Career Advice – Borrowing Wise Words from a Sailing Hacker

On researching SSL-related hacks, I have stumbled upon the website of notable security researcher Moxie Marlinspike.

Marlinspike is also a sailor and working on diverse projects, such as Audio Anarchy – a project for transcribing anarchist books into audio format. On his About page he says:

I like computer security and software development, particularly in the areas of secure protocols, cryptography, privacy, and anonymity. But I also secretly hate technology, am partially horrified with the direction “geek” culture has gone.


In general, I hope to contribute to a world where we value skills and relationships over careers and money, where we know better than to trust cops or politicians, and where we’re passionate about building and creating things in a self-motivated and self-directed way.

I call myself Subversive El(k)ement, Security Consultant, Search Term Poet, and Luddite in Disguise … how could I not relate

So it was not a surprise that I found myself in total agreement with his career advice.

Moxie’s post starts with

What I want to say, more often than not, is something along the lines of don’t do it;

This is reminiscent of Via Negativa I learned about from Nassim Taleb’s writings. I have also  found it more helpful to state what I don’t like instead of phrasing so-called SMART goals. When planning positively you try to target a small point in the vast space of options – likely to be missed – in contrast to the negative approach of avoiding a subset of options and keeping a considerable part of them in reach.

From the famous Stanford Prison experiment Moxie draws a simpler lesson as an individual – and it seems more palpable to me than that grand discussions about morals and free will:

 … just be careful what job you take, because your job will change you.

You should look at the people working in a certain environment or industry sector and think twice if you want to become like them. This is not self-evident: At times I was dead set to break into a world whose representatives were anti-role-models – but of course I wanted to revolutionize the whole sector. Finally I have found out that it is more rewarding to go where the people are to whom you can relate with.

Moxie talks about choices we all make, and how the first of those, early in our careers, are defined by supporting structures like family, school, or university:

When we arrive at the ends of these funnels, it’s possible that the direction we’re facing is more a reflection of those structures than it is a reflection of ourselves. Self-determination in a moment like that can’t simply be about making a choice, it has to start with transforming the conditions that constitute our choices. It requires challenging the “self” in “self-determination” by stepping as far outside of those supporting structures as possible, for as long as possible.

It is silly to attempt at rushing through our lives, taking conscious decisions as early as possible and trying to cast your perfect CV in stone, as

There’s no rush to get started early on a never-ending task.

Moxie concludes that in relation to the inquiries about career advice, he is:

… likely to respond with something like “if I were you, I’d hitchhike to Alaska this summer instead.”

He advocates

… doing the absolute minimum amount of work necessary to prevent starvation, and then doing something that’s not about money, completely outside of supporting structures, and not simply a matter of “consuming experience”

I can anticipate objections, and you can also find them in the comments on Moxie’s post. How to pay the bills? How to feed the kids?

Actually I have re-written this post several times because of this – but, alas, I will not be able to avoid all ambiguity. All I want to say is that Moxie’s post struck a chord with me. Though targeted to students it is this classical advice to the younger self that exactly that self might not like. It took me ~20 years to come to that conclusion and act accordingly.

I think the primary target group of articles like this are people who arguably have choices but don’t use them – people who err on the side of caution. I don’t want to downplay the predicament of the single mum working two jobs but rather speak to the unhappy Head Chief Architect Officer of Something Sounding Really Impressive But Actually Doing Unnerving Grunt Work That Just Happens To Be Extremely Well Paid.

I am also not at all trying to evangelize among those who wholeheartedly enjoy their stressful jobs. There is this subtle dance of intriguing yet stressful work and inspiration that makes it enjoyable nonetheless. The big caveat here is that you need to find out on your own what exactly stresses you out in a fatal way – and this is not necessarily straight-forward. It is to be experienced, not to be determined by theorizing.

