Getting Lost - Career Moves
Breaking my own career in pursuit of discovery
Next week I’m going to return to a very different role, a very different career, and a very different path. Our industry is shifting, and I wanted to approach that change from a different perspective. To do that, I had to make some changes.
Earlier this year I was leading the largest organization of my career as a Sr Director at Workday, overseeing engineering teams across both our Financials and Professional/Business Services pillars. This organization was composed of 6 major product areas across two group GMs, and I was honored to have had the chance to take on this multi-industry and multi-product engineering area. Supporting these teams and leading this area was a huge growth experience.
By all accounts my career was on the right path, but something felt off. At first I thought that I needed to shift my mindset about the next stages of my career, to get more comfortable with the demands of a growing organization. As I worked with a coach and talked to others about what I was seeing, feeling, and getting energy from, the path forward became more clear. To really address what I was sensing, I would need to exit this career path and go another direction.
What I’m seeing
Memorial Day 2025, the weekend after the release of Sonnet 4, my personal experience building with AI turned a corner. That weekend I shifted from arguing with Sonnet to cranking out features. Feature after feature fell into place and just worked. By Sunday night I was out of ideas. It felt to me like a switch had flipped and building with AI became completely viable. The only thing that had changed was a model version.
Overnight, with a single model release, an entire product category of AI coding agents gained new capabilities. I hadn’t written a line of code in over 8 years, but here I was building functional apps in a weekend. In the coming weeks I built another, and another, and suddenly found myself distracted in my day job by what I was going to work on when I got home. My evenings and weekends became consumed by building, learning, and trying to understand how to harness these new tools.
This step change would happen a few more times in 2025, and each time we are able to do things one day that we couldn’t do the day before. This reminded me of when I started in tech back in 1997, the Internet was new and technology was moving fast. To keep up you had to be resourceful, hungry, and take your own initiative.
To take your own initiative takes energy and time…
What I’m feeling
While I spent my evenings and weekends cranking on apps using every AI tool I could get my hands on, something else was changing. Our workforces were shrinking and companies were rapidly expecting AI to improve the bottom line for them and their customers. Talk of AI replacing jobs gave way to actual layoffs. Whether or not these two things were related doesn’t matter - the trajectory became clear to me.
What I was seeing in my own use of AI made me increasingly uneasy about being a manager of hundreds of people. I wasn’t very worried about whether or not I’d have a job - I was worried about what that job would be. How many people would I be responsible for? How much connection to those people would I have? How would our drive for efficiency re-shape what it meant to be an organizational leader? My hypothesis was that I would be expected to lead a flatter organization, with less operational support, less leadership support, and more interrupt-driven work than ever. While coding with AI had felt revolutionary, the tools available to leaders operating a large organization were not experiencing this same pace of advancement.
My daily experience became an energy drain. My pessimism about the future of roles like mine, combined with an insatiable pull toward returning to a maker’s life - building and shipping things - made daily work more difficult. More than anything else I wanted to learn and experiment and build and ship - and doing that while holding up a day job leading a large organization felt incompatible.
What seemed inevitable to me was that the shape, size, operating model, and basic principles of running organizations would need to change in dramatic ways. I am deeply interested in exploring this, but that option is rarely available in large established organizations. These ways of working haven’t been written yet, and the exploration of what’s possible is mostly taking place in small teams and small organizations.
So, after careful consideration, I blew everything up…
What I’m doing
Next week, I return to a part-time IC role at Workday after a six-week sabbatical. Aside from one week spent on vacation, I spent the other 5 weeks of this time building a new business. You can see the beginnings of our ideas at nodaste.com. The site is very light on details, which is probably the biggest story here, we don’t know exactly what the world needs from us yet.
What has become clear is that tiny teams have a lot more oomph than they did this time last year. I’m grateful to have 3 partners who round out a very capable set of experiences and skills. We enjoy working together, we care about doing that in sustainable ways, and we care about helping others in the process. That’s really all I need to get going.
In a very real sense, we are getting lost for a reason. With these tools, the pace of learning is magnified so much when you are outside the constraints of the corporate world. While corporate policy and structure serve important purposes, rapid experimentation and access to the latest emerging tools are not their strengths.
What’s next
We are deep in discovery mode, connecting with as many people as possible about what they are experiencing in their own organizations as AI comes charging in. We’re exploring different approaches we could take - from providing professional services to building and operating our own products.
You’ve read this far, maybe you have thoughts to share that would help shape this.
Over a few short months we’ve proven to ourselves that we can build and ship products. We’ve proven that we can operate an organization in new ways with new tools, and we’re convinced that these tools are going to re-shape organizations of all sizes. We’re excited to work with teams on that journey, figuring out together what the future looks like, and my goal is to write about what we find as we go.
There are so many things that I don’t have answers to, and I think that’s what excites me the most. This book isn’t written, the playbooks are all out of date, and we’re going to have to work together to navigate the future.
Synchronicity
I asked a friend to read through this and she pointed me to an article from Ryan Martens published earlier this month: We Sit At a Precipice Between Systems . I have deep respect for Ryan, I learned a lot of what I hold dear about how humans can work together from working at one of his companies - Rally Software. In this article Ryan writes:
Today, something rare is happening. We sit at a precipice between systems: an old system in which human intelligence commands instrumental technology, and a new system defined by the interaction between human intelligence and superintelligent technology.
It is at this threshold that systems thinking doesn’t ask us to make incremental tweaks to the existing system, but rather to leap into the new one. In the old system, we adjust the variables of a known game. In the new system, we discover new, unknown games. In the old system, we accept and work within the established rules. In the new system, we help shape the future rules.
In new systems, the difference between those who thrive and those who flounder is one thing: the ability to take responsibility.
This nicely describes that anxiety I felt earlier this year to jump into this new system with both feet. Ryan made connections back to that period in the late 20th century where it seemed clear the world would never be the same. We are there again, and I’m here for it.
If you too are jumping in with both feet and want to connect, I would love to hear your story.