Midlife Crisis outsourced: a chat with SuperBoss

Hi RIP friends,

today we have another personal post about my Midlife Crisis. The blog will get back on “personal finance” after the series is completed.

In the previous episode I was heading toward the end of June 2019 with a foggy head.

in mid June, before my dinner with KM Finanzen, I spent a few days retreating in Tuttlingen, Black Forest (south Germany). I talked about that in my June 2019 update post, where I also said:

I’m on sick leave. Burnout. Since forever – it seems to me. The likelihood I’d be back to work at Hooli after my sick leave ends is low.

During my retreat I took time to review my last 2-3 years of journal entries. Yes, I write a lot. Whenever I feel like I have a thought I want to keep around forever I just write it down. I also journal each day since more or less 2014.

During my retreat I took time to think, to ask myself big questions, to review my last 2-3 years of journal entries – especially those related to Hooli. I cut & pasted all docs I wrote about frustration, dissatisfaction, anger, sadness, helplessness at Hooli into a new doc. 29 pages of rants. “I can’t keep doing this”, “I will quit by the end of the week”, “I have no idea what I am doing here” and so on. 29 pages. That made me realize: “I’m done here. So long and thanks for all the fish”. I’ll write a separate post (probably another series of posts) about the content of my rants, and what can make a dream job like Hooli unbearable.

Anyway, as I said in my June Update:

After 3 months of medical leave I just wanted to quit Hooli for good.

That was June 27th.

Few days earlier, while in Tuttlingen, I posted my May 2019 Financial Update, where I said for the first time “I’m considering leaving Hooli soon” and ranted a bit.

[Note about financial updates: I hope to post a quarterly update early in October 2019, covering July-September. It’s been a good quarter. Many financial events and decisions that I want to share. Stay tuned]

Few days after my May 2019 Update post I received an email from SuperBoss: “hey RIP, I’ve read your latest post and I’m sorry to hear you’re burning out. Wanna talk?

SuperBoss! What a pleasure to hear from you 🙂 Of course I want to talk to you. Let’s have a video call whenever you’re available! Cool, June 28th sounds perfect!

I was so excited! I couldn’t wait to hear from…


Who is SuperBoss??

Right, I never mentioned him before…

SuperBoss is the best manager I have ever had in my career. He was one of my first managers at Hooli, the one who brought me to Superb performances and got me promoted. He’s also an occasional RIP reader and, more importantly, a good friend.

My story at Hooli is more or less the following:

  • First year in team A: just joined Hooli, super excited about anything. Didn’t achieve much though: many reorgs, manager changes, corporate BS that I couldn’t even perceive back then. I was too busy eating free food and going to Pilates lessons at 2pm.
  • Following 2 years: still in team A (renamed and rebranded 10 times, corporate BS), managed by SuperBoss. growing from “Meets Expectations” to “Exceeds” to “Strongly Exceeds” to “Superb”. Had an amazing time, worked on cool projects, had smart and friendly coworkers. Loved Hooli, loved life.
  • Following 6 months: SuperBoss quit, many teammates left either Hooli or the team, team direction unclear, reorg’d in a way to became a service team for some US-based corporate-BS-based Product Manager (from being a proactive, engineering-driven team). I resisted longer than I should have done, then I quit the team after 3.5 years.
  • Following 2 years: team B. Decided to change product area and find the team where I liked the people the most. The product is irrelevant, I want to be with colleagues I like! Turned out to be a very bad decision. Worked on a “search ranking” team, which means fine tuning parameters and handling a shitload legacy code. Writing almost no code, doing A/B experiments, human evals, side by side evals… having to get 100 permissions to push a 2 lines of code change into “the big ranking algorithm”. A huge amount of corporate BS. I forgot how to code. I hated my job, even though I loved my coworkers. That’s where my burnout originated, I guess. By the end of 2017 I just wanted to quit, even though I was able to work 80% for most of 2017 and I was exceeding expectations. Actually, in October 2017 I felt the need to come back at 100% to try to get promoted. It used to be kind of mandatory to be promoted after a while. It was expected that you exceeded your expectations… can you smell corporate BS? I decided “either I ragequit or try a new – a last one – team change”. I started this blog few months into team B, before the descent into darkness. Coincidence? Cause of? Don’t think so.
  • Following year: team C. I wanted to focus on both working on a product that I love and solving complex and challenging engineering problems. I joined a team in a product area I really love, on a product that I and all of you use everyday, working on new features that would have made user experience better for every kind of user. Friendly teammates, interesting problems, lines of code to be written. Still a lot of corporate BS, a lot of communication to get things done, agile sprints, daily stand-ups, legacy code, feeling of helplessness, lack of mastery, lack of contextual knowledge, so many TLAs, and a burnout condition already going on. Performance went from “exceeding expectations” to “meets expectations” to “dangerously close to below expectations”.
  • Last 6 months: medical leave. That’s where I’m right now.
  • Next? No spoiler 🙂 But you’ll be disappointed 🙁

