A Very Long Break

This post was originally written on August 15, 2014. What’s most unusual is that I didn’t publish it as I typically publish everything that I pen here on this personal blog (and then I promptly forget that I wrote it).

For whatever reason, I just felt like I couldn’t and I’m not entirely sure why as I was very comfortable with the idea of taking a very long break from building software.

Of course, I was terribly wrong and I haven’t stopped writing software since. In fact, I’m doing more of it than I ever thought I would be doing at this point in my career.

I guess I’m just not done… yet. That’s fine. But, I wanted to publish it anyways and I’m going to publish it without a single edit, so, remember… this was more than 3 years ago…

Here you go:


There’s nothing more scary than making a public commitment to something and then having to follow through with that commitment.

I’m not sure if it’s the commitment itself or rather expressing that commitment that’s actually more scary – perhaps both in a variety of different ways.

I have used this technique for my own benefit a number of times when I’ve really wanted to lock in some goals that I have for myself so that I might receive accountability from people that care about me and the work that I do.

But perhaps more than that I have done it because it hardens and steels my resolve to move forward with the commitment with an even greater earnest and creates “weight” around the commitment that limits me from bailing.

And I’ve made yet another large-scale commitment that has completely wrecked me emotionally in the past few months as I’ve been sharing it with others; and I’m ready to go public with it here on this blog.

For the last 17 years I have been building software, software products, and applications for fun, for profit, for the small startup company all the way to the largest companies on the planet.

I have loved it immensely and I have derived an incredible amount of identity and self-worth from it. I believe I have also changed people’s lives with not just the products that I’ve built and the customers who have purchased and used those products but perhaps more importantly the people that I have hired to help make those visions a reality.

To think that people have come alongside me (and their families) and spent years helping me build out my visions, my obsessions, my hopes, and my desires is simply too humbling for words. I have asked them of their most precious resource and many have given me much – I am eternally grateful for that.

And for 17 years I’ve been building, creating, expressing myself through software. In many ways I have found my existence. My calling. My purpose. The reason that I was created.

And so it’s hard to imagine that I would do anything else. It’s hard to imagine an existence where the next project, the next app wasn’t on the horizon of my own mind. For years I’ve expressed to people that the most exciting project that I’ve ever had is the one that I haven’t quite yet started. That my favorite project is the next one.

And up until now that’s been the case as there has always been “the next app” that I’ve wanted to build and that I’ve been paper-napkin sketching or that I’ve been toying around in my IDE.

But not this time… and that’s scary as fuck.

For those that have been following me for a while then you know that the most recent applications and products that I’ve been obsessed over are Pressgram (that I leveraged Kickstarter to start and then raised a round of venture money to support) and in (maybe) this month Pressgram’s desktop brother, Desk Publishing Machine, an OS X native publishing client that I’ve been dreaming about for more than a decade.

I have spent thousands of hours building these applications and I have had thousands upon thousands of people use them (and I hope that number continues to grow). For Pressgram specifically I have been awarded the very prestigious recognition of becoming a Featured App in the Apple App Store and have had more press than I deserved.

And with the soon-to-be released Desk PM I couldn’t be more happy with my work as it’s the most personal and emotional product that I’ve put together. It’s not complex nor is it necessarily revolutionary – but it’s distinct, incredibly functional, and I generally think it’ll kick some serious ass in a technological ecosystem that’s been entirely starved and ignored for real tangible advancement. Here’s hoping anyways.

And in every case prior to these applications there’s always been “the app” on the horizon, the next app that I’m excited to build once these things ship. In many instances the fact that I had one that I hoped to begin development on was the motivation to finish and ship the current one.

But I don’t have that this time and I’ve entered a very precarious mental state as I simply do not have that “next app” in my head. I’ve been drawing blanks for the last year and it’s scared the shit out of me.

For a while I thought that I had lost it completely, that I had entered into some crazy sort of mental doldrums and that all I needed was major refresh or perhaps a vacation. Or maybe I needed a breakthrough in the existing apps that would jumpstart my passion for the next big thing.

