This week, I've been sitting with and mulling over Charity Majors's recent blog post Thoughts on Motivation and My 40-Year Career. I also had a chance to have a conversation with her about it, not only about how I connected with the post, but also reflecting a bit about how I've been thinking ahead as I cross into the second half of my career. My conversation with Charity helped me pull together a range of disorganized themes that her post brought up in me that I'm going to try to articulate here.
THINGS OF ENDURING VALUE
For me, the main heart of her blog post expresses why it’s important to be in the business of building the kinds of things that have enduring value. She describes them as institutions:
I’ve come to believe that the most quietly radical, rebellious thing I can possibly do is to be an institutionalist, someone who builds instead of performatively tearing it all down.
People need institutions. We crave the feeling of belonging to something much larger than ourselves. It’s one of the most universal experiences of our species.
When I take stock of the many people and organizations who have been building and doing this kind of work, I see them building communities that serve as the fundamental component of what I believe Charity is calling institutions, and they are not unlike social institutions. The social institutions described in sociology usually include entities like family, education, religion, government, and the economy. What we crave within social institutions like these are things that support us, provide aid, safety, a sense of belonging, and other fundamental, basic needs. These are things of enduring value.
One example of this in the digital space that comes to mind is Rudy Fraser’s work building Blacksky. Blacksky is a decentralized, open source set of social media tools and infrastructure built on the AT Protocol (the same protocol as Bluesky), but with a specific emphasis on empowering marginalized communities by giving them the tools needed to curate and moderate safe, self-governing online spaces.
Building communities like this has enduring value, especially when they are grounded by an ethos that prioritizes equal value, agency, access, and leverage. I strive to embody these principles, and it is a major reason why I recently joined Kim Crayton’s community Profit Without Oppression, a community space for business leaders to connect with one another who believe that business profit should never come at the cost of people. I see Kim building something of enduring value here too, because the guiding principles of Profit Without Oppression helped me gain a better understanding of what will be required to build enduring, inclusive, safe communities.
As I’m crossing into the second half of my career, putting my energy into building these kinds of communities becomes even more important to me. Part of being able to do that means acknowledging what got me to the present moment in the first place.
THE DUTY OF THE TRAVELER
Yours is a long road, my friend, and it stretches on to places beyond imagining.
With your every step, these grand adventures shall grow more distant and faint.
And there may come a day when you forget the faces and voices of those you have met along the way.
On that day, I bid you remember this…
That no matter how far your journey may take you, you stand where you stand by virtue of the road you walked to get there.
For in times of hardship, when you fear you cannot go on…
The joy you have known, the pain you have felt, the prayers you have whispered and answered—they shall ever be your strength and your comfort.
This I hope—I believe, here at memory’s end.
On my personal journey, the roads that I have walked upon and the paths I have taken are ones I know have been wrought by the efforts of countless individuals who built them before I got here. Maybe yours are too. For me, it is simultaneously true that the totality of my journey is unique to me and could not have happened without those who came before me.
Over the past 4 or 5 years or so, I’ve shifted my perspective and practices about what to do about all of the experiences I’ve had and all of the things that I’ve learned along these roads. I deeply resonate with how Dr. Cat Hicks describes the duty of the traveler when she talks about citation as pilgrimage (emphasis mine):
One of the specific ideas mentioned in this episode [Phil Cousineau’s Turning travel into pilgrimage] clicked in my head with citations as well: the long-held many-cultures notion that it is the duty of the traveler who succeeds to come back and share with those at the beginning of the trail.
You are required to pass along what you have learned to others embarking on the journey you have survived. This communal and socially shared obligation is an uncomfortable fit in an isolation-biased world. Do you owe other people your knowledge? I think my answer is yes. We do owe each other. Why? Because my mind was built with other people’s knowledge.
For me, this goes hand-in-hand with building things of enduring value. This is part of how I will do that. I recognize that it is time for me to go back to the beginning of the trail and to share with my communities what I’ve learned. I owe it to both the people who built the roads that made my journey possible and to the people who will come after me.
But why am I choosing to do this?
OWING OTHERS MY KNOWLEDGE IS AN EXTENSION OF MY DEEPEST PROFESSIONAL JOY
As a teenager in the mid- to late-1990s, I felt really comfortable being around computers and tech. I felt a natural affinity and fluidity when I put my energy into solving technical problems.
I also distinctly remember how utterly dismayed I felt bearing witness to people sharing anecdotes of miserable and shitty experiences calling professional technical support to solve the problems they had. In their recounting, they would often describe the worst possible outcomes: their problems weren’t fixed, they felt more angry, jaded, and distrustful of tech, and the practitioners responsible for shepherding the process were either oblivious, indifferent, or unwilling to learn from the experience.
What were the technical support professionals doing that led to these outcomes? I spent a lot of time grappling with this question, because I knew deep down that I would eventually find myself as the technical professional in other people’s experiences. I desperately did not want to repeat their mistakes and I held onto the belief that better outcomes were possible.
So, I shifted my practice of technical problem solving and communication and explicitly chose to meet people where they were, with compassion. I adapted what I said based on the customer’s proficiency and comfort with tech. I followed their lead but used my skill to guide them through the process. When I was successfully able to do those things, I witnessed magic and transformation. I helped a lot of people—family, friends, family of friends, friends of family, strangers—who came to me with their technical problems feeling frustrated by, intimidated by, or scared of tech, and left feeling a little bit of relief, satisfaction, and in some special cases, curiosity to learn more (which I was always more than happy to share my knowledge).
