Starting by Quitting

I've been struggling for three years now to get my company off the ground. I've wanted to develop apps for iOS for some time and finally had the idea I wanted to work on. I formed an LLC, got a domain name, and joined the Apple iOS Developer Program. I started prototyping the app I wanted to build and made some progress. I even started playing around with basic animation to see what I could do. 

Then I did nothing for a long time. 

WWDC rolled around, new developer videos were posted, and I got excited again. I picked up the code and started fleshing out more features. I even managed to get it running on my iPhone and found and resolved my first significant performance issue.

Then I did nothing for a long time. Again. 

Again, another WWDC rolled around, new developer videos were posted, and I got excited again. I started clean: The prototype code was bad (even to a beginner it was obviously bad), so I needed a fresh slate. I started over. I decided to take advantage of ARC and Auto Layout this time. I experimented with animation using Auto Layout, which proved more challenging than I expected. I was confident enough in my ability to build out the features I was interested in that I started to focus on properly designing the app, sketching options and thinking through how I wanted the app to work.

Then I did nothing for a long time. Yet again. 

Why? Why do I keep stopping every time it seems like significant progress is being made? 

Back to Work

At the same time, my joby-job has been going really well of late. I got promoted and a raise. I ended up in a position I like. The company has a major IT-wide effort that I fully support, feel like I can make contributions to, crosses projects, and seems to have the upper-level support necessary to let me make those contributions. I've finally gotten into the GTD methodology and feel like I'm on top of things. Based on what others tell me, I've got a pretty good handle on how to do my job, and am really growing into the roll. For a corporate stooge job, things aren't too bad.

In that area of my life, at least, I'm capable of making progress. Clearly it isn't a matter of ability (though, admittedly, the skills I use at work have limited carryover to an app business).

Expectational Debt

Over the last year or so, I've really started to "get" Back to Work

I didn't at first. I could get my joby-job work done without much of a problem. I wasn't as organized or efficient as I might have liked, but it wasn't significantly holding my career back. I had a side effort I was interested in, it was just that my interest waned at various times for good reasons: I met my now-wife; I got married. 

It was only really with this last collapse in ambition that I began to realize something else was at work. I didn't know what, but it was clearly more than changing life circumstances. What was holding me back?

I remember when it all clicked for me. It was about two weeks before my first child was born. Work had settled down enough that I had time to consider broader matters than just the next thing that needs to be done. The breathing room let me think, and one phrase kept running through my head:

Fear of success. 

This is a phrase Dan and Merlin have used repeatedly. It sounded like an absurd concept when I first heard of it. You wouldn't try to do something unless you wanted to succeed. I listened to them explain it and still didn't understand how this could actually hold anyone back. 

Now I realize that is exactly what has happened to me. I'm afraid of successfully building an app that I sell. I've built up all these expectations about the demands on my time if I succeed: I'll have customers to support, which means I'll need to deal with email, Twitter, ADN, etc. There will inevitably be bugs which need to be fixed, some of which will likely cause people to be upset at me. I could ship a "bug fix" that ends up wiping out customers' data, which would be a Really Bad Thing. There is no vacation from support (at least not if you want to be an excellent company). Simply maintaining the app will take time, and working on the next version of the app will take even more time. Once money is coming in I'll have to start worrying about paying taxes on it, which will take more time to manage.

With a wife and a new child, do I really want to give up that time? 

Those are just the reasonable expectations.  Then there are the "nice problem to have" concerns that are already weighing on me without justification: If this becomes successful and it becomes clear I can't manage the business and my job, would I really be willing to take the risk of quitting to work on the business full-time? If not, could I really sustain the business as a side-effort for any real period of time? To get the app to where I eventually want it, I'll have to build a bunch of new skills I've never had before. Will I have the time to learn what I need to?

All of these questions, doubts, and unjustified fears (for the time being) have paralyzed me. Whenever I've made enough progress to see possible success, the weight of what might happen shuts me down to ensure I never have to deal with those issues.

Ready to Quit!

I think I've figured out how to get over this fear and get moving again. Marco Arment has a great deal to do with it, indirectly.

In the last month or so, Marco has sold everything he does. Instapaper? Sold. The Magazine? Gone. Tumblr? Not really his and he hasn't been involved in years, but still gone.

In the case of Instapaper and The Magazine, Marco was very clear that the reason he sold them is because, effectively, he didn't want to handle their success. They'd both grown to the point where he would have to confront the problems of success which would require him to do things he has no desire to do. His solution was to sell off the products, making the successes someone else's "problem". 

The key lesson is one can always walk away.  Gracefully, hopefully.

I think the key for me getting started is knowing I'm not permanently committing to anything. If I fail, well then I don't have a problem. If I succeed and things go really well, either I build a real business out of it and quit my day job, or try to sell it to someone who can. If I can't sell it...well, I'll figure that out if I get there.

Knowing there is an "exit strategy" no matter what happens is oddly liberating. I feel like I'm ready to get going again. If I'm right about what I've written here, you'll be seeing my first app in a few months. With some luck, you'll see it when iOS 7 ships. 

I'm ready to begin because I finally understand I can always quit.