My Software Engineer Journey – (10x Income in 5 Years)

In the beginning...

Let's go back to where my Software Engineering career begin. Back to 2015, 5 years ago, where I experienced one of the most challenging times of my life at the age of 23.


It was February 2015, a month from my 24th birthday, and I worked at T-Mobile making $35,000 a year (including commission) in California, a high Cost of Living area. Needless to say, I lived paycheck to paycheck, taking hand-outs from food banks and churches, making payment arrangements, and borrowing from family to keep food in the house.

I was married, but going through a divorce after my (now ex) wife had an affair and decided to stay with the guy. I found out about this affair the day before Thanksgiving in 2014.

The divorce was the driving factor that finally caused a change in my life, and it lit a fire that is still burning strong today. I consider it one of the best things that's ever happened to me because of that.

I decided to get a fresh start in life and moved out of state to Boise, ID. A friend of mine offered to put me up for free for a month, and I took advantage, transferring to a local store in Idaho and maintaining my roughly $35,000 a year income.

Forming a plan...

With the mindset of wanting a fresh start, now was the time to form a plan. I was about to turn 24, and I decided I was finally going to do the things I wanted to have already accomplished. I made the following list of 5 goals that I wanted to complete by the time I turned 30 in March of 2021:

  1. Go back to school, earn a Bachelor's degree
  2. Break into the IT Industry and start my career
  3. Pay off all of my debts
  4. Purchase my first home
  5. Get back into the physical shape I was in while in the Army

With a plan outlined, I knew my goals and I set out to tackle them one at a time.

Getting my foot in the door...

In August of 2015, I enrolled in school at Western Governor's University (WGU), an online school that has full accreditation and a better reputation than say, University of Phoenix or ITT Tech, but it's definitely not a top school by any means (sorry to my fellow alumni, but it's the truth). The classes weren't bad, but not the best either. That said, it's what helped me get into the career field. My favorite thing about WGU, was that they allowed me to test out of classes as soon as I felt ready. This could mean within a day, I could finish a class with full credit, or I could take a few months, it was all in my hands.

Around this same time, my roommate referred me to a position as a contractor for Hewlett Packard (HP Inc). I was doing manual software testing (QA), following test plans, writing bug reports, and staring at printer outputs all day. It wasn't glamorous, but it was a start and I truly believe the test-first mindset I carry came from this first experience. This role increased my annual income to about $40,000 a year, and was a stepping stone in the right direction for me.

My first Software Developer role...

A year later in August 2016, I was about halfway through my full "four year" degree with WGU. Again, I was able to complete this so quickly due to what they call, "accelerate your learning," which allowed me to test out of courses as soon as I enrolled in them. I was doing upwards of 30 units or more per term, with a goal to finish as soon as possible.

I co-founded a Slack workspace for WGU IT students to connect, network, form study groups, and more since the school had little in offerings for students to collaborate together. The group was founded in April of 2016, and we had over 1750 members within a year. The Slack workspace has since been replaced by Discord with a new admin, however at termination we had over 5000 students and alumni working together, networking, and sharing best practices.

Through networking within this Slack group, I was able to get an interview with Hewlett Packard Enterprise (HPE) as a junior Software Engineer (SWE), not as a contractor, but as a full time employee, working in Java. This role netted me a sweet $50,000 a year, my first salary role, and it felt amazing.

Moving on up...

By March of 2017, I graduated from WGU with my Bachelor's degree in Software Development, and I had begun looking for new-graduate and new-hire jobs.

I was able to find a local position at a start-up, and accepted a role as a Software Development Engineer in Test (SDET) at $70,000 a year, working in C# .NET. I was ecstatic to have doubled my income in just two years, and the company benefits were fantastic as well. I really shined in this role, and started delivering Lunch and Learns (Brown Bags) to the engineering organization on aspects of the Test Automation world, with an emphasis on "shifting left."

Through initiatives I ran, we were able to improve developer productivity, improve quality, ship faster, and decrease sprint interrupters in the form of critical bugs in production, and I had earned a name for myself within the engineering organization.

I wanted to continue my education, so I applied to and was accepted into the Online Master of Science in Computer Science (OMSCS) program from Georgia Tech, a school ranked in the top 10 in the nation (and the world), for Computer Science graduate programs. I planned to start at Georgia Tech in Spring of 2018.

My first stumble...

Now, you may be reading this and wondering how I found some crazy path to success without making mistakes. This section is about my first stumble, my first mistake, and a hard lesson learned.

In November 2017, I decided it was time for a change. I had no family in Idaho, a few friends, but I felt like there may be better opportunities for me in another state. I had family in the Raleigh, NC area and decided to work with a staffing agency to find a position there.

After a few rounds of interviews, a flight out to see the office in person, and a little bit of negotiation, I accepted an offer for $95,000 a year as a Java developer. The cost of living was only about $10,000 a year more, so it was still a significant bump in income.

Unfortunately, this new company had pulled a bit of a bait and switch on me, and the culture (and even the position) were grossly misrepresented when they were interviewing me. For these reasons, I am not naming the company. If you've ever seen the movie Office Space, this company was basically that on steroids.

