How to Have a Low-Risk Life And Achieve Success at the Same Time

Have you ever seen a package with a label “Fragile, please handle carefully”?

Of course, you have. Certain items like glassware are very easy to break and need to be handled carefully.

Imagine you saw a box with a different title “Antifragile — please mishandle.” I learned about the concept of antifragility from the book Antifragile by Nassim Taleb. The concept is so important that I’m dedicating an entire section to paraphrasing it and giving you ideas derived from it that will help you live a better life.

Per the book, there are three types of states:

  • Fragile — doesn’t like volatility
  • Robust — indifferent to volatility
  • Antifragile — loves volatility

Being antifragile means you’re capable of thriving in a chaotic environment with lots of chance involved. Being fragile means you need everything in your life to go smoothly or else you’re screwed.

I’ll dive into the concepts soon, but a great example of an antifragile career is being a writer.

There’s a ton of chance involved in becoming successful and chaotic/random situations can fuel your career — think 50 shades of grey. You want buzz and press, regardless of whether or not it’s good press. Some of the most wildly popular books aren’t the ones with 5-star reviews across the board.

They’re the ones with an equal amount of positive and negative reviews. All the disagreement makes you want to see for yourself.

Being antifragile means you set your life up in a way that has a minimal downside and high upside. To make the picture clearer, let’s dive deep into the fragile lifestyle most people live.

Are you a Turkey?

“Consider a turkey that is fed every day. Every single feeding will firm up the bird’s belief that it is the general rule of life to be fed every day by friendly members of the human race ‘looking out for its best interests,’ as a politician would say. On the afternoon of the Wednesday before Thanksgiving, something unexpected will happen to the turkey. It will incur a revision of belief.”

People treat real estate like a religion. Seriously, make a negative comment about real estate and you will be treated as an apostate. People will genuinely get upset with you. Warren Buffet has a saying about debt. “Debt is almost always good. Until it’s not.”

It’s not that taking on debt is bad in and of itself, but it makes you fragile. Everything needs to go smoothly for you to thrive off of debt. But if you lose your job, the economy goes south, and all the sudden you’re underwater on your mortgage, that “great investment” will eat you alive. See 2008.

This isn’t a post about real estate investing, though. It’s just one of the perfect portraits of a fragile lifestyle. One of the core philosophies of antifragility is “don’t go bust.” You want to keep yourself from being exposed to a “ruin event,” meaning something that can completely wipe you out.

Buying a house above your means and taking on a ton of debt is like playing Russian roulette with a revolver that has a billion cylinders in it. 99% of the time you’re fine, but one bullet can kill you.

The average person is living the life of a turkey:

  • “The average U.S. household with credit card debt has an estimated $6,929 in revolving balances” (source)
  • Only 39% of Americans have enough money to cover a $1,000 emergency (source)
  • Student loan debt and default rates now match the same numbers of the housing bubble (source)

I’m not saying these easy situation to get out of, but ask yourself? How far away are you from being destitute, really? An injury that keeps you out of work, a major medical scare, a divorce, lost job, economy tanking — all of the situations create a very real and possible path to ruin.

This is why I included a section in the book about starting a home-based business or side business.

Do I think everybody needs to be a capital E entrepreneur? Absolutely not. But having an extra stream of income makes you less fragile. And choose the right side gigs or businesses and you can create an antifragile environment to make dramatic leaps in success.

The Antifragile Lifestyle

This book could sell zero copies. It could also sell a million copies — unlikely but possible. It could also land in a wide range of number in the middle, some of which would be very satisfying. But here’s the key to book writing being antifragile — I can’t sell negative books.

The downside is known. Sure, I spent a couple of thousand dollars to produce the book, but even if I never sold a copy, I couldn’t lose more than that original investment. Writing books is antifragile because it has a low downside and a potentially extremely high upside.

Photo by NeONBRAND on Unsplash

When it comes to careers, internet businesses are as antifragile as you can get. For a few hundred dollars, you can start an e-commerce store online without having to write a single line of code, process any orders, or needing to package and ship items. With “drop shipping” you don’t need to buy and carry any inventory. You find a supplier who will ship the items for you when somebody orders.

