7 Antifragile Alternative Investments


Here are my  suggestions for “alternative” investments that will make you a more antifragile person. That is to say, after implementing these, you will have less fear of chaos, stress, and volatility entering your life — your downside risks will less, while your upside potential will be greater.  For a quick definition of antifragile see here.

1. Cash

Ideally you’d have the following:

  • Savings account with at least 6 months living expenses
  • Cold hard cash that you keep under the mattress, in a strong box or what have you
  • Foreign cash in two different currencies


  • If you’re out of job, you’ll need the savings to live on.
  • If you have a job, but need to pounce on an great investment opportunity (or pay a ransom) immediately, you’ll need something very liquid.  This will put you in a more advantageous position than someone whose assets are tied up.
  • If the banking system fails as it almost did in 2008, you’ll be happy you’re one of the few with big stash of real money.  Cash will be king.
  • If you’re country’s cash is no longer accepted or inflation is skyrocketing, you’ll at least have some foreign cash to get by

2. Alternative Energy


  • Solar panels
  • Windmill/wind power
  • Extra diesel fuel and a generator (diesel fuel stores the longest)
  • Tesla power wall or back up battery
  • Gasoline futures.  See http://www.mygallons.com/


  • High optionality. If one power supply is unavailable or too expensive, you can use another method.
  • In a case of a real calamity, if you are able to produce your own power and sell it, you become much more valuable than you were in normal times, so you’re almost hoping for chaos! — at least from a financial perspective.  That’s antifragile.

3. Dual Citizenship

Imagine something terrible happens in your home country, such as a civil war or financial collapse.  Wouldn’t it be nice to be able to just buy a plane ticket and be on your way to another (home) country?  In today’s globalized and interconnected world, no country is immune to collapse.  I happen to live in the United States, which seems powerful and stable, but is also the country that people would love to bring down the most.  It would be nice to know that I could make me way to Canada, if need be.

This idea is not just for doomsday scenarios.  Perhaps you want to purchase real estate for investment or retirement purposes — or there are better job opportunities in your other country.  If you’re a citizen, it’s no problem.  Speaking of…

4. Foreign Real Estate

This a good hedge against other investments in your home country that are tightly correlated, but it also gives you that alternate place to live in case the zombie apocalypse  hits your home town.

It also you encourages you to travel more to a foreign country and learn about the culture there, which is another excellent antifragile strategy.

5. A Garden  / Extra land

A garden or farm allows you to grow your own food.  This is good for several reasons:

  • you get highly nutritious, organic food which keeps you healthier and protects you more effectively from disease, free radicals, toxic chemicals, and stress
  • you can sell excess food for profit.  As chaos rises, your food prices should go up
  • if the land becomes super valuable, you can just sell it and set up a garden/farm somewhere else

Extra land has similar benefits. It’s a place you can:

  • put your garden,
  • construct a greenhouse,
  • construct some other type of building for your benefit,
  • move to if your current living situation is undesirable,
  • or just sell to someone else if the price is right.

6. Friends

True friends do not require a high degree of maintenance (low downside) and will come through for you in times of need (big upside).  From a practical perspective they also provide the following  benefits (and there are hundreds more):

  • access to jobs
  • someone to share your feelings with
  • ideas to help with your kids, finances, home repair,  recipes, etc…
  • conduits/introductions to other acquaintances that can help with literally anything
  • backup/duplicate functions such as house sitting, pet sitting, babysitting or even backup friends or mating partners if you encounter a loss.

7. Yourself

It’s safe to say the best investment you can always make is in yourself.  This could be a whole other blog post or even a separate book, but it should be obvious that the more time and money you spend on bettering yourself, the more adaptable, stronger, smarter, and healthier you’ll be.  Which means you can survive and thrive even when the world is in disarray.

The foundations are always nutrition and mental health in my opinion. Stay on the cutting edge of health and always try eat as well as possible.  See a therapist or read inspiring self improvement books.  Engage in activities that bring you joy.   Everything else should take off from there.  Here are some people and resources in no particular order that have helped me greatly and which I highly recommend:

