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!


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