Reflecting on the first ~20 years of my career

Reflecting on the first ~20 years of my career

I was part of the Microsoft layoffs in June 2023. While I was initially upset with it, and particularly with how it happened (though I can't share details), it turned out to be one of the more positive things that happened for me recently.

You see, I was burned out. Now, there is a ton of reading available on burnout. Tons of blogposts, tons of Twitter/X posts, tons of books. And yet, a lot (I'd argue most - maybe 80%?) of people dismiss this feeling. "I'm managing", is a sentence I'd often say to myself. I felt like I was in control of my burnout. In reality, I was working for 16+ hours a day, and not spending any time with my family. I'd constantly tell myself that "just this one more call with my manager". The situation was untenable. So, in hindsight, while it looked devastating at that point in time, it was the best thing that could have happened. I spent the next few months getting better again. I lost weight, started exercising and started training for my first marathon (on inline skates).

Tinkara and me at the family stage of the L'etape Slovenie.

I finally started spending more time with the kids. Intentional time, proper time. Where the focus is on them, not on Teams, trying to put out fires thrown at you by your manager.

I finished the Berlin marathon (on inline skates) in 1:54, which is 20+ minutes faster than I hoped for.

I started looking for a job immediately but realized that is not the smart thing to do. On one side, the market was not ideal, and on the other, I wasn't ready to start until early next year anyway. I was incredibly fortunate to still have some amazing offers on the table and I am incredibly humbled to be in this position even now, when so many of my colleagues continue to look. I recognize my privilege...

All of this aside, however, it has enabled me to seriously reflect on a lot of things about my 20-ish years in the industry. I started thinking deeply about what I want to do next, and what lessons I can highlight up to this point. This post is a collection of those reflections and learnings.

1. Follow your dreams/goals

When I wrote my first CV those 20+ years back, I said "I want to work on technology that will improve people's lives - like MSN Messenger or Microsoft Word". In my 8 years at Microsoft, I contributed in different ways to some amazing projects (like Movesense, computer vision or the NWG water hackathon) and products including Visual Studio for Mac (with contributions to all of its sister products), Codespaces, Roslyn and Playwright. During my last 2 years at Microsoft, I worked in their Tech for Social Impact part of the organization. This falls under Philanthropies, and basically my team was responsible for delivering the Cloud for Nonprofits, which is a suite of products to help non-profits fundraise better.

While I set a trajectory for myself very early on, it's fine if you change your mind. We all go through different phases in life. We meet people who inspire us, see technology that we think can have a profound impact, etc. That should shape our view of where we want to skate to. It took me almost 10 years to get into Microsoft, which is where I wanted to be. Funny story, when I got there, it was really a difficult time because I now lost my one north star. It took me a long time to figure out what motivates & drives me again, and what I want to aspire towards.

Not having this made work harder than it was before this. Not all people are like this - which is great. But for me, I need to know what I'm working towards. Questions like "Where do you see yourself in 5 years" are actually relevant here. I remember having a conversation with a former skip-manager (i.e., manager of my manager) and he explained to me how he has a slide deck of his next 5 years. He says for each task he takes on, he looks at his set of goals and see if it's working towards any of them. If it doesn't, he doesn't do it.

For me, I realized that I care less about promotions as such (i.e., the default answer for what do you want to do in 5 years) and more about the type of work I do. In my particular case, the work in the non-profit sector gave me a lot of personal satisfaction. It also sparked the institute I'm setting up this year. I also discovered my passion for engineering leadership. Helping people grow in their career was truly great. I strongly believe that whatever I pick next, has to empower me to write the rest of my story.

2. Your fit matters more than a good/bad manager

Hanlon's razor suggests to "never attribute to malice that which is adequately explained by stupidity". In my career, I've had the fortune of working with some truly great managers. Sadly, I also had the misfortune of working with some bad managers. Note, at Microsoft, I think by my last count, I had ~15 managers in 8 years, so I have some historical data to go by... But, in my 20 years, I think I only ever had 1 manager that I would genuinely consider malicious to a point I would actively discourage people from working with them. What does malicious mean? They would essentially gaslight their directs.

