Last time I wrote about Marco Arment selling Instapaper to Betaworks. I talked a little about Marco’s state of mind and a few of my own thoughts on that. I can relate to Marco’s feelings as I have had many of them myself.

At the end of the day what I believe every independent (indie) developer wants is financial security and the freedom to work on whatever interests him. I’m not sure Marco makes this same decision if he doesn’t have income coming in from other places.

Let me be clear that I have no insight into Instapaper’s revenues and Marco hasn’t talked about them specifically. Maybe the revenues, in the face of competition, has dwindled to the point where the revenues aren’t helping that much. But when it comes to indie developers, sole proprietorship in general, every extra dollar helps and diversity of income is critical. If The Magazine revenue drops then blog revenues are there to pick up the slack. Marco, on the surface, has four revenue streams that all related to each other: a blog, a podcast, The Magazine and Instapaper. All were geared around reading and listening. They all appealed to the same audience and thus could cross-sell those services. He has dropped one of those — or at least now has less of a stream from it — meaning at least in the short term his stool has three legs instead of four.

The financial security earned from a combination of revenue streams means almost everything to an indie dev. It is the backbone by which creative security is built. After all, if I need to make money to pay the bills then I am beholden to other people to earn that money, whether it is a job or contract work or something else. That financial security enables folks like Marco to do whatever he wants. There is nothing like knowing that you have less than three months in your personal bank account. It makes it nearly impossible to focus.

Marco talked, on various podcasts, about the stress and guilt of Instapaper. The stress of working on a product he no longer wanted to work on, the guilt of ignoring his customers, and feeling this way when he has had so much success. That, too, is palpable. I’ve spent plenty of days stressing over the code I can’t bring myself to touch. The motivations are done, whether it is because the app isn’t making you any money or because the code is old and break-prone or because heart and sole was already dumped into the project long ago and there is just nothing more to give. I think, give it a week, give myself a break. But a week passes and I’m still not ready to touch the code.

That’s when the spiral happens. The guilt over not touching it takes my brain to bad places which makes it even harder to focus on touching the code. Breaking that spiral is nearly impossible. And when coupled with the constant 24 hour a day worry over the servers going down, a worry that plays in the brain all night, a worry that keeps the head awake even when the body needs to sleep, well, there is no recovery from years of that. There are plenty of mornings I wake up at 6am after 8 hours in bed and feel like I just did an all-nighter. After four years, that gets really old.

The catch to all this is that there is a clear path forward for Instapaper, one that could potentially provide the security Marco, I believe, is looking for. More on that later. But maybe the stress and guilt had gotten to be too much. Maybe Marco just felt like it was time to do something different. That’s okay, too. I know I’ll be watching closely to see what it is.

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This concludes Part 2. Part 1 | Part 3