My Introduction
From WYSIWYG editors to pizza delivery to six figures 💰
Hey, I’m Aken 👋🏼
I’m the author of Become a Senior Engineer, a new educational and community endeavor. I’ve been been in professional software development for 20 years as a full-stack engineer.
Here’s my story of getting started in software development and where it has taken me along the way!
The Early Days
Like many people, I was likely predisposed to some sort of computer-based career due to my father. An electrical designer by day, we would spend evenings in his office playing with an old Apple IIe. It had a black-and-green screen that I’m reminded of every time I see The Matrix. I loved finding the large 5.5” floppy disks that had my favorite games to play. As I got older, Dad would show me some of the silly cartoons and newsletters he’d make on his Apple Macintosh (that he still has today).
When I was around 9 or 10 years old (1995-ish) we got a regular PC tower and the internet. 🤯 I thought websites were the coolest thing on the planet, and I wanted to learn how to make them.
The next few years or so was a trial-and-error journey of self teaching. Checking the source code of web pages, copying and pasting, changing things and seeing what happened. Netscape Navigator and Geocities dominated my desktop.
(I have a hand-drawn wireframe of a Geocities website somewhere that I desperately wanted to show in this article – couldn’t find it 😡. Literally drawings of gifs with their filenames listed underneath! The internet was so cute back then.)
Eventually I had a pretty good handle on HTML and CSS, and started introducing dynamic elements with JavaScript and PHP. Macromedia Dreamweaver was my editor of choice, allowing me to be hands-on with the code when I knew what I was doing, and using the WYSIWYG editor and built-in scripts when I didn’t.
First Paid Gigs & University
After graduating high school (secondary school), I began freelancing as a PSD slicer. I would receive website designs as Photoshop files and turned them into static HTML and CSS. Freelancing taught me a lot about client communication, pricing and invoicing, and other fun intro to business lessons. Though I was still very much an 18-year-old not really thinking about careers. Web development was always just fun.
I began going to a local state university right after high school. I made it three semesters. School was never my favorite thing to do. University felt like more high school, except I was not forced to go and it cost money. I knew the university wasn’t for me when I had to take an “Intro to Computers” class as part of the computer science program.
I ended up taking a few basic jobs for a university-aged guy – retail, pizza delivery, that sort of thing. Meanwhile, I continued to freelance occasionally while learning and exploring more complex dynamic code solutions, particularly on the back-end which I am most drawn to.
This is the stage in my career I regret the most – not thinking of development as a permanent job. I very likely could’ve found a job as a junior engineer, or focused on freelancing full-time. I had a great time at this age with many friends and hobbies and shenanigans, but I could’ve incorporated my career also and progressed a lot quicker.
E-Commerce
In 2006 at 21 I moved to the East Bay area of California to join a friend’s online retail business. He had outgrown his solo home-based setup and rented a warehouse next to a small airport. Since we were friends for a while and often exchanged help and ideas for his business, he asked me to come be Employee #1.
Along with all the usual e-commerce tasks of logistics, customer support, purchasing, etc., he and I rebuilt the store platform from an off-the-shelf solution to a homegrown one. (Do NOT build your own e-commerce software platform unless you absolutely have to.)
Unfortunately I ended up pretty homesick, and moved back home near the end of the year. After a little more freelancing and another service industry job, I landed another online retail job, this time 100% focused on development. From then on, software engineering was my full-time career, that I’ve been doing ever since.
My next e-commerce gig was one of the more interesting ones, at least for the type of work. It seemed like every few months the owner would pivot to some new idea, and we’d have to build some custom functionality for it. Logistics integrations. Custom candle configurator. Pricing calculators. And for a while I was the only dev there doing everything.
Startup Life
In 2013 I joined a local e-commerce agency startup. Literally overnight – I emailed about the job opening on a Wednesday afternoon, interviewed that evening, accepted their offer in a follow-up email, and started the very next day. What a turnaround!
I was employee #5, and we all worked out of the founder’s condo. The East Side of Milwaukee isn’t Silicon Valley, but it was still startup magic. There is nothing like a small group of people all invested in growing a business, working next to each other without formality or bureaucracy. Shit gets done, and it’s some of the most fun I’ve had in this industry.
