Yet Another Year in Review - Year 04.5
I’ve now been working for myself longer than I’ve had any other job. May 2024 marked 4 years and it felt a bit surreal, not because I didn’t think that I would get here, but because being here has felt so gratifying.
Many of you who know me have heard me struggle to explain what I do over the years. I’ve used broad and ambiguous descriptions (“I work for myself.” “I’m a consultant and advisor.”), specific and somehow-still-ambiguous descriptions (“I help companies make better decisions.”), and specific-but-incomplete descriptions (“I help companies build and scale research practices.”). By now, I’ve realized that the best way to describe what I do is perhaps the simplest (and the closest to what I first wrote when I made a /projects page a few years ago) — I work on projects I care about with people I respect.
This privilege is not lost on me.
While I tend to do a mix of looking back and looking ahead, because we’re 4+ years in, I thought I’d do a more comprehensive retrospective than just the last year and save most of the looking ahead for a later time.
Looking Back
Since May 2020, I’ve been fortunate to do paid projects with 24 organizations (and unpaid projects with a number of others) ranging from single day workshops to multi-year advising relationships, over 90% of which have been with former colleagues or the result of a direct referral from someone I know. I’ve given over 30 talks at public and private events (not including podcasts), and built 3 courses with Reforge which have had over 1,000 members participate live (and many multiples of that engage with the content on demand).
As I’ve looked back across all of this work and my partners, I’ve noticed four different eras, roughly corresponding to each year:
Y1 — Scaling Research Practices
Y2 — Research as a Trojan Horse
Y3 — Problems, Not Projects
Y4 — Being Hired to Care
Year One — Scaling Research Practices
My first year was exploring in an attempt to answer the questions “Can I do this?” And “Will anyone pay me?” I owe a ton to Cristen Torrey who brought me to Figma (my first real client) and gave me the space and encouragement to bring my whole self to the work.
In this first year, no two projects I did looked similar, and I intentionally took on work that was different to help me calibrate on what I actually enjoyed doing versus just what I thought I was good at. While I knew that things were going to be different and challenging, I hadn’t predicted that we’d see a global pandemic or that I’d be spending the vast majority of my time in a loft in San Francisco.
Thankfully, this year came with the development of my first Reforge course and the groundwork for what followed.
Some of the most important things I learned in year one:
Start warm — I had an idea of what I wanted to do and who I wanted to partner with. This made it much easier to build momentum as I could reach out to people and have conversations instead of pitch and it allowed us to shape the work together rather than have me show up with a menu of options (which I most certainly did not have at this point).
Be flexible — I didn't know what my offerings were, outside of being “me-as-a-service.”, so the best way to learn was to try different things and iterate on what worked.
Say no quickly — Everything has an opportunity cost, and you should do your best to focus on the things that you're uniquely qualified to do AND excited about doing. When you think something isn't a fit, don't waste people's time.
More lessons in my year one review.
Year Two — Research as a Trojan Horse
As I started year two, I got a glimpse of how powerful network effects are when it comes to being self-employed. Both former colleagues and new connections through Reforge made up the vast majority of my inbound inquiries and actual projects.
Conversations during this year shifted from being just about research to being about what research enables; the decisions that needed to be made because of research and the next steps to take. It was during this year I was able to move beyond just research conversations and into work that clients were doing around product and growth. In many ways, research was a Trojan horse that got me into the conversations, but the work started to feel less about research itself and more that research was necessary to do the work that the team wanted. Over time, I was being invited into more and more of the latter.
Some of the most important things I learned in year two:
Manage your energy, not your time — Working for myself has a very different rhythm and I realized that certain activities were a better fit for different times of day based on my energy. I experimented with my calendar a lot this year to block out time for what mattered and learned a lot about what I needed to be the best version of myself personally and professionally.
Playing an infinite game — I strengthened my conviction that I wanted work to be a set of things that nourished and challenged me with people I respected and could learn from. This shifted my approach to projects and my offerings as I started to focus less on the products or projects and more on who I got to play with and what those games looked like.
