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Decisions, Decisions

I’ve had a number of follow up questions related to my decision to leave management. While none of the questions are quite the same, many of them have one common theme: the individual asking is facing a major career decision and is trying to figure out how to make that decision. They recognize that in choosing to go into management, to leave management and pick the team to join after, I have some perspective on decisions similar to what they’re struggling with. The fact of the matter is that I’m not going to be able to tell anyone else what the right choice is for him or her. I can explain what I would choose and why I made a decision or things that I would consider. I can listen to someone think out loud, but the right decision for me may not be the right decision for someone else. That said, I did learn a few things through the process of making several hard decisions in a relatively short amount of time that I found helpful both in making those decisions but also for facing future decisions.

Figure out what you want

Figuring out what you want is probably the most important, but also the hardest to do. What you like, what makes you happy and what you are trying to optimize for are all very individual. When people ask me what I want for my career, I often don’t have a good answer. When I try to spell it out, things start to get very vague and hazy. Sometimes the options are almost overwhelming. That doesn’t mean that it’s not worth thinking about. Having some idea of what I like or where I might be trying to get or even that I want to explore a few things gives me some structure to the decisions that I make.

It can be hard to think about the big picture when focused on a very specific decision. I’ve found it useful to try to have some thoughts on my goals and values outside of any particular decision or situation. For example, I’ve found that one of the most important things for me to enjoy my work environment is the people I’m working with. I find that most companies have interesting technical problems and while some things may interest me more than others, getting along with my co-workers matters much more to me. To that end, when I was last looking for a job, I picked Box because I liked the people here the most. Without thinking about that ahead of time, it would be easy to get bogged down with the specific benefits at different places or the specific technologies or a hundred other differences that I ultimately care a lot less about.

Likewise, when making the decision of leaving management, I thought about which days I felt happy and energized and when I felt drained or frustrated. What aspects of those days were different? What was the same? What tasks did I find myself dreading? Was I unhappy because of the role or the specific team or the company? Was there something I could fix within the role or did I just need to switch roles? By figuring out exactly what was making me unhappy and what wasn’t, I was able to more clearly see what the underlying causes might be and what I would need to do to change things.

I also found that there are some tasks that I like in theory, but not in practice, so it is important to be able to make that distinction. For example, I really like the idea of helping other people grow in their careers (and in some cases, I do enjoy it), but I found that I didn’t enjoy it as a manager. As a manager, you need to try to grow everyone on your team and in every aspect. Additionally you have these competing goals of both trying to grow one individual, but you’re also trying to grow others on the team and sometimes what helps one person will hurt another. On top of all of that, you need to make sure the entire project moves forward which may run counter to any individual’s growth. I found I also felt an extra layer of pressure — if I recommend something as a mentor that was wrong, I was just some random person offering advice. As a manager, however, I had some added air of authority and was much more directly responsible. It was hard for me to admit that I didn’t enjoy growing people, but the truth was that I didn’t enjoy growing people as a manager. Recognizing this made my decision easier.

Decisions are reversible

When I was first considering going into management, one of my big hesitations was that I was worried that I would hate it. As it turned out, that fear wasn’t unfounded. However, it’s not like I was stuck in management forever. When making that decision, one of my turning points was when I realized that I could reverse that decision. If I hated it, I’d be able to move back. I still had options. I feared that in management, I won’t be technical anymore, but you don’t lose these things immediately. Looking back, even if I had somehow gotten really rusty, then doing a side project or two or attending a hackathon or just getting a friend to practice a few interview questions with me would have quickly gotten me back in the game. Even apart from moving back to a previous role, there are always other options — new decisions that can take your career in new directions.

There are no wasted experiences

My other big fear was that if I made the wrong decision, I’d be wasting time on a sub-optimal career path. Now this holds a grain of truth, but it’s much less true than I originally thought. While management may not be the most direct path to a top engineering role, I learned a lot and gained perspective that will still help me out. Some of the perspectives and skills clearly directly help me out, such as perspective on how managers approach conversations with their reports that has helped me talk with my own manager. Beyond that though, many of the other skills, which at first glance are much less applicable, are still valuable. As I recently discussed with several friends, some of the skills you learn in other roles actually help diversify a team and make it stronger as a whole. Having someone really good at organizing projects or communicating or approaching problems from a user perspective will make any engineering team much stronger. If everyone on the team grew into his or her role in the exact same way, we would lose out on a lot of diversity. These skills learned from a different role can actually be our biggest asset. Even if you think you might reverse your decision later, focus on learning as much as possible in the new role and it won’t be wasted.

Make a decision and own it!

When I was first deciding whether to go into management or not, one of my mentors really pushed me to do it. When I later told her that I decided to leave, I was surprised that she was really excited for me. When I asked her about that, she told me that she pushed me because she thought I needed to make a decision and move forward. I was staying undecided and I was leaving my career on hold as I was trying to keep myself in a place where I could keep all my options open. By doing that, I was holding myself back from both paths. Ultimately, she didn’t care if I was in management or not, but she wanted to see me on a path moving forward and owning my decisions. While I still think it’s important to really consider decisions and to leave options open as much as possible, it’s also important to recognize when you’re just waffling and need to move ahead.

Have a support group

Throughout all of this, it’s helpful to have a support group — friends to pick you up if things fail spectacularly, mentors to give you that little extra push when you’re waffling, peers to give other perspectives on unforeseen pros and cons. While a support group isn’t strictly necessary, I’ve found it incredibly useful to have people I can talk through my thoughts with or people who can point out considerations I haven’t even thought of. Even if everything goes amazingly and I know what I want to pick, just knowing that they’re there for me makes that initial plunge easier.

No matter what the options, if we’re feeling truly torn, then it’s rare that the decision we make will be a total disaster. No matter what your decision is, go into it knowing what you want. Don’t worry overly much about getting stuck since decisions are almost always reversible and even if you do reverse your decision, you will have learned something valuable in the process. Own your decision and use your friends and network to make it all easier.

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