The system is centered on a tool called Kinkless GTD. This is my master vault, where I keep all my to-dos, organized by project. On the surface, it is simply an outline written in the excellent OmniOutliner. Underneath the surface, however, are scads of scripting and formatting rules developed by one Ethan Schoonover, using OmniOutliner’s support for third-party scripting. He calls the package Kinkless GTD, or kGTD.

This system is not for everyone. It can be clunky at times. For me, it works, because it embodies the principal of GTD I value most, which is to Get Things Out of My Brain. Everytime I have a thought about a project, I write it down in my kGTD document, filing it under the proper project. Everytime I get an email from a client, saying she’s going to delivery something by X date, I write it down in kGTD, tag it as “Waiting on” and list the date it’s supposed to arrive. Everything anything happens, it goes down in my kGTD outline.

The benefit being, if all my to-dos are one place, they’re easy to retrieve. The first thing I do everyday is open up my kGTD file, sync (which removes done items and changes the formatting of due items so they stand out more), and then scan the document for items to do today. I write those down on a separate list—usually a notepad next to my keboard—then work exclusively off that list for the rest of the day. If I’m feeling really energetic, I’ll even mark down time slots for each task, so I know, realistically, what I’ll be getting done today for sure.

What was revelatory for me about GTD was not the specific systems it describes, but the philosophies behind them. Get stuff off your brain and onto paper. If you’re frustrated, fix the process. Put stuff where it belongs. I’ve tried lots of other tools, and I keep coming back to kGTD, because it’s the easiest tool that allows me to accomplish those goals.

Nevertheless, it’s always really tough to take a vacation as a full-time freelancer. As much as I try to plan them, project schedules are a beast of their own desires. I got lucky this time; the week could have just as easily been one of hectic deadlines, forcing me to bust out my laptop at inopportune times, like on the subway, or at my sister’s wedding.

On the flip side, of course, is that a freelancer’s life gives one the chance to take vacations whenever they mood, and pocketbook, pleases. We are a highly mobile class; it’s just as easy for me to respond to email in, say, New Delhi, as it is from my desk. For this, I feel very fortunate. I have the kind of mind that requires consistently fresh stimuli in order to avoid boredom. That I can take my work with me to the porch, or a coffeeshop, or to Boston, and get just as much done—or quite likely more—makes me a very happy worker bee.

The tricky part is avoiding the guilt. (Oh, but isn’t that always the case for sons of Jewish mothers?) It comes from both sides. If it’s not the guilt of waking up in a foreign city with all sorts of lovely stuff to do and finding myself working instead, then it’s the guilt of having fun while my to-do list remains untended. The solution I’ve found is to set some short-term, project-based goals, work until I meet them, then feel free to spend the rest of the day galavanting, guilt-free.

It’s easy to think, as a independent worker, that without constant attention, your whole business will fall apart. I’m finding this to be less and less true. There were days on this trip when circumstances prevented me from working or getting online until late at night. And yet, nothing caught fire or broke down. Instead, I was able to check out and enjoy my vacation. In the long run, this makes me feel healthier and more creative and, in turn, more excited to get back and do my job.

As a freelancer, I spend all my days at home, by myself. This has its perks, but I find myself missing the human interaction of the office environment. No one to bounce ideas off of, or get over-the-shouler critiques from, or scam a free lunch out of. Fortunately, I have the ability to pack up all my work into my 13-inch laptop and move my butt to wherever I care to. Often this ends up being a coffeeshop.

I like the coffeeshop atmosphere, and I’m not alone. I know this because even though there are three wifi-enabled coffeeshops within walking distance of my home, it’s becoming harder to find a seat at any of them, thanks to other bedouins like myself. And who can blame them? Free wifi, a change of scenery, lunch made while you wait by a staff of highly trained professionals—all for the cost of…

Well, that’s my question. I’m beginning to wonder what the proper exchange rate is for time spent on another business’ network. I’ve seen a few places put up signs asking people to be courteous with their time, but it usually doesn’t get more specific than that. And I can understand why—they don’t want to appear ungrateful for the business, and certainly they don’t want it to seem like they’re counting minutes or bandwidth.

