As I write this post, its the first time in over a decade that I am not employed. Please don’t feel bad for me. I am privileged enough to take a well-deserved break from the hustle and bustle of everyday software development. As I sit here with my two dogs, Samson and Guinness, I have to ponder my future and what I want to do next.

As an experienced software developer, I’ve accomplished so much, and I am proud of each one of those accomplishments. But victories fade, and I have so much more to learn. As clichéd as it may sound, the possibilities for my next career move are infinite. To understand where I want to go, first I’d like to talk about where I’ve been. I hope you take the time to read about my journey: past, present, and future.

The Last Six Years (2014 - 2020)

In my last position, I held the title of Director of Software Development, leading a diverse cross-national team. It was the first time I was officially the leader of a group, and when I was interviewing for the position, I was asked: “how would you lead a team of software developers differently?” My answer was brief: empathy.

Upon arriving, the existing processes were suffocating the team. Timesheets, daily checklists of activity, rigid style-guides and coding practices, and round table meetings where “everything was ok”, it wasn’t. The development team was shown through these practices that management had an overall lack of trust in them.

My first task was to fix a lingering project that had overrun its deadline for three years. The app was an exercise in user brutality, but we completed it none the less (we would later replace it with a static site, go JAMstack!). Once completed, we could focus on what mattered, the people.

The evolution of the team happened almost immediately. My initial efforts focused on building team rapport and understanding the roles of individuals. I was attempting to give everyone a voice, and I was shifting philosophies around the concept of teamwork. “We are in this together,” I thought. Soon after, our team would work openly and collaboratively. We built packages to enable each other to work more efficiently, questioned our processes, adjusted where we needed to, and grew our methods and ideologies organically.

During that early period when our strategies were shifting,our team’s productivity stagnated. If I had to sum up my failure, it was due to false ideas of what I “believed “ we could do, versus what we could actually accomplish. If I could go back and tell my past self something important, it would be:

Meet folks where they are, not where you think they should be.–Khalid Abuhakmeh

I made it a team goal to make sure all associates within the company could share the same knowledge. The existence of many applications caused different departmental realities to emerge, causing disagreement and unnecessary conflict. We wanted to bring everyone together professionally. It wasn’t easy. The execution may have faltered at times, but the vision was sound, and we all believed in it.

Our team’s efforts were succeeding, one project at a time. Success was short-lived, and that wasn’t enough to pull the organization together. When you don’t have time to celebrate your wins, and your mistakes are magnified, what do you have?

Burning Out Is A Journey

Well, two words, burn out. The personal cost of pulling decision makers into a future they can’t imagine is excruciatingly taxing on many levels: physically, mentally, and emotionally. Change is terrifying to most, and it takes a lot of trust and energy to keep positive momentum.

Collaborators can shoulder some of the burden, and team members helped, but over time it wasn’t enough. I had lost my passion for the goals we had set out to accomplish, and what I was adding to the team dynamic felt like a fraction of what I was contributing previously.

So what contributed to my burn out?

  • What was once an a risky vision, became a successful reality. Success meant many “stakeholders” started indulging in drive-by design and attempted to cease control.
  • Shiny-object syndrome undermined the longterm goals of the team.
  • Vision driven initiatives turned to short-sighted goals on a checklist.
  • Processes and organizational structure began to replace trust. If DISC and AMP ring a bell, then I feel bad for you.
  • The reward for taking action didn’t outweigh my personal energy expenditure.
  • Our team’s success bred disproportionate responsibilities. “No good deed goes unpunished.”
  • Disagreements about management styles and visions for a productive team.
  • Unrealistic expectations for all tasks, since all goals are weighted equally by the stakeholders. “Is it done yet?”

For me, what started as a collaborative environment with business stakeholders morphed into a series of “do what you’re told” and “it is just a business decision” responses.

I had believed, as a director, that I was in a position to help the organization imagine a new future. In reality, I was an executor of finite-minded checklists. In the context of checking boxes, I felt I had completed my job and checked that box, and there was nothing more I could bring to the table.

