Growing Your Career in the Evolving Tech Field

Growing Your Career in the Evolving Tech Field

Today is my last day at Tyler Technologies. I’ve been here for just about 11 years.

10 years, 8 months, 4 weeks, and 5 days to be exact. I’ve built my entire professional career at this job. And I’ve loved every second of it.

I was hired one month before I graduated college. I joke that last month was the hardest one not because of my finals, but because I already had a full-time job that didn’t care if I had a degree or not.

For the first 7 years of my career, I was a .NET thick-client application developer. I started as a junior developer and gradually worked up to a lead engineer over a few products. In early 2019, I was given the chance to run multiple cloud teams as we entered the cloud.

It was a whirlwind of an opportunity. I built a team of engineers and we dove into learning cloud concepts. We moved fast. We were agile. We adopted a rapid iteration mindset that accelerated development faster than I had ever experienced before. It was intense. I loved it.

I grew more in those first two years running the cloud teams than I had the prior seven. But why? Was it because of the workload? Was it the team around me? Was it the content?


There were many lessons I had to learn as an individual that helped me grow exponentially faster. Lessons that weren’t obvious early on in my career that I stumbled into as I grew as a leader and learned more about myself.

Find What Motivates You

I don’t think anybody would argue with me when I say you tend to do the things you like more than the things you don’t. If you don’t like something, why spend more time than you have to on it?

Hopefully, you’ve made a career out of something you’re passionate about. Consider the graph below on passion vs skills.

Passion vs skills matrix

If you aren’t passionate and don’t have the skills to perform a specific task, you’re destined for failure. You have no motivation to get better.

Contrast that with something you love but aren’t great at….yet. You’ll enter an intentional growth area where you find the time to enhance your skills.

If you find something you’re good at but are not motivated to get better, you’ll coast and stop growing.

But if you can find something you are good at that you love, you’ve found the sweet spot. You found the thing that motivates you and enables you to easily accomplish your goals.

Not everybody finds their sweet spot. Some people are completely satisfied grinding at something they’re good at without it being something they love. There’s absolutely nothing wrong with that.

But for others, we seek to incorporate what we’re passionate about in every aspect of our lives. We want to live and breathe that one thing that gets us up in the morning. It’s just a matter of finding it along the way.

Make Your Own Opportunities

My career has always been tech-oriented. For the majority of it, I was an individual contributor writing code every day. Early in the cloud portion of my career, I found my passion for writing. Unfortunately, there is not much overlap in the job description of developer and blog writer.

So I had to make my own opportunity. I started writing on Medium in 2019 in my free time. I wrote about some of the ideas I had at work and some of the early successes I had as a manager driving engagement of my dev team.

I didn’t wait for an opportunity to present itself at work. Looking back now, it’s a good thing I didn’t wait because that opportunity never really came. I made my opportunity by starting small. I grew comfortable with writing and eventually built my personal website so I could have greater control over the look and feel of my content.

I remained consistent, writing about things I was doing at work, and started being approached by people who loved what I was doing. I started writing guest blog posts, giving conference talks, and speaking on podcasts.

Of course, I was still doing my day job. But I began realizing that writing was something that was taking my career to a different level. I could feel the quality of my work rising, my desire to fully comprehend everything I encountered was skyrocketing, and honestly, I felt more confident in my day-to-day work.

Turns out I had found my sweet spot. While it didn’t have direct parallels to my daily work, I could see the tangents coming in more and more.

Build On A Solid Foundation

Early last year I planted a grapefruit tree. It was about 2 feet tall and honestly not much more than a stick with a few leaves on it. I watered it regularly and gave it fertilizer as needed. About 3 months after I planted it, a fruit started to grow. I was excited at the prospect of having a grapefruit I grew myself, so I let it be.

But there was a problem. This was a baby tree. It needed to set its roots and focus on getting bigger, not on fruit production. But I let it continue to grow because I was excited about the fruit.

About 6 weeks go by and I have something reminiscent of what Charlie Brown had at Christmas.

Small tree that can’t support the weight of a Christmas ornament

When it came time to harvest the fruit, I’ll be honest. It wasn’t good. It never reached full size because the tree couldn’t support it. It was splitting energy building a foundation and growing fruit.

Now I’m set back a year of growth for this grapefruit tree and what do I have to show for it? Not much.

Had I snipped the fruit off at the beginning, the tree could have put all its energy into growing. The trunk would have gotten bigger and it could have supported multiple fruits next year. But I allowed the tree to rush into production without establishing a foundation.

