving into the discussion. I finally found a point to jump in, saying with a smile, “I have a thought, and while I’m at it, I’ll also introduce myself.”

The moderator profusely apologized, not just in the moment, but throughout the rest of the discussion. I was touched by how badly he clearly felt. It was fine, I knew it wasn’t intentional, and I would have been okay regardless. And everyone in the group was lovely. What really stuck out for me, though, was how no one else in the group noticed or said anything, especially after all of the talk beforehand about the importance of seeing each other, of being seen, and of being good allies.

I’ll say it again: This work is hard, but maybe not in the way most of us think it is. The muscles required to create a more equitable society are the same ones needed to be skilled collaboration practitioners, and they can only be developed through practice and repetition. The key is to focus on the right things and to do them over and over again.

I’ve worked with all kinds of groups over the years, including many social justice groups, and I’m constantly struck by how bad most of us are at the fundamentals. It’s why I’ve moved away from larger systems change projects and have focused my energies on training and coaching. If you’re trying to create a more equitable world, but you can’t even run an equitable meeting, much less an equitable organization, you’re focused on the wrong problem. Everything is connected. If we just stepped back and started with smaller, simpler (but by no means simple) challenges, giving ourselves plenty of permission to make mistakes along the way, we would be far more likely to make headway with the bigger, harder societal problems that so many of us care so much about.

Which brings me to the thing I really want to say to collaboration practitioners and organizations who want to contribute to a more racially just world. Urgency is the enemy of equity. If you really want to make a difference, start by slowing down.

All of the racial equity training in the world won’t make a lick of difference if you don’t have the mechanisms and the right mindsets in place to get clear and aligned about success, to adjust based on what you’re learning, and to hold yourselves accountable to your stated values. In many ways, these are the easiest things to implement, and yet they’re the things groups are most likely to skip. I can’t tell you how many groups have approached me over the years wanting to change their culture somehow, someway, and yet weren’t willing to schedule regular time to assess how they were doing. Frankly, most practitioners I know skip these steps too, and our impact suffers as a result. We get away with it, because no one holds us accountable to long-term success, and the status quo continues merrily on its way.

Earlier this year, I wrote about my six-year journey to learn how to slow down. I know how hard it is to change these habits, and I don’t want to suggest that what I did will work for everyone. All I know is that it matters, that it’s an affliction that infects many of us, and that you’re more likely to propagate than address inequity if you don’t figure out how to fix this. It won’t be worthy of a press release, but it’s more likely to result in the impact you want to have in the long run. Moreover, if enough of us do this, the right things will start to happen in society at large.

Update: I clarified the number of victims since George Floyd’s death (91) above, explaining that I focused on the Black and white victims (19 and 32 respectively, for a total of 51). Thanks to Travis Kriplean for the suggestion.

Illustration from Black Illustrations: The Movement Pack.

Case Study: Designing and Facilitating a Small Nonprofit Board Retreat with Zoe Tamaki


Over the past two years, I helped designed and facilitate two annual board retreats for a small nonprofit with my colleague, Zoe Tamaki. I don’t typically do one-offs like this, but the executive director was a friend of mine, and I was looking for an excuse to work with and learn from Zoe. After last year’s retreat, Zoe and I sat down in front of a camera and discussed some things we learned from the experience and from each other, including:

  • The importance of designing with your stakeholders
  • When relationship-building trumps task work
  • How I handled a funky facilitation moment

I’d like to share stories like this more frequently, and I hope to explore other mediums in which to do this, especially video. I want to share a lot more about design, which contributes much more to the success of group process than facilitation. I especially want to talk about the harder stuff — the challenging moments or the stuff that flat out fails. Since my focus over the past few years has shifted to supporting and coaching other collaboration practitioners such as Zoe, I’m especially excited to be sharing things I’m learning from them.

Finally, I hope to inspire other practitioners to share stories from their work more frequently and without concern about polish. This work is hard. It’s better to show all the rough edges.

Many thanks to Zoe for doing this work with me and for being willing to candidly debrief it on camera afterward! As I think you’ll be able to tell from the video, it was super fun working with her.

Lemon Meringue Pie, Stiff Peaks, and What Effective Collaboration Feels Like

Stiff Peaks

Stiff Peaks

The summer after my junior year in college, I decided that it was finally time to learn how to cook. I had barely managed to feed myself in previous summers, largely subsisting on pasta and jarred sauce and also "pizza" made with slices of bread, cheese, and jarred sauce. (I ate a lot of jarred sauce.) I was able to survive, but I like to eat, so survival felt like too low of a bar.

Rather than start with something simple, I figured that if I could cook something difficult, I could cook anything. I decided that the hardest thing to cook was lemon meringue pie. I recruited my friends, Justin and Jay (who similarly enjoyed eating food and lacked competence in preparing it) to join me in this experiment. Miraculously, they were persuaded by my convoluted reasoning and enthusiastically agreed to participate.

Our first mistake was to search for a recipe on the Internet. This was in 1995. Recipes on the Internet weren't very good back then. Still, that was the least of our problems. The bigger problem was that we couldn't understand the recipe that we found. The crust required that we quickly roll slices of frozen butter and drops of water around in flour until they formed "marbles." The lemon custard required "tempering" eggs so that they cooked without scrambling.