What I did seemed to consistently work, because I kept witnessing these same transformations. It engendered mutual trust and dependability. I was driven by wanting to demonstrate to people that the shitty technical support experiences did not have to be that way. I stuck with it because there was nothing more professionally fulfilling and joyful to me than being a part of seeing those transformations happen in people. It was a cornerstone upon which I built my professional life.
I felt a sense of duty when others asked me to solve a technical problem, both to shepherd people through the process, and always being ready to share my knowledge. I felt like there was no reason for me to hoard my knowledge. I shared my knowledge because my technical mind was built with other people’s knowledge. I owed it to those who wanted to hear it.
Now that I’m further along in my career, the shape of all of my experiences and knowledge as a technical professional is very different than it was as a teenager. Nevertheless, there is a familiarity I feel, a comfort in the idea of going back to the beginning of the trail and sharing what I’ve learned with my community and with those who are about to embark on the paths I’ve taken. I owe it to them too.
FATHER TIME REMAINS UNDEFEATED
I said earlier that I feel like it is time for me to go back to the beginning of the trail. Why now? What’s the rush? There are actually a few reasons why I feel like it’s time. One of those reasons has to do with how I confront and contend with the amount of time and energy I feel like I have left to do what I do professionally while also maintaining a standard of high quality.
My melancholic self cannot help but notice the growing number of days when I feel a step slower, a little less sharp, or a little more tired than usual. The days when I feel at my absolute best don’t come as often as they used to, though I do occasionally still see flashes of it. As a result, I actively calibrate and adjust what it means to be the best version of myself today, so that I can protect and reserve what I feel like I have left.
I sometimes think about how this kind of thing happens in professional sports a lot. How professional athletes will do this thing where they push themselves to play just one more season, or do one more special event. It’s usually driven by an unquenchable thirst to experience the rush of competition, or chasing down an elusive goal. Invariably in these situations, the athlete confronts the reality that their mind may be willing, but their body, at some point, cannot oblige. Sports writers often invoke the looming figure “Father Time” in these situations, and sports history is littered with many, many examples. Father Time comes for everybody eventually. It will come for me too one day. Father Time remains undefeated, after all. So, I’m planning and acting accordingly.
It should be pointed out, of course, that the demands of professional sports and the demands of being a professional in tech are very different. What I’m saying is that even if the end of my career is, at most, two decades away, I’m making my accommodations now to focus on sharing my knowledge with my communities. Building the things of enduring value takes time to build, and it cannot be done alone. It is important to me to have the mentality to build and liberally share my knowledge as willingly as I can for as long as I can on my way back to the beginning of the trail.
GOING TO THE BEGINNING OF THE TRAIL DOES NOT MEAN MOVING BACKWARDS
Building things of enduring value is a nonstop process, and the work never truly ends. Maybe it sounds like I’m sailing off into the sunset by deciding to go back to the beginning of the trail, but that’s not quite right. The way I see this particular work is that I’m building for a future I probably won’t see in my lifetime. I’m contributing to the roads and infrastructure that others will need to walk on after I’m done, with the hope that they will go on to build a safer, healthier, fairer, more equitable, more inclusive world than I could. I will build roads I hope they will use to enact transformative experiences in their communities.
I hope, perhaps naively, that we are entering into a new era of rebuilding, sadder but wiser. An era of building institutions with accountability and integrity, institutions with enduring value, that we can belong to and take pride in… not because we were coerced or deceived, not because they were the only option, but because they bring us joy and meaning. Because we freely choose them, because they are good for us.
My hope is that more and more people get comfortable with the idea of building for something they will never get to see the fruits of, especially if they truly want to build things of enduring value. So much of American or similarly Westernized norms taught me to expect and demand returns for my investments of time, energy, and finances (and modeling measures of worth around ROI). For this work, I have to let go of that idea. I’ve made peace with this. Maybe this is a sobering thought for you, but the reality is that the work still needs to be done and you may not see the return of your investment.
By going to the beginning of the trail, I’m actually aiming my sights to a world of people who will be here well beyond the end of my life. I owe them my knowledge too.
HEALTHY COMMUNITY VALUES ARE RECIPROCAL
I’ve talked a lot about what I owe my communities at the beginning of the trail. But it needs to be said that community values rooted in inclusion, equity, fairness, trust, and justice are reciprocal. The enduring communities to be built, cultivated, gardened, and maintained will also hold me accountable, will value psychological safety, and will be ones I can safely trust.
A lot of the communities I grew up around were not those things. I made myself invisible to communities rooted in inclusion, equity, fairness, trust, and justice because I had grown up believing what my communities taught me about the importance of individualized independence from others and reliance on authoritarian wisdom. I’ve also had to let go and unlearn the ideas of the supposed moral failings of asking others for help. Healthy communities will not cast those same judgments when someone in their community needs help. I choose to follow that lead.
FIND YOUR COMMUNITY
You will know best which communities are right for you. But you need to try to find them and reach out to them if you aren’t doing that. The communities that will be best for you will be the ones that will incorporate you, meet you where you are, and will share with you. People within communities will do this because we all crave that in one another.
The communities I’m investing in are ones that are extensions of my deepest and most profound joys. A lot of the knowledge I have to share with my communities comes from what I’ve learned in my tech career. Those communities may change and they may go on to do things I cannot fathom. As I venture to the beginning of the trail, I will keep asking myself whether what got me here still works for me. I may leave some communities and join others. That’s ok.
The roads of the second half of my career are what I hope will carry enduring value—what I leave behind for others. I want them to be lined with the kinds of communities I’ve learned to treasure and want to see in this world.