The Antifragile Career, Part 2: Finding a job

In Part 1 of The Antifragile Career, we talked about the types of jobs that tended to be more

Needle in a haystackantifragile than not.  In this post, I will lay out some strategies for actually landing that job.

The job search process can be one of the more grueling, energy draining, and humbling experience of your lifetime.  And chances are you’ll do it over and over again as you work your way through your career.
The average person changes jobs about every four years, so it’s critical that you constantly learn and improve your job searching skills.
Since the age of 16, I’ve changed jobs at least 15 times.  Just within the technology sector, I’ve worked for ten different companies, so I guess that qualifies me to be a bit of an expert at finding a job!  Here are some of the different titles I’ve held:


  • Food Vendor
  • Deliver truck driver
  • Basketball Referee
  • Blackjack dealer
  • Off Track Betting Manger
  • Web Designer
  • Software Engineer
  • Database Developer
  • Small business owner
  • Lyft Driver
 I have learned something from each one of these, and each one had it’s own interesting aspect to it, but you need to have the skills to get hired in the first place.
It’s especially important in this phase to try and be as antifragile as you can and not get mentally crushed when you don’t land that job that you thought would be “just perfect”.   The fragile person quits the search or makes up excuses about why they can’t find work — again, I’ve been there.  Let’s look at some strategies for being antifragile in our search.  Again, this means taking actions that have small downside risk and a large upside potential.


  1. Apply to lots.  Pretty obvious, right?  The more you apply to, the greater your chance of getting hired is.  Make it a goal each day to find say, 4 good possibilities and apply to them.
  2.  Use recruiters.  I sometimes hear people say, they don’t like using recruiters.  I don’t understand this.  They have lots of jobs!!  Why would you ignore this group of potential jobs.  Sure, some of them are sketchy or they blast out emails of jobs you have no interest it, but there are also many good ones.  Get better about working with ones you trust.  They are connected!
  3. Apply yourself too.  On the other hand you can’t just rely on recruiters.  They may have a good network, but they don’t have everything. Apply directly online, talk to people in your industry, whatever it takes.
  4. Learn from mistakes.  Get feedback from every interview, whether it’s explicit or implicit.  Meaning, you can directly ask at the end how did.  There’s no law against doing this… 🙂  Many times you won’t get a direct answer, but if you do all the better. Often times though, you can tell how you’re doing during the interview, so try to make a mental note of it.  Did the interview start glancing out the window as you blathered on about something?  Maybe you talked to long.  Did you feel nervous talking about a certain topic or not know it well enough?  Study up for next time.
  5. Apply to some outside of ones you normally would.  If have gotten a job several times doing this. One job I applied for was a 60 mile commute each way, but I asked if I could work remotely two days a week and they said sure.  Another job had listed “Embedded software development” as a major bullet point, which I had never done.  I almost didn’t apply, but I asked the recruiter about it and he said, “oh, they don’t really care if you know that or not…”.
  6.  Tailor your resume.  It takes a bit of time, but in most cases you’ll need to modify your resume for each job you apply to.  It’s got to mention the things the company cares about most.  This at least gives you a better shot to get in the door.
  7. Network/Talk to people.  But be interested in what others are saying too.  This is free and you never know what you might hear about.
  8. Start your own company.  In most cases, this is much easier than you think.  And it’s a great idea for several reasons:
    1. You could be successful immediately and not need a job.  Hooray!
    2. It’s a fall-back in case you hate your job or get fired.
    3. Most importantly, it’s a great resume builder. If people see you started your own business in the field you are applying for, you have instant credibility, whether you were any good or not!  I’ve used this my advantage several times.
    4. It looks like you were doing something if there are gaps in your resume ( like if you got fired).  You can just say you were “consulting” or working on your own business.

All of these suggestions are meant to be low risk, high reward.  I’m sure there are many others.  Have more ideas?  Please share them with me!