Needless to say, we mostly got it wrong. Our crust barely held together and tasted like… well, it didn't taste like anything. Our lemon custard was actually lemony scrambled eggs — strangely compelling in their own way, but not good. At the very least, our results were edible and even resembled the bottom of a lemon meringue pie.

We could not say the same for the meringue. The recipe called for us to mix egg whites with cream of tartar and to whip them until they formed "stiff peaks." None of us knew what "stiff peaks" were, but we figured we'd know them when we saw them. None of us owned an electric mixer, much less a whisk, so we went to the store, bought a hand mixer, and proceeded to mix away.

And mix. And mix. One of us would mix until exhaustion, then another would take over and continue. We kept stopping to examine our results and debate whether we had achieved "stiff peaks." It didn't look very stiff, but we still had no idea what "stiff peaks" were, so we kept mixing. All told, we mixed for over an hour until finally giving up. My forearms were so tired, I could barely make a fist. We poured our runny egg whites over the custard, baked the darn thing, and celebrated over slices of glazed, scrambled egg and lemon pie.

The next day, we debriefed with a friend who knew how to cook and who somehow found our whole ordeal hilarious. She laughed heartily at most of our story, but paused in surprise when she heard about our failed meringue. "You mixed for over an hour?!" she remarked. "It shouldn't have taken that long, even by hand."

"How long should it have taken?" we asked.

"Five minutes, maybe ten," she responded.

We started speculating about why our meringue had failed, finally concluding that we should just buy an electric mixer and try again. We did, and this time, it worked. We all stood around the bowl and marveled, "So that's what a stiff peak looks like!"

What Do the Different Stages of Effective Collaboration Feel Like?

Last year, Amy Wu and I announced version 2.0 of our DIY Strategy / Culture toolkits. The following week, I spoke with my friend and colleague, June Kim, who had generously pored over our work and had lots of helpful feedback to share. He said, "You do a pretty good job of explaining how to use your toolkits, but you don't explain how it should feel and what it should look like when you're finished."

This hit a nerve. One of my core mantras is, "Chefs, not recipes." In a previous blog post explaining this principle, I wrote:

Recipes and tools have their place, but they are relatively meaningless without the literacy to wield and interpret them.

In a later blog post detailing the design philosophy underlying the toolkits, I confessed:

Initially, I was biased against tool development as a possible path to scale, largely because I felt that most people viewed tools as a silver bullet whose mere presence would magically make any group better. Even though this was the opposite of how I viewed tools, I didn’t want to unintentionally contribute to this problematic mindset, which I felt discouraged practice.

June's feedback felt like my worst fears come true. Without a clear sense of how it should feel to do strategy or culture work or what it looked like when done well, my toolkits would not be as effective as I wanted them to be for "cultivating chefs." I had written recipes that called for "stiff peaks" without explaining what they were or what the process of creating them should feel like. I swore I would fix this immediately.

Almost a year and a half later, I am happy to announce that… I am still at a loss as to how to do this.

My blog post about alignment was a first attempt, but more still needs to be done. I think my Good Goal-Setting Peer Coaching Workshop is also a step in the right direction. It exposes people to how others use the Goals + Success Spectrum, and it helps develop muscles around looking to peers for feedback, rather than biasing toward self-proclaimed experts. I’m in the process of designing similar offerings for other aspects of the work.

Still, I want to do better. The reason this bugs me so much is that I see groups going through collaborative processes all the time without really understanding how the outcomes are supposed to help them. Consequently, they end up blindly following a recipe, often at great expense, both in money and time. They think they've made lemon meringue pie, but they're actually eating glazed lemon and scrambled egg pie.

If people knew what the equivalent of lemon meringue pie actually looked and tasted like, this would simply be the beginning of a learning process. They'd be able to debrief and make adjustments, in the same way that me and my friends did when we were learning how to cook. But because many people don't, they just end up making and eating glazed lemon and scrambled egg pie over and over and over again. Most people sense that something is wrong, but because they don't know what right is, they keep doing the same things over and over again, hoping that the benefits will eventually present themselves.

The best way I know how to do this is to bring people along in my own work, encouraging them to "taste" along the way, pointing out when things feel right and wrong. It's how I learned, and I think we as a field can create many more opportunities for this. I think it's extremely important that all of us, as practitioners, take time to shadow others and create opportunities for others to shadow us. I continue to experiment with this.

A greater emphasis on storytelling is also critical, and I think that video is a particularly good and under-explored opportunity. If I were trying to learn how to make a lemon meringue pie today, a quick YouTube search would turn up hundreds of examples of what "stiff peaks" are and how to create them. What would be the equivalent videos for all things collaboration? What videos could we, as practitioners, easily make that would help the field understand what effective collaboration feels like? (Here's one of my early attempts.)

What do you think? Have you run across or created really good examples of what a good collaborative process feels like, with all of its ups and downs, be it strategy, culture, experimentation / innovation, or any other process? Please share in the comments below. Don’t feel shy about sharing your own work!

Photo by Tracy Benjamin. CC BY-NC-ND 2.0