It’s been around ten years since I quit my job and decided to go on my own. Since then I’ve traveled around the world while building all kinds of different online businesses. I won’t lie and say that things have been easy because they haven’t. The correct word is challenging.


The biggest change—and the most drastic—one experiences after leaving the 9–5 is the complete absence of specialization. After all, the beauty of a regular job is that you’re hired to do one or two things really well and that’s it. The caliber of the specialization differs from one job to the next job. Sometimes it’s as simple as taking orders at a McDonald’s; other times it can be as complicated as building embedded software at a tech company. The bottom line is that you do one thing and, as a result of lots of experience and practice, you probably tend to do it pretty well.

Specialization comes with two important benefits: stability and security. These two are pretty much the core of the “9–5.” You come in at a set time (e.g., 9 am), work and then leave at a set time (e.g., 5 pm). The times may change around (you can come in early or later), but the type of work you do is typically the same for many years as well as the majority of your life.

Specialization ends as soon as you leave your job and decide to go on your own. You no longer have a “specific” responsibility; you now have an entire array of them. Instead of being a specialist, you’re now essentially the jack of all trades, master of none.

Not being specialized is actually a blessing in disguise. Specialization gives you a false sense of stability. If there’s one thing that all successful people share is that they’re capable not only of doing all kinds of different tasks, but doing them pretty well. The CEO of Coca-Cola, Muhtar Kent, started off working in the mailroom before rising through the ranks and eventually becoming the boss of one of the most recognized global brands. Specialization is a new term that gained prominence after the Industrial revolution and the assembly line.

Selling the world

I spent ten years living in San Francisco (and surrounding areas). During that period, I was permanently immersed in the startup scene, either working for one or building one. Building a startup (a type of business) is so common, and so much has been written about it, that the entire process has been almost reduced to a science. Typically, when you build a startup, a very common pattern is to have two co-founders: a technical one and a non-technical one.

This pattern reflects the psychology of an individual. Some people excel at building something. They are writers, designers developers, engineers, tinkers, and the like. They’re really good at putting things together. What they aren’t good is communicating with people and selling to them. They tend to be introverted.

On the other side of the spectrum, there are people that are really good at selling. These people love to be surrounded by other people and, from an early age, learn to read people well. I’m guessing that if you’re reading this now, you’re probably more of a builder type than a seller type.

I’m going to be very blunt with you: I don’t care what kind of business you have, but if you want to be successful, you must be able to market and sell. You simply can’t expect to do the same kind of work as you did when you were part of a company. Being able to build something just isn’t enough. If you’re too shy, or you don’t want to talk to people, or you can’t write sales letters (or videos) that tout your product’s benefits (you, know, because you’re proud of the product you built), it will be that much harder to become successful. I’m not saying you won’t become successful, it’ll just take an unnecessarily long time to get there.

This is precisely why most startups — and most companies — fail. A guy (usually a developer) thinks he has an idea, locks himself in his closet, builds the first prototype, but then realizes he can’t sell it because 1) he can’t sell/doesn’t want to sell and 2) the product doesn’t sell itself. Out of all the skills that you must possess when leaving your 9–5, the most important skill is being able to sell.

When I say selling, I’m also talking about it in a broader sense: you must be comfortable meeting and talking to new people. Most of the time it will be dealing with people you do not know, so you must be comfortable at least talking to people you do not know, so you can later pitch to them your products and services.

Fortunately, selling isn’t as hard as they make it out to be. It’s a skill like any other. It can be learned and mastered.

Toughening the work ethic

Most people naturally think working for yourself is a lot easier than working for a super tough and demanding boss. Actually, it’s quite the opposite. I’ve worked harder for myself than I’ve ever worked during my time in Silicon Valley (well, almost).

There’s a certain freedom and commitment that comes with working for yourself. When you’re working for someone else, you don’t have the freedom to not work — if your boss tells you must do something, then you know you must do it or else your office’s door key may stop working the following morning. Thus, one of the biggest challenges has been to do things when you don’t have a boss standing barking out orders and waiting for you to finish them while he stands over your shoulders.