So, who is this SuperBoss that made the miracle of getting me passionate and over-performing?

I always wanted to write a post named “ode to a Super Boss”, praising the quality of my best manager. I guess now is the right time.

SuperBoss has been my perfect manager. Not a standard manager, like you have plenty today in Silicon Valley. Not a polite, nice, detached manager who always tells you “awesome, good job, thanks, nice, cool”. I don’t need that. I need one who challenges me. One who codes more and better than me. I need a mentor, a coach, a source of inspiration, an unreachable genius. I’m the scholar who needs to get inspired by a 100x stronger master, that one day will be overthrown by my growing skills. I need my Miyagi, and SuperBoss was all I needed. Sadly he quit before I could even get 1% closer to his greatness.

He was also very sharp and direct. No corporate BS, not even when facing stakeholders. Team A was a strongly engineer-directed team, where we – the engineers – decided what to do next in full autonomy. Never experienced that again at Hooli, which is slowly transitioning into a PM-driven company, when not a [competitors/news/governments/military]-driven one.

On the technical side he was – again – the best I have ever met. Awesome and prolific coder, obsessed with code quality, famous – and feared – for his tough code reviews. When he quit Hooli in Fall 2015 he was the software engineer who submitted more code into Hooli codebase worldwide. Worldwide! Second was 20% behind. I guess by the end of 2015 he was still on top, even after having quit a few months earlier! And he had a team of ~10 engineers to manage, with regular 1:1 meetings, other teams to meet, strategies to define and so on. After his “normal” work day being a manager, he used to spend his evenings and nights submitting code into Hooli repository “for fun”. Submitting more code than the sum of his direct reports.

One would expect to meet a nerd with no life outside of work, but that’s not the case. He has a family with many children – last time I checked… 3? 4? 5? Let’s blur things to hide his identity anyway – and he spend quality family time every day. He had also time to do volunteering, do sports, have many interests, and… holy crap how the hell does he manage to do all of that??

On a side: I used to be the strongest Ping Pong player of the team, beating everyone in our team several times over. My legend spread quickly until he wanted to play against me. He destroyed me several times. I was not able to score more than half his points in each game. Holy crap, what the f**k? He said he wanted to play against me earlier, but he was too busy having fun writing code. No way!

Having a so strong boss who continuously challenged me and kicked my ass when I was slacking off motivated me to do my best and kick some asses back. I felt an expert in my field, a go-to person for many and a praised host for an Intern back in summer 2015, an intern who successfully converted into full time employee at Hooli.

Life was amazing, until SuperBoss left the company. He loved Hooli, but for family reasons he decided to go back in his home country. He announced the thing in spring 2015, after my promotion. He was allowed to work fully remote, go figure why (hint: because he was awesome? Btw, during the 2 years I needed to get promoted he got promoted twice), and he did it for a few months until Fall 2015. He then quit because “it was not fun to work alone from a remote location”. I guess Hooli did everything possible to try to retain him. In the meantime I changed a couple of managers and slowly entered the burnout avenue.

He left Hooli without an immediate plan, a kind of mini retirement. Even though he had no intention to stop working, he had enough means to if he wanted, I guess. Several years at Hooli, you know. He’s probably already FI, or almost there.