I will forever be thankful for the opportunity to grow a team of talented individuals. We achieved goals more significant than any one of us could accomplish by ourselves. Through out my tenure, many open source packages were built, a team-driven blog was established, empowered multiple departments, mentoring became a focus among colleagues, and we were able to foster a culture that will always make me unapologetically proud. It’s humbling to work with great people, even when it doesn’t work out.

Future Possibilities

I just completed reading Simon Sinek’s The Infinite Game, and it is incredible how someone you’ve never met can echo your values. I almost want to scream, “get out of my head!” as if through social osmosis, he knows what I want. The ideas within the book encapsulate the kind of organization I want to work for next.

Infinite-Minded Vision

A company with a clear vision is critical for my next role. I want to work for an organization grounded by their belief, but elevated by the thought of their future. A vision shouldn’t change because of investors, competitors, or any external forces.

Just Cause

I want to work towards a Just Cause. A just cause means I can always strive to be better and make the world better. The cause can depend on each organization, but it gives purpose and meaning to our actions. It’s the reason to get up in the morning and be excited to work.

Trusting Teams

One of the critical aspects I want in a team is a collaborative environment stemming from a collective trust. I want to work with a team that expects failure and understands that learning from our mistakes is a necessary part of any successful organization.

Existential Flexibility

I want to work at an organization that is continuously evolving and trying to work towards achieving its vision. The organization sees the future and is unafraid to change course if it deems it necessary. Flexibility is not to be confused with the shiny-object syndrome.

Companies That Fit The Mold

I am a life long learner and have an appetite for knowledge. My current skills are in .NET, but I also have many other valuable skills. I am currently researching organizations I would enjoy working for, and a few come to mind. While these seem like good fits for my philosophical background, I am also open to other organizations.


Netlify is one of the most exciting companies I have seen in a long time. Their vision is clear, and they seem to hire team members who believe in the mission.

By unifying the elements of the modern decoupled web, from local development to advanced edge logic, Netlify enables a 10x faster path to much more performant, secure, and scalable websites and apps. –Netlify

It doesn’t hurt that I am a JAMstack lover and believe their bet on the future of web development is a winner.


I have been a JetBrains customer since I can remember using .NET. Their tools are top-notch, and their community-driven approach is one to admire.

We make professional software development a more productive and enjoyable experience. –JetBrains

JetBrain’s mission is one I can get behind, and it would be humbling to work with some of the smartest people involved in the .NET community. Additionally, it would be great to explore the other tech communities outside of my comfort zone.


Elastic, creators of Elasticsearch, provide some of the most transformative technologies in the past decade. I also love Elastic’s emphasis on transparency through open-source.

Open source is a strength for our community and our business, and it’s at the heart of all that we do. –Elastic

I have delivered organization-changing solutions with the help of the Elastic stack. Contributing to the Elastic ecosystem, and helping other developers would be thrilling.


The Dev community is an exciting one to watch flourish. A clear vision drives the company.

DEV is a community of software developers getting together to help one another out. The software industry relies on collaboration and networked learning. We provide a place for that to happen.–DEV

I am a long-time blogger, and working on a platform to bring folks together in the spirit of a just cause greater than themselves would be exciting.


Glitch is the spirtual succesor for the ways of the old web. It’s a place where folks can experiment with fun ideas with zero judgement. It welcomes everyone and has a clear mission.

Glitch is the friendly community where everyone builds for the web. –Glitch

Their efforts to democratize apps and build a platform is refreshing in the context of a modern web ecosystem. The values of the company are in full public display for all to see. It also doesn’t hurt that they are currently led by Anil Dash, whom I respect.


I learned so much being a director, but I would prefer my next role to be more technically hands-on. I’m not saying I won’t ever lead a team again, but I need some time to recharge. I still want to work within a team and be responsible for helping shape an organization’s future on a strong vision, but I won’t miss the drudgery of approving days off and managing up the food chain.

Like I said before, I will miss the former team I collaborated with, but I am also excited about new teams and new challenges. My next steps are to write some cover letters, do more research, reach out to some organizations, and see what happens. In the meantime, my “funemployment” continues, and you should expect to see more blog posts as I try to recharge my emotional, mental, and physical batteries.

P.S. Feel free to share this post with anyone. I am always open to discussions about new opportunities and challenges teams face.