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Weekly 3: Pursuing passions & making money

Summary: Don't end your search too early. Keep your day job. Strike the right balance. (~7 min read)

Idea Journal Weekly 3

June 23 · Issue #92 · View online
We combine 3 ideas to help you think differently and be more creative.

Summary: Don’t end your search too early. Keep your day job. Strike the right balance. (~7 min read)

#1. Finding work that you love doing
Entrepreneur and investor Paul Graham writes in an essay that most of us realize that in order to do something well, you have to like it.
But just how much are you supposed to enjoy what you do for a living?
As Graham suggests, unless you know that, you won’t know when to stop searching. If you underestimate how much you’re supposed to enjoy the activity, you may stop your search too early. In that case, you’ll likely “end up doing something chosen for you by your parents, or the desire to make money, or prestige – or sheer inertia.”
He recommends using two constraints to help narrow your search for work that you love: an upper bound, and a lower bound.
Upper Bound
As an upper bound, doing what you love doesn’t mean do what you would most like to do this second: “Even Einstein probably had moments when he wanted to have a cup of coffee, but told himself he ought to finish what he was working on first.”
As Graham points out, the rule of doing what you love assumes a certain length of time. At any given moment, almost anyone would rather eat delicious food, or have sex, or relax in the Caribbean than work on hard problems.
Doing what you love means doing what will make you happiest over some longer period, like weeks or months.
That’s because the allure of unproductive pleasures eventually fades: “After a while you get tired of lying on the beach. If you want to stay happy, you have to do something.”
Lower Bound
Graham’s rule for doing what you love does assume that you have to like your work more than some unproductive pleasure.
As he puts it, you have to like what you do enough that the concept of spare time seems mistaken. It’s not that you have to spend all of your time working. After all, you can only work so much before you get tired and start messing up.
But if your work isn’t your favorite thing to do, you’ll have problems with procrastination: “You’ll have to force yourself to work, and when you resort to that the results are distinctly inferior.”
Testing for Admiration
For Graham, to be happy with your work, you have to be doing something you not only enjoy, but admire. You have to be able to say, in the end, That’s pretty cool!
An alternative to the above test is to try to do things that will make your friends say, Wow!
#2. Chasing inspiration while paying the bills
Author and cartoonist Hugh MacLeod writes in his manifesto How to Be Creative that he advises creators to keep their day job, but not for the usual reason – that their idea will likely fail.
Instead, he gives that advice because someone to suddenly quitting their job in “a big ol’ creative drama-queen moment” is in conflict with what he calls the “Sex and Cash Theory.”
For MacLeod, a creative person has two kinds of jobs: one is the sexy, creative kind and the other is the kind that pays the bills.
Once in a while, a person’s job can serve both functions, but that’s rare.
As MacLeod points out, it’s important to remember that the tense duality between the two jobs will always exist: “It will never be transcended.”
Here are some examples of the Sex and Cash Theory in practice:
  • MacLeod tells the story of his friend Phil, who’s a photographer based in New York. Phil does “really wild stuff for the indie magazines – it pays nothing, but it allows him to build his portfolio.” Then he’ll shoot some catalogs on assignment for a while – it’s not exciting, but it pays the bills.
  • As a painter, you may spend a month painting blue pictures because that’s the color the celebrity collectors are buying this season (“Cash”), and then you spend the next month painting red pictures because you secretly hate the color blue and love the color red (“Sex”).
  • Or say you’re a programmer. You spend weekdays writing code for a faceless corporation (“Cash”), and you spend your nights and weekends creating weird computer games to impress your friends (“Sex”).
The key is to balance making a living while keeping your creative sovereignty.
#3. See your job and your art for what they are
Entrepreneur and musician Derek Sivers would seem to agree with Hugh MacLeod’s Sex and Cash Theory from Idea #2 above.
Sivers writes on his blog that the key to managing the balance between what you do for stability, and what you do for creative expression is having the right perspective.
The happiest people he knows have the following views:
How to view your job
What you’re looking for is a well-paying job that has a solid future. You’ll likely need to spend time developing the rare skills that are well-rewarded.
As Sivers points out, this is “a head choice, not a heart choice.” You’re not trying to make your job your entire life, and you don’t need it to fulfill all your emotional needs.
How to view your art
Sivers defines “art” as anything you do for expression.
He suggests that you pursue your art seriously – make weekly progress and keep improving, even if you’ve been doing it for decades. Release and sell your work just like a professional – find some fans, let them pay you.
The difference is that your attitude isn’t the same as someone who needs the money. You don’t need to worry if it doesn’t sell, and you aren’t pressured to please the marketplace.
You’re doing your art for its own sake.
How to view the balance between your job and your art
The trick is to look at each as “a remedy for the other.”
We all have a need for certainty and uncertainty, money and expression, stability and adventure. When you have too much stability, you get bored. If you don’t have enough stability, you panic.
You want to keep the balance: you get paid stability for part of your day, but then you need time for creative expression. You then push yourself creatively, “expose your vulnerable art to the public, feel the frustration of rejection and apathy, and then long for some stability again.”
Quote of the Week
“Too often we make a separation in our lives – there is work and there is life outside work, where we find real pleasure and fulfillment. Work is often seen as a means for making so we can enjoy that second life that we lead. Even if we derive some satisfaction from our careers we still tend to compartmentalize our lives in this way. This is a depressing attitude, because in the end we spend a substantial part of our waking life at work. If we experience this time as something to get through on the way to real pleasure, then our hours at work represent a tragic waste of the short time we have to live.”
- Author Robert Greene in his book Mastery
Idea Journal
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