Despite never once suggesting that I am some sort of authority on making money, the number one question I get is an expanded form of, "I have a job. I want to do whatever I want. How should I make money?" So today I'm going to answer this question. My answer will probably not be very satisfying, as the short answer is "I have no idea", and I'm primarily writing this to link to when people send me emails asking about how to make money.
No one is going to tell you an easy way to make money
In the beginning days of my gambling thing, it was very easy to make money. The system was basically foolproof and anyone with a credit card could make a good yearly income. I wasn't making money through any sort of skill, I was essentially exploiting a loophole. But here's the thing about loopholes: no one is going to tell you how to do them, especially not someone you don't really know personally. Because if too many people find out about a loophole, it closes. So if you want to make "easy money", you're probably going to have to stumble upon it yourself. If someone IS trying to share a loophole with you (especially aggressively, by email) it's probably a scam like a HYIP or a Forex trading scheme.
Most of the people who were gambling like I was now play poker. You can play poker online or in casinos and make six figures a year. But it's not a loophole, so it's okay to tell everyone. The barrier to entry is a few years of exhaustive practice, thousands of dollars to lose while learning, and the ability to sustain that lifestyle while you struggle to break even.
You should probably do something you like to do
As someone whose income has oscillated in the past 10 years by a factor of 10 or so, I can tell you that by far the most important factor in terms of life satisfaction is that you're doing something you enjoy doing. For me that's mostly writing books, working on my site, and programming. If you hate, or are just ambivalent, about these things, they're probably not for you. I would rather make $40,000 a year doing something I love than $400,000 a year doing something I hate. Your daily life will affect your happiness a lot more than your bankroll will, assuming you make enough to cover the basics.
This rule alone makes it impossible for me to offer any sort of meaningful career advice to anyone other than my close friends. I don't know what you love to do, and I'm not going to suggest anything you don't love.
Whatever you do, don't get a real job
This goes hand in hand with #2, but I'm separating it out because it's something I feel pretty strongly about. If you're writing me for advice, it probably has something to do with you subscribing to my ideas about the importance of freedom and travel. Jobs don't give you freedom or let you travel (much). So if you want my heavily-influenced-by-my-own-experience advice, don't get a job.
The Key to My Lifestyle is NOT on the Earning Side
I can live life like I do because I've mostly divorced myself from materialism and spending money. I don't buy things I can't afford, and I don't buy things I can barely afford. I buy things that I can easily afford. When I bought my RV in cash, it only used up about half of my cash reserves. The reason I had those cash reserves were because of a many-year-long pattern of spending significantly less than I could afford to spend. Money is worth a lot more to me in the bank because it is then a big chunk of freedom. Once I buy something with it, it reduces my freedom.
Some people think I'm really rich, and others think I'm really poor. That's because I have the best of everything I want, and pretty much nothing else. That's intentional.
I'm particularly cautious about monthly costs. My only fixed monthly costs are $18 for cell phone and internet (it was a loophole, you can't get that deal now), $109 for a spa membership (hey, I need to shower everyday and gym showers suck), around $40/month for my server and accompanying services that run this site, $50 for cryonics related stuff, and $30 for RV insurance. That's $227. Most people spend at least five to ten times that on rent, cable, phones, and junk like that.
So, if you want a lifestyle that looks like mine...
My advice is to RIGHT NOW cut your expenses to the bare minimum. In fact, cut them to as close as zero as possible. Cancel everything that doesn't have a termination fee, sell everything you own, and live at your parents' house for a couple months. That's how you find out what you actually need and want. I found out by selling everything and traveling around out of a 28L backpack. I discovered that I needed even less than I thought, and now I'm looking for a smaller backpack.
Once you find out the bare minimum of what you need to be happy (hint: most people who have tried this are HAPPIER with less stuff. It removes a lot of stress), then start thinking about how to move from working a job to living a life.
Next post: How to write a book
Gear post STILL coming soon. Todd and I are looking at smaller backpacks because I've downsized significantly since last time. I'm really excited to share all the stuff I've found, but I'm hoarding it for one big post that will blow your GD mind.
I'm getting into this two posts a week thing... seems to be the right balance for the site. Thanks for all the great comments recently... I read them all on my phone, but don't do a good job of remembering to reply to them.
Bonus points if you know what the picture is of...
If you paid me fifty times what I make now to work at a regular job, I wouldn't do it.
Over the past few weeks I've informally asked some of my other entrepreneur friends how much they'd have to be paid to work a normal job in their industry. None of them quoted any reasonable figure. Some of them didn't want to answer the question because it was so uncomfortable to think about.
When Justin Frankel, creator of Winamp, quit AOL, he was offered a job by Microsoft. They asked what he needed to work there, and he responded with a written offer. In his list of necessities were things like a private jet, the ability to work remotely 100% of the time, and all boat rental fees to be reimbursed. It was a joke, but he sent it to them anyway. That's how abhorrent the idea of a real job was to him.
I have on big fear in life that trumps all my other fears. That fear is the fear of having a job and being mediocre.
I don't really believe in jobs. I know that sounds weird to say, considering in order for society to function jobs need to exist, but I just feel that a lot of times, and for a lot of people, jobs are a waste of time, mental energy, and skill. Due to socio-economic factors, sometimes complex, sometimes not, a lot of people end up getting jobs they don't like, and sometimes even worse, to keep up with a life they don't enjoy.
I know a lot of people out there truly love their jobs and waking up everyday brings them great satisfaction, but ultimately for me, the lack of flexibility is just too much. Flexibility and freedom to me are the most important things in life. Being able to wake up and decide to do nothing and just watch a movie, or get on an airplane because of some amazing discount, or just go to the beach or what not is something that is extremely important to me. A job doesn't allow me to do this in most cases.
Ultimately I would like to work for myself either through starting a business, becoming a professional trader, or finding some loophole of the sort. Once I feel like I have a stronger base of the sort I would really like to venture to maybe doing something like specialty coffee, photography/travel blogging and the like. I have a huge passion for travel, languages learning, skill building, and specialty coffee/foods.
With the market in turmoil these past few days, and me not seeing it coming, and not properly taking steps to hedge against it, I have let stress effect me again. The fear of needing to have a normal job to make ends meet almost paralyzes me. Its funny because in 2012 when I wasn't making money and wasn't as ambitious to achieve my goals as this year and last year I never had any stress. Only when you feel like you have something to lose or that you might not get the closure you want does one start experiencing stress and second thoughts. Better handling my emotions, not letting impulsivity get to me, which could lead to bad trading mistakes.