This article, btw, is great to understand how to start dealing with it. If you're experiencing gaslighting from your manager, reach out to your HR people, please. Every (bigger) company will have a department designed to help you. If you need a chat, though, I'm happy to talk! Reach out. Just don't suffer through it.

I saw first-hand, this manager give positive comments to one of the team members, then talked negatively about them in a separate 1:1. They failed to provide any clarity in the face of uncertainty and would instead blame everyone up and down the chain. They would let disagreements fester, instead of supporting individuals to resolve them, creating opposing teams. They spent a lot of time in meaningless meetings to seem productive, but never really delivered anything. On top of that, they were just a bad manager where they genuinely didn't do a good job.

There are some important nuances to consider here. What I usually consider "bad" manager doesn't mean they don't know how to do their job. All barring that one manager mentioned above, were good in that respect. But some were still a bad fit with me. This last bit is important. How you fit with your manager is crucial. Their preferred communication style is important. Their ability to read you is important. I still remember one of the best managers I worked with and how they approached conversations. They were a coach 80% of the time, and a director the remaining 20% of the time, when it really mattered.

All this to say, I have since learned to ask questions that determine if I'm a good fit for that manager. This will be different for each individual, but for me, some are:

  • How do you convey information in the fact of uncertainty? Do you prefer to over- or under-share?
  • Do you prefer reassuring directs when they're doing a good job, or waiting to give praise when it's finished?
  • Do you prefer async or sync updates, and if so, how frequently?

I bring this up because as I reflect on the reasons why I left those roles, it was almost never (barring that one) the manager's fault. It was mostly because they (or I) were a bad fit for each other. For me, that translates to not being able to be confident in myself, which ends up reflecting in my work, etc. Which breeds insecurity, which leads me to the next point...

3. Clarity trumps insecurity

I love the buzzwordiness of this one. But it's true. As a manager, the most important thing I could do was create clarity. You need a supportive management chain for this, of course, and I am 100% I could do an even better job at this in hindsight. If I continue on the manager journey, I will strive to do better here. But, back to the lesson learned. Most of the criticism I've seen coming from my team was around uncertainty on what comes next, or decisions that were made.

When I thought about moving to a manager role, I reflected on what was the hardest part of the job as an Individual Contributor (IC) for me. This is something deeply personal to everyone, and it's possible you might not care about the same thing. But for me, the key motivational factor was knowing why something is happening. I was a part of an organisation in Microsoft, where the leader flat-out said "I will be reorging every 6 months, because I feel this creates a better culture". I hated that, and changed the first moment I could. There was no particular reason behind it, and (to me) the choices seemed arbitrary. In fairness, I don't think they were, as in, I think there was a reason behind them, but I wasn't aware.

In my mind, a good manager, will always do their best to create a perception of some stability. As a manager, I did my best to explain the decisions I was able to, sharing the reasoning behind them, and the steps we hoped to achieve. Transparency is a key pillar of my management philosophy and the take-away for me here is that I fit in better with organizations that share this belief. I strongly believe that insecurity is driven by lack of clarity, and that insecurity can quickly spiral out of control.

Over the past 20 years, the roles I enjoyed the most were the ones where there was the most clarity - either about what we are doing, or what's coming next. In retrospect, the (times in those) roles I hated the most, were usually exactly the opposite - when it was completely uncertain what is coming next.