My usual rule of thumb is an over/under of three hours. If I’m spending less than three hours there, I can get away with just buying a coffee or tea. More than three hours there, I’m obliged to buy a sandwich. More than six hours, and I start washing dishes.

I’ve yet to get to a point, fortunately, where a barista has come up to me and asked me to either buy more food or get walking. And I’d like to avoid that situation. So I wonder, should I be more generous? What would you do?

It’s not a lack of confidence about my own abilities. If I didn’t have that, I’d be a fool to be starting my own thing like this. If I had to hire a web developer, there’s no question who I’d hire. I’ve seen my own work, and for my money, there’s no one I’d rather have on my side but myself. The hard part is translating that confidence to the page. Or more precisely, translating it to the page in a way that’s relevant to the client.

So much of the value of the work I do is hard to quantify. How do I put a number on the extra care I take with my eye to the screen making sure no pixels are out of line? Or the drafts of unpresentable design comps that come before the one that finally hits and ends up in the client’s hands? Or the way I accommodate client’s requests for changes well past the sensible break-off point, because I’d rather have a happy client than a few more hours to kill?

I can’t, so instead I turn to the tropes of our business—of being able to increasing the the value of their brand, of being able to optimize their search rankings, of a standards-based codebase. None of which is untrue or misleading. Those are important things; everyone says it. But that’s just it: everyone says it.

I’m learning—as we’re all destined to someday—that it’s all about the details. The qualitative, rather than the quantitative. This is why I prefer to meet a potential client in person before even submitting a proposal, and why I address them directly in the proposal, instead of as a headless entity. These touches, which I’ll admit I’m still no expert at, go a long way toward making a personal connection. My hope is that the person on the other end of the proposal will recognize that—and more importantly, value it, to the tune of a signature on the bottom line.

None of this is revolutionary. Yet it’s new to me. I guess that’s because I prefer to see things—everything—as a problem of analytics. Everything should be solvable by a process. It’s disconcerting to me when there is no definite, for sure, 100% way to say that what I’m doing is going to garner the result I desire. Yet, such is the job at hand. Funny place for a CS boy to find himself.

I was recently hired for one day of training work. The job entailed a short amount of travel and eight hours of on-site, one-on-one CSS training. I priced the work out at X dollars, to which the client agreed. When the day came, I found myself working with an interested, attentive client, and the training proceeded smoothly and successfully. At the end of the day, the client asked if I could come back again, the next week. I told him I’d check with his boss.

When I spoke with the boss, I told him I was asked back by his employee, and I’d be happy to do so, but that I’d have to charge a little more, due to the short notice—my upcoming week was already booked up with work. He agreed to this price, which we’ll call Y, and which was roughly 25% more than X.

After the second day of training, which also proved successful, I submitted my invoice of X+Y to the boss. I didn’t hear anything for a couple weeks, and then an envelope came from the company. Inside was not a check, but a contract, detailing the nature of my work, and all the typical legal mumbo jumbo that they have all contractors sign. I hadn’t signed it before starting, and they needed it on the books before I got my money. No problem, except for one thing: the contract included a breakdown of my fees, and they were not what we agreed on. Instead, they were much higher. Instead of X dollars for day one and Y for day two, it showed X+Y for day one and Y again for day two. They (or their contract-writing secretary) wanted to pay me more than 50% more than what I billed.

Of course I’m tempted to sign it as is, send it back and see what happens. There are a few strongly mitigating factors: 1) I’ve already sent them an invoice for the proper amount; 2) if they catch their mistake and my subsequent exploitation of their mistake, it could come back to bite me in the ass; 3) it feels gloriously unethical.

What would you do?