I’ve been feeling more contemplative than usual in the hours approaching the flip to the new year. Perhaps it’s the combination of my various Twitter homies making year-end observations, and the fact that so much is in flux right now for me. So I’m going to bloviate a bit over what happened in 2010, as much to help me make sense of it all and to put myself on track for next year.

The Business Angle
On the face of it, my web development business did extremely well in 2010. The year before had been difficult, though it ended well enough. But after several years of no growth, sales this year went up quite a bit in 2010, mostly owing to a simple action: I asked for more money for my work, and I got it. That’s a good takeaway for anyone in this business. If you’re not getting mass complaint about your rates, you’re leaving money on the table.

The extra cash didn’t seem to come in as handy, though, owing to a larger and more systemic issue: I just haven’t been getting paid on time. Clients in 2009 and 2010 had far less trouble holding out on me than in previous years, and it’s been grating at me more than anything else in my work. Programming requires focus more than anything, and it’s been consistently difficult when you have to worry about whether you can pay the mortgage. And I truly did spend hours and sleepless nights wondering how I could extract the cash from these reticent clients.

It got to the point where I was seriously considering a career change. The stress of having to manage the business was starting to overwhelm the incredible benefits of working from home and flexibility. It got to the point where I started looking at job postings. Maybe, just maybe, there’d be something that would both let me continue to enjoy the freedom of my current life, while providing a steady income.

I found such an opportunity. I can’t really talk about it yet, because it’s a startup, but I’ll say this about it: I’m now employed with them full-time, I work from home exclusively, and I’ve arranged to maintain my existing business. That latter move was made possible by the acquisition of a contractor, who has proven to be absolutely amazing: very skilled, very talented, and moreover, totally reliable. I can’t enthuse enough about what a difference it makes to have this kind of talent at my disposal. My business will almost certainly shrink in 2011, but this beats shutting it down altogether. Best of all, my clients haven’t noticed a difference, except for the mentions I make in our emails about my “team”. That’s not a bad feeling to have.

Personal Goals
I’ve always been burdened by what I call “crazy ideas” — those business ideas that end up going nowhere. I try to find projects that combine my strong web development powers, with my long-term goal of becoming a Mac/iOS developer, with a desire to become unnaturally wealthy.

As it turns out, I’ve got a long way to go.

I began last year with this great idea for a backup and versioning service for writers. Called PageSquirrel, it was essentially a web-based service that died almost as soon as it got into the testers’ hands. Dropbox was just becoming well-known at that point, so it seemed I’d been a little late to the party, and so I let it go.

I also joined one of my clients in creating a group-buying site (like Groupon) called WebPiggy. In the year that’s been around, it has done very modestly, while Groupon and others have literally exploded in size and reach. While we get by with modest resources, it seems unlikely to take off in a big way without a change in direction and commitment.

I wrote a book! It was a ton of work to produce Web Development with the Mac for Wiley, but seeing an actual box of real books arrive was a thrill, and one I’ll remember for the rest of my life. But the fact is, sales have been miserable and it looks like this book will join the legion of technology books that sink into obscurity, forever part of the Long Tail. So the book is bittersweet.

In the same vein, I met another personal goal at about the same time as the book launch: I wrote and published my first iPhone app. Code for iPhone and iPad lets you view the source code of any web page. It was a great moment, having published iOS software. And while I wrote the app with no expectation of reward, I was still disappointed by the extremely poor sales. Let’s face it: there’s not a big market for web page source code viewers. An early request from the enormously popular John Gruber to see the app could have led to a huge breakout win for the app. But his silence after getting a promo code said everything about the quality of my software. The pennies I’ve made on it haven’t inspired much confidence in my ability to make money on the app store, but the experience was worthwhile.

A few months ago, I started thinking seriously about another project. It’s a Mac app that I plan on pushing out to the Mac App Store. This plan addresses the weaknesses that I found in my first project, so it’s with my usual (naive? idiotic?) hope that I proceed with this new plan.

Looking Forward
So 2010 was a funny year: I ostensibly met a lot of long-term goals (best sales ever, book published, app produced), but it netted me so little that I wonder what the effort was for.

At the same time, I have new opportunities, both with a brilliant new startup, and with my own ideas in my spare time. As with any of our lives, stay tuned to see how this crap turns out.