More lessons in my year two review.
Year Three — Problems, Not Projects
By year three, I felt as though my inbound was divided. Half of the organizations coming my way needed research help and the other half needed my help, though they couldn’t necessarily describe what that was.
Writing and speaking had created surface area for people to engage with me and my ideas, and I found more people reaching not for what I have done, but for how I thought about things. I was being invited into problems, not just projects.
In my Year 03.5 review, I noted "it’s easy for me to see that I’ve been much more of a speaker, writer, and teacher than a consultant" and that this was a bit disorienting. But I used that as fuel to take consulting seriously, and I think that meant I was able to separate out writing and speaking about things I noticed or experienced from the work itself and let them fuel each other, rather than be directly connected.
Some of the important reflections I shared in year three:
Leverage — This was a key idea, both in my own work (how do I function as leverage for the people who hire me?) and for those I'm engaging with (instead of working on "the most important thing" go focus on contributing in the highest leverage way). It showed up in a number of talks and workshops and is still an idea that feels like it needs more exploration.
Sabbaticals — Even though I was better at managing my energy on a day to day level, I wasn't thinking intentionally about the on-season and off-season over the course of the year. I intentionally carved out periods without work so that I could exhale, reflect on the work itself, and recharge. These have become a more regular rhythm in my year.
Side Projects — At various points throughout the year, I felt that I was looking externally for inspiration rather than tapping into what's inside. I decided to give myself permission and space to play on my own, doing things (like sending postcards) that maybe didn't make sense or seem valuable to the business, but were crucial for helping me stay nourished. These had different expectations and rhythms, but became apart of the fabric of the year and challenged and stimulated me in different ways.
More lessons in my year three review.
Year Four — Being Hired to Care
The last year has felt like the biggest shift in my work since I started, with the kinds of people and problems that come my way having the least consistency or legibility.
I've had the chance to work with a city chamber of commerce, facilitate workshops for entire companies, help reimagine what innovation looks like within an organization I've long respected, and advise CxOs in industries ranging from construction automation to healthcare. I've also started coaching a few individuals at their request. Across all of this, I've felt empowered to be myself (all of myself) and do whatever I can to help the people I'm working with.
Throughout this year I realized that this orientation is because I'm hired to care — both about the people and the companies I'm supporting. While this sounds a bit generic, it reminds me a lot of the only "rule" I was told when I worked at Nordstrom; "use good judgement."
As I mention in the linked post above:
The empowering aspect of this is that without a lane or a specific role that you're supposed to play, you can draw from your full toolkit. This quickly shifts you from playing sheet music to jazz... When you're hired to care you have to trust yourself a bit more and ruthlessly prioritize what you believe will move the business forward, since people will rarely specify how you should contribute.
I think that I'm still internalizing what this shift means, beyond feeling more emboldened to trust myself and do the things I think are right, regardless of whether or not they seem fitting initially. But this orientation has opened more doors, allowed me to have more interesting (and useful) conversations inside of organizations, and do better work.
Note — I'm continuing to chew on this idea as a part of series I'm writing about consulting. If this is interesting, let me know. I have some drafts of upcoming essays I'd love your feedback on.
What I (Still) Love
If it was not already clear, I'm so grateful to be able to work with people I respect on things I care about and earn a living. Almost nothing on my journey so far has been consistent except for that fact.
Before I left Slack, my brilliant coach Sunil Arora told me that close contact partnership (like coaching, advising, etc) doesn't scale. This wasn't a challenge so much as a reminder that the work I wanted to do would not require dozens of clients at the same time. I've realized that I do my best work with a small portfolio of things in parallel, often of different modalities (coaching, teaching, consulting, etc). I'm thankful that I've created a vehicle by which I can do that and continue rebalancing the portfolio across seasons and years based on my curiosity and potential partners.
Over the past few years I've gotten to play, explore, learn, build, and engage with so many different people across so many different topics. While I imagine I could create this kind of experience within an organization, it's hard to imagine that it would have been as nourishing or come with as much growth.