It never came. I still hasn’t. And I’m not expecting that it will. I’ve battled some serious depression in the past year and the corner of my bed and pillow have been a very dear friend. I’ve spent the day in bed unable to get up thinking that my entire existence was on the brink of destruction as I peered into a future where I had no value and no point; it’s as if my contribution to mankind had evaporated.

This was change on a scale that I had never experienced. It was an evolution that was so uncomfortable, so foreign, that I throw away all the previous thinking around my own existence and begin to build a new mental foundation from scratch.

And like the slow and painful recovery time from a complete drunken blackout I walked through my mental hangover and realized, in a rare moment of clarity, that perhaps I needed to stop fighting the inevitable and unreasonable truth: I needed a very long break.

This isn’t like one of those sports superstar announcements of retirement only to find them come out of retirement and back into the game a year or so later because they couldn’t quite find a reason to live without the sport; no, it’s not like that at all.

I’m not retiring from software development. I just need a seriously-long break. I didn’t know at first but I’v settled on a starting point: 8 years.

Why 8? For number of reasons most of which are somewhat arbitrary. But it provided a helpful starting place that seems to make more sense the more I think about it:

  • I’ve been building software for 17 years professionally and so spending half of that amount of time away from building is pretty significant.
  • 8 years is a serious amount of time so that I might invest in some other areas of life in a consistent and concerted way. It’s not just some 6-month sabbatical where I’m spending 3 months adjusting to the said sabbatical…
  • I turn 40 in 8 years and some change. I think shooting for 40 is a pretty big deal.
  • And finally, relating to the last bullet point, this post here about The Stages of Man.

What does this mean practically? It means that once I ship Desk PM I’m going to find to supper the application by hiring a team around it to take over the development full-time and take a back seat to actually shipping code myself. It means that I’m going to put on pause my incessant need to open any IDE of any kind and write lines.

Don’t misunderstand me – I’m going to fully support Pressgram and Desk PM in the best way possible; it’s just that I won’t be writing code for the two apps myself. I have big hopes for the two apps and I’m praying that they do amazing. I think they will. I’m counting on it.

8 years… now that’s a long time. Is it set in stone? No, not entirely. It could be shorter it could be longer (now wouldn’t that be incredible…). But outside of a cataclysmic life event I’m going to aim for 40 years of age as the next time I take a serious look at building any type of software (or starting yet another software startup and venture).

So there’s my announcement and now that I’ve made it public I’ll be referring back to it constantly, for my own sake mostly as I know that it’ll require an incredible amount of resolve to stay the course.

What does this mean for me practically-speaking as a professional in the software space? I think it means a few things, most namely an intense focus on my staff and coworkers @ The Iron Yard. We are growing so fast it’s freaky and I want to give it the very best run that I can possibly give it.

Second, I think I’m going to invest in other areas that I think are relatively weak, such as areas of leadership, public communication, and mentorship. I’ve investing in these areas as an amateur and I think it’s time that I go “pro” with it. If you were to ask me what that actually looked like I wouldn’t be able to tell you succinctly but I have some thoughts on where I might start.

Finally, my family has given me nearly a decade of their time and attention with my passions and obsessions; I have moved them too many times to count and they have given up more than their fair share over the past decade.

And they have done it willingly and have loved me every single step of the way. Especially my incredible spouse, partner, and friend. I cannot believe the sacrifice that she’s made for my crazy ideas.

Consequently, I’d like to spend more time in that area, focusing my time on investing in them. Again, I don’t know what that practically looks like but I’ve got some great ideas and I’ve already made some new commitments that will help steer my time and attention. I can’t wait to get started.

I love software. I love engineering. I love building great products for the web and my heart skips a beat every time someone confronts me out of the blue and they tell me that they use what I’ve build and that they love it. I will never tire of that.

But it’s time for a long break so that I can become someone even greater than who I am now. And that means I must be courageous enough to throw away the patterns of previous behavior and experience and be willing to risk something entirely new.

I am an entrepreneur, I will always be one; I just want to learn more about what that really means.

And oh… what a story it will be.

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