So, to recap, the second half of June looked like this:

  • Mid June: retreat in black forest, realized I’m unhappy at Hooli since 2016. I just wanted to quit.
  • Around June 20th: dinner with KM Finanzen
  • June 27th chat with doctor, told him I just wanted to quit. He gave me another month of medical leave “clean your resume, work on your (coding) projects!
  • June 28th video call with SuperBoss

This chat was obviously different from the one with KM Finanzen. While KM acted as a mirror and helped me clarifying my own thoughts, SuperBoss acted as a mentor, answering my questions and showing me “the way”.

I didn’t take detailed notes, like I did last time. This chat was more emotional and personal. But I still want to share the key points, a bit obfuscated for privacy reasons – and fading memory.

Enters SuperBoss, dressed in dark green

RIP: “Dear SB, what a pleasure to meet you 🙂 How is life??

SB: “Blah blah awesome blah blah super! What about you? How’s the Baby?

Blah blah so and so blah blah baby is wonderful!

Awesome! Ok, what’s up with this burnout thing?

Blah blah blah… so I just want to quit, and maybe jump all-in on another project. It could be about coding, or writing (not just this blog, I have plenty of ideas), or education, or even acting – or a mix of them… but a tiny fraction of my brain doesn’t like it. It keeps telling me that I’m a quitter, that I’m leaving because I’m weak, not good enough for Hooli…

You’re not a quitter if you quit Hooli! You’re progressing to the next step of your life. Your blog is so successful that you don’t have time to work at Hooli anymore! You need meaning. I also needed meaning when I quit Hooli and joined an NGO [RIP Note: his version of Barista FIRE?]. Tell yourself the full story, don’t just say ‘I quit Hooli because I was a failure, didn’t reach level X or achieved Y’. In a year from now everything will be fine and you’ll regret not having done it before! You only regret the things you don’t do!

Thanks 🙂 Well, ‘my blog is so successful’ is a very extreme claim… but I see the point. Right now, working on my blog is the short term answer to the question ‘what would you do if money were out of the equation?’. Btw, can you tell me more about your story after Hooli? How was it emotionally? How did you find your way?

I had trouble in the first 6 months after Hooli, since I didn’t have a concrete project. I started having some regrets… I tried a few things that didn’t work out, but then I found a project I love and now I’m happy with it. I have full control, mastery, autonomy… perfect! I didn’t quit to do nothing, I didn’t retire. I moved on with my life. What you ‘retire to’ is much more important than what you ‘retire from’.

I see… thanks for sharing 🙂 About geo arbitrage: you moved back to France. I know it was because of family reasons, not financial ones. how did it feel? Did you feel fine leaving one of the richest countries in the world? Don’t you feel like your kids would miss some opportunities?

We moved to France also because we didn’t want to spoil/overprotect our kids. Switzerland is a bubble! We moved to a shitty neighborhood of Lyon, where our kids adapted just fine. They have friends whose name we couldn’t pronounce, and that’s fine 🙂 Hedonistic adaptation works both ways, you’d adapt anyway. We didn’t want our kids to be living in the richest country so that everything else would look shitty in comparison. You can try to be ‘semi retired’ in Switzerland, but you can also move back to Italy and you – and your family – will be fine.

So.. you’re recommending me to quit, work on my project (this blog?), be semi retired in Switzerland or move back to Italy… am I correct?

You have more options than you think. You just don’t see them now. You could also semi retire in Switzerland and accept some job here and there. Freelancing and consultancy for ex Hooli employees is very lucrative. If you can keep your expenses low you can work sporadically and still be cashflow positive, or burn very little – less than your investment income. Call it Semi Retirement, or whatever you like it 🙂

I don’t know… I think I just want to clean myself from ‘professional software engineering’. I want to stay away from giant corporations, maybe even from small companies. I hate corporate bullshit, you know. I either quit now or keep pushing the pedal a bit more to prove myself I’m not a quitter and to accumulate ‘enough money’ to not have to look back anymore. You know, our expenses are growing…

Don’t overstress about money, you’ve plenty of it and you’ve skills and passions. You’re a great Software Engineer, and the fact that you got a job at Hooli, where they hire the top 0.1% proves it.  Don’t stay there for the money. Ok, I get that it’s a quantitative thing, not a qualitative one. I get that if you were working at a crappier company you won’t be around just for the money. I get that it’s Hooli-level money, and Hooli environment (which last time I checked was 100x better than coal mining for example)… But don’t keep grinding because of money, it would contradict your own philosophy!

