Bullish: Every Weird Thing You Do Will Help You

I recently spoke at Yale University, where it was icy and Gothic, everyone was very nice and very smart, and I was reminded of what it was like to be 21 and not know how to order a cocktail yet. I was also reminded of what it was like to be able to say, “I study literature” (or philosophy, or economics) and have that mean basically full-time: I LIVE THE LIFE OF THE MIND. Oh, college!

Specifically, I was the guest at a Master’s Tea, wherein the master of one of Yale’s residential colleges chats with a guest about some interesting topic. We drank Earl Grey. It was very civilized. Although the posters for my talk said nothing gender-specific, almost everyone who showed up was female. I just have that vibe, I guess.

Master (and Dr.) Paul Hudak of Saybrook College provided a kind introduction about my many careers, and I told the tale of majoring in philosophy, starting a company as an undergraduate, having my company fail five years later, moving to NYC with $400, getting my car stolen immediately, getting hired for a job when the company doesn’t want to commit, developing expertise, and starting more businesses. I gave a list of Bullish bullet points — here are the notes I spoke from:

What people call a “scattered” career or life, I prefer to think of as a “richness of experience.” And it’s worked. Very well. Every weird thing I’ve ever done has come back and helped me somehow. I’ve written about bodybuilding; I’m starting a luxury cat-services company. Standup comedy isn’t a great way to make money, but it’s a huge selling point for other things I’ve wanted to do (everyone wants education products written and produced by funny people). “Focus” is overrated. In 10 years, many of us will be working in professions that do not yet exist. You want to diversify your experience. Even in traditional fields — say you want to go into medical research and try to find a cure for Alzheimer’s — there’s value in getting ideas from unusual places. “Scattered” is an outmoded insult.

Failing early inoculates you against the impact of future failure. My company failed when I was 23. I don’t mean that my home business wasn’t getting any orders so I had to get a job. I mean that the sheriff padlocked the door to my office and legally prohibited me from entering it, and then the landlord sued me and I declared bankruptcy. I didn’t have anyone to help me. I went to court without a lawyer. (I told this story in Bullish: Actually, We’re All Kind of the 1%.) Having failed young gave me a sangfroid worth two masters degrees, at least. My fiance is pretty worried about wedding planning. I sleep like a baby. (See Bullish: To Give Up or Not to Give Up? A Column About Bankruptcy.)


Working at home: I believe in it. Or at least I believe in working on your own schedule. I think best in the morning. Why waste that on the performance of womanhood, and commuting? I refuse to spend my best thinking hours making my hair look pretty. Also, I work within eight feet of an espresso machine, a bathroom, a pullup bar, and a kitchen. Am I really going to be more productive drinking worse coffee, getting less exercise, eating takeout, and wondering which coworker always pees on the seat? My assistant, similarly, makes things happen on the Internet, and I have no idea where she does that from. Do I really need to waste her time making her wonder if I’ll object to her ripped neon Pegasus tights? (I think that’s what the cool kids are wearing these days, right?)

It’s always a good time to be an entrepreneur. Economy sucks? Cool, sell an affordable alternative to something expensive. Labor is expensive? Start an Internet business that doesn’t require employees, or go into headhunting. Labor is cheap? (It’s very cheap right now.) That means you can hire talented people at bargain rates.

Most people don’t do things. Full stop. Learn that you can. Want to get a product manufactured in a factory? It’s not that complicated, in the sense that factories want your business and send out business agents to try to get business from people just like you. Sometimes there are language difficulties, which is why there’s a whole layer of middlemen (middle-people?) who can help broker these things for you. They also want your business! Not only will they explain it to you, they kind of have to be nice to you, or you’ll take your business to one of their competitors. If we have to live with the many flaws of capitalism, how about we enjoy the upside, which is that doing things is easier than ever before due to the Internet and a relatively unfettered free market full of small businesspeople ardently competing to put some shit together for other small businesspeople.

Relatively small amounts of money can change the world. I celebrated my thirtieth birthday with a male beauty pageant in a bar. I put up a cash prize, recruited male models, singers, poets, etc., and invited lady-bloggers to judge. I hired two male models to hand out bonbons. Literally, I paid handsome men to verbally encourage women to eat more chocolate. It led me to conclude that all you really need to be omnipotent is about $2,000 and access to Craigslist. My beauty pageant was just for fun, but that lesson has stuck with me. Once, I tried to work with an adult literacy nonprofit. At a morning meeting with this nonprofit, I offered to teach a class for free. When I learned that the organization had a lack of classroom space, I marched over to the company I was working for if we could use their space, and successfully convinced the company president that we would not start getting phone calls and visits from the homeless. I got approval, as well as a cash donation for supplies, WITHIN THE DAY. When I got back to the nonprofit (“Remember our meeting this morning? DONE.”), they delayed for WEEKS. What do these two things have to do with each other? You don’t have to work for a nonprofit to be an activist. You don’t have to give up living a gentlewomanly life in order to make the world better. Richard Branson makes the world better. He owns an island. Next time some black teenager gets roughed up by the police for no good reason, maybe you would like to find him and pay for his books during his first year of college. Next time a teenage rape victim is threatened with jail over naming her (convicted!) rapists on Twitter, perhaps you would like to make sure she has a very good lawyer. (See Bullish: How to Ask for More Money, Part I and Part II.)

Do things that don’t have applications. The “opportunities” that everyone can recognize as opportunities have too much competition, and probably won’t fit you that well anyway. I counsel high school students about college admissions, and the one piece of advice they all nod at but rarely take: Don’t spend your summer just doing rich-kid programs your parents sign you up for. Everyone sees through that. You say you want to major in business? Start a business. Or or do anything that was entirely your own idea. In all my years of telling kids this, I had one kid take a photography class for adults and put together a photography project, just because. It was awesome. Oh, and I hired my assistant after I mentioned, offhandedly, around paragraph 22 of one of these columns, that I was thinking of hiring an assistant. She wrote, “I’m sure you got a ton of emails about that.” I didn’t, actually. Just hers.

