On Quitting

Reflecting on two years of unemployment and self-development.

An Anniversary

Two years ago I quit my job.

October 2nd was my last day. Nowadays, October 2nd is one of the most important dates imprinted in my brain. I guess October 3rd (my first unemployed day) makes more sense... whatever, today is my unemployment anniversary.

The Beginning

The first couple months were hard. Not because I second-guessed my decision (I didn't) or because I was anxious about the future (I wasn't really), but because I missed people. When you go from being around people every day to being by yourself it can be a bit of a shock. There is so much interaction with other people when you have a job. Coffee chats, phone calls, meetings, after-work beers, lunch! Boy, did I miss those lunches. But when you make a decision to quit your job and work at home all day everyday, well, you have to understand that there are fewer people there.

It's a good thing I'm an introvert! Seriously though, finding peace in solitude comes naturally to some people, and before long I found comfort, even happiness, in working alone at my home office desk all day. This certainly isn't for everyone, but it's probably pretty easy to tell if it's for you. How does the idea of working at a desk in your house everyday sound to you? Assume your "work" doesn't require talking to other people. At all. Does this sound like bliss, or a nightmare? There's your answer.

What Are You Doing?

I sometimes get tripped up by the simplest question, "What are you doing these days?" Early on I did a little consulting, so sometimes I would just say that. But I also had some real ambitions to "start a startup", and occasionally I would have the guts to say it even though it can sound overly ambitious or even downright silly (more on this later). Other times I would take the more modest approach and say, "I'm on a learning sabbatical, which is kind of like going to grad school, but, you know, entirely self-directed and without all the pesky tuition". This is probably the most accurate response, especially you when you consider that I would never have made this much progress if I had a day job to distract me.

But perhaps the best response is this:  I'm building stuff.

This was the real reason I decided to quit my job. I just wanted to build stuff. In my previous career I never got to build anything. Well, I mean we built teams, and reports, and models, and processes, and culture, and... well, whatever. But we never built anything tangible. I wanted to build stuff. That stuff happens to be software. So that's what I'm doing now.

How Are You Doing This?

This is something I often gloss over, but it's important. I worked for 10 years and saved as much money as possible. Thanks to my awesome parents I had no student loans when I started out, which certainly helped, though I don't think this was crucial. What's more important is that my parents taught me how to save and not be wasteful. With persistence and smart financial decisions, I truly think a sabbatical like mine is attainable by anyone.

And another thing, do you really want to wait until you are 65 to enjoy some free time? I decided that taking a few years off in my 30s would be a much better option.

Self Identity

I'd be lying if I said I haven't struggled with some self identity issues these past two years. It's interesting when your identity is no longer tied to a company and a job title; you have a bit more free rein.

For example, I've called myself a freelance software developer, even though I have not yet developed software for anyone, on a freelance basis or otherwise. I've also referred to myself as a consultant. This is closer to the truth, as I actually did some paid consulting work, but it was only for one month out of 24.

My Nevada business license says that I am the Managing Director of a consulting company. Yet I haven't taken a consulting gig this year, in order to focus on software projects.

My business cards say that I'm the CEO of a software company. That company doesn't yet have a product nor any revenue. While I certainly hope that the projects I'm working on now lead to something, now it's hard to say if they constitute a business or justify the CEO title.

One thing I know for sure:  I'm now a software developer. That's an important first step, and I'm happy with it.


To be honest, I thought I would be farther along at the two-year mark than I am. It's really the classic problem when you are learning something new:  you don't know what you don't know. You take it one step at a time, and as your understanding of a subject grows, the world gets bigger and you have a clearer picture of the path forward.

I do think I have come a long way. While I'm certainly no expert, I now have a very serviceable understanding of several programming languages, most notably JavaScript and Python. I am now very comfortable with web technology. I love tweaking designs with CSS, and I feel I have an above-average knowledge of HTML, including many important new HTML5 technologies and APIs. The web has become my primary focus because I believe it is the most unstoppable force in modern-day programming. I love that I can now build a decent website in a day or two when it used to take weeks. I'm also thrilled that I can now tie together my love of data with my newly found passion for web design by building data-driven web applications.

Perhaps I'm naive, but I feel that if I continue to focus on building software, eventually money will happen. I feel like I'm on the cusp. The next project could be the one.

Lessons Learned

I'm going to spin this off into a separate post:  Lessons I Think I've Learned.

Next Steps

I need to find a partner. This has been very top-of-mind, but honestly after an initial push to seek out like-minded people to build software with, things kind of fizzled out. It's very similar to dating—I sought out people through various channels, reviewed dozens if not hundreds of profiles, and met with 4 or 5 individuals to try to see if there was a fit. It's very draining, but I need to kickstart this effort again, because working alone kind of sucks. Well, as I said before I am comfortable working alone, but it's not a long-term solution. Having a team is crucial.

I have come to one important conclusion on something I mentioned earlier, "starting a startup". I want to start a company. I don't want to start a "startup".

It's weird to think that these are notably different things, but in recent years being a "startup company" implies certain things. I think "startups" typically share the following traits:

  1. Their existence is tied to raising money, typically from venture capitalists
  2. They often join "accelerators" to get attention from these VCs
  3. They target extremely high growth rates (the VCs demand it)
  4. They have a goal to reach a $1B valuation (they call this being a unicorn for some stupid reason)

To me, this sounds like a recipe for disaster. What is the old saying, four out of every five new companies fails? Well, if you're a "startup" aiming for $1B then you are setting yourself up for a >99.99% chance of failure. Yikes.

I don't want to be a "startup". I don't want to raise money. Boy, I can't emphasize enough how much I don't want to raise money. At least not at the "startup" phase. Taking other people's money when you only have a vague product or idea just seems wrong.

No, I think I'd rather start a company the old fashioned way. I think they call this "bootstrapping". Those in the Silicon Valley startup world call companies with goals that are more modest than $1B "lifestyle" companies. Whatever. I'm just going to call it starting a company and be done with it.

To Summarize

No income, but no regrets. Here's to another year of building things.

Like what you read? I'm seeking cofounders in Las Vegas! If you're interested you can reach me anytime on Twitter @cschidle to discuss.