I'm a New Media entrepreneur in New York City. I create things to make our government more efficient, and our democracy more transparent.

Formerly: Intelligence analyst to the U.S. Government
Currently: Tech consultant to the U.S. Intelligence Community
Founder: ReadableLaws.org and Speechology.org

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I’m almost at my 1-year anniversary of working for myself. I think everyone who wants to do such a thing should be able to. So I’ve put together some thoughts on how I came to this point, and the challenges I’m facing.

First, I want to explain why I think self-employment is so crucial to happiness. I’ve learned that it’s not just about waking up when you want to and having as many vacation days as you like. It’s about spending your life—or at least, a third of it—pursuing your own curiosities instead of someone else’s. It means no office culture. It means you can pursue multiple tracks and avoid the ups and downs of any one industry, staying safe while your friends get laid off. It means you can navigate into other fields when you become bored with others. And when you wake up in the middle of the night with the stomach flu, there’s nothing more comforting than knowing that your boss will have no problem with you taking the day off.

How did this happen?

I wanted all of these things. I did it through work and luck: hard work put me in the position to get lucky.

1. Publish your name

Without question, publishing my writings online is the best thing I’ve ever done for my work life. Every job I’ve ever had–with the exception of selling videos at the Pentagon City mall—was the result of someone seeing an article or paper of mine. Most of those jobs were unsolicited—I didn’t apply for them. Instead, they found the paper and contacted me. That ability to attract work without looking for it is vital if you want to work independently. You attract it by stamping your name on things that help people.

Don’t be shy about this. Post anything and everything that someone else might find useful or interesting. The first thing I posted online was a software manual I wrote for a nonprofit. That got me a job at the Duke library, where I helped faculty use computers. After that, it was a few mediocre research papers I wrote in college. One got me my job at DIA. Another got the attention of a media nonprofit that I helped with some cool projects. That job was unpaid, but it gave me even more exposure.

Then it got serious. On my own time, I wrote a diatribe about the Intelligence Community’s shoddy intranet. It got some attention. I got some praise. Then I decided—again, on my own time—to adapt the paper for the CIA’s journal, precisely because I knew it would help my ideas gain traction.

It did. I spent the summer working in DC helping the Intelligence Community do exactly what I proposed. A few months later, Clive Thompson bumped into the article, and just like that, I was the lead for a New York Times Magazine cover story. That article comes up again and again when potential clients write to me out of the blue and ask me for help.

The unsolicited offers are nice, but I think the most gratifying experience so far came last April. I was down in DC having dinner with some friends, and some friends of friends. In talking to one of the latter, we discovered that we work in very similar fields. I eventually asked him if he’d seen my article. Not only had he seen it. He said that his company refers to it all the time, and that he even had a printed copy of it in the bag at his feet. Priceless.

Now, this will be somewhat frightening, but people attach incredible value to a printed name. It is, whether warranted or not, the ultimate symbol of expertise. Let’s say you write and publish a paper about Garfield. Congratulations: you are now a Garfield expert. You may not feel like one, but expertise is more about the public’s perception of you than about your actual knowledge. See? Frightening.

Even more frightening: it doesn’t matter where that name is. This rule of expertise applies even if you’re “published” on Blogger. Of the papers I mentioned earlier, only one of them has been published outside my personal Web site. So get yourself a personal site this instant.

To modest for/disgusted by self-promotion? Redefine the term.

2. Do free work

In the last section, I mentioned more than once that I wrote all those things for free. I did so in the hopes that the free work would pay off later. It did. This attitude is vital. When you’re young, you have to prove yourself to people who aren’t willing to risk money on someone of unknown ability.

There’s a book out there called The 5 Patterns of Extraordinary Careers. The authors explain what they call the “permission paradox”: you can’t get a job without prior experience, and you can’t get experience if you don’t get the job. How do you work your way out of that one? Their solution: give yourself permission. Start making your own experience.

I couldn’t get hired to do what I wanted to do. So I started doing it on my own time. I helped a few nonprofits with their technology issues, developed their Web sites, ran mailing lists, and, of course, wrote about what I wanted to do (again: paper = expertise). After that, nobody could tell me I didn’t have experience.

An added bonus of working for free is that you’re free to screw up–that is, experiment. Experimenting helps you learn. Free jobs will, in the long run, be much more rewarding and valuable than being a paid Yes-man.

Where did I get the time to do that stuff for free? I did it at home when I got off work. Brutal. Exhausting. Worth it.

3. Ask for advice and help

Here’s how to turn someone you admire into your mentor:

• Make a list of people whose work you admire
• Write to them and ask them to be your mentor
• Set it and forget it

It really is just that easy. Wouldn’t you be flattered if someone emailed you out of nowhere and told you they loved your work? These people are no different. They are very eager to give you advice. But there’s very little chance that they’ll contact you first, so it’s up to you. Tell them what you like about their work. Ask them about their path, and for advice on the path you should take. Tell them you want to do X, Y and Z over the next few years. Don’t be surprised when they respond and ask you for your resume because a friend of theirs is looking for people that do X, Y and Z. (You’d be working for someone else, but you’d be doing what you love, and that’s a good start.)

