What is it about my job that makes it so damned enjoyable? I was discussing this earlier today with a friend and came to the conclusion, perhaps obvious, that it’s fun because running an indie software business feels like playing a game.

I imagine that other small business owners, and larger venture entrepreneurs feel the same way. What a luxury to be immersed in this environment where every decision ultimately rests upon my shoulders. Whether I win or lose depends entirely on how I choose to move the pieces.

Of course this freedom and autonomy comes with a few downsides. In particular, playing the game can be stressful, and the consequences of losing can be dire. The indie software business is a long, sometimes tedious game with no extra lives.

I believe that the best game players are those who acknowledge they might lose, but who really, really, really, really, really, really don’t want to.

By acknowledging a risk of failure, you implicitly acknowledge:

1. You are willing to accept the consequences of losing.
2. The choices you make in playing the game affect the outcome.

This is good. Somebody who is blindly assured of winning is liable to play games that they can’t afford to lose, and to play them with foolish ignorance of the rules. Knowing you can afford to lose liberates your thinking so that you can play the game for the game’s sake. And your strong desire to win encourages you to seek out the wisest moves at all stages of play.

I often hear the opposite mentality celebrated. “Failure is not an option.” “Nobody told me it was impossible, so I did it.” “If you build it, they will come.” These are fantastic rallying cries, but they don’t reflect the true attitudes of a wise game player. They make a romantic postscript to games that were, ultimately, won.

Running your own business isn’t the only way to treat your job as a game. I always found framing the expectations and achievements of work in a game context made the work more fun, even when I was working for other people. Whether that was racing to fix bugs in time for a deadline, or counting the number of envelopes I could stuff in 60 seconds.

But the game has never been as complex or enjoyable as it is now. Running Red Sweater is incredibly challenging. I make decisions every day that could be the foolish move that leads to my failure, or the stroke of genius that guarantees my success.

I know there is a chance of losing, but I really, really, really, really, really, really don’t want to.

Yesterday Favrd, a site that monitored the number of favorite stars a particular Twitter update has received, was suddenly shut down.

Twitter erupted with reaction, much of which was more earnest and emotional than I expected. I had learned about Favrd and used it myself from time to time, but I assumed it was one of those sites that you should feel slightly embarrassed about loading. Or at the very least, you should be ashamed if you were caught trying to get your own tweets to be featured.

But Dean Allen, who created the site, is apparently some massively famous, well-loved internet superstar. I had never heard of him, even though many bloggers whose opinions I respect obviously had. Disorder is good for a system, so I guess it was my healthy function to be ignorant of this man so that I could experience the curious emotion of respecting him not for what he built, but for why he dismantled it.

Mr. Allen’s goodbye message, which now occupies the entire content of the site, was matter-of-fact and sincere, but its declaratory tone gave it a tinge of self-aggrandizement. To learn some of the really interesting rationale behind this fascinating end, you need to visit the comments section of Jeffrey Zeldman’s blog (thanks, Gruber), where Mr. Allen responds to Jeffrey’s criticism of the abrupt shutdown:

“I’ve spent the past year or so reading and writing and doing my level best to chip away at 40 years of belief in the logical fallacy that one’s identity meaning – self-worth, self-image, whatever you want to call it – can accurately be measured in the thoughts of others.”

Many folks use the internet as a valuable tool for research and connectedness, but also as a dubious source for ego-validation. Some of us are more vulnerable than others. How many of the following questions do you care to know the answer to?

• How many people are following me on Twitter
• How many hits on my home page?
• Has any high-profile blogger linked to me recently?
• How many people are @responding to my tweets?
• How many comments on my latest blog post?
• How early does my name show up in a Google search?
• How many people are buying my app/t-shirt/CD/craft?
• Who left positive feedback on eBay/Amazon/iTunes?

If you’re interested in the answers to these questions, it’s probably because you are concerned on some level about whether you matter or not. But more specifically, when it comes to the internet and other people you may reach by way of it, all these questions boil down to whether you have pleased anybody lately.