While most of our customers were e-commerce focused, I worked on custom applications or individual components. Two of my largest accomplishments were SaaS apps for employee recognition and a learning management system.
The startup eventually got a real office and grew to nearly 40 employees, which included a satellite office in Europe. A little more formality and bureaucracy, but still a wonderful job. I doubled my salary, and even received a minor partnership stake.
I left when the custom application side of the agency was removed to focus on e-commerce. I took with me a lot of experience in both engineering and business growth, and long-term relationships with colleagues I still enjoy spending time with 10 years later.
Solo Founder Failure
When I left the startup my family was living with my in-laws. With a fresh start, a savings runway, and the cheapest cost of living I’d probably ever have, I decided to give my own startup a shot.
In 2018 I started developing Nicheket, the “niche marketplace”. I’m a toy collector, and I wanted to create a marketplace that would compete with eBay but be focused on specific niches. Interested only in diecast cars? Visit that section and you can search, buy, and sell within it. Buy from multiple sellers in the same transaction with one payment. All the bells and whistles.
I spent about 10 months building the first production release. I registered the business, got a bank account, all the usual new business actions.
Except I never built a customer following. No customers knew about Nicheket. No marketing was done. Nicheket made about $20 in revenue.
After about 6 months of expecting customers to appear out of thin air (pro tip: it never happens), I admitted to myself I didn’t have enough runway left to stay full-time on it. After considering starting another type of business with my wife, I began searching for another full-time dev job.
Six Figure SaaS
After one bad employer that only lasted a month, I found a stable SaaS in the data collection ecosystem. They had a recent investment and were growing their engineering department by 2-3x.
After all of my experience at this point, I really wanted to break the six-figure barrier: $100,000+ USD in compensation. It’s one of those milestones that really helps you feel like you made it. At least to this millennial who had 15 years of experience already – those of you new to the field in the last 3-5 years might have this salary even at a junior or mid position.
Because of a bit of self-doubt and imposter syndrome, I didn’t feel like I was worth asking for much more. So, I asked for $105-110k as an initial range.
They hired me at $110k. I made it! 🎊
Later on, I learned from the hiring manager that one of the lead engineers messaged him in the middle of one interview saying “Can we just hire Aken right now?” So much for that self-doubt, eh?
Over the next four years I was a part of many major projects and features, CI/CD improvements, hiring processes, mid-level mentoring, healthy debates about code organization, and all the fun and nuance that comes with it. I was part of an engineering team who helped deliver the shift in our product to a more valuable B2B offering, that resulted in regularly increasing revenues.
Along the way, I also received a substantial pay increase as part of a market adjustment. Kudos to the organization for recognizing some of our turnover and hiring challenges were due to lower rates, and they made the adjustment for both existing and new engineers.
Fired Into Today
In September 2023, I was fired from that SaaS position.
It’s important to tell you that for many reasons. I want to be honest, relatable, vulnerable. I want to show that failure doesn’t define you, and you will always be better for it.
I was a great employee in many ways, and difficult in others. Those difficulties were a combination of traits that were incompatible with the company and the team (sometimes things aren’t a good fit, not really anyone’s fault), and skills which I need to improve on. Skills I intend to practice along with you, because you should never stop learning and seeking to improve yourself.
After taking time to process, grieve, and adjust, I found myself back in the same spot as 2018. A fresh start, a savings runway, and a new found desire to never be in a position to be fired again.
That brings us to today! I’m once again a solo entrepreneur, attempting to create one or more successful products that can sustain a full-time income as a founder and business owner.
Become a Senior Engineer is one of those products, and this newsletter is only the beginning. Please consider becoming a subscriber. Paid subscribers receive exclusive actionable content, and as part of the founding audience you can receive 50% forever. Check with your employer to see if you can expense educational content at no cost to you!
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Thank You! 😊
I appreciate you taking the time to learn a bit about my professional background. I’m looking forward to more opportunities to share stories and anecdotes, and to hear yours!
Hit reply and tell me your favorite part of becoming a software engineer, or one of your best career wins.
For more of me personally, you can find me on X at @AkenRoberts and on the web at AkenRoberts.com
#KeepSpritzing 💙
Aken
This was a great piece, and it felt very personal. Thank you for sharing your journey :)
This was such a fun read! A good reminder to capture more photos of the seemingly "boring" but significant-in-hindsight moments in life.