At the end of October I quit my job as a director of software engineering. Many (most?) people view this as insane given the amount of money I was making. I'm not going to give a precise figure here, but if you're really curious you can check out software director salaries on I was making enough that in another 5-10 years I could very comfortably retire with a reasonably high standard of living.

Working on my own terms

So why did I leave this behind? The concept is simple – I want to see how it feels to work on my own terms. I know how that sounds. If you've hung out for any period of time in tech-oriented communities like Hacker News it's likely that you've seen at least a few posts about people losing motivation at their high-paying tech jobs and wanting to strike out on their own. I always felt a little cognitive dissonance over those posts. On the one hand I completely identified with the desire to firmly seize control of my time and spend it on things that I wanted to do, but I also had this voice in the back of my head that said, "What a ridiculous first-world problem. Sure, other people set their priorities, but they have a pretty high degree of freedom compared to other roles and industries, so they should be thankful for what they've got. Why risk it?"

Everyone's situation is unique, but I think in my case the downside is limited. At the risk of sounding overconfident, I am very good at my job, and if things go south I believe I can join a large software organization again. The upside is that I can work on lots of different projects, spend more time with my family, and build things that I want to build.


A huge reason for leaving was that my second child was recently born, and my company had no official paternity leave (if a company is small enough they're not bound by FMLA). With the pandemic raging and my toddler cooped up in the house, I wanted to spend more time with my toddler so my wife could focus on our new son.

This has been going fantastically so far. We're spending time outside, getting exercise, playing games, and making progress on simple academics. If my wife had to take care of a two year old and a newborn by herself with no support during the workday it would have been a nightmare.

It can be occasionally tedious (two year olds aren't the most sophisticated conversationalists), and we are all looking forward to the day where my daughter can engage more fully with other kids, go back to the rec center and library, travel with us, etc, but for now our schedule works. I'm very much enjoying our time together.

Financial stability

I don't have the funds to retire – this post would read very differently if I did. I have enough savings to feel secure, but it will be necessary for me to take on contract projects to support my family.

I may write another post on the financial details of working freelance down the road, but if you're interested in the types of expenses I took into account when quitting Daniel Vassallo has a fantastic post on it:

I'm currently paying for COBRA health insurance through my old employer, and in general it was important to me that all my insurance coverages continue uninterrupted. I think that the most important points that Daniel emphasizes are ways to avoid financial ruin when you no longer have many of the safety nets that come with large tech employers.

What's next?

I've already started contracting! I have a fairly broad network of friends that I've developed over the last decade in tech, and for now I'm happy sharing my expertise with them and helping to build new products.

This blog

I've always enjoyed writing about things I'm interested in and helping others level up their skills. This blog,, will be focused on news about the major cloud providers (AWS, Azure, and GCP), along with comparisons between the platforms and tips and tricks I've learned while building enterprise software in the cloud. I'm hoping you'll find it easy to read and educational. My secondary objective is to build a conduit to meet potential clients who need help with their cloud projects.

Please feel free to reach out if you have cloud questions! I'll be looking for interesting cloud topics to post about every week. I plan on making conversational-style posts that will help you keep up to date in a less painful way than just reading Amazon/Microsoft/Google press releases.

My next post will be a recap of the major cloud feature releases of 2020 – if that sounds interesting, sign up for my mailing list below!

Until next time,