Career Inflection Points: Chicago and Learning
By Annie Hedgpeth · October 8, 2023
Career Inflection Points: Chicago and Learning

When I tell the story of how I got my first job in tech, it’s always a fun celebratory vibe, but in reality I was so scared and overwhelmed. I had an immense amount of grit, energy, and desire to accomplish my goal, but then it was time to make new goals, over and over again. Such is the life of a technologist.

The Setup

As I alluded to in the story, my first job in tech was for a small Azure consultancy. I was hired when the company was only about 30–35 people. They hired me first on a four-week contract. It was a smart move. If I didn’t work out, they could simply move on and not bring me on full-time. This lowered the pressure for me, as well. (Thankfully, I had the privilege of already being on Michael’s health insurance policy, so that wasn’t a point of stress for me.)

During the interview and onboarding process, Trevor, the person that had recruited me, had gotten his big break to work at the software company that he had been trying to get hired at for a while, none other than Chef, so he was going to be out of the picture for my training. This left me with a huge amount of anxiety. What if no one else at the company had the vision for what I was capable of, and I was left without a mentor or trainer?

I flew to the home office in downtown Chicago for my first two days, and I don’t know if I looked like one or not, but I sure felt like a deer in headlights. I was dressed to the nines in a nice blazer, dark jeans, slinky white blouse, heels, and jewelry, ya know, like a typical engineer. ;) (This is the pic of me trying on the jacket I bought for the occasion.)

A typical engineer

I did the tour and met everyone. I was feeling pretty good but a bit nervous and uncertain of what the next two days would look like. The office space was one of those open concept seating situations with enclosed offices lining the halls for the phone call people, so I took a workstation and got comfortable. A little while later someone booted me from my seat because that’s where he always sat. Everything that seemed to go wrong, no matter how seemingly small, would increase my heart rate tenfold. I pressed on and tried to keep feeling the fear and doing it anyway, faking it until I made it.

The Problem

In the average technology company, you will get about a month to onboard, making sure your email is set up, installing all of the software you need onto your new laptop, meeting the team, etc. Only a couple of hours into my onboarding, however, they told me to start looking at my very first project: configuring an Elasticsearch cluster with Chef. I didn’t know it at the time, because I didn’t know what was normal, but looking back on it, they threw me into the deep end. I had no idea how to configure Elasticsearch manually let alone with Chef, and I had never even heard of Elasticsearch until that day. I don’t think they meant to throw me into the deep end, but it was a consultancy, they were at the mercy of whichever deal was coming through at the time, and those things are very hard to time with onboarding.

The other engineer I would be working with on this project was kind, a nice person to chat with, and we got along well as work pals, but for this project I remember him being pretty hands-off. I don’t think he knew how much one-on-one onboarding help I actually needed. In addition, I was too scared of asking for help for fear that I would expose myself as an imposter. In reality, they knew who they were hiring.

Being a startup, there was no official onboarding guide. (I eventually wrote it up myself to help those that came after me.) I was given an extra laptop that was sitting around in the CTO’s office and told by the engineer to go familiarize myself with the project. I sat down to look at the code, and I froze. Everything that I had learned in the last few months was out the window.

I ended up texting Michael because I didn’t know what to do. I wouldn’t call him because I didn’t want anyone to know that I needed help. I was so uncertain of what was expected for me to know and what wasn’t. I was already being hired as a risky candidate; I didn’t want to do anything to jeopardize myself. Michael would tell me what was appropriate for me to ask for clarification about and what I needed to look up on my own. I was still sweating bullets, but the guidance helped to ease some of my anxiety.

The Inflection Point–Learning My Way Off the Bench

I realized a very sobering truth in those days–that I was in a unique position to have a husband that was such a good and willing teacher. I realized that most engineers weren’t like him. I became extremely grateful for him. And if you know Michael, you will know that he is a rule-follower through and through. He never gave me answers, but he was so apt at telling me what I needed to learn in order to get the job done. He would direct me to the appropriate tutorials and sit with me through some of those, answering questions and guiding me. He was patient when I was not. Sometimes I didn’t want to hear that I needed to learn an entirely new segment of technology before I could move forward, but he was always right.

I had two or three Chef and InSpec projects right at the beginning (yes, they ended up hiring me full time) with a bonus of a Terraform project (another one I learned on the fly). But after those, the configuration management and infrastructure as code jobs dried up. I ended up on the bench a lot, which gave me a great chance to do a ton of learning, but that wasn’t sustainable, obviously.

They started putting me on Azure Site Recovery projects, which had nothing to do with the things I had been learning, so I realized that I had to be aggressive in learning more. At one point when things just weren’t clicking for me with the online courses, Michael suggested that I build my own computer so that I could see all of the components and make it make sense faster. He was right; that helped a ton. (My son still uses that computer for gaming.)

I did, however, need to focus my learning and become a subject-matter expert of something so that I could be better utilized. I decided to go all in on Chef and InSpec. I got every certification that Chef offered, and I did training to be able to teach Chef. It definitely helped to be better utilized! I ended up getting to teach a one-week Chef training that didn’t go so well because the client said I was too green, but after that I got more contracts on which to sharpen my skills. When I was good and comfortable with Chef, InSpec, and Terraform, I got a long term contract embedded on a team using those skills to bring integration testing via test kitchen to an organization.

Conclusion / Call to Action

I saw learning as an opportunity and an invaluable tool in my toolbelt. I have always believed that I can learn anything that I need to accomplish any job. It may require patience with myself or to deliver more slowly, but it’s better to take the time to learn to do it the right way than to half-ass my way through a project. As time has passed and deadlines loom, I definitely need to remind myself of this truth from time to time.

While my company may have struggled to have the time and leeway to train me themselves in those early days (I don’t fault them–it was a startup), they did allow me to hang on and learn during those times that I was on the bench (and expense the courses!). Also, when I was interviewing with them, I told them that while I was ramping up, I could use my non-technical skills to deliver value to them, and I did! I blogged. I spoke at conferences. I was on podcasts. And I helped to align their brand with one of learning, inclusivity, empowerment, empathy, and drive.

And their investment paid off; I spent year two and three at that long-term client building out their Chef and Azure infrastructure. I spoke at a Chef conference with one of the engineers there, and whenever I came onsite we all had a happy hour because we all genuinely enjoyed each others’ company.

Chef Conf Talk

I talked to numerous companies when I was trying to break in, and most of them probably had a better onboarding process than the one I describe above. However, none of them would hire me. I needed a cowboy company to take a chance on me and have patience with my growth enough to see the ultimate return on investment. Most companies frankly lack that patience, foresight, and creativity.

So in today’s call to action, I would love for you to think about how successful I would have been at your company. Would you have had a superior onboarding experience but an inferior hiring process that would have excluded me? Do you have people on your team who would have believed in me enough to spend their cycles on me? Are you rewarding those people? Or are you rewarding the ones who put their heads down and deliver right now?

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