I relate strongly to this urge, because I find most of my time at the computer ultimately boils down to striving to get another “fix” of pleasure acknowledgment. When I’m working on my apps, I’m hoping the features I add will move somebody to send positive feedback, or to buy the software. When I’m writing on Twitter, it feels great to have people declare their enthusiasm for something I’ve said. And yes, when I’m writing on this blog, it’s ultimately because I hope what I’ve shared will resonate with other people, and some percentage of those readers will share their satisfaction with me.

What can I say? I aim to please. And I think this is a pretty common “problem.” It’s not exactly humanity’s worst defect. The expectation that our help and amusement be acknowledged has probably fueled a lot of important help and amusement. While a few saints work tirelessly and without need of emotional coddling, the rest of us always benefit from a pat on the head and an “atta boy”.

Sites like Favrd, and even Twitter itself, demonstrate how the internet has facilitated an ever-increasing diversity of positive feedback. A witty remark to an appreciative cluster of people at a party was once chalked up as a major win, but nowadays you might find yourself recognizing the wasted potential of that line, and quickly cc’ing it to Twitter. Then what? If 10 people favorite it, you’re a rock star. Until 10 people favoriting you is an everyday occurrence, then it takes 100 to move the meter. When does it end?

While the desire for praise and acknowledgement that we do matter is a healthy instinct that motivates us to do life-affirming things, I believe it can be fed inappropriately. Compare this need with hunger, which can be sated easily at first, but which tends to become harder to satisfy as your meals become larger, richer, and less complex.

It’s become relatively easy to find praise on the internet. A quip on Twitter yields a simple reply of “Hilarious!” from somebody you’ve never met. Not the most illustrious validation you’ve ever received, but it will get you through the hour. If you don’t pay attention to what you’re feeding your ego, it might develop health problems. Adulation by way of Twitter replies, favorite counts, blog comments, etc., are all fast food gratification. They are invaluable when you’re stuck in a lonely place and are desperate for a boost, but if it’s all you consume day in and day out, you’re heading for an epic fall.

The folks at The Unofficial Apple Weblog were kind enough to invite me to write a guest post about my experience at the recent Apple iPhone Tech Talks in New York City:

Inside view of the iPhone Tech Talks from Daniel Jalkut

Thanks to Mike Rose for approaching me about writing this up!

Starting a blog changed my life. Before Red Sweater Blog, nobody knew who I was, nobody cared what I was working on, and nobody (relatively speaking) bought any of my products.

I’m not saying the blog changed everything overnight, but my first post, on June 24, 2005, set the stage for what has been an exciting 4 year adventure. At the time, I was fresh from graduating with my second BA degree (in Music!), and was scraping by doing freelance development for an assortment of clients. Today, I spend every day working on my own software, which sustains me and my small family.

So what changed? The moment I started blogging, I became part of a community. Sure, the community was just myself and a few readers at first, but as my readership grew, it merged with other readerships, and connected me to other bloggers and readers, many of whom have become good friends. Every opportunity I’ve had the privilege to take advantage of over these years can be traced back to the reputation I earned and the friends I made by blogging.

Dan Wood wrote about the value of blogging on his excellent marketing blog. The Importance of Blogging discusses the benefits of writing a blog in more concrete terms than I have here. Check it out!

Some of you consider yourself more adept at reading than at writing. I know you’re with me, because you’re the type of person who had no problem digesting the content of this post, and you’re still reading five paragraphs later. You might be tempted to think you can’t start a blog because you’re not the world’s best writer. Think again. I covered this a couple years ago in another post: No More Excuses. I stand by those thoughts today.

If starting a blog is so great for your reputation, and will make you lots of friends, and bring you fame and fortune, why should I share the secret with you? Why not keep it to myself? Because I write blog editing software? Well, sure, more blogging is good for me. But much more importantly, it’s good for you. Helping others has always been a mission of this blog. It’s one of the things that led to its success, and it is one of the aspects of my work that gives me the biggest charge.

So start a blog intent on helping others. You’ll reap personal benefits and feel good all at the same time. Furthermore, everybody who ever helped me over the years holds a special place in my heart and they’ll always have my deep respect. If this post gets you to start blogging and achieve the level of success you deserve, maybe I’ll earn a similar spot in your heart. Bonus!