Management

I got into management about a year ago, and it has been one hell of a ride. There’s sort of a running joke that “management isn’t for everyone”, and I can certainly verify that.

I had moved into management with the hopes of it being a great way to advance my career further, push me closer to the goal of getting a Director position, and hopefully scratching the same problem solving itch that solving technical problems and helping organize my team as a lead did.

To start off with the (possibly obvious) point from the list above - it does not scratch that same itch. Not even close. While handling logistical/people problems is indeed interesting and engaging, the politics that come with it are exhausting and not at all in an intriguing way.

Maybe this has to do with changes as the company scales, but the overall concept of analyzing everything down to the most minute detail before implementation is downright exhausting. Add to that conflicting points of view, many of which are often objectively wrong, and you get a recipe for extremely slow movement and low return on investment for projects undertaken. I suspect this is the same at most companies, to be clear, but it was far more drastic than I had anticipated going in.

Insofar as career growth - it’s a very slow move from senior manager to Director, especially considering that you’re likely needing significant organization growth to ever facilitate it, or a Director leaving and you being the next most likely person to take the job. The other thing that comes with this, though, that I had not appreciated in advance is that the politics and disconnect from the actual jobs being done increase somewhat exponentially as you move up the ladder. It’s no longer surprising to me that executives know next to nothing about day to day operations. Still depressing… just not surprising.

Moving into management was absolutely a valuable experience, however, and I’d suggest folks who are curious do it at least once to see if it sticks. I don’t think I’d be interested in doing it again though, at least not with the team sizes here. For reference, I’ve got 13 engineers as direct reports, I could see a team of ~5 being quite enjoyable.

Despite all this, I’ve gotten a hell of a lot done over the past year. I’ve helped double the size of the organization, I’ve found ways to continue to increase revenue while decreasing workload, I’ve promoted several folks and helped others move on to their dream jobs, and I’ve helped bring visibility to several areas that need significant long-term attention. It has been productive, and seeing the outcomes is very rewarding, but I can’t help but feel that I could have done a lot of this from an IC role as well.

Leadership != Management

Burnout

This, I think, is a case of right place wrong/wrong time. The organization I’m a part of has primarily hired managers externally over the past few years (both for backfill and growth), and as a result of this we excellent people managers, but most have little/no knowledge of our tech stack, or any interest in learning it.

Unfortunately for me, I’m still super interested in it, and this has meant that I still have a tremendous amount of responsibility when dealing with technical escalations or complex problems. I’ve effectively been doing the role of “L3” Support, escalation management, and people management. This would be fine if the other managers were also in this boat as it could be load balanced, but it hasn’t been the case.

I did go into this expecting 50 hour weeks to be the norm, and honestly it has been pretty well aligned with that. There’s the usual ebb and flow - some weeks are closer to 40, some weeks are closer to 60, but the average is probably in that 50 range. Again, another thing I had known but didn’t really appreciate, is that virtually every one of those hours is going to be spent in meetings… and most of those meetings could have been done async or could have not happened at all with little to not loss in effectiveness.

For clarity, I highly value the 1on1 meetings I have with my team members. While I probably should have been scheduling those bi-weekly instead of weekly, the value is there either way. My challenge here was mostly around working in a company that is globally distributed, has a majority of its organizations working in a highly async fashion, but being part of an organization that (through growth and a focus on external hiring from non-“async” companies) has almost completely lost the ability to work asynchronously.

Whether this is good, or bad, I don’t know and I’m not going to comment. I just know that I don’t enjoy it.

In any case, this has lead to a level of burnout I haven’t experienced since routinely pulling 70+ hour weeks in the startup world as a single point of failure for nearly all customer operations at a previous job. I needed a change.

Changes

I first realized that I really was not enjoying my job, or interested in pursuing that career path, back around Christmas time. I started entertaining some interviews, and in several of them I actually got some great insight from folks who had taken a similar path that maybe I should reconsider what I was doing. Most interestingly, this often came after job offers for management positions, so it was at the cost of them losing a candidate they wanted. I deeply appreciate that level of honesty, and it won’t be forgotten.

At this point I think it’s important to note how incredibly supportive my management chain was in helping me find something that was a better fit, whether in the company or outside of it. I knew I wanted to move back into an individual contributor role, but I wasn’t sure if it was going to be in the Support world, engineering, or something else (e.g. SRE, Solutions Engineering, etc…).

I had an opoprtunity to do a part-time internship with one of our engineering teams for a period of 3 months, and that was extremely valuable. It showed me that I do probably have more knowledge in that space than I thought, and it really allowed me to learn more about my unknown unknowns… one of which is that having a position where a majority of your time is spent working on top of/fixing someone else’s code has a lot of the same frustrations as what I had been doing previously in Support. Combine it with an area of our tech stack that I don’t have a lot of love for, and I decided maybe that wasn’t the path for me despite being an awesome opportunity. Maybe I’ll swing back in that direction though? Time will tell…

Turn a passion into a job?

After quite a saga of hunting and experimenting over the past 6 months, I finally found something that I think will be an awesome way to spend a few years. It does have some risks, in that it is turning a life-long passion into a job, but it’s also one that I think will keep me engaged long term.

In July I’ll be moving (back) into the cybersecurity world!

Without going into details (you can lurk my LinkedIn for that), I think this new position will combine my hobbies with my existing work-related skills, for a pretty fantastic mix of entertaining and productive work.

More to come on this topic as time goes on!