4. Spend (more) time creating a culture

This hurts me the most. It's where I think I have the biggest improvement to make, as a manager and people leader in the future. Despite writing about this way back when, I somehow didn't do enough here. The lesson is that no matter how much time you think you're dedicating to creating a good culture, you can probably do even more. This applies to ICs and managers. If I had a do-over, I would spend more time doing informal calls with the team, coffee chats, wine/juice tastings, even board game nights (yes, there's an option to do those remotely/hybrid). Work will change, priorities will get shuffled around, products might be renamed/killed/deprioritized, but a culture is forever. I worked in some amazing teams where the culture was phenomenal. I'm still in touch with most people from those teams in one way or another, and we continue to have good banter, debate and general conversations. Much like everything else, this takes intent & work. Prioritize it, either as an IC, or as a manager.

5. Put yourself first.

Despite this learning being last, it's probably the most important one in my list. Nothing else matters as much as yourself. Not even your kids, or your family. Why? Because if you don't look after yourself, you can't look after those who need you.

I messed up this part. I didn't see the signs of burnout. I didn't see that I never really disconnected from work. I let go of all my hobbies, most of my friends and things I did for fun. It was literally going to work, then being to tired to do anything else. Working from home didn't help either because despite me trying to create one, there simply was no barrier between the two realities. I let work creep into my personal life too much. This is the only time in this post I will ever criticize other people, namely my former manager, but I strongly feel a good manager will spot these signs and actively work against it. It's still a lesson for me, because I know I did see some of those signs in some of my directs and I hope I was able to stop them on the path of self-destructions. A manager has a lot of power - they can choose not to email you during non-working hours. They can choose to not Teams message you, especially if they know you're quick to respond (the exact opposite of their first instinct of "it's just a quick question, sorry I'm bothering you right now"). They can choose to not invite you to meetings at 9pm+. They can choose to respect your calendar and not book over existing items, especially personal ones. As a manager, this is my number one priority. I cannot let this happen to anyone else, or me.

No role is as important as this. Admitting this sounds a bit entitled, especially in the current economic/job situation, but you can (almost) always find a new job, or a new role. It is much harder to find another you, and fix things on yourself.

Dealing with burnout

So, what am I doing to cope with this? I am obviously too late now, and as suggested, this messed my life up quite dramatically. That's a post all in its own, but... Anyway, I started doing a lot more sports. I have a character trait where I'll over-target myself, either at work, or in my personal ambitions. The marathon was a good start. I set myself a nice, doable pace, and I achieved it. It took a lot of work to not sign up for the next one a couple weeks after Berlin, but I needed a break. So I set myself an achievable goal - a triathlon before I'm 40. Before that, I want to do one 150km+ bike race, but I have my eyes set for Istria 300. Depending on how life moves on, I might setup a fundraising event for the non-profit I'm setting up, and doing the 300km bike ride as a challenge.

I started playing more guitar/bass again. I intentionally take time every day to play something. My perfectionist self is making this harder, but I try.

I spend more time with my kids. I plan day trips for just us, we try to cook together, just us, I bought more board games that we can play, and I have a full living room table just for books I can read to them, if they want. Not having to go to the next meeting, has also done wonders for my bedtime routine with them, although I still have much to learn.

The only people who will remember that you worked overtime will be your children.

This quote hit me hard. I must have heard it a few months before getting laid off and it moved me deeply. Work will never stop. It will never be done, there will always be more of it. It's similar to liquids - it will always fill the container. And work will always find all the time you're willing to give it.

If you don't feel good with yourself, you can't feel good with others. You can't spend meaningful, quality time with your children, if you don't feel positive, energetic yourself. So, do whatever (healthy thing) it takes, for you to feel that way. The rest will follow.

What's next?

Recognizing the privilige of this statement, I am incredibly grateful to people in my life that have enabled me to do and say this. I'm continuing to take time off from working for the next few months more. Overall, I'll not be working for almost a year, which is probably the longest I've not worked since I started high-school (yes, I started working at Cosylab in high-school and am incredibly grateful for that).

On the other hand, I had some incredible offers on the table. As I suggested earlier, I am incredibly humbled by this, and I recognize not everyone in the current job market is in this position.

I can't wait to announce the next step, and start thew new journey. Until then, the search for the next 20 years continues...

Show Comments
Mastodon Verification