The Antifragile Career , Part 1: Choosing a Career

One of the biggest parts of life for many of us is the work that we do.  If you include commute time, time thinking about work outside of work, and the time inside of work, it’s easy to see that this can be 50 hours per week at the minimum.  Not to mention it’s how most of us earn our money, so yeah, it’s important.
There are three aspects to consider when thinking about an antifragile career:  1) Choosing a career, 2) finding a job, and then 3) thriving at your job.  Let’s focus on the first and more philosophical question of choosing a career.
The first question we should ask is: Which job or career ( or combination of jobs) is the most antifragile?  Or better yet, which careers make our lives the most antifragile?  The difference is subtle,  but important.  Although a career itself may be somewhat fragile, such as CEO or a professional athlete, if you did it for just a few years, you may have store up enough cash to make yourself “set for life”.  So the end goal is not just about the fragility of your current job, but what it does for you and how it affects your life in the long term.

To illustrate, let’s first think of which careers are the most fragile.  The ones where if you make one bad mistake, you’re gone.  And not only gone, but also stand to lose a lot — meaning it will be hard to get back to the same level you were at.

If you are scared to send a tweet (for fear of saying something politically incorrect or that be construed as something that doesn’t jibe with your company policy), you are fragile.  If you’re scared about getting an email from someone, you are fragile.  If one major error at work means you’re fired you are fragile — even if that firing is justified.

Let’s say you’re a truck driver or school bus driver and you are arrested for driving drunk or cause and accident, you’re likely done — and rightly so — with a small chance of catching on with another job of the same type.

Or take the real life example of former Vante CFO Adam Smith.  In 2012, he decided that he wanted to voice his displeasure against the Christian-based fast food restaurant Chick-Fil-A and their opposition to same-sex marriage.  He made and posted a video to YouTube where talked about his views on the matter and films himself berating a Chick-Fil-A employee.  The video immediately went viral and when he came to work the next morning, his secretary was in tears because of the flood of calls and even death threats he was receiving.  He was promptly fired.  Smith not only lost his $200,000 base pay, but also reportedly $1 million in stock options.   He was able to find another job in Portland, but two weeks into it they found out who was and let him go as well.  As of 2014, he was still not able to find a job, his wife has had to return to work and they have been using food stamps to help get by.  I’d say that’s the definition of large downside, small upside.

Does this mean that you should not take a CFO job?  No.  Again, if he had made better choices and realized what an interconnected world he was now living in and what the consequences were of speaking out like he did, the payoff from his job would have been enough that he wouldn’t have needed to worry about it.  Now, if speaking out and voicing your opinion in this manner is that important to you, then no, it might not be the best job to take.

Let’s take a look at structuring your career so that it as antifragile as possible.  Here are some of the factors that go into creating that ideal career:

  1. Transferable skills  (like exits on a freeway)
  2. Multiple skills
  3. Low probability of getting fired
  4. Potential high pay
  5. Liking your work

Think of your career as a long cross country road trip, but without an exact city in mind — just a direction.  For example, let’s pretend we’re driving accross the United States and West represents the best career direction.  We want to go this way because we know it will be the most antifragile, but don’t know ahead of time which area is best for us — we can’t plan it too far in advance.  So whether we end up in Los Angeles, San Francisco, Seattle, or anywhere in between doesn’t matter now.  We just want to get there.  That’s how we can think of our career.  We may think we want to be a Sr. Engineer with Facebook, but Facebook may not exist 30 years from now.  The same holds true with many other industries.  The best strategy is to picks skills that are as transferable as possible and several of them.

Would your job skills translate to another job or similar job fairly easily?  If you’re a blacksmith or typewriter repariman, perhaps not.  If you’re a restaurant server, electrician, or a good salesman, then you’re probably ok.