I’m not a very disciplined person. I’m always getting writer’s blocks. I need a certain push, motivation and inspiration to get started. If I didn’t feel like working, I would do something else. Disciplined I’m not.

One huge mindset hack I’ve learned is that you must do something even if you don’t feel like doing it. You must work when you don’t feel like working. You must write when you don’t feel like writing. You must create products even when you don’t feel like creating products. If something needs to be done, it needs to be done. It doesn’t matter if you feel like doing something else; feelings should have no impact on your output. If you need to do something, then you must do it regardless of how you feel.

What helped me get through this is to “decouple” my own physical state from how I feel about my state. Now, whenever I “feel” something (e.g., “not working” or “tired”), I simply acknowledge that it’s something that I’m feeling and is thus separate from me. Then I start working. Realizing that who I am and what I feel when I think about who I am has made a huge impact on my productivity. After all, willpower is a muscle.

With all the businesses I’ve started, I’ve discovered businesses have distinct two phases. There’s the growth phase and the maintenance phase. During the growth phase, you’re feverishly working, trying to get the business of the ground. It’s during this time that you’re working the hardest (12-hour days are not uncommon).

This is the toughest part, and where most people give up. It’s also something you don’t experience when you’re working for a company because the top management takes care of that.

Once you’ve scaled the business, and it’s more or less running by itself, you don’t need to work as much. Nevertheless, because of the constant competition, you still must innovate by adding new features and fixing problems/bugs.

Stretching the boundaries of knowledge

When I worked as a software engineer, I spent hours and hours devouring every kind of article and book in the bookstores as well as on the Internet related to programming—and nothing else. I was obsessed with computer science and various programming languages. While I enjoyed it, I never needed to venture outside these topics.

Nowadays, as a result of diligently working on various businesses, my interests span all kinds of areas including history, economics, politics, consumer psychology, marketing, copywriting, etc. At first, learning about all these topics seemed overwhelming, but I realized early on that this is something that needed to be done. Not surprisingly, one area that I no longer actively study or care as much is programming and computer science.

A lot of tools I use are already pre-built (e.g., WordPress) so there’s absolutely no need to code anything. Thus, programming and computer science (and engineering in general) isn’t something that I need to concern myself with. This means solving different types of problems and never re-inventing the wheel if a problem is already solved.

The natural extension of yourself

When I was working for a software company, I viewed small businesses and those who started them as a sort of an anomaly. I imagine running that running your own business must be fraught with lots of risk and confusion. Now, it’s the opposite. I view working for myself as something that’s “natural,” something that must be done, and not something that’s “different.”

On the other hand, it’s the specialization that now feels so strange and unnatural. In fact, when you give up specialization and embark on building a business, the business you build becomes a natural extension of who you are. It’s something that you believe in, something that represents you, something that completes you.

The best part about leaving the 9–5 is that you’re continuously operating outside your comfort zone. You need to find new customers/leads, but you’re introverted and hate talking to people? Too bad. You must do it. You need to sell your products, but you’re afraid of rejection? Too bad. You have to go out and try new things, even it means being rejected most of the time.

In this sense, entrepreneurship is the very best thing you can do for personal growth. It’s where you learn about yourself and test the limits. It’s where you find out what you’re really made of. There’s nothing else out there that makes you grow as much. And starting is super easy: my program, the Maverick Entrepreneur Bootcamp makes it super easy to start any kind of business you want to the point where failure isn’t even an option.

I don’t know about you, but I certainly wouldn’t have it any other way. And neither should you.

Tired of working for an ungrateful boss and seeing your life slip away? Want to turn your ideas into a profitable business that can run from anywhere in the world? If so, check out the Maverick Entrepreneur Bootcamp, the premier course that freed thousands of guys from the tyranny of the 9-5. Click here to learn more.

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James Maverick

James Maverick

James Maverick used to work in a cubicle as a code monkey in Silicon Valley. Then, in 2007, he quit his job and a one-way ticket to Brazil. Ever since, he continued to travel, visiting over 85 countries and living in more than a dozen of them. He loved his location-independent lifestyle and has no plans to live in America.

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