How To Achieve Massive Success Without Taking Massive Risks

The following is an excerpt of my book — Real Help: An Honest Guide to Self-Improvement

“Risky” is a loaded word. First, people don’t understand it fully. Second, risk isn’t always the same when you want a certain outcome — context matters. Last, people often get it backward. They find safety in what’s truly risky and see risk in what’s truly safe.

I learned many of these concepts from the author Nassim Nicholas Taleb (you can see his influence on me, as I’ve quoted him 47 times in this book). His Incerto series is all about understanding risk. My favorite book in his series Antifragile: The Things That Gain From Disorder teaches you how to live a low-risk life and benefit from luck at the same time.

You need to learn how to become antifragile. It’s the key to experiencing the rewards life has to offer without many of the risks that can set people back permanently. Remember that earlier in the book I told you that luck and chance play a large role in your life. If you become antifragile, you set yourself up for serendipity.

Per the book Antifragile, there are three types of states:

  • Fragile — doesn’t like volatility
  • Robust — indifferent to volatility
  • Antifragile — can benefit from volatility

An example of something fragile is a glass vase. A rock is robust. But what is something that benefits from volatility? The universe itself was birthed from volatility. Ecosystems are volatile. Many of the systems we don’t truly understand, like nature, emerge over time from seemingly random events. Evolution doesn’t happen in a quiet, orderly, pain-free way. So while parts of the system get phased out, the system itself survives and improves. Take something like the restaurant industry. Many random restaurants open, some close, but the best survive. Individual pockets of the system don’t always win, but the system itself does.

If you want to be antifragile, expose yourself to the upsides of randomness while at the same time protecting yourself from the risks. Make many small bets with high upside. Some will fail and some will succeed, but the overall payoff of the combined actions can be huge.

A great example of an antifragile career is being a writer. There are a ton of chances involved in getting high book sales or even building a small but cultlike following of dedicated readers. Plus, chaotic/random situations can often fuel your career. Think Fifty Shades of Grey — both the good and the bad random press fueled the success of the book. Antifragility doesn’t mean you definitely experience benefits from randomness, but you have the possibility to.

Some of the most wildly popular books and underground classics aren’t the ones with 5-star reviews across the board. They’re the ones with an equal number of positive and negative reviews. All the disagreement makes you want to see for yourself.

When you write a book, you know the downside. You can’t sell negative books. But with effort and luck, you can have a bestseller. Write more books, get better at writing, and continue taking “at bats” in the publishing world, and you can set yourself up for a great career.

If the concept doesn’t make sense to you yet, let’s take a look at what the fragile lifestyle looks like.

Are You a Turkey?

This quote from the book describes something called the turkey problem. A turkey problem happens when you put yourself in a situation that can go south really fast and without warning, even if it works well for a long time.

Real estate in 2008 was a great example of the turkey problem. As long as the economy worked well, you could get away with buying a house you couldn’t afford and financing it with debt. The key to understand here, even during those good times, is that you’re fragile.

Just because something works out for you now, it doesn’t make it a good decision, nor does it put you in a stable situation. You get a false sense of security.

Putting yourself into debt is a scenario where you won’t put yourself into a disastrous financial position most of the time, but you can sometimes lose everything, and then some, depending on the circumstances. It’s not that taking on debt is bad in and of itself, but everything needs to go smoothly for you to thrive from debt. If you lose your job or the economy goes south, all of a sudden you’ll be underwater on your mortgage, and that “great investment” will eat you alive.

This isn’t a post about buying a home, 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 or 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 that one bullet can kill you.

The average person today is living the life of a turkey.

  • The average American now has about $38,000 in personal debt, [excluding home mortgages] (emphasis mine).
  • Only 39% of Americans can afford a $1,000 emergency.
  • Student loan debt and default rates now match the same numbers of the housing bubble.

I’m not an economist. But I don’t have to be to understand what a fragile lifestyle looks like.

Any situation that can cause real harm to your life, unexpectedly, is a fragile situation. Working for someone else and relying on one sole source of income is fragile. Businesses come and go, even ones that have been around for decades. Same with job titles. People get laid off, with high mortgages, and little savings. Their lives are ruined in mere moments after experiencing many years of “stability.”

I’m not saying this is an 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, a job lost, the economy tanking are all situations that can create a very real and possible path to ruin.

Do I think everybody needs to be a capital E entrepreneur? Absolutely not. But having an extra stream of income makes you less fragile. Saving that money, and paying off debts makes you more robust.

Choose the right side gigs or businesses, and you can create an antifragile environment to make dramatic leaps in success. And yes, even income.

The Antifragile Lifestyle

This book could sell zero copies (but since you’re reading this, that’s not true!). It could also sell a million copies, which is also unlikely, but possible. It could also land in a wide range of numbers 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 the original investment. This is my third book, so I have a good idea of whether or not my investment will pay off.

A new writer wouldn’t need to spend as much. In fact, I personally know those who’ve created books for a few hundred dollars or less. If you didn’t have that money to begin with, you could try an even lower-cost option, like starting an affiliate blog that costs no more than $10/month for hosting; then use those funds to create a book. Writing books is antifragile because it has a low downside and a potential for an extremely high upside.

When it comes to careers, internet businesses are as antifragile as you can get. For as low as $30/month on Shopify, you can start an e-commerce store online without having to write a single line of code, process any orders, or package and ship items. With dropshipping, you don’t need to buy and carry any inventory. You find a supplier who will ship the items for you when somebody orders through your website.

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 email list. With cheap web hosting and YouTube videos to learn marketing for free, this could be done even by someone who didn’t have a ton of money for materials.