I don’t think I’m overstressing about it. It’s much more than this. I’m trying to give myself permission to quit

from the amazing blog livingafi

Anyway, I always loved working with you. You said I am an awesome Software Engineer, so why don’t you recommend me to launch a startup, join a startup, revolutionize the world and stuff like that? We both know that freelancing and consultancy… well… they really are ‘just for the money’.

I was just showing options if money is a concern, if you lack self confidence. I think you should not focus on ‘coding’ right now. I think you should move on, and eventually come back later. Don’t think about the far future now. Don’t think about 5 years from today. Think of what to do in the next 6 months. And just pick one of your passions. Blog, write a book, work on EERG, write fantasy novels, work on improving education system, become a financial advisor… really, whatever. Get started. Do something. Don’t overplan it. In 6 months from now your project would have moved in directions you don’t know today. You don’t know what you want, where your future project will head to, what feedback will you get… and that’s the amazing part! And it’s ok to fail, it’s just 6 months of your time. Then you can pick another project! You’ve plenty of options and plenty of time, thanks to your skills and your financial security. What are you waiting for?

Thanks… wow… that’s huge. Eye opening. Thanks my friend. But what if things go really south? I’d be soon unemployable by standard criteria. What if I need to get a real job in 5 years? I’m scared that I won’t be able to get back into the industry.

This is a motivation catch 22. If you ever want to find a Hooli-like job you’ll get it. It will be easier than it was to get hired by Hooli. Today you know much better what you need to get there. You know how to code, what it means to be in a giant tech corp, how to write a design doc, how to effectively communicate and so on. They know that you know your trade… it’s just a matter of motivation: do you REALLY want to get it? If you’re not motivated you won’t get the job. And who cares, why do you even apply if you don’t want the job? So it’s pointless to try to go to Smithereens right now if you’re not motivated. Don’t obsess over the fact you won’t be able to get a good job again in case you need it.

Thank you SuperBoss, thank you for reading my blog and having reached me out. Any technical feedback for the blog? How can I improve it? Be honest and harsh – I know you know I like how you don’t bullshit around things and go straight to the point 🙂

I love the personal parts in your blog, and the fake dialogues are super funny… but you’re lagging behind in appearing as an expert. It’s becoming more ‘a blog’ than a ‘personal finance website’. Monthly updates are boring, personal facts are hidden and interleaved with metrics and financial events that may be more interesting for readers. Maybe you should have a section (a static page?) with metrics and the shit, while moving to the ‘meta’ level on the blog.

Copy that! Oh, SuperBoss, I miss you so much! When was the last time you came here? Mrs RIP was pregnant if I remember correctly 🙂

Come visiting me whenever you want 🙂

This was my mental state at the end of June.

I took the extra month of “paid vacation”, i.e. medical leave, knowing that 99% I’d quit right after.

Financial-wise, in June ~30k USD Hooli stocks vested: milestone achieved (in Hooli Jargoon: Key Result score 1.0). Next significative income jackpot would be December/January (another 30k stocks, yearly bonus, 13th salary). The odds of getting there are close to zero.

It seems the right moment to say GG to Hooli.

Let’s enjoy the summer and leave this door still open for an extra month.

Then something happened… stay tuned 😉


  1. After a long time again reading on your blog!

    Hope you‘re doing more well now, I wasn‘t aware of the midlife crisis. I can‘t imagine how this is, probably not nice. I wish you all the best.

    but back to the topic. I think the „Superboss“ as a lot of points which you should dig deeper. I remember we‘ve had lunch right after I resigned. I could guess I would be sooner or later be in a similar situation like you if I have not resigned my Job at UBS.

