The next important inflection point in my career life happened at dinner one night. If you are following along, I walked you through how I got to that dinner by way of the kindness of family, an actor who believed in me, and the decision to be a stay-at-home parent. Fast-forward ten years…no wait, let’s hit some highlights of those ten years first.

The Setup

I ended up having three boys in five years, and I was your typical stay-at-home mom overachiever. I went to the mom groups and the library singalongs for toddlers, had a lifestyle blog when those had first started to gain traction, ground my own wheat for my homemade bread, made sourdough before pandemic made it cool, made yogurt and baby food, cloth-diapered for a stint, was the chair of the welcoming committee for my neighborhood association, started running half-marathons and went to the gym 4—5 days a week, helped build the garden at the kids’ school, had a high school foreign exchange student; you get the point. I was busy and needed outlets for my energy.

At the time, I was committed to being a stay-at-home parent for the long haul, but I also had this growing desire to cut my chops in the work world and see what I was capable of. While I was learning this about myself, I had started a few side projects. I blogged for YNAB when they first started doing it. I started a home decorating business. And I made home decor pieces out of reclaimed wood. As you can imagine, none of that was very lucrative, but it gave me the itch to go back to work.

The Problem

I didn’t think that I could go back to casting because my former casting company had relocated, and I would have to start from scratch, making peanuts. I wasn’t too keen on that idea. I had been home for ten years, so I wanted to jump into a new career that would give me a better starting income that would better reflect the value I thought I could bring. That was going to be a challenge, but I was up for it.

The spring semester before my youngest kid was to start kindergarten in the fall, I started experimenting. How could I use the experience that I had to transfer into another career? I started interviewing people in careers to ask them about their jobs and get an idea of whether it was possible for me to make the leap into those careers. I also started studying for the GMAT, thinking that I would need to get an MBA to make a meaningful career transition. I didn’t know what I wanted to do, but after studying for the GMAT, I knew that I didn’t want to be in school for another two years.

Meanwhile, during these past ten years, Michael had been growing his career, starting out as a software engineer, then architect, then engineering manager, then director. He began a huge DevOps initiative at his company and was really successful in moving his products to the cloud, providing faster, safer, more reliable delivery of their products. It was quite a gutsy venture for him to take this on as he was at an old school, behemoth of a company that wasn’t exactly known for the popular DevOps maxims like move fast and break shit.

Every day, he would go off to work and come back home and vent. He’d vent about not getting traction with his initiatives and how there were people just resistant to change. There was one particular sticking point that went on for about a year, and it centered around security and compliance.

We’d talk it out together, and I would urge him to see how he could approach these blockers from a social and emotional perspective. What did his blocking colleagues really want? They were, after all, responsible for the security of a major point of sale software through which millions of credit card transactions were run. They weren’t just trying to be difficult. They had a lot of responsibility on their shoulders. How could he come to a compromise? How could he show them a better path forward? They had to have valid reasons for blocking; how could his solutions help them?

So the DevOps transformation that Michael was pushing at his company was centered largely around Chef tooling for configuration management to better enable cloud migrations. His company was also required to be PCI-compliant, and what fortuitous timing, Chef had just acquired the up-and-coming auditing framework, InSpec.

I wrote about the whole fantastic transformation here, but the

TL;DR is that InSpec was created with empathy in mind first. The creators knew that many security and compliance folks at the time weren’t developers and that these folks were getting nervous about everything moving to code. InSpec provided a way for them to write their audits as code, but the framework they created to codify everything was simple, elegant, and actually pretty fun to write. So while all the IT folks in organizations were moving to an Infrastructure as Code (IaC)and Configuration Management mentality, the Security and Compliance folks wouldn’t be left behind. They could have Compliance as Code using InSpec.

This changed everything for Michael’s initiative. He was excited to learn how to codify a bunch of the compliance audits himself and show it to the Security folks, teach them how to do it, and change their minds. But he still faced resistance. He realized that while he was out building relationships with people in the Chef ecosystem, the Security folks weren’t a part of that world at all. They were missing out on a crucial part of the solution-people and community.

