Assuming that anything could be learned, and then going into The Cave to do it
In 2007, I learned that the top company in my field paid the world’s best GMAT teachers very, very well. I had many important qualifications (classroom experience, public speaking skills), and I’ve previously written (Bullish: How To Do Many Different Things At Once) about how my standup comedy experience has been far more valuable to me as an add-on to other services than it ever was for its own sake, which was also the case here — everyone loves the idea of being taught otherwise dry material by a comedian. But then there was the GMAT itself. In short, I spent about seven months of unpaid study and training time teaching myself to ace the GMAT, and weeping bitterly when, after the first five months, I took the test and scored 20 points below the goal. I probably lost $10,000 in income that year, taking time to teach myself a skill that I knew would pay off. I have since made back that investment many times over.
While there are many paths from A to B, as it were, I often note that extroverts have some serious disadvantages. Surely, extroverts find networking much easier! But I feel as though it must be a very shallow networking. Someone who likes everybody flatters no one with his attention. People who always need to be around people lack the ability to “go into the cave” and build the skills needed to leap ahead. Be comfortable with solitude. Blithe, lazy friends you lose along the way will later be replaced with new friends who have also catapulted themselves ahead through clever and focused effort.
Cultivating multiple income streams
I am a broken record about multiple income streams. You need to have your money coming from more than one place so that no one can exploit you, so you have security, and so you don’t need your employers more than they need you. Having multiple income streams creates a healthy balance of power.
I’m not suggesting that you have to run three totally separate careers at once or anything of the sort. I believe in exploiting efficiencies. If you already sell something to a group of people, is there something else you can sell to those same people? Or if you’ve already set yourself up with a web designer and a telephone answering service for one business, isn’t it now fantastically easier and cheaper to do it again for a second business?
I also believe in the principle of low-hanging fruit. A small business might bring in $10,000 a year without having to advertise, and $50,000 a year if you really work it. Or … you could run five of those $10,000 a year businesses that dont require much effort. At the simplest level, I discovered when I first started SAT tutoring that I didn’t have enough business to do it full-time, but that doing it about half-time was pretty easy. I also discovered that I would never be a full-time model, but doing it half-time was pretty easy. Once I stopped hustling on both fronts and just took the work that came in, I was able to direct my mojo to the next income stream.
Selling Services to Rich People
This is just the easiest way to get started making money. Obviously, there are many other ways to make money. But I think this is the easiest one.
Rich people pay other people to do everything for them. Not just things like personal training and getting their kids into college. Everything. Including many normal, human activities that anyone could do. Rich people just don’t feel like it, or else they are so busy making all that money that it makes sense to outsource the basic tasks of life. Here are some positions held by people I know, serving the rich:
Personal trainer for kids (takes kids to the park, where they toss a ball around).
Overqualified handyman paid to hang pictures on walls.
Guitar teacher to three year olds (um, their hands are too small to play the guitar).
Stretcher. A person who helps people stretch. I am not joking.
Rich people also order meal delivery services, hire carpet cleaning services even for small Oriental rugs, pay extra for babysitters who teach their kids foreign languages, and teach their babies yoga.
Here are some more ideas, just off the top of my head:
Babysitter who specializes in self-expression through music (or French, or vocabulary)
Personal coach for girls and sports (offer to help get people’s daughters into sports, which is an excellent way to prevent future eating disorders and self-esteem issues)
Auto detailing for ladies, by ladies (spritz people’s cars with essential oils when you’re done!)
Errand running service (if you went to a prestigious college, advertise this)
Memoir ghostwriter (lots of people want to write their memoirs but are lazy)
Cat hair removal service (clean furniture and floors and never indicate that what you are doing is ridiculous)
Of course, to get started, you’ll have to meet some rich people. So, never turn down an opportunity to meet rich people. Taking a low-paying job that puts you in contact with many wealthy people might be worthwhile. Volunteering or reconnecting with family friends might also do the trick. Once you meet the first few clients, do a good job and they’ll pass your name around. Many wealthy people have much more money than time. They may or may not be price sensitive, but they are always very concerned about trustworthiness. If you seem professional, friendly, and normal — and as though you understand them — you’ve just started a business.
That said, it always helps to get the basics out of the way first; being able to pay your bills is helpful in creating the mental space to think big. This might mean pursuing particularly cheap rent, taking a temp job, or otherwise sucking it up with some line of work you don’t really want to do but which (hopefully) isn’t too exhausting. (You might enjoy Bullish: How to Make an Extra $100 a Month).
Financial basics are important. I’ve never pursued nor even been particularly attracted to wealthy guys, but once I started making a real income, I dated completely differently. I stopped trying to get men to like me and instead scrutinized whether I liked them. I realized that my precarious finances had been making me feel vulnerable without my realizing that that was the reason. Making money is deeply feminist.
I do talk a lot about entrepreneurship, and I want to emphasize — everyone needs to be an entrepreneur, even if just a little. Even for employees, having a side business or serious interest can create novel opportunities — you could end up doing business with your company as a peer rather than as an employee, or you insinuate yourself into leading a new project at your company due to your diverse experiences. You could pitch something within your company — starting a new division, or marketing the company’s product to a new group of people you know something about. Doing two things at once for five years is in some ways equivalent to having had a ten-year career.
So, whatever your goals, I hope you’ve found something here that will give you your next move from A to B. You can get started now. You don’t have to play three moves ahead. Just take one step, and then the next.