Bullish: How To Make A Career Out Of The 10,000 Things You Want To Do

If you grow up being told that you can achieve anything you set your mind to, and that girls can be President and go to the moon, it kind of leaves you a little paralyzed by all options, doesn’t it? Or even guilty that you’re not an astronaut. (Or better: PRESIDENT ASTRONAUT!)

Let’s hear today from a reader who dubbed herself, “99-talents-and-practicality-ain’t-one” (or, for the rest of this column, “99”).

Dear Jen,

I am dying. Please, help me. I often struggle with my self-perception, so I will describe my most recent career path, and thus dilemma, to you the way most everyone describes it to me.

Among the most popular in respect to my work-life from friends, family, and HR reps are:

– flighty
– wasting my potential
– making dead-end career choices
– unfocused
– lazy
– undisciplined
– unwilling to grow/stay put in a single venture

I would love to argue against this laundry list of pleasantries, but since the time I graduated from school in 2007 – and maybe even as long as I have been on this earth – what I tend to do is start 10,000 different ventures a year/week/day, succeed to a certain extent, and then never complete them to mastery.

I feel that you being the bullish woman that you are, would provide me with the next bit advice: f- them! do all that you want as long as you make profit from it (probably worded more eloquently and sans grammatical errors), but I cannot. I feel stuck. For every random skill I have — and I have many — I have a shortcoming that halts its development into a successful business plan. Not only that, these feelings of floundering have consumed my ambition. The only thing that keeps my head afloat is the fear of submitting to a mediocre 9-to-5.

In short, I love my random adventures and quirky collection of inapplicable (and some very practical) skills, but I do not know what to do with the dissonance I feel between their value in my life and their ability to bring me real financial and personal success.

Signed,

99-talents-and-practicality-ain’t-one

Oh, we all contain multitudes, don’t we? A couple months ago I wrote Bullish: Cultivating a Career When You Have Too Many Choices, in which I suggested that you can indeed fuck all the haters and do all the things you want, as long as you can make a profit. Except that most of us can’t just randomly do a bunch of crazy shit and somehow be able to pay the rent.

More specifically, I wrote that workaholism is valid in certain seasons of life, but it should be pursued cleverly, not just hard. Doing a lot of different things is a good plan when you can cobble together a career from the low-hanging fruit of a few different careers (I was once a part-time SAT teacher and a part-time model at a time when it would’ve been hard to do either full-time), or when those things work together synergistically, taking advantage of common resources.

For instance, I am hiring a publicist to promote (at least) three of my projects at once. Even when you pay someone to do something for you, you spend a substantial amount of time interacting with that person (writing emails, checking to see that the work is done correctly, trying to understand what people who are better than you at things have actually been doing so you don’t seem like an idiot when you ask them to do the next thing, sending people checks and Paypal payments, etc.) Similarly, the publicist also has to spend then same kind of time talking to me. So, by bundling three projects together, we are both able to get more value out of our relationship, meaning that more actual work gets done for the amount of time spent (in theory – I’ll keep you updated).

The opposite of this approach would be something like hiring three unrelated publicists for a single project, or constantly hiring and firing publicists. To an outside observer, all of this might look like the same flurry of activity. However, what looks to others like mere “business” can actually be more or less efficient than appearances suggest.

Needless to say, 99 is not pursuing lots of different but overlapping professions in a synergistic, functional, streamlined way wherein each reverberates with the others (for instance, people who need Pilates also need their dogs walked; people who graduate from a weight-loss program might need a personal shopper; teaching the GMAT might be a great way to meet people who, in ten years, will do business with companies I start).

I’m going to link to a book that I don’t exactly recommend: Refuse to Choose! A Revolutionary Program For Doing Everything That You Love. I bought this book for $1.99 at a discount warehouse I visited with my mother in Virginia. I started reading the book and was struck by the personal stories of women who sound a lot like 99, except that these women all seemed to be at least fifty and not employed. One woman wanted to learn to make Navajo blankets and then just make one Navajo blanket and put it on her wall and then move on to the next thing. Sure, if your husband pays the bills, or if you’ve got some free time, why the hell not? You don’t need permission for that.

But then the book went all crazysauce. It said that, if you keep starting things and not finishing, or getting great ideas and never following up, you could create a journal, where you write about or sketch out your ideas, and then you date the pages, and it’s like a scrapbook of all the things you never accomplished, and then you can leave it behind for your children so they will really know you after you are dead.

And then I realized what I was reading. The book didn’t say “Refuse to Choose: You Can Still Be Successful!” It just said that you can refuse to choose. Never anywhere did the author even remotely suggest that this would lead to a fruitful career or even solvency.

I put the book down. I said: This is exactly what I must never become.

That was the best $1.99 cautionary tale of my life.

Dear 99 here is going to get one big piece of advice from me, in several steps:

– List all the skills and talents you don’t hate doing.
– All these people whose opinions you find credible, at least in aggregate? Ask them which of these things would make the most money.
– Become the very, very best in the world at that one. Give it about 80% of your time for at least the first few months.
– You can still do the other things. But you have to make them relate to the thing you do for all the money.

If you do the above steps, once you’re financially stable, have saved up an emergency fund, and your reputation greatly precedes you in the field that pays you all the money, then you can think about changing things up. But until then: Don’t fuck with the model.

When I say “the model,” let’s actually visualize it. Instead of a giant mess of random stuff, imagine spokes on a wheel. The thing that pays you the money is the hub of the wheel. Don’t necessarily choose the thing you love the most. The thing you love the most is probably something other people love also, so there are too many people wanting to do it and therefore the laws of supply and demand work against you. Pick something you don’t hate but that other people find difficult, scary, boring, etc. Get so deep into that thing that you learn to love it more.

From that thing proceed all the spokes of the other things you want to do. More exciting, more gratifying, less lucrative things, perhaps. Start with the ones you can try to sell to the same people “in the hub,” people who already know you as an expert in your main field.

You know what the most gratifying part of my career is? This column. You know how it exists, financially? (I do get paid for freelance writing, but freelance writing is a terrible way to try to make an entire living.) Because people pay me boatloads of money to help them beat the GMAT. You know how I know how to do that? I spent seven months of my life doing nothing but becoming obsessed with prime theory and combinatorics and factoring things most people dare not factor. Why did I do that? I had no designs on attending business school myself. I did it so I would make enough money that I could do the things I want to do. At the time, I had no idea that Bullish would ever exist. But I knew I would be opening up options and that my future self would come up with something. (See here, here, here, here, and here where I discuss setting up your future self.)

99, I’m glad you realize that you can’t continue in this way. You wrote yourself that the “floundering” is “consuming your ambition.” What you’re doing right now has no path from A to B. You literally began your letter with “I am dying,” which for several seconds made me worry that I had actually gotten a letter from a terminally ill person and that I wouldn’t know what to say.

Your future self needs you to work some shit out. You don’t have to pick just one thing, but you have to pick a main thing. You have to put everything else in a lockbox for a little bit (see this for more on choosing what to devote your mental space to.) Whatever you lock away will be there later. You won’t run out of ideas. That’s just the way you are. (Me, too.)

Take a deep breath, make some decisions, and get to work. In that order, please. Good luck!

originally published on The Grindstone