The last time I had an introspective post was in my sign-off to 2017 post. As I'm flying from Chicago to Toronto on a work trip, I felt inspired to write another piece. During the summer I came to the realization that I've reached the end of the growth that I can gain at The Fellowship, and that it is time for the next phase in my career. Over the last ten years, I have found what I am passionate about and now I need to find the right company with the culture that can support those passions and where we will have a mutually beneficial relationship.

The First Four Years at The Fellowship

Over the first four years, my title changed from "Senior .NET Developer" to ".NET Developer Team Lead" to "Manager of Application Development". Not a lot changed in my position description with each title change - more the title catching up to what I was actually doing. During the entire period I was reporting to the "Director of Information Services", who in turn reported to the COO. The Information Services department oversaw all technology related aspects of operations for the organization, split roughly between the Infrastructure team (which included the one-man helpdesk and the network engineer) and the App Dev team (a DBA, me, and a few jr. devs).

I had always been the senior most developer on the team, working in frequent and close collaboration with the DBA. My boss determined the priority of various projects that were in our pipeline, and I was tasked with ensuring that the day-to-day operations were being met while keeping the projects moving along. I handled most interactions with our users - be it for requirements gathering, user testing, user training, or general good will.

There were a couple of signature projects that I look back on fondly, including: overhauling the way receipts and letters are printed (replacing a manual Word mail-merge process with an automated PDF output), changing the way the entire organization spoke and looked at donor "contact preferences" (including architecting a new CRM module to better track and reflect these preferences), and moving our code base from web forms to ASP.NET MVC with Razor and from ADO.NET to DBMLs and then to Entity Framework. This was a period marked by a lot of wins and very few failures. I had a lot of time and freedom to experiment with new frameworks, to teach myself new technologies, and to help my team learn and grow.

By the time the one-year mark was coming up at the manager level, my career growth had seemed to stall. There were no more titles to squeeze in before moving to Director and there was no indication that an opening was going to happen.

One Fateful Week

The Fellowship has had a known problem internally of having a lack of project management on large initiatives. At this point, we were looking to move off of our web services / email marketing platform for a myriad number of reasons. However, there was no obvious department to lead and project manage this multi-phase, cross-department initiative. There were a few high-level discussions about who should take on that role, but the decision was lingering for weeks as various directors and departments demurred that they didn't have the bandwidth to fully take it on.

Eventually (from my understanding), the COO laid down a final call for ideas about who should take on the responsibility. When I heard about this, I spent my weekend putting together a comprehensive proposal for a new "Director of Technology" position and department that would combine my internal team of developers with the team of developers for our external website. This department's purpose would be to ensure that departments across The Fellowship had the best software tools and training that the organization could afford to help them be the best at their jobs. This would include market research, departmental interviews, handling bids and contracts, vendor management, and user training and support. It would also include project management for these cross-departmental initiatives such as just the one that we were about to engage in. I had outlined a transition plan, a budget, and preliminary measures of success. That Sunday evening and Monday morning, I lobbied hard for my boss, the "Director of Information Services", to pitch this proposal to his boss, the "Global Chief Operating Officer".

This was a position that I was extremely excited and passionate about. The more I studied similar positions at other organizations, wrote about it in my proposal, and envisioned how I could grow the department, I found a renewed sense of enthusiasm for the company. For the first time in a while, I came into the office excited and filled with a renewed sense of purpose. I had finally discovered, in a weekend of writing down one giant hypothetical, what I was passionate about and where I wanted to take my career. I was on an incredible high that week, giddy with a sense of what the future could hold.

An Unexpected, Disappointing Promotion

I hadn't heard anything during the week about whether my boss had actually done anything with my proposal, but I had faith in him and hoped that while he would lose me as a direct report, he would see that The Fellowship would be better for it and that I would be able to continue to grow instead of stagnate where I was. Friday morning came around and he pulled me into a conference room. Without preamble, he held out his hand and congratulated me on becoming the new "Director of Information Services".

"What. The. Fuck."

It was the only thought I had; I was completely dumbfounded. I didn't know what this was, but it was not good – not at all what I wanted. I kind-of-sort-of recovered, shook his hand, said my thanks, and then (very characteristically, but much more so than usual) skeptically asked where he was going. He was positively beaming and announced that he was being promoted to the brand new position of "Vice President of Technology" and that I would continue to be reporting to him.

"What. The. Fuck."

I just could not stop thinking it. I've never been so blindsided by news then I had in that moment. He went on to tell me that the infrastructure/helpdesk team would continue to report to him, but our DBA would be reporting to me. The Web Services department was being moved under him and a different director was given a lateral move to a new position to specifically project manage the email marketing platform and web services migration project. I spent the rest of the day in a complete haze. HR sent out an email announcing the various promotions. Everyone was congratulating me on the new opportunity, which (I think/hope) I managed to gracefully and humbly accept.

The weekend was a baffling mixture of emotions ranging from disappointment to anger to resignation to renewed belief that it was time for me to find another opportunity. I don't think I had a single honest moment of positivity about these organizational changes. I can only imagine how rough it was for my wife to see me go through all this. I can't even imagine how grumpy and hostile I must have been that weekend.

"I'll Give It a Year"

By the time I came into the office on Monday, I had convinced myself that I would give it a year. At a minimum, one year would look good on a resume. I felt that was a reasonable amount of time to guide and shape this modified department, to help the organization transition with the new structure, and to support my boss in his new role. It wasn't a lot, but it was something. It got me through that first week, and then the first month, and then through a lot of hard adjustments the company had to make during the first six months.

Looking back on the last 18 months, I can honestly say that I gave it my best effort. I have added a significant number of services that the IS team is able to provide to other departments. I have been able to transition almost the entirety of day-to-day operations onto my team. I have mentored them in how to better engage with the different needs and personalities of each department.

I architected a solution to create a secure API and pipeline to ingest data from the website, including processing credit cards and sending email confirmations. Throughout that project, I taught the developers why this was the right solution and the right design patterns. The foundation has been laid, and next is an expansion of the API into two-way communication for an upcoming greenfield Donor Portal project - giving our users a comprehensive online view of their account, one they've never had before. I've guided the team from being told what technologies and frameworks to use, to now ensuring they have the confidence and tools to search for or create the right solution.

In Conclusion, Continued...

Years ago, I was the only person who was able to look at a problem and understand what the entirety of the solution would be; now, my team is almost always able to get there on their own and they just come to me for confirmation. It is a satisfying sense of accomplishment to know where my team has come from and where I've taken them. Even as I see the growth they've achieved, I am worried that I have stalled my own growth. At conferences that I've been to, I feel as if I'm slipping further behind my peers in knowledge share, community engagement, and breadth of impact. I want to go back to working on Big Projects that have significant positive impacts on whole organizations. I want to foster and mentor another team of developers. I want to explore and experiment on a grander scale.

I am really good at my job; but is my job still really good for me?