Independent Software Development

It was a little over a year ago that I set out to try and turn a few mockups into a full-fledged revenue-generating piece of software. For the most part, it’s been a pretty smooth ride, but there have definitely been some lessons learned. In January of ‘08, I woke up to the first day on the job. I was free of the daily grind. I could work anywhere and anytime I wanted. I could attend any web conference without seeking approval. I could write and share to my heart’s content. But most importantly, I could spend every single day working on things that I loved.

As it turns out, only the last one is 100% true. In retrospect, I wouldn’t trade it for the world, but making ends meet and building a software empire, err, uhh, village, can be quite the juggling act.

The Daily Grind

I didn’t have to commute or work set hours, but being highly self-motivated and loving what I was doing led to a self-imposed grind where I felt guilty about every moment that wasn’t paying the bills or finishing Sifter. By blogging so openly about our plans, I had unintentionally created some expectations that loomed over me. Combine that with loving what you’re doing, and it was, and still is, hard to put the mouse down so to speak.

The really daily grind for me was making time for friends and family. Working was easy. It was fun. And, unfortunately, it can be pretty addictive as well. I’d like to think I kept a reasonable balance, but I probably averaged 60 hour weeks. That may not seem like a lot, but one of my goals in becoming self-employed was to find more time away from the desk. It hasn’t exactly worked out that way, but it’s getting closer.

Working Anywhere and Anytime

In theory, this is attractive, and it was until Sifter launched. Now, with customers all over the world representing different time zones, the reality is that I’ve always got an eye on Sifter and support. Instead of working a boxed in 8 hour day, I’m regularly working a bunch of separate 2-4 hour shifts. I don’t mind so much, but Lauren, my fiancée, is, quite simply, over it. I can’t say I blame her, and one of my highest priorities is to bring in some backup for support.

Working anywhere is another thing that sounds great. I’ve romanticized about working on coffee shops or coworking spots for as long I’ve seen others doing it, but it turns out that I’m not too effective in that environment. At home, I have a meticulously crafted setup that includes a desk and chair high enough and large enough for someone that’s 6’6” and 225 lbs. I also have a printer/scanner, large monitor and various other amenities. Most importantly, it’s quiet, and there aren’t any distractions. (Yet.)

It turns out that I’m most productive from home, but there is a huge drawback in that I don’t have anyone to spin around in my chair and bounce ideas off of. That’s really tough at times. I blast friends with mockups over IM or call them up to make them listen to my new ideas, but it’s not the same. Frankly, it gets a bit lonely at times.

Web Conferences

I don’t need approval or justification to attend web conferences, but I’m too heads down to jet set from conference to conference like some people. Switching from a full-time job to part-time consulting constrains the cash-flow considerably. So, while I have been able to attend a handful of conferences, it hasn’t been the free-for-all that I had hoped. The most significant challenge is that it’s hard for me to justify work time that isn’t paying the bills or improving Sifter.

Writing, Blogging, and Sharing

This was probably one of the most exciting facets of being self-employed and building my own web applications. I’d finally have more than enough material to update the blog regularly and share ideas free of NDA coverage. Unfortunately, it turns out that the amount of time one has for blogging is inversely proportional to the amount of fun cool things that you’re working on and able to discuss publicly.

I’ve learned more in the last year than I have in probably the last 3 years, and none of that new knowledge is under NDA. (Well, some of the client work is, but it’s a very small amount.) I have a backlog of ideas that I want to share and talk about so that you don’t trip over the same silly mistakes that I made. Lessons about the business, interface design, development, customer support, and more are all there with rough drafts that I just haven’t made time to finish.

I’m dying to sit down and type it all up, but improving Sifter wins out every time. For every new paying customer that spends their hard-earned money on our application, I feel even more obligation to make sure that Sifter makes them happy. So blogging loses out, for now.

Loving What You Do

Despite all of the challenges, there’s something to be said for waking up every morning and pouring your heart into work that you love. I consider myself incredibly lucky to have that opportunity, and I consider myself even luckier that it seems to be working out financially as well. I’ve always believed that work and passion should go hand in hand. That is, we should all want to work to find a way to pursue our passions rather than just trudging through another 8 hour day just so we can pay the bills.

It’s not easy, but nothing worth doing ever is. So, if there’s anything I’ve learned this last 14 months, it’s that it’s definitely worth it. Whether it’s web development, music, writing, tight-rope walking, or creating and marketing your own BBQ sauce, being able to spend your work hours doing something that you enjoy makes all of the difference in the world.