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!