Don’t rush into new things. Focus on establishing a good foundation and understanding the nuance of what you’re learning. Build up your expertise and proficiency in your current skill set. When you feel comfortable with what you know, branch out a little bit. Pick up the next thing that may or may not be related to what you know.

I wrote blog posts for 3 years before I branched out and began a newsletter. I honed my writing abilities and developed an audience before trying out a new medium.

As a result, I had a successful launch of the newsletter that continues to grow week after week. It is growing not only in the number of subscribers but also in quality. I learn something new with every issue I write. I also take lessons I’ve learned in other areas and apply them to make writing the newsletter easier. Like building my newsletter platform. There’s no way I would have been able to do that if I started writing the newsletter when I started blogging.

A year after the newsletter launched, I started a podcast. This new medium steps away completely from my writing foundation and pushes me out of my comfort zone. But because I have a solid foundation around content creation, I was able to pick it up and just….start. I know how to create content. I’ve built a strong network of industry leaders who are willing to come and talk on the show and teach me about trending topics in the cloud.

Because I didn’t rush into it at the beginning, I’ve set myself up for an easier launch and didn’t get overwhelmed with new tasks.

Look At The End Game

Somebody asked me recently, “when you retire and look back at your career, what will make you feel successful?”.

I immediately fumbled at that answer. I had no idea.

If you asked me five years ago, I would have said the number of applications I’ve built or the number of lines of code in production I’ve written. But that’s not the case anymore.

As I’ve grown over the years, my priorities have changed. I care much less about slinging hundreds of lines of code than I used to. I care more about enabling others to be their best self, both personally and professionally.

It’s not something new, I’ve been mentoring others for years. But as I progress in my career and find what truly motivates me, I’ve learned that helping others is my end game.

For the past year at Tyler Technologies, I’ve been playing a long game. I am on a research and development team, pouring my efforts into exploring new topics ranging from things like serverless cold starts, to designing applications for growth, to deciding if disaster recovery is worth the effort with serverless systems.

I take the lessons I learn, boil them down into blog posts and internal Confluence articles, and share them with others. I do the work so others don’t have to. I love it. If I can enable a team to move quickly because they don’t have to do a research spike, then I’m a happy camper.

If you can find something that motivates you that also defines success in your career, you need to capitalize on it. Find ways to expand that and grow yourself around it.

For me, enabling others to succeed is how I’m defining success in my career. For now, anyway.

To maximize that effort, I made the incredibly hard decision to leave my job in pursuit of something that more directly enables me to reach the serverless community.

Chances are as you continue to grow, so will your definition of career success. That’s ok! Do regular checks to make sure you’re tracking goals that are important to you. Never feel like you’re locked into a personal goal.

I love Tyler Technologies and all the people that work there. But as I’ve grown, I realized my passion has drifted away from what I was doing. I want to dream BIGGER.

Final Thoughts

Without realizing it, I developed a growth mindset. Subconsciously, I started positioning myself in ways that would help me grow in the things I’m passionate about. I put a heavy focus on content creation and realized that above anything else, I want to help others succeed.

I want to grow by growing others. Building developer tools, diving deep into hard topics and simplifying the results, and bringing to light the opinions of industry leaders are in my end game. I want to be the catalyst that makes you a better engineer. Heck, that might be one of the reasons I was named an AWS serverless hero.

With the end game in mind, I had to make an incredibly hard decision to leave my job after 11 years. I’ve grown in this direction as much as I can in my current position and couldn’t be more thankful for the opportunities, friendships, and knowledge I’ve picked up along the way.

Don’t be afraid to make hard decisions.

On Monday, I’ll be starting a new chapter with Momento as an Ecosystem Engineer, focusing on everything I’m passionate about. It’s a scary transition going from a large enterprise to an early startup, but nobody said the path to growth was easy.

I battled self-doubt and dealt with so much unnecessary stress when trying to decide what to do next. I wondered if I was making the right move, or if next year might be a better time to make a change. But once I drew the lines around where my passion was and where the opportunities were, it became clear that while this is the hardest decision of my career, it’s probably the best one as well.

I hope you continue to follow my journey and that we can do something together in the future. Above all, I hope my story has inspired you to make your own opportunities, develop expertise, and focus on the end game.

Happy coding!

Allen Helton

About Allen

Allen is an AWS Serverless Hero passionate about educating others about the cloud, serverless, and APIs. He is the host of the Ready, Set, Cloud podcast and creator of this website. More about Allen.

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