I realized I needed to find something else, as I was getting depressed, upset, and being really hard on myself for thinking that moving across the country was a good idea.

Finding the unicorn...

In January 2018, after less than 90 days in this "literal hell" of a role, I knew I had to find something new. I had just started at Georgia Tech and after about 8 weeks, I was loving the class I was in and maintaining an A through the course. Unfortunately, I found the time commitment to benefit ratio was not worth it for me, as I was spending 30 hours or more a week in what was the "easiest" class in the program, and I just didn't have the time to dedicate to it. I withdrew from Georgia Tech after this first semester, and still hope to go back one day when I have more time.

Luckily, I had started interviewing with what I considered to be one of my "unicorn companies." By unicorn, I mean a rare, highly desirable, near unbelievable company and role. This unicorn, was GitHub inc. I accepted a role as a Professional Services Engineer for just under $120,000 a year, plus private stock options (as we hadn't been acquired yet), and absolutely amazing benefits. The role was 100% remote, and I still work out of my home office now.

With this new-found passion and drive for my career, I decided it was finally time to take care of my student loans, credit card debt, car payment, and other miscellaneous debts. I am happy to say that as of January 2019, I was completely debt-free. I attribute this accomplishment to Dave Ramsey's program, and highly recommend his book.

I found my calling...

As a Professional Services Engineer at GitHub, I worked as a subject matter expert to help Enterprise customers in all sorts of industries succeed with GitHub, their Software Development Life Cycle (SDLC), and more. These industries included finance and banking, healthcare, start-ups, AI and Machine Learning (ML), government agencies, stock exchanges, power companies, car companies, retail stores, and more.

I continued to excel in my role, and began delivering Lunch and Learns (Brown Bags) again, as I found that sharing knowledge, providing thought leadership, and having a growth mindset has really worked well for me. These trainings were incorporated into the on-boarding process of all future employees in the Professional Services organization, and were truly just an avenue for me to share passions of mine in areas of the industry I had expertise in.

In May of 2019, I changed roles and joined the Partner Engineering group under the Business Development organization with a raise to the $120,000s a year. As a Partner Engineer, I contributed to the GitHub Slack and GitHub Jira integrations, and even posted a blog post on the GitHub Blog about features I shipped. I also got to work with large cloud providers and SaaS platforms in the software industry to build better integrations with GitHub, to reach more users, and increase their business and GitHub's platform. Through 2019 I saved for a house, and became a homeowner in December of 2019.

In April 2020, I accepted a role change as a Senior DevOps Engineer back in the Professional Services organization. Due to the work I had done previously with Lunch and Learns (Brown Bags), the interview process was actually very easy and I accepted this senior role (my current role as of this writing) for around $140,000 a year. This marked 5 years into this journey, and a base salary 4 times higher than where I started at $35,000.

But you said 10x the income...

Astute readers may be asking the question, "But Thomas, you said you 10x'd your income in 5 years, where did the rest of the income come from?" Well, let me tell you. In the IT Industry, especially Software Engineering, there's a concept called total compensation. This is a combination of your base salary, plus bonuses, plus stock options' value, and sometimes people add in their benefits to the equation.

If you've been around in the software world, you likely know that GitHub Inc. was acquired by Microsoft Corp. in November of 2018 for $7.5 Billion. This meant that my private GitHub stock options became Microsoft Stock (MSFT), and I was actually able to do something with them. Through stock sales and base salary, my total compensation and income for tax year 2019 was a little over $350,000, just over 10 times the annual income reported on my tax return in 2015.

The past...

As you can tell, I am proud of this journey and what I've accomplished. That said, I also remain very humble. I know the feeling of not having money to pay your power bill, to feed yourself, and the overwhelming stress and depression that comes as you try to stay afloat.

In 2015, I felt like my life had started over from 0. If you asked me then where I thought I'd be in 5 years, I would not have said anything close to where I am now.

What about that checklist...

Do you recall the 5 goals that I set myself? Well, today I am 29 years old, with 1 year to go, and this is my current status:

  1. Go back to school, earn a Bachelor's degree
  2. Break into the IT Industry and start my career
  3. Pay off all of my debts
  4. Purchase my first home
  5. Get back into the physical shape I was in while in the Army

I've crossed off all the items except my physical fitness, which I am happy to say I am working on now and have consistently moved in the general right direction since June of 2019. I've since set a few more goals such as paying off my home, learning a foreign language, and more, but I'll save those for another post.

The futureā€¦

As for the future, I recently began speaking at conferences, and you may have seen me at GitHub Universe 2019 in San Francisco. I hope to do many more of these talks and workshops in the future, so please contact me if you'd like me to come speak at your conference, your workplace, or at a local MeetUp.

You can find me here at, and you can follow me on GitHub to keep tabs on my latest projects. I'll be posting tutorials, white pages, guides, cheat sheets, and more to help you with your career, your current role in your company, and more.

I hope this post motivates you, and provides the inspiration to know that you can make it too. With hard work, dedication, focus, and determination, you can achieve your goals.

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