Adam Jacob: Rebuilding DevOps with System Initiative

Adam Jacob is the original creator of the configuration management tool Chef, as well as the co-founder and former CTO of Chef Software. But he’s got a new perspective as the co-founder of the company behind the new DevOps-simplifying tool System Initiative.

“It’s time to rebuild DevOps” reads the headline on the company home page…

Jacob once famously said that tools influence culture, and culture influences tools. But in September Jacob revisited the topic on an episode of the Arrested DevOps podcast, with Jacob trying to re-emphasize the tooling side of the equation. Now he stated simply that “tooling is culture” — and that people are misunderstanding what he meant by “culture.”

“The idea that it’s about culture and not about tools — was wrong from the jump. And I have regrets that we ever said it. Because look — culture is what you do. That’s what culture is… It’s expressed in our actions.” Jacob thinks much of the DevOps world instead defined culture as the principles you’re aspiring to adhere to — whereas in truth, “it’s a little more works-oriented… The idea that you are going to change your culture toward a more collaborative approach without the tooling forcing a more collaborative approach — was lies. It was never going to work… The tooling must push you together, because individual people won’t do it alone. You have to coach them to it.”

Making the rounds for various podcast interviews, Jacob is now laying out his vision for a tool that can transform DevOps. It’s the product of years of development — and a little soul-searching — distilling what the 45-year-old software engineer has learned from a lifetime spent “building great tools for systems people.”

Taken together, the interviews seem to document the long evolution that has finally led him — and us — to this moment.

But along the way, Jacob is also sharing what he’s learned about the possibilities — and the perils — of the software engineering profession itself.

A Second Wave of DevOps Tooling

In June Jacob appeared on an episode of the Changelog podcast, arguing that his goal was not just to rebuild DevOps from the ground up, but also “change the outcomes for what I think are kind of mediocre outcomes that the majority of us have sort of come to experience…

“We need this second wave of DevOps tooling, where people realize that the problem was systemic and that we need to actually build new solutions that change some of the fundamental rules of how these things worked.”

The original pitch deck for System Initiative had used the phrase “Way more intuitive!” and in the interview Jacob described the product as “basically building this really full-fidelity model of all the stuff that you use.”

There’s a powerful visual interface/configuration diagram with a simulator showing all the relationships within the infrastructure that underlies and attaches to your applications. In an introductory video, Jacob calls it “an intelligent automation platform that allows you to make detailed, interactive simulations of your infrastructure, and use it to manage your real-world systems.”

The podcast even titled the interview “the new DevOps.”

“The tools and the process and the culture I’m trying to create is all attached,” Jacob explained. “It’s one holistic thing — and that is the way that we have to think about DevOps.” System Initiative can drill all the way down from a high-level strategy — even the pitch deck being used to raise money — to an individual story that’s being worked by an engineer. So engineers truly understand why they’re doing what they’re doing…

On Changelog Jacob had stressed that it’s part of a larger goal. “I want to see a second wave of DevOps that’s full of new, interesting stuff.”

Toward that end, in September Jacob made another appearance on the YouTube channel for the Wing programming language. Titled “Bridging DevOps Divides with Adam Jacob,” the episode found the creator of Chef decrying that imaginary gap between sys-admin/operations folks and software developers — usually with software developers at the top of the hierarchy. “For me, that’s one of the reasons I started building great tools for systems people. Because I just — that was always bullshit. It remains bullshit today.”

“If you’re a great operations person, there are skills that you have and things that you can do that a fabulous software developers who don’t know anything about how operational things work can’t do. And in both cases, you’re software developers — you’re writing software. They’re just different kinds of software, for different purposes.

“In fact, all of us were programmers the whole time. The only difference was what kind of language are we working in, what kind of problems are we trying to resolve, and how do we solve them?”

A Continuum of Work

Appearing in September on the Corecursive podcast, Jacob cited specific examples of the way organizations had been undervaluing systems administrators over the decades. The first sign was that there was one lone day in the year designated as “Systems Administrator Appreciation Day” — but that was just a symptom of a larger problem. Jacob remembered a boss’s boss buying beers for a team of nearly two dozen, and actually saying “Happy Systems Administrator Appreciation Day. Too bad none of you are smart enough to be software developers.”

On the Arrested DevOps podcast Jacob looked back to the pre-DevOps era, with companies grappling with a new world where applications ran on the internet. This eventually created an “operations” silo — much like today’s platform engineers.

The problem? “They would try to build systems that would allow the developers to do whatever the developers needed to do without thinking about how the infrastructure worked,” he remembered with a laugh.” And never the twain shall meet….

“More than anything, the number one thing that the DevOps movement did was it recognized that that was a single continuum of work.”

Collaboration would have to happen — a big difference from a world where the explicit goal was to not collaborate. Still today, Jacob sees efforts to just build a better silo — when it’s collaboration makes the difference. “The big problem is that the tooling itself, to me, never was designed for collaboration…

“We’ve rebuilt every single piece of that stack 10 times over in the last 10 years, and it hasn’t made an appreciable difference in the outcomes…”

A CTO’s Epiphany

In reimagining DevOps, Jacob brings a wide variety of experiences. On the Corecursive podcast, Jacob remembered feeling moments of CTO-level imposter syndrome during his tenure at Chef. There are heavy responsibilities in being a CTO — to the company, and to the larger community — and Chef was facing competition from tools like Puppet, and then Ansible, Docker, and Kubernetes.

Somehow this could even raise the stakes of simple internal discussions about the shape of an API endpoint, Jacob remembered in the interview. “Because again, riding on it was not just that API call. It was my identity. If it failed and fell apart, what did that say about me as a person? Does that mean I’m a bad person? Does it mean I never belonged here…?”

“It was lot of pressure on what is essentially, ‘Should it be RESTful or RPC over JSON?'”

But this led to a kind of epiphany — about how startups in general “tend to mythologize everything but the work.” Jacob shared his belief the most impressive thing about someone like Mitchell Hashimoto (former HashiCorp CTO and creator of Vagrant software) isn’t the founding story, or the wildly successful outcome. It’s “that Mitchell stayed in that company, still is in that company, and found a way to be useful and to grow and to change as that company needed him to grow and change… learned how to do the work, and to keep doing it, and to be good at it, and to stay good at it over a very long time through a huge amount of change…”

“It was the work that did it, right? It was all those people who showed up every day and decided to believe in whatever it was you’d ask them to believe in. The work is good and valuable in its own right, and actually the only thing that ever mattered.”

Jacob decided to set some limits on how much of his identity he’d tie to “the outcomes of this capricious monster… you have to be the one to figure out how to professionalize it so that it can be work.” And in the end, it turned out to be a life-changing insight — a kind of total self-empowerment simply by valuing the act of work itself.

It will be interesting to see if Jacob and his team can now apply that same valuing of the work toward their mission of rebuilding DevOps from scratch.

And if this potential-unlocking philosophy can find its way into System Initiative.