Based on my experience, anecdotal as it is, I dare hypothesize that there is an impressive percentage of respected middle-class corporate employees who do ponder about an alternative life as that iconic free sailor. My job role had been that of a technical consultant ever since but I had become more of a project psychologist at times. I was to hear surprising confessions – after we had left the formalities of the professional negotiations behind and people started philosophizing over coffee.

Generally speaking, I believe that most of us living in stable democracies are freer than we think. I am saying this as the inhabitant of a country whose primary mentality is not exactly shaped by entrepreneurial spirit and daring. I know how the collective submission to alleged obligations work.

As for using kids as a main counter-argument to a ‘free’ life-style, I was reminded of that most recent controversy about adventurous parents living and rising their kids on boats. – an impossible life for most people. Considering their life-styles too risky gives proof of how warped our sense of risks and probabilities is, and how over-valued spectacular risks of The Uncommon are in comparison to the dull, but near certain health risks of the accepted, sedentary living in a modern civilization.

We do make choices all the way, and be it just choosing the life expected from us by those supporting structures. When we are grown up we don’t have much excuses for not taking accountability – and this does not at all mean a perfectly streamlined career plan.

Quoting Moxie again:

Be careful not to discover a career before you’ve discovered yourself.

The best advice is not to follow any advice (incl. this one), question everything, and decide for yourself.

This post will be filed under Life – a collection that recently struck me as much too serious and solemn. In any case – if that happens again, I would just like everybody to know that I have never been happier; and I am weighing my words carefully.

22 Comments Add yours

  1. I have been deleting old tweets and facebook posts today. I found this post on my timeline and moved it over to Google+. I was delighted to find it again, as I really have thought about this particular post many, many times since you wrote it.

    1. elkement says:

      Thanks a lot, Michelle! It is own my favorite posts – one that was years in the making, in a sense!!

      1. I am working on a post that cites it. I finally have reached the right time to write about how (or why) to do this with kids.

        1. elkement says:

          I am just reading another beautiful post you shared on G+: “this site is more a museum of me, my posts like exhibits behind panes of glass.”. Yes, exactly. This post is like that :-)
          Looking forward to your next post!!

  2. YOU TOTALLY ANTICIPATED MY RESPONSE TO THIS ELKE! I hate to be negative or questioning or suspicious … but might Moxie be independently wealthy? Does he have a family? Health insurance? I read through all the advice and agree that it is all very good … even great …. but I fear most of it may only be put into practice in a theoretical sense. Much of what he advocates can’t easily be done in this very real world of ours … can it?

    … doing the absolute minimum amount of work necessary to prevent starvation, and then doing something that’s not about money, completely outside of supporting structures, and not simply a matter of “consuming experience”.

    I wish … I wish … if only it were possible.

    Sorry Elke.


    1. elkement says:

      Thanks, Dave! Now this comment is what I call a challenge :-) I don’t take such objections lightly. I think I will not be able to get across my points better in a comment than I did in that post, but I give it a try:

      ‘Not avoiding starvation’ might by hyperbolic but I believe the essence is that people (e.g. students) should be nudged / challenged to think along these lines rather than instilling in them the desire to start that well paying career as soon as possible, go for stretch goals, know exactly ‘what you want to do in 5 years’ etc. When I read any other career advice for young people today I usually cringe – it is all about starting to ‘optimize’ your career from the earliest age on. You might better want to work a bit more than just avoiding poverty – but you could work much less than what so-called common career wisdom says though.

      As I said, the target group of this are people who definitely could afford it to live that ‘free’ life-style, at least at some point in their lives, but don’t because they simply cannot stop doing what they did since they entered the workforce.

      It would be an interesting project to collect tangible evidence that a ‘free life-style’ is possible. I am wary to interpret other people’s lives, but Moxie seems / seemed to have lived what I call a project-based life, having founded a startup in security that has been sold to Twitter.

