Career Inflection Points: Networking
By Annie Hedgpeth · October 5, 2023
Career Inflection Points: Networking

In my last post in the Career Inflection Points series I walked you through a nice evening of inspiration called A Big Dinner where I made the huge decision to try my hand at technology. I left that story remembering how full of hope I was. I also remember how terrified and overwhelmed I was. Today, though, I’m going to talk about the inflection points that made the hard work a little more worth it as I started to see it all come together.

The Setup

After that dinner, we got to work. When I say we, I mean me and Michael. He is the one that designed my learning program, a very patient and wise teacher without whom I would have had no idea where to start. We started with some basic Git, and it was hard and confusing and I hated it oh so much. I remember one day crying out of frustration, and Michael said, “Don’t worry, everyone cries when they first learn Git.”

Just straight learning for the sake of learning was difficult and not very motivating, though, so we had to build in the two magic ingredients: a problem to solve and a sense of urgency. After getting to a basic knowledge of Git and InSpec, I had begun creating the blog series on InSpec that I told you about, and it definitely had those two magic ingredients.

I had created a following on Twitter composed mostly of Chef community folks, and to create a manufactured sense of urgency, I would tweet about my upcoming posts. This held myself accountable as well as served as marketing for myself ( and free marketing for InSpec).

The blogging and the tweeting were going well, but the learning was still a grind. I was stretching brain muscles that had never been used before. It was very smart that Michael suggested that I combine the learning with something that I enjoyed, blogging. This took the edge off of the pain of tech-learning and let me use my writing muscles, muscles that were already in good shape.

The Problem

Still, though, it wasn’t enough to break into the industry. How was I going to know where the opportunities were? How were people going to know me and see how passionate I was about the change I wanted to make in my career and life? I was going to need to do some networking and see people in person to show them what I was made of. But how? I didn’t have a job and wasn’t yet part of that world.

The Inflection Point–Conferences

I started looking for opportunities and making them if I had to. I started talking to recruiters and to whomever would talk to me. I also started looking for conferences. Michael had heard that DevOpsDays Dallas was in its infancy and planned on doing their first conference that year, so I emailed them. What did I have to lose? I was so eager and desperate, and they graciously gave me an amazing opportunity to be the sponsor liaison, soliciting all of the vendors for sponsorships. I ended up meeting dozens of people through that role! It was perfect.

During the time that I was organizing for DevOpsDays, ChefConf 2016 was just around the corner, and it was in Austin, just a three-hour drive from where I used to live. Michael was already planning on going, as his company was paying for it. I, however, was unemployed, and let’s face it–those conferences aren’t priced for folks to pay out of pocket but rather for employers to pay for them. So I had heard about a scholarship I could apply for, wrote a letter for my application, and got in! I was so excited to get to meet all the folks I had been interacting with on Twitter. (Here's a pic of Michael and I yucking it up at the photo booth at that conference.)

Michael and I at the photo booth at ChefConf 2016

And then the coolest thing happened. Matt Stratton was working at Chef at the time, and he knew Michael from being his customer success architect (or something), and he followed me on Twitter. Well, he hosted (and still does) a podcast called Arrested DevOps, and he asked me if I wanted to be on the live podcast that they broadcast from ChefConf to talk about my experience. I still can’t bring myself to listen to it because I was so green and just excited to be there, but it was such a great opportunity and a perfect example of someone lending their privilege to someone. They saw my passion, excitement, and dedication and gave me the benefit of the doubt.

Arrested DevOps Live at ChefConf 2016

While I was there, I met Trevor Hess, an Arrested DevOps co-host who recruited me to the cloud consultancy that he worked for at the time. And when I say recruited, I really mean fought for me. I was a huge risk to a consultancy. Bench time is money down the drain. I didn’t know enough to be fully billable as a consultant yet, but he saw the potential. It wasn’t just him, either. The folks that interviewed me liked me and had to convince the CEO that I was worth taking a chance on. But it worked! I fought tooth and nail for it, but I was able to show up to DevOpsDays Dallas as a Cloud Infrastructure Engineer representing my new employer.

DevOpsDays Dallas 2016

Conclusion / Call to Action

Was getting my first job in tech in this way the easy way? Absolutely not. Was there any other way that would have yielded the same results in the same amount of time? Absolutely not. Would I recommend others do it the same way that I did? Absolutely not. There are definitely some fundamental pieces that I do recommend, but overall, I think I got lucky. I have seen a lot of people work just as hard as I did who didn’t get the big break that I did, and it’s not their fault. I think it’s largely the fault of crappy culture in the industry. People aren’t willing to incur any risk, even if the upside is far greater than the potential downside.

It’s wild to think that I got my first job in tech in this way, but the math adds up after you consider the equation. If Michael didn’t have an established network that I could piggyback on and if he didn’t spend all of that time teaching me, none of this would have been possible. So what do people do that don’t have a Michael? They struggle!

So why don’t more people decide to take a risk on folks like 2016-me and invest in the upside? It’s a lot of reasons, really–rather excuses. They don’t think they can support the new person’s learning. They are afraid that the new person will be a burden. They don’t have support from leadership to take the risk. They aren’t organized enough to know how to manage and teach the new person.

In my humble opinion, I think that all of those excuses are unfounded. If you have been in the industry more than 3 years, then you should not only be growing your own technical skills, but you should also be growing your leadership skills. Even if you are learning how to lead your first solo project, part of that is learning how to impart your knowledge to others. This is a skill that is sorely lacking in technology.

Growing someone so new to technology is the perfect engineering problem to solve! How better to learn how to create efficiency and performance in a system than to develop those skills in others. I urge you to start this in whatever work you’re currently doing. Is there someone junior on your team that you can practice on to build your confidence in this area? If you are wholehearted in this endeavor and treat it as important as learning the last difficult technical skill that you learned, then I promise you will both yield impressive results.