Let’s say you want to be an artist. Again, the downside is known. Instead of going into debt for an art degree (fragile), save up some money and buy your paint and canvases. Set up a website to sell your art. Learn how to do SEO, run Facebook ads, and build an e-mail list. Again, it’s a type of business that doesn’t kill you if it completely collapses and has the potential to change your life. You can become a freelancer who only does work when it’s requested — known downside.

So why don’t people choose to live an antifragile lifestyle? Because of fear and unpredictability. With a paycheck, you know how much money you’re going to get and you can rely on it coming.

You have “job security.” And I get it. You can’t just up and leave your job. You need health insurance, and a home, and food.

I have a solution for you. It’s a remix of the antifragile lifestyle and it’s also the new American Dream.

The New American Dream

The old American Dream is dead. The days of being a “company man” for 40 years, getting your gold watch and your pension, and taking care of your family with a single income are long gone. You know that.

But, despite what you hear on the news, you’re living in the best possible time to make a dramatic shift in your life and career (unless we all get nuked or chemically attacked, the world is fragile). We’re in the 3rd inning of the New American Dream.

So how does this all work?

Keep your job. You need it. The steady income is good and it will support you when you try your side business. Contrary to popular belief, entrepreneurs hate risk. Ask most company founders and they’ll tell you their business started off as a side project they worked on while holding a job.

Most people don’t quit their job until they have enough cash saved up and they’re confident the cash flow will be steady. I’m in that position right now. I’m a marketing director at a digital agency. I actually make about 3 to 4 times as much money with my side business than I do at my job. So why am I still working?



First, I have the advantage of liking my job and the skill set I learn in my job helps me in my side business.

Second, I’m building my “fuck you” fund. I’m squirreling away cash until, one day, I’ll have enough money to never have to listen to anybody again if I don’t want to.

Third, I have options now. It feels better to work because I want to, not because I have to.

Start a side business that makes you an extra $1,000 a month and see how much your life changes. What kind of impact would an extra $12,000 a year have on your life? I’m guessing quite a bit.

I say this with no hyperbole — almost any reasonably intelligent adult can start a side business that makes them an extra $1,000 a month. That means you.

You can keep your side business as a hobby. You don’t even have to work extremely hard or anything. You can half-ass your way to $1,000 a month by spending a few hours a week working on your side gig until you get some traction.

Then, what do you do next? You pay off your credit cards, student loan debt, and other bullshit you accumulated over time. You don’t upgrade your lifestyle yet (fragile)! Start building your “fuck you fund.”

Invest some of it back into your business and education. Take some and throw it in an index fund (don’t try to become an investor because you will fail).

Spend a few years doing this. 5 years from now you have a six-figure career and an antifragile future. This is not unrealistic at all.

The end goal is stated eloquently by John Goodman’s character in The Gambler:

“You get up [a large amount of money], any asshole in the world knows what to do. You get a house with a 25-year roof, an indestructible Japenese-economy shitbox, you put the rest into the system at three to five percent to pay your taxes and that’s your base, get me? That’s your fortress of fucking solitude. That puts you, for the rest of your life, at a level of fuck you. Somebody wants you to do something, fuck you. Boss pisses you off, fuck you! Own your house. Have a couple bucks in the bank. Don’t drink. That’s all I have to say to anybody on any social level. “

Until you can say “fuck you,” you’re fragile. You’re fragile if you have to do what you hate to survive. You’re fragile if your life can’t handle stress and chaos. Becoming antifragile isn’t just a fun idea to motivate you, it’s the antidote to ruin. It’s imperative you adopt some sort of antifragile mechanism in your life. Next, I’ll break down your best options and strategies to have an antifragile life.

How to Live an Antifragile Life

The concept goes much deeper than economics and money.

Always thinking about having a low downside and a high upside is key to living not only a great life but an exciting one.

So how do you live an antifragile life — increase your options and put yourself in situations that favor chance? Let’s paint the picture of a fragile vs antifragile lifestyle in an example we can all relate to — vacations.

Which type of vacation is more fun? One with regimented activities, itineraries, tourist traps, and spending tons of time standing in line. Or one where you go to spots the tourists don’t know about, have no plan and spend your time exploring the local areas.