I'm excited to continue playing this infinite game, learning from others on similar journeys, as well as those in other industries who have professional lives of the same shape.
What I (Still) Struggle With
No journey worth going on comes without a challenge (or many), but two have really stood out, especially over the past year or so.
Communication & Management
One of the biggest lessons this year showed up in a few different places as I failed to manage clients effectively. The benefit of being hired to care is that you're given incredible latitude to do the work you think needs to be done. But in working across different altitudes and with different teams, I often failed to create the right anchors around the work.
In one case, this meant that I went from talking to a key stakeholder multiple times a day to only once every few weeks. This was a miss on my end and something I noticed too late, as even a lightweight (async) check in on a weekly basis would have helped me better focus my time and energy. While I'm only in favor of processes or systems that support the work you're doing, I've learned that certain structures are worth setting up initially and then opting out of, while others are much more build as you go.
My learning here was "over-communication" looks a lot more like "good communication" than I probably think, especially when you're on the outside.
Trusting Myself
I've talked about the importance of hard and fast no's, but I think that four years in, I've learned that the ideal projects to take on are a hard and fast yes. In most cases that I took a few days or weeks to think about an opportunity, it probably wasn't the right call (as measured by whether or not I felt like I did my best work).
I mentioned to a friend recently that I think about every opportunity in terms of learning and earning. I need to write more about this, but I've found that the following diagram helps me think about how to prioritize potential partnerships:
There are reasons to take on projects in each of the quadrants, as much as I'd prefer to stay on the (top) left side of the diagram. But being clear on what the opportunity looks like and what I want out of it (especially compared to what I can get out of it) is critical for my own happiness and sustainability. There are times where I want to play in a new space or learn about a new area, and I'll do that for less money than another project may pay. This is one of the benefits of the portfolio approach I mentioned above — I can pull the learn lever or earn lever as I want or need with each opportunity.
Looking Ahead
I generally try to take some space in these reviews to look ahead at what's to come and call out some themes or vectors that I'm exploring. However, I'm currently in the thick of a few projects and some significant personal life events, so I've been a bit more heads down than heads up lately. (I’m hoping to actually get back on schedule and post Year 05 this May with more words dedicated to the future, but man plans and God laughs, so here we are.)
I'll wrap this up with a few hopes for the year ahead:
I hope that the fifth year of the studio comes with the same kinds of opportunities to work on good projects with great people that I've had in the first four.
I hope that writing and speaking continues to be a tuning fork that helps me identify people with whom my ideas resonate and can push my thinking.
I hope that I can continue to bring together good people for meals and events, creating meaningful relationships that exist on their own.
Thank you to the many people who I've been able to partner with and learn from over the past year. As I mentioned, I don't take this privilege for granted.
Appendix
Here's some of the public-facing things I've done since November 2023:
Writing
I partnered with Adam Fishman on writing Mastering Product Discovery Part 1 and Part 2.
I wrote about "Me-As-A-Service"
I wrote about "Being Hired to Care"
I contributed to the Maze playbook on Embracing the Evolving Role of User Research.
Speaking/Interviews
I appeared on Reforge's Unsolicited Feedback Podcast with Fareed Mosavat and Ravi Mehta (Part 1 and Part 2).
I spoke with Kate Syuma for Growthmates about making decisions with user research.
I was interviewed for the Calyx Consulting Substack on when to do research versus go with your gut.
I spoke about Investing in Insights Infrastructure at Dovetail's Insight Out Conference.
I spoke about the Four Pillars of Voice of Customer Practices at Monterey.ai's VOC24 event.
I was interviewed by Elan Miller for Off-Menu’s Newsletter about how rules are meant to be bent.
I spoke at the Adverb Founders and Friends offsite about understanding customers.
Other
I taught cohorts of Effective Customer Conversations in December, January, March, July, and September.
I partnered with Fable on an Accessibility Roundtable for UX leaders.
I co-hosted the Niche Research event in Seattle with Sarah Sled + Learners.