    Try not to focus too much about money, this is probably the cause of this midlife crisis now. The comfort of a high paying job, and now going a big step back is hard. But I do belive at some point one has to make a decision not for their financial security/wealth but for their own well beeing. Money strangely enough follows close up when you do something you like and it creates value for someone.

    Kind Regards

    1. Hi Thomas, thanks for stopping by!
      As I said, I’m finally ok with sharing this because I’m much better now, I see things more clearly.
      It’s been a tough period, but also deep and life changing. Much better to face life than to live on autopilot 🙂

      I’m looking forward to meeting you in October and to see how are you doing after you quit. You spoiled that you’re doing “better than expected”, so I’m excited about hearing that from you!

      Please, be contagious 😀

  2. I know this is a big struggle for you but I love this series and I wait for the next episode more than I did with the GoT ending 🙂 I also think that you should not worry much, your dedication and passion will get you through anything and you could go in any direction you want. What about the following thought experiment: what would be an unfortunate case? Imagine moving back to Italy, I guess it would not be the end of the world as you were considering it, so take it as the worse option. How much would life cost there? 2k euros a month would be enough, I guess. So you could be totally FI there but just for the sake of the game imagine that you withdraw your money from everywhere and head back to Italy with a couple of bags containing 1m euros. Let leave inflation out of the game or assume that you put your money into something which does not earn anything but tracking inflation. So your 1m euros would pay for 500 consecutive months of living there. That’s more than 40 years. That’s a helluva lot of time to find out how to fund the next x decades living as a cyborg or whatever will be the trend by then 🙂 Even if you stay in Switzerland and blow, let’s say, 8k euros per month and invest for nothing more than just for tracking inflation and you will still end up with 10+ years to figure out what’s next. Then be honest and tell me if you could sit on your ass and not doing anything that can make at least a small chunk of money for ten years. I don’t think so. 🙂

    1. Hahaha! You made my day HCF!
      I’m writing third episode, and there will be a mention to the game of RIPthrones for you 😀

      Spoiler alert: the finale might be as disappointing as GOT’s one, but nobody dies 😀

      About the thought experiment: good suggestion! I should have thought about it earlier, just facing directly all my fears. This is a stoic exercise named “fear setting”. Tim Ferriss wrote about it (here’s a blog post with his TED talk about it: https://tim.blog/2017/05/15/fear-setting/), plus also fear rehearsal, which is another great exercise to face and kill your fears.

      I don’t have a “fear setting”-like answer right now to your thought experiment, but will do and come back here 🙂 thanks for triggering me in the right way!

      And yes, the 40 years (say 30, say 3k per month.. we’re fucking addicted to luxury now) in Italy / 15 years in Switzerland before having actual financial problems, assuming we earn ZERO should be reassuring enough 🙂

  3. Hello RIP,

    greetings from a fellow Italian working in Brussels! I just wanted to thank you for sharing your experience, especially during the last months… working in a big bureaucracy (guess where) I can certainly relate to what you say.

    Maybe what SuperBoss says will work… if you quit, you can try different things for, say, one year and then see where those lead you. If nothing works, one year is not long enough from preventing you from returning to the job market totally out of shape. It would be a short sabbatical, a gap year.

    And obviously Switzerland is not the only good place in the world… in Europe, in particular, there are a lot of good places where quality of life is high (Italy doesn’t work for me).

    Wishing you all the best whatever you decide to do,

    1. Hi Saramago, thanks for stopping by and un abbraccio dalla Svizzera 🙂

      I wonder what are the “good places” in Europe that you think of. Switzerland is addictive, it’s perfect. We’re now into the third week of a 3 weeks vacation in Portugal.
      It’s a nice place… nice food… nice people… but holy crap cars, noise, dog’s shit on the streets, cars everywhere… Switzerland is really addictive!

      1. Hello RIP,

        well, I have never been in Switzerland, so I can’t really compare. But, yes, I would consider Portugal and Spain (not Madrid/BCN) as options, maybe France… and certainly Germany – it’s a big country, with lots of places where quality of life is high (Cologne, Dusseldorf, Munich, Berlin… these are the places I know, there must be others as well).

        As superboss says, you don’t need to be in a perfect place to be happy. Even a place with some grit could be ok…

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