  • Sally HogsheadHow to Fascinate.  In this book, Sally talks about how each of us has one or two distinctive personality types ( out of 49)  that can makes us effective and powerful.  The main takeaway for me was don’t worry about your weaknesses, play to your strengths.  This makes us more “fascinating” to others.  Simple, yet very effective advice.  It changed the way I approached my career and thought about myself, in general.
  • James Altucher — Listen to his podcasts, read his blog posts and/or his book Choose Yourself.  You can’t go wrong with James.  He’s so brutally honest that if nothing else, it makes a great read or listen.  He has so many unbelievable guests on his podcasts, that you’re bound to learn something new and amazing each time.
  • Jack CanfieldThe Success Principles.  I was a little skeptical at first because this is the guy who wrote the Chicken Soup for the Soul series, which I figured was too cheesy for me (even though I had never read it), but this dude lays out some awesome advice.  The book is like a bible of success habits — something you can turn to again and again.  I’ve listened to it on audio book three times now on my way to and from work.
  • Jon GabrielThe Gabriel Method.  Equal parts nutrition book, weight loss book, and  mental health book, Jon combines visualization and mediation with expert-level bio-chemistry and nutrition information.  This guys knows his stuff.  It’s also the first time I remember hearing the idea that you’re overweight because your body wants you to be.  Until you can conquer things like emotional pain and stress, toxicity, and bad poor nutrition habits, you won’t lose the weight no matter what kind of diet you’re on.  In fact it’s an anti-diet book.



The Antifragile Career, Part 3: Thriving at Your Job


“You don’t understand, you’re out.” These were the words my dad heard from the principal at the high school where he was a social studies teacher during the 1980s.  The school year was wrapping up and due to budgetary restraints and lower enrollment in the district, some of the teachers would be out of a job next year.  He had known there were some layoffs coming for some staff, but had been trying to negotiate for why his job should be secure.  At the time, he had three children under 13 years old and no backup plan.  He was the sole income earner for the family.  What he thought was a stable, steady public school teaching job, was suddenly very tenuous.

In today’s environment, it’s not enough  just to get a job and go on automatic pilot.  Jobs tend to be fragile.  Companies go out of business unexpectedly, governments are under increasing pressure to cut taxes, and technology advances at such a fast rate that what was once state of the art is now obsolete.  The list could go on and on.  Most people don’t realize how insecure their career actually is.

When my dad was told his bad news, he knew he had to spring into action immediately.  He had been unprepared at the moment, but there was still a slight chance he could be in a better position by the time next school year started.

He found a clause in the union contract that said if was qualified to teach a second subject, they would have to find a spot for him, due to his seniority.  So during one mad scramble of a summer, he was able to go back to school, call in a couple favors, and take a bunch of English classes — which enabled him to get certified to teach by the time the fall rolled around.  He had saved his job (even if he wasn’t the most popular teacher with the administration).

Things were stable for the moment, but this must have been a wake-up call for him, because the next year, he enrolled in law school and by working nights, weekends, and summers completed his law degree four years later.  Even though he chose to remain a teacher until he retired, he nonetheless had put him self in a much more powerful position.  He had taken a stressful event (getting a layoff notice) and turned it into something better ( a teacher with dual certification and a law degree).  That’s the definition of antifragile, right there.

You never know when you could receive a bolt of bad news out of the blue, but you can always do your best to prepare for the worst.  Here are some strategies for thriving at your job and keep your options open in case you have to switch jobs or even careers.

  1. Learn new skills on the job.  This is almost always free (no risk!). Some companies offer additional skills training.  Some might offer management training.  Both are good — and management skills are broadly transferable, even it is harder to move laterally sometimes.
  2. If your company offers international travel, take it.  It opens up new doors personally and professionally and you learn things about other cultures that you normally never would.  Plus it probably makes you a stronger player within the organization itself.  Double plus… they pay for it!
  3. Learn a new language.  See above.
  4. Take on a new project.  If you can’t travel, you can at least “explore” within the organization.  The more sills you have, the more valuable you become.
  5. Be friendly.  Be likable.  Go to lunch with people.  Hang out and chat with people once in a while.  This does two things:  1) it makes you more popular within the company (harder to fire) and 2) if you are let go, it gives you other connections in case you are looking for work.  Those people will want to help you and pass along any openings or advice that they have.
  6. Learn a non-related skill in your off time (or when you are at work, if you can pull it off).  If you have to (or want to) switch careers entirely, you need some kind of skill.  There are hundreds of things you could do but here’s a few ideas:
    1. Take some computer programming classes or just learn online and practice
    2. Learn how to cut hair, go to beauty school
    3. Learn about plumbing
    4. Make things and try selling them online ( cookies, crafts, t-shirts, artwork, etc..)
    5. Bartend or wait tables a few hours a week
  7. If nothing else, just do a good job at your current company.  It probably goes without saying, but the more valuable you are to your boss and your company, the more likely you are to thrive there. That will at least get you to robust within your own company.  Then you can start apply some of the other antifragile ideas above.

The more of these things you do while at your current job, the more relaxed you feel.  Eventually, you’ll be so confident about handling any situation that you will get bored if things are just the same old, same old every day.   You’ll actually crave variability and some randomness!  You may want to start that side (or second career).  And if one doesn’t work out, that’s fine… there is always another more exciting option to try….


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!