      I can personally attest to the fact that it is possible – also without employees, and without selling a product, just as a mundane contractor – to work intensely for some years (as long as you enjoy it) and then cut back drastically – but it is (mentally!!) challenging to change the switch. I started tinkering with my workload after I had once been accidentally forced not to travel to clients’ site for a full month – I thought I ‘can’t work at all’ but yet that modest amount of ‘remote work’ was able ‘to pay the bills’. It would have been easy to do the math before, and I actually did, but I absolutely needed to be forced to do that experiment as I was so set for ‘working as much as possible’.

      What remains to be proven is that that these are not exceptions or ‘first world problems for the lucky few that happened to have ended up in a lucrative sector’ (You see, I am anticipating objections all the way :-)) but something in reach for at least some considerable part of the middle-class workforce.
      I am just reading an interesting book about the ‘corporate’ culture at Automattic, the company that runs It is a company made up of a geographically dispersed workforce only, fiercely independent and funny individuals working together in a way that seems unusual and peculiar to most – and I am sure wouldn’t they be so successful skeptics would say that can’t work at all in real life.

      1. The following is telling … ” … Moxie seems to have lived what I call a project-based life, having founded a startup in security that has been sold to Twitter.” What you mean is … he’s a millionaire and can afford to tell the rest of us what we should do in the absence of his very deep pockets. Yes, yes, I agree that there are rewards higher than money that we should all pursue for our own good as well as the good of others … but that’s tough. D

        1. elkement says:

          I was just interpreting his Wikipedia entry and some other articles I have found, I don’t know any more details:
          From his technical writings and conference presentations I can just say that he seems to be a really smart guy, down-to-earth, unpretentious, funny, and experienced – representing the best of what I admire in members of the security community. He deserves any dollar he might have earned in that deal … and we don’t know this after all!! I rather give somebody whose writings I consider convincing the benefit of doubt.

          So it seems we have to agree to disagree here, and generally I would not even have any issues with somebody being a millionaire based on talents and hard work – in contrast to inherited wealth.

          Successful or famous people are often asked for their “secret” or career advice – as it might have been the case here. I haven’t at all interpreted his post as “telling the rest of us …”.
          Then such people try their best to generalize based on their experience. We all might be prone to narrative fallacy – crafting stories of cause and effect with hindsight instead of appreciating the role of luck. But saying that “rich people” have no right in making such conclusions – because they can do that so easily – would basically mean that (financial) success would always deprive you of the right to “philosophical insights”. I had to abandon all books by Nassim Taleb if I would agree with that – but I rather indulge in his truly irreverent writings.

          What if somebody worked hard for 25 years, then suddenly made a great invention and sold patents? What would that person have to do to regain his / her right to ponder (in public) about life and career? Isn’t it sufficient to return to your modest life-style “as quickly as possible”? Thinking of successful self-made people who are millionaires: It seems whatever these people do – donate like crazy, setup foundations… it is never considered enough, it is never considered convincing or said to be just a PR campaign.

          I am rather in agreement with Nassim Taleb who admires Seneca, the Stoic philosopher that happened to be rich though he lived as he wasn’t.

  3. This definitely struck a chord in me, too (your representation of it – I’ve yet to click through to the original). A lot of us are definitely freer than we think. Not everyone, of course, and being free doesn’t always mean making unconventional choices – we’re always free to make the conventional one. But then there’s a difference between consciously choosing the status quo and just getting wrapped up in it.

    1. elkement says:

      Thanks for your comment, and you made a good point: I didn’t want to advocate unconventional choices only, and it feels definitely different to make so-called conventional choices consciously.
      Sometimes I think the most important thing when taking ‘career and life decisions’ is to pick a path that rather increases options than reducing them so that you are always able to pick something actively.

      1. To me, your take definitely included the option to make a conventional choice.

        1. elkement says:

          Thanks a lot – as I indicated in the post, I re-wrote that quite often (as not to alienate anybody who had taken or not taken any choice whatsoever) – so I was not quite sure.