Nobody has crazy cool stories about Disney land and scheduled dolphin swims. No, great travel stories always include things like interactions with the locals, secluded off the grid destinations, danger, adventure.

The philosophy is the same too. Your vacation becomes fragile when you put together meticulous plans because those plans come with expectations. If one of your destination spots isn’t as fun as you planned, especially if it’s toward the end of the trip, the trip will seem kinda meh.

The opposite is true with ‘flanuering’ — Taleb’s word for doing whatever you want whenever you want. When you flaneur, your upside for having out of this world experiences is high.

You can see elements of this lifestyle in many more activities.

Go to Parties

I’ve been to a “networking conference” before. Talk about an event that produces the exact opposite outcome of its name. Events have the same issues as pre-planned vacations — the sterile unadventurous atmosphere where fun seems forced on you instead of something that emerges from the experience.

Contrast that with a party — one that’s not geared specifically toward business connections.

Casual parties create ten times more business deals than any networking conference. Parties are out in the wild. The natural characteristics of people emerge from the environment because people aren’t on guard and trying super hard to be their best.

They’re also just fun. People don’t like to work with people they don’t like. Exposing yourself to meeting more people in a non-forced way is the best way to create genuine friendships and build a network.

Photo by Brooke Lark on Unsplash

Hobbies With No Goal

Getting better at something for the sake of getting better at something has unlimited potential benefits. Think of the things people try to force themselves to do — work out, make money, look cool, etc. It’s always harder to do something you think you have to do.

When you find a hobby that you want to do for pure exploration and joy, it can lead to the results you generally want.

Instead of hitting the gym, forcing yourself to move pieces of metal for set periods of time, you could just hike, rock climb, ride a bike with your kids, whatever. Many companies were formed out of hobbies.

Derek Sivers, a well-known entrepreneur, and author started a multimillion dollar company called CD baby because he was a musician and he realized it was hard for indie artists to sell their CDs. He started a website to put his own CDs on the site and a few buddies.

More people asked him to put their CDs up, then more, then more, until it became a full-blown business. He was just toying around with computer programming because he thought it was interesting and he happened to be a musician — two hobbies that had idea sex with each other and birthed a company.

Making, doing, or experience for the sake of it has a way of opening up your life to serendipity, which is what antifragility is about. We live in a complex world we don’t understand. Instead of always trying to “figure it out” we can expose ourselves to life in a way that doesn’t hurt us and has the potential for life-changing benefits.

Read More

Ah, yes, another self-help writer telling you to read more books. I have to talk about books because books are the most antifragile opportunity out there. I read a lot. Most of what I read isn’t mindblowing, but a small handful of books completely changed the way I think about the world like:

  • Antifragile
  • The Meditations
  • Fooled by Randomness
  • Rich Dad Poor Dad
  • The War of Art
  • Zero to One

I’ve read all of these books more than once, more than twice, more than three times. I experience something new each time and jump through a mental wormhole when I read passages the second time that hit me in a totally different way — because my life is different during the second pass, some lessons don’t present themselves until you’re ready for them, and book retention is just low so you flat out forget or miss stuff.

As corny as it sounds I credit much of what’s happened in my life — starting businesses, becoming a writer, increasing my sanity, getting healthier, being able to handle being alive — to books.

When I had no money, no hope, no network, and no opportunities, I bought a bunch of books. Books obviously fostered my interest in writing. There’s a bond you can create with other people when you’ve both read the same book (see: parties and business connections). Little tidbits and ideas from books can become your ally in tough times.

There is an 80/20 principle involved with books too. Sometimes you have to wade through the dirt to find diamonds. Hell, I plan on writing at least a few books per year for this same reason. I put all my effort into my work, but I can’t know how well they’ll do. J.K. Rowling didn’t know. E.L. James, the author of 50 Shade of Grey, sure as fucking hell didn’t know.

You, when it comes to your life, will never truly know the future.

You have two choices, try to force the world into your cookie cutter mentality and suffer downside for it or become antifragile and increase your odds of serendipitous magic.


This is a test section for a new book I’m working on. Tentative title Real Help: A B.S. Free Guide to Self-Improvement. I’d love your feedback. I’m trying to test out ideas like a comedian at an open mic night.

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