Michael began to realize that his initiatives were benefiting from him being part of a thriving DevOps community. He had access to solutions, people to help and bounce ideas off of, and excitement! He realized that he needed to bring his Security friends into this experience so that they could make informed decisions from a similar perspective. So we decided to do what we do and invite everyone to our house for dinner for some good face-to-face community building.

We invited the two main Security and Compliance guys at his company, Michael’s VP of Engineering, the Chef salesperson who was so instrumental in getting Michael unblocked on the Chef side of things, and the two creators of InSpec who were so humble and excited to see their product solving real world problems. Michael and I were excited, too. We saw how people were enabled to come together to solve a problem with kindness and empathy and how the design of a product enabled that, and we thought that was something really special.

We had a lovely dinner where we discussed that specialness and thanked Christoph and Dominic for building empathy and kindness into their product. I loved how it was about so much more than just helping a major company make more money. It was about humanizing the people that make the world go ‘round and helping them to be just a little bit more joyful while they go about their work life, building a community of kindness, knowing that other people are looking out for them.

Sure the dinner was a strategic move on Michael’s part, but he just really liked this way of working—in community, with empathy, and seeing his colleagues as people and not hurdles. We invited them into our personal space to eat our food and drink our wine with the risk that our elementary aged boys could get in a screaming match at any moment. And he invited the Security people to bring all their objections to the table, literally! They had the opportunity to bring their fears, their disagreements, their skepticism, all of it, to the creators of the tooling themselves to talk it out in a setting of community and warmth.

By the end of the dinner, everyone felt heard and ended up on the same page. It really was a celebratory moment because it not only accelerated their DevOps transformation, but it changed the culture in their organization to one of an automation-first mentality and even more important—empathy.

The Inflection Point — Just Give It Two Weeks

After everyone left and Michael and I were clearing the table off, and he said, “Why don’t you learn InSpec as a way of getting into technology?” Oh dear reader, I cannot express how dumb of an idea I thought this was at the time. “Uh, because I don’t know the first thing about computers, maybe,” was my response. “No, I’m serious. They say that it’s such an easy framework to learn. You could learn it, as someone who doesn’t know coding, and you could blog about your experience and report if it’s really as easy as they say.”

He had my wheels turning at this point, but I still thought that I was the worst person for this job. I had never even opened a terminal before, but I didn’t even know enough about technology to use that as an argument in that moment. It was nuts. “Give it two weeks,” he said. “If you hate it, then you never have to do it again. But if you start getting the hang of it, then you can use that as a jumping off point to learn more.”

I wasn’t convinced yet, but the thing I loved was witnessing the power connecting the social problem with the technical problem. It gave me a view of tech outside of what I had been conditioned to think—that it was just about sitting behind a desk all day coding. It was more than that! It was about problem-solving, sure, but if you embrace the humanness required, you can create win-win situations all the way around.

So I reluctantly started learning it. The process was painful, but Michael was the most patient tutor. We would wait until the kids were in bed, and we’d stay up until 12—1AM every night. Ugh, just thinking about it stresses me out all over again. I had to start from scratch. The genius behind Michael’s scheme, however, is that since I had to start from zero knowledge, the resulting blog posts that I wrote to teach people how to use InSpec assumed that the reader was just as uninformed as I was. This resulted in extremely simple and useful tutorials for a wide range of skill levels. Michael’s idea was pretty genius.

Conclusion / Call to Action

Part of the reason that my transition into tech is so difficult to replicate is that there aren’t many Michael's in the world. I honestly don’t know many people that are willing to sit with someone, even someone they love, for hours each day for months to teach them something that may or may not work. He had a dogged determination to give me opportunities for which my education and upbringing had robbed me. He knew that I was smart enough, determined enough, and stubborn enough to make it work, but it was still a huge amount of work for him.

So this is not a call to action for all the folks that want to be in tech to just work hard to learn a technology as a jumping off point. This is a call to action for all of you with the means to help someone. Is there someone in your life struggling to make ends meet that has the drive, intellect, and potential to make it in tech and make a salary that could change their lives and their family trees?

I will say that being a double-tech-income family has changed our lives significantly. Our children have opportunities that we didn’t dream of before. I don’t want any of us to be knowledgeable-hoarders or gatekeepers. The more folks from non-traditional backgrounds that we can bring into tech, the better it is for everyone. I hope you will look for opportunities to be a Michael for someone.