You can craft your own career out of the zillion things you want to do. But narcissism — and everyone’s a narcissist on some level — is costly. You will make more money by killing your narcissism. It’s the difference between, “I have my own business” (That’s so nice for you) and “I own a business.” (Great, which one? What does it sell?) You want to produce things that people would still want and need even if you didn’t exist or nobody liked you. You want to provide something people want for their own purposes.

By this point, my Earl Grey was cold. It was time for questions. Here are a few I remember answering:

Do you have any tips for getting everything done? If you try to do a lot of things, how do you finish your to-do list?

I don’t! It’s great! I once dated a guy who had a three-item to-do list every day. He wrote it out each morning on an index card, and that was it. I asked, “Three?! Three?! What if something urgent pops up?” (He would bump something else from the list.) I guess he was focused. I didn’t date him that long, but I wouldn’t have expected him to remember my birthday. I don’t want his life.

I realized at some point that I was only finishing about 15% of the items on my to-do list, which felt bad, but I was actually still doing way more than most people. I stopped feeling bad. Many items we put on our to-do lists are actually just ideas, not action items. Some of these ideas are very large and need to be broken down into dozens of to-do list items. Some of these ideas are nice, but the time expenditure is too high and the payoff is too low, so we’re just not going to do them. Some of these ideas are just bad.

So it was at this point during the Yale presentation that I coined the term “idea menstruation,” the monthly flushing out of all the bad ideas and the good ideas that just didn’t take. I’m pretty sure at least one person in that room is going to remember nothing but “idea menstruation.”

(See Bullish: How to Be a Productivity Unicorn.)

Starting businesses is great, but what if you don’t have any money? Like, no money.


I got started in my first company by making some cash doing campus jobs that paid $10-15 an hour. I got these jobs by teaching myself web design in my dorm room, scouring all the applications for on-campus jobs, and pitching various campus departments on what my mad crazy web design skills could do for them. Then I started a business with zero overhead. That happened when I was in the computer lab trying to teach myself Perl, which was apparently the “it” web programming language of my sophomore year in college. I was a little out of my element. And then I noticed the greasy dude next to me in the hoodie, coding away, and I thought, “That guy will work for me for $8 an hour.” I didn’t hire that specific guy, but soon thereafter I put up ads on the campus job board, and I had a small staff of contractors who worked out of their own dorm rooms on their own computers. So, I didn’t spend any money to do that. (See Bullish: You Can Start a Business by Tuesday.)

In a way, not being rich (Dartmouth is really full of rich people!) was very freeing. My parents never questioned that I was majoring in philosophy. (Mom: “That sounds interesting!”) They weren’t really aware that I was running a company from my coed-fraternity-house bedroom. They did not try to set me up with internships at my dad’s friends’ companies. Only years later did I realize that the reason none of my classmates were starting businesses (the economy was AWESOME back then and really stupid startups were getting all kinds of venture capital) was that they were born and bred to go into investment banking (mostly the men), or at least to get a masters (mostly the women) before thinking about anything else. If you’ve been raised to think that living on less than six figures is a deprivation, you’re pretty locked in to a small number of career options.

As an entrepreneur, I lived on very little money. I ate Wal-Mart vegetable soup (54 cents a can!) I later moved and lived in NYC on about $17,000 a year. I’m just not sure I would have understood how to do this if I had been born rich. If you think Wal-Mart soup will kill you and Target sweatpants are humiliating and only doormen buildings are suitable for “nice people,” you are not going to take the same kinds of risks. You won’t make the decision to undergo some calculated suffering for a greater goal.

Can you tell us the first thought that went through your head — and then the next six or seven — when your car was stolen?

Ha! So, I moved to New York in 2003 with $400. (See Bullish: When To Make Massive and Ballsy Life Changes For Your Career.) My car was stolen a couple weeks later. After driving to New York, I had let the insurance lapse, because I couldn’t pay it but also because I was storing the car in a garage and it wasn’t even being driven. In retrospect, everything is clear: I had no money. I had a car I had no use for. I should have sold the car. But I was 23 and everything was a blur of youth and moxie and estrogen and failure and confusion. The car was stolen. Specifically, the parking garage in which the car was stored went out of business and when I went back, I was told that it was new management and they didn’t have my car. The NYPD offered to write a report but refused to investigate. They suggested I walk around and talk to doormen to see whether they knew anything. (I actually tried this. It was not the kind of neighborhood that had doormen.)

I still owed money on the car and my dad had co-signed. So my response to this problem was the same response I have had ever since to losing money: go find new and better ways to make money. I owed about $7,000 on that car. Even if I had somehow tracked down the car or sued someone to get back my $7,000, that’s a lot of risk and effort and time just to end up back where you started. You know what would be better? Making $7,000 in some way related to my profession or my mission in life. I end up in the same place financially, but with new connections and accomplishments and cool shit on my resume. I don’t beat myself up about losing or wasting money. It’s the cost of doing business. (See Bullish: A Metaphor About Shoe-Shopping That is 100% Related to Hard-Nosed Business Thinking.)


After the Q&A, I went out to dinner with Dr. Hudak and six lovely Yale women. I drank an old-fashioned — rye, not bourbon — and was delighted to be at Yale, and also delighted not to be in my early twenties anymore. But if my early twenties were fraught with catastrophe and confusion, it was all for a good cause. If I weren’t already a risk-taker, it would be too late to become one now.


Our Latest Products