Peggy's Progress
        (Not to be confused with John Bunyan's tale of agony and doom!)

Here at Outside the Lines we repeatedly encourage each of you to pursue your life's dream, live your passion or follow your heart. No matter what you call it though, actually taking that path is truly easier said than done. It should be so easy.

No one describes this quandary as astutely or as amusingly as Paul Graham.

Since I'm pretty far removed from the tech world, I had never heard of Mr. Graham, but have come to find that he is a really smart entrepreneur and apparently really talented hacker (his choice of words, not mine). He's an author and founder of both failed and successful tech start ups. One success has become YahooStore. And if that isn't enough he's a painter who studied at the Rhode Island School of Design and the Accademia di Belle Arti in Florence.

No matter what titles you attach to his name, what it comes down to is he's a big thinker and a doer. He's very much an outside the lines thinker and way back in the 90's he launched on online web based art gallery named Artix. It didn't succeed, and I'd be curious to know if he was just ahead of his time or if it really is a flawed concept. While his audience may be more typically hackers (he notes that it's the term software engineers and designers use to refer to themselves) his topics are of broad interest.

As someone who hasn't really made the leap to a more creative path, I found his comments particularly pertinent to anyone wanting to follow their own heart but who doesn't quite know where to start.

Graham is the author of the book, Hackers & Painters: Big Ideas from the Computer Age and founder of startup launch group Y-Combinator but I was recently introduced to him when I came across this interesting piece (How to Do What You Love) that he wrote back in 2006 in which he speaks to the creative stirrings in all of us:

"The test of whether people love what they do is whether they'd do it even if they weren't paid for it—even if they had to work at another job to make a living. How many corporate lawyers would do their current work if they had to do it for free, in their spare time, and take day jobs as waiters to support themselves?"

"It's hard to find work you love; it must be, if so few do. So don't underestimate this task. And don't feel bad if you haven't succeeded yet. In fact, if you admit to yourself that you're discontented, you're a step ahead of most people, who are still in denial. If you're surrounded by colleagues who claim to enjoy work that you find contemptible, odds are they're lying to themselves. Not necessarily, but probably."

"Although doing great work takes less discipline than people think—because the way to do great work is to find something you like so much that you don't have to force yourself to do it—finding work you love does usually require discipline. Some people are lucky enough to know what they want to do when they're 12, and just glide along as if they were on railroad tracks. But this seems the exception. More often people who do great things have careers with the trajectory of a ping-pong ball. They go to school to study A, drop out and get a job doing B, and then become famous for C after taking it up on the side."

Thankfully, fame hasn't found me and instead of mimicking ping pong the trajectory of my life has been more "go with the flow." I had no idea what to study in college until the Registrar at UC Santa Cruz wouldn't let me register for classes for my first quarter of my senior year of college until I formally declared a major. Forced to make a choice, instead of having some great epiphany about my academic path (much less a life path) I looked at where I had the most units completed and what classes I had liked the most, and declared myself a History major. Graduating with a B.A. in History with no real sense of what kind of job to get, I went to graduate school at UCLA. Though I enjoyed my year of a pre-doctoral program in History clearly it wasn't something I was committed to continuing and so I quit school and got married. I got a job as a secretary at San Jose State and four jobs later I embarked on a professional career of 20 years as a University planner. There was no way I could have known as a kid, much less as a college student that I would have ended up involved in hundreds of millions of dollars worth of planning, design and construction projects.

Although he's generally speaking to a younger generation, Graham's advice struck me as meaningful to folks of most any age and stage of life because it's not just about work. I think it applies to the path I've been on for years, and since I'm still working, it offers some serious food for thought:

"In the design of lives, as in the design of most other things, you get better results if you use flexible media . . . It's also wise, early on, to seek jobs that let you do many different things, so you can learn faster what various kinds of work are like. Conversely, the extreme version of the two-job route (to work at things you don't like to get money to work on things you do) is dangerous because it teaches you so little about what you like. If you work hard at being a bond trader for ten years, thinking that you'll quit and write novels when you have enough money, what happens when you quit and then discover that you don't actually like writing novels? Most people would say, I'd take that problem. Give me a million dollars and I'll figure out what to do. But it's harder than it looks. Constraints give your life shape. Remove them and most people have no idea what to do: look at what happens to those who win lotteries or inherit money. Much as everyone thinks they want financial security, the happiest people are not those who have it, but those who like what they do. So a plan that promises freedom at the expense of knowing what to do with it may not be as good as it seems . . . To be happy I think you have to be doing something you not only enjoy, but admire. You have to be able to say, at the end, wow, that's pretty cool.

Is there some test you can use to keep yourself honest? One is to try to do a good job at whatever you're doing, even if you don't like it. Then at least you'll know you're not using dissatisfaction as an excuse for being lazy. Perhaps more importantly, you'll get into the habit of doing things well. Another test you can use is: always produce. For example, if you have a day job you don't take seriously because you plan to be a novelist, are you producing? Are you writing pages of fiction, however bad? As long as you're producing, you'll know you're not merely using the hazy vision of the grand novel you plan to write one day as an opiate. The view of it will be obstructed by the all too palpably flawed one you're actually writing. 'Always produce' is also a heuristic for finding the work you love. If you subject yourself to that constraint, it will automatically push you away from things you think you're supposed to work on, toward things you actually like. 'Always produce' will discover your life's work the way water, with the aid of gravity, finds the hole in your roof."

I know for a fact that I've thoroughly enjoyed the creativity of master planning campuses, site planning for buildings and designing new buildings and implementing construction projects. I really didn't like the people management part of my previous jobs. My current job is similar, but full of flexibility for me to learn new things and skills, and without the people management. But I haven't really figured out what I want to do when I'm not doing that work. I've enjoyed it, and have even been able to stand back and admire the fruits of my labor. But that doesn't make me immune from my internal naysayer. You've heard me talk about this before when I lamented the fact that I can't draw, I can't paint, etc., etc. I could swear Graham was talking to me when he wrote:

"Of course, figuring out what you like to work on doesn't mean you get to work on it. That's a separate question. And if you're ambitious you have to keep them separate: you have to make a conscious effort to keep your ideas about what you want from being contaminated by what seems possible. It's painful to keep them apart, because it's painful to observe the gap between them. So most people pre-emptively lower their expectations. For example, if you asked random people on the street if they'd like to be able to draw like Leonardo, you'd find most would say something like "Oh, I can't draw." This is more a statement of intention than fact; it means, I'm not going to try. Because the fact is, if you took a random person off the street and somehow got them to work as hard as they possibly could at drawing for the next twenty years, they'd get surprisingly far. But it would require a great moral effort; it would mean staring failure in the eye every day for years. And so to protect themselves people say "I can't."

I need to stop saying "I can't do this or that" and just start "producing" as Graham calls it. In my case I just have to pull out the sketch pad and start drawings and get my hands dirty in the concrete. And if that doesn't work, I'll just keep at it—just keep producing or be flexible enough to move on to something else.