Again, it’s a type of business that doesn’t kill you if it completely collapses, but has the potential to change your life. You can become a freelancer who only does work when it’s requested (a known downside). At worst, a client doesn’t pay you, and you wasted time doing a project for them. That sucks, but it isn’t life-ending.

Another benefit of the antifragile lifestyle is that it keeps you on your toes. I heard somewhere that too many street signs actually make people worse drivers because they have an illusion of safety. In areas where there are fewer signs, people tend to drive better because they have to pay attention.

This makes for a great analogy for how being in business for yourself or freelancing work. Since your income isn’t “stable” like a paycheck, you work harder and with a higher level of awareness. You can’t “coast” when you’re on your own, which means you make more conscious decisions.

This hyperawareness makes you a more skilled and aware person. A skilled and aware person can spot opportunities. Contrast this with the employee who is satiated by paychecks and asleep at the wheel. This isn’t a moral judgment. I’m simply talking about the risks, rewards, upsides, and downsides of different life paths you choose.

Of course, there is no guarantee of a risk-free life under any scenario. But the antifragile lifestyle at least makes sure you’re aware of this fact.

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 when you’re going to get it, 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, we’re in the third 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 or even try to shift to a new career. 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 waited until I had six months cash saved and the monthly revenue for my business was 2–3x my job income and but consistent for six months at that level.

While I was employed, I started my “fuck you” fund. This is when you squirrel away cash until one day you have enough money to never have to listen to anybody again. if you don’t want to. I’m free now, but I still have to build enough revenue to be set for life. Once I’m there, fuck you.

Start a side business that makes you an extra $1,000 a month, and see how much your life changes. I believe that most people can start a side business and eventually make 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 get to $1,000 a month by spending a few hours a week working on your side gig, until you get some traction.

Even if you don’t want to start a business, switching to the career you actually want, learning how to earn more, and then saving the extra money and investing it works well, too. Aside from the route you choose, 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. Spend a few years doing this. Five years from now, you could have an amazing 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 Jap-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.”62

Until you can say “fuck you,” you’re fragile. You’re fragile if you have to do what you hate to do, just 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. The antifragile lifestyle extends beyond money, career, and business.

You can look at many areas of your life and expose yourself to the kind of healthy volatility that can improve it. Let me explain.

How To Live an Antifragile Life

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? By increasing your options, putting yourself in situations that favor chance. Let’s imagine a fragile versus 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 Disneyland and scheduled dolphin swims. No, great travel stories always include things like interactions with the locals, secluded off-the-gridoff the grid destinations, danger, adventure, experimentation. 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 flaneuring — 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 preplanned vacations. The sterile unadventurous atmosphere where fun seems forced upon you instead of something that emerges from the experience.

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

Casual parties create 10 times more business deals than any networking conference. Parties are more organic. The natural characteristics of people emerge from the environment because people aren’t on guard and trying super hard to be their best professional selves. They’re just fun. People don’t want to work with people they don’t like.

Exposing yourself to meeting more people, without forcing it, is the best way to create genuine friendships and build a network.

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, save money, “manage time,” 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 want, and then some.

Instead of “hitting the gym,” forcing yourself to move pieces of metal for set periods of time, you could just hike, rock climb, go for a walk, ride a bike with your kids, whatever. You’re getting in better shape without trying to get in better shape.

Also, many can attest to these forms of exercise helping them be more creative. When you go for a walk, experience nature, do an activity that lets you enjoy some scenery. Great insights often come when you’re not trying to get them, so having a more open and free lifestyle opens you up to serendipity.

Hobbies can have a weird way of coming in handy well down the road. This is an overused example, but I like it. Steve Jobs took a calligraphy class in college just for the fun of it. Decades later, the insights he gained from this class became useful when coming up with the typography for the iPhone. Sometimes, hobbies themselves can turn into businesses, too.

Derek Sivers started a multi-million 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 just to put his own CDs on the site. He also added a few of his friends’ CDs to the site because they asked him to.

He wasn’t trying to start a business.

Over time, 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 experiencing 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 mind-blowing, but a small handful of books completely changed the way I think about the world like these:

  • Antifragile
  • 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. My life is different during each pass, so each time I read these books, I catch new insights and experience them in a different way. Some lessons don’t present themselves until you’re ready for them, and book retention is low, so you flat out forget or miss stuff.

I credit much of my success to reading. When I had no money, no hope, no network, and no opportunities, I bought a bunch of books or even read them for free at the library. 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: Go to Parties). 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 many books for this same reason. I put all my effort into my work, but I can’t know how well they’ll do.

When it comes to your life, you will never truly know the future. So 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 random magic.

The Equation That Almost Always Works in Your Favor

Life comes with many downsides. Half of the self-improvement battle is simply avoiding being dumb. Once you cover that part, you can focus on finding opportunities that can help you improve your life without putting everything at stake in the process.

There’s no need to overcomplicate this. Everything in this chapter focuses on the simple concept of low downside with high upside potential.

Do you want to live your life with a sense of heightened awareness, always looking for antifragile opportunities? Or like the turkey, do you want to believe in safety and security until it’s too late? The choice is yours.

Noticing a theme yet? Living a successful life isn’t about being over the top, bold, and daring. No, it’s about doing little experiments, having a measured view of success, and doing what you can to increase your odds of living a good life because there’s no guarantee.

I live the life I want not because I’m a genius but because I used the tools and opportunities gifted to me. There are many skills I wish I had, but don’t. There are many connections I wish I had, but don’t. But there’s no use in focusing on what I don’t have. That’s what losers do. You’re here to win. The next chapter will show you how.

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