Even more useful than job leads are the motivation and moral support they’ll provide. You’ll only understand what I mean once you start getting responses, so get on it.

This step is easy, but it might take some guts at first. What if they respond negatively? Just remember that if someone does respond negatively to something so positive, you don’t want to consort with such people, and it’ll probably benefit your character to stay away from them.

Has it been worth it?

True, I’m much more independent than most of my friends. But this question is worth asking, because this life has its down sides:

1: I’m not exactly loaded. My friends at Yahoo are pummeling me in this category. They’re taking home six figures and they know they’re going to get a paycheck twice a month. I, on the other hand, haven’t a clue what I’ll make over the next year. Money doesn’t come regularly, either. I’ll get a few small checks one month, nothing else for a few months, and then *BOOM*, something big. Independence at this age means uncertainty. But I work for myself precisely because I value independence over money, so I’m not envious of my friends’ salaries. And I make enough to live in Manhattan and enjoy city life, and for now, that’s good enough for me. It beats Sunnyvale.

I’m a food fanatic, so one of the downsides of the small wallet is my inability to make the most of Manhattan’s restaurants. But I’ve discovered something else, a perk of self-employment that ends up saving me money: the working lunch. I have time and permission to go anywhere in the city for lunch, and unlike dinner, lunch can be had at nice places for reasonable prices. Also, it helps my work, as the conversation at lunch is much more work-oriented than at dinner. This helps me justify it as a part of the job, not a luxury.

Oh, yeah: I also have to pay double taxes, as I’m both an employer and employee. Aggravating? Yes. Worth it? No question.

2: Working for myself means I do my own marketing, recruiting, record keeping, couriering and receptionisting. It’s boring. It also means that sometimes, I feel like I’m not working enough, because the amount of creative work I do is dwarfed by errands. The issue here is not the amount of boring stuff I have to do. Rather, it’s that I’m unable to gauge whether I’m spending enough hours on the job.

For example, let’s say that in my first year, I want to end up making the equivalent of $40/hour for 40 hours per week. Should my trip to Kinko’s count as work time? The practical answer is yes, as my trip to Kinko’s is a business necessity. But the time at Kinko’s was spent ordering new stationery (or whatever one does at Kinko’s). I’m not doing work for a client, so I end up asking myself: was the time spent at Kinko’s really worth $40/hour? Should I spend extra time tonight doing real work to offset this errand?

I’m still not sure what the answer is. It’s something I have to live with for now. But it beats living with my old schizophrenic cube neighbor, who provided color commentary of his mouse clicks.

How to keep it up

All those things I said at the beginning about sick days and freedom and the absence of bureaucracy–it’s easy to forget about them once they’re no longer in your life, and thus forget why you’re working for yourself in the first place. With that gone, and no looming boss telling you to do work, it’s easy to start loafing.

I constantly have to remind myself just how lucky I am to be doing what I’m doing, lest I find myself among the gainfully employed. Here are a few things that help:

• The cube placard from my old job. I kept it. It’s on my wall. My cube number—C5-822F—smacks of an inmate number. From my desk, it is always within view. “Don’t go back to that life!” it screams. The cream-colored construction paper is wise: I don’t deserve to be called C5-822F.
• The occasional rush hour trip on the subway or train. It’s only 8 am, and those people already look defeated.
• Office Space and The Office. Their observations of cube life are so spot-on, if I weren’t already working for myself, I think they’d inspire me to quit my job.
• Thoreau’s Life Without Principle. This paper convinces me again and again that humans were not meant to spend eight hours a day in an office. “What is it to be born free and not to live free?”

These are my own unique sources of inspiration. Everyone has their own. I’m curious to know what yours are. Use the comments section.

On top of maintaining the drive to work, I need to figure out the mechanics of this lifestyle. The right to work whenever I want is a mixed blessing. I’m writing this at 2 am because I got a sudden burst of energy...Alternatively, I could do it tomorrow during sane work hours and thus reserve this hour for something healthier, like sleep. That would help me maintain a balance between my work and my life...Then again, I like to think that a job like this should be fun, that it isn’t work at all–that if I like what I do, I’ll never have to work a day in my life, so who cares about life/work balance?…Of course, if I only did work during bursts of creative energy, I would be pretty unproductive. So if I force myself to work by going to the library, I get a lot more done…But, since it isn’t as inspired as the middle-of-the-night diatribe, is the quality as good?

I have this conversation with myself over and over. I haven’t figured it out yet. But at this age, I have time.