  4. danielmullin81 says:

    Excellent post as usual. Great advice about looking at the people in your sector and asking yourself if that’s the person you want to become. Although I didn’t formulate it quite that way, that was part of my reason for leaving academia: I didn’t want to become part of the wine-sipping literati out of touch with ‘common people.’

    Also, I agree with ‘do what you have to do to survive, then do something else for love.’ I’ve given up on being a professional philosopher, because the profession saps the joy out of it, at least for me. I’d much rather be an amateur (etymologically, somebody who does it for love, not money).

    1. elkement says:

      Thanks, Dan! I am really grateful for the comments on this post. Though such posts basically write themselves I am never sure if they sound too much like “follow your bliss” cliché or if they are overly sarcastic.

      It really took me an embarrassingly long time to find that totally straight-forward heuristic of watching the people in your intended profession / sector though it seems so common sense.
      Probably it is tricky to find out what people who really consider role models have in common. As a student or graduate you might pay too much attention to a tag like “physicist” or other professional label tied to a discipline. It is actually not easy for me to define today what exactly is a worthy career (if career is the right word). I can relate to people who are techies / geeks / engineers, but who have a philosophical / “renaissance” bent nonetheless. They are often entrepreneurs or freelancers or affiliated with different institutions … in a way that they basically represent themselves, but not some organization.

      As for “amateur”: I like “dilettante” for similar etymological reasons! :-)

  5. I am saddened that this would be odd career advice: it doesn’t get more sensible. We don’t get dropped onto earth to become VP Insurance Sales. We get here to enjoy it.

    There is an implicit opposite wisdom of the sailor’s point that careers shape us: if we live to be the person we want to be, than our careers will morph around that. That includes finding ways to pay bills and raise good kids.

    It’s worked well for me and I don’t sail around the Pacific. Though, perhaps, there is the good idea of the day. 

    1. elkement says:

      Thanks – I like your point of career being a by-product of personal growth. Of course any HR / professional development manager would say that corporate jobs – incl. VP Of Something – are offering just that ;-)
      It’s probably about: You get what you want if you don’t try to hard or don’t target any “goal” at all.

  6. M. Hatzel says:

    You have spared me the post I was intending to write this morning, but went outside and found tulips instead. I have finally accepted a decision I have been slowly drawing toward over this past year. I agree with all your points, actually. And since part of my imagined composition would address the issue of alternative choices with kids, I might create the post still… and link concluding thoughts to yours.

    1. elkement says:

      Thanks, Michelle! This was an interesting coincidence then: The post sat in my Drafts folder for nearly a week – and yesterday I decided that I didn’t want to be tempted to edit it anymore.
      I am looking forward to your additions to these ideas – as “family obligations” are often used as the main counter-argument to an unconventional, free, whatever-you-call-it life-style.

      1. M. Hatzel says:

        I am glad you published it; it’s a great essay! I will focus on “Family Obligations.”

  7. Fascinating, and something to which I can relate very well.
    Last year I retired from my eLearning position from the public school system–a job I loved very much. I took retirement as a process though, and prepared for it in various ways–financially, academically and “in my own head.” Looking back I can see now that it–all of it–was the right thing to do.
    These days I’m still working, but as an independent agent, and once again I find myself doing things I love. I think the advice that both of you agree on is something that I, too agree with, namely we have to currently seek that which works best for us at the time.
    And that thing is very much a moving target so perhaps it’s wise to always keep a least some of our thoughts on the career and thinking of what we need to be doing next. Maybe the quantum shift will nly be small; to the next energy level, and maybe it will be great.

    1. elkement says:

      Thanks, Maurice – I really appreciate your comment. I have re-written this so often to get my points across so I am happy to see yours and Michelle’s comments here.

      I sometimes figured it is important to change something (often something unexpected – at least for me) in order to keep the aspects of a job you really like and care about. To my own utmost surprise I still do security and certificates – in that strange combination / in parallel with the heat pump stuff. I totally enjoy this, and I think I would never been happy with any standard “career track” in corporations or academia.

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