Better yet, if you have more than one marketable skill, you will be in a much better position.  If the skills are also tranferable, valuable, and you like doing them, you’re gold!  Ideally these skills won’t be too closely related or else the value wont be as great.  For instance, if you’re a computer programmer and you know C# and are also learning Python, that’s nice and it will help you in your career, but if for some strange reason there is a big slowdown in information technology, it would be nice to know how to do something else.  Remember, it’s best to be prepared for worst-case scenario, because that scenario is probably much more likely to occur than you think — and furthermore is probabaly not even the worst case scenario!
In no particular order, here is a sampling of some of the more antifragile careers:
    1. Driver (Taxi/Lyft/Uber).  Variability is no problem.  Rain, snow, holidays, large events all have potential to increase rides.  There is no boss to fire you.  If you make a mistake, you learn and start gong to a new part of town or trying at a different time of day.  If Taxis become obsolete, you can drive for Uber or Lyft.  If they all go down the tubes, there are many other places that need drivers.
    2. Bartender/server.  People drink when they’re happy.  People drink when they are sad.  People drink just because it’s Friday.  I think you get the idea.  It’s unlikely drinking alcohol is going to go away.  If we do have a second prohibition, you’ve be glad you developed great social skills as well.  It’s also an excellent way to meet people and create a bigger network of friends and acquaintances.
    3. Dentist.  People will need dental work for the foreseeable future, even in financial downturns.  It pays well and there is high barrier to entry so not just anyone can do it.  If own your own practice you can’t be fired.  If you do lose your job, it’s fairly easy to transfer to another place.
    4. Mechanic.  Knowing how to fix things is a good skill to have, especially if it’s somewhat transferable, like fixing engines.  You have to keep your skills up to date, but there’s no doubt that machines will continue to be very important in modern society and they will continue to break.
    5. Carpenter.  Similar to mechanic, if you can build things of high-quality and high usefulness, you will most likely survive in good times and bad.
    6. Software Engineer / IT expert.  Technology is only increasing in complexity and importance.  When times are good, companies must build new features and devices to keep up with the competition.  If things break down then someone will need to fix them!
    7. Hair Stylist / Barber.  This career is at least robust.  It’s hard to imagine a time when people won’t pay for someone else to cut there hair.  A great skill to pair with another career.
    8. Writer.  Communication is always important.  If you can write well, you can survive whether the medium is newspapers, magazines, books, or digital.
    9. Accountant.  Each new “random event” — tax laws and corporate regulations, and the like — make it even more important to have a top notch accountant.  As the world gets even more globalized, companies and individuals will be looking for the most advantageous place to earn income.

Have more ideas for antifragile careers?  Please let me know!


Stewart Copeland, The Police, and Antifragile Beginnings



“We were a punk group and we wanted to ruffle feathers.”   This was the mindset of Stewart Copeland, drummer for The Police, in the late 1970’s and it may have created fame and fortune for the group.
I came across  this quote while watching this great interview of Copeland from the Later with Bob Costas show.  Great because I am a fan of the Police and there aren’t many interviews of Copeland that I could find online.  And secondly, because he talks about two antifragile concepts in just the first couple minutes!
Early on in The Police’s career, they released a single called Can’t Stand Losing You.  The BBC wouldn’t play it because the subject of the song was suicide.  Costas asks, “Did you raise a voice in protest and say ‘Wait a minute!  This is not an advocacy of suicide…'”?  I was expecting Copeland to explain how they tried, but the BBC was just too big, etc., but instead he gave a wry smile and said, “No, the more we irritated the BBC, the better we felt about things”.
Of course their career went straight up from there and they eventually sold millions of records (even if they did lose the “punk” label).  Did they consciously know the notoriety would help them?  Probably not — and of course it didn’t hurt that they wrote great songs — but this is exactly what Nassim Taleb talks about in his book Antifragile.  Sometimes, paradoxically,  the more bad press you get, the more popular you get.  Especially if you’re pissing off the right kind of people.  Think, Elvis, The Beatles, Led Zeppelin, even Donald Trump.
So, The Police had great songs and the right attitude to go with it. They were poor, hungry, and had nothing to lose.  Very antifragile!  All upside.
Then they became a sensation and they all got rich.  Now what?  Did their motivations change?  Fortunately, Costas asked this exact question as a follow up.  Stewart answers this way:
 “It’s amazing how you start out as a firebrand, but then you start getting rewarded for you revolutionary fervor.  And you become a lot less revolutionary.  In fact, you become part of the status quo.  You think, ‘If they knock the world over, what’s going to happen to my bank accounts?’  It’s terrible.”

The more you start to worry about losing you possessions, your relationships, the more fragile you become.  The more fragile you become, the more likely it is that you will lose these things!

Best to develop an attitude free of attachments and try to maintain your zest for life no mater what.

In 1924, Thomas Edison’s laboratories burned to the ground.  Ten buildings in all.  Years of work, all of it gone.   “It’s all right.”, he told his son. “We’ve just got rid of a lot of rubbish.  Go get your mother and all her friends. They’ll never see a fire like this again.