At the beginning of the month, I finally quit my job after planning to leave for the six months prior. Naturally, I’ve had many conversations with friends and family over these six months about what I’m going to do next. Even with all that time to practice, I’m pretty sure I've just confused everyone by ominously referring to “personal projects.” If you’re one of those people (or not!) here’s a much better explanation of what I’m doing next.

While I’ve truly enjoyed my job over the last seven years, it’s still always felt like, well, a job. I’ve been able to find passion for specific technical challenges over that time, but I’ve never had any particular passion for the business itself. This has led me to struggle with procrastination and motivation on a day-to-day basis, and I’ve rarely been able to hit the level of productivity that I know I can. (Not that productivity should be anyone’s only goal, but when the alternative is mindlessly scrolling the internet, it does seem like the better option.)

A few times during my career, I’ve been able to summon the motivation to play around with a side project, and have found that working on something I’m passionate about is energizing even during the boring tasks. These experiences have always made me wonder what would happen if you dedicated a long period of time to only working on passion projects. With few responsibilities and some good savings from an extended time working, now seems like the perfect time to find out!

What Am I Doing?

In order to maximize the value of this experience, I’ve spent some time thinking about exactly what I want to get out of it, and have come up with the following priorities:

Creating

When I think back to times in my career where I’ve had the most professional fulfillment, it’s always been during intense periods of creation. I love tinkering and getting my hands dirty (just not, like, literally), and creating something from nothing has always been what’s attracted me to programming. On the other side, I’ve never been as enamored with the minutiae of the business side, and time spent in meetings and planning has always felt to me like time that could be better spent coding. So, at least for the short term, I'm going to prioritize creation at the exclusion of almost anything else.

To be clear, I would never claim that the BusinessStuff™️ is less valuable than creating (I am married to an MBA). And I’m fully aware of the cliché that programmers who start businesses often try to code their way out of problems that could have been avoided with a bit more planning or research. So I guess I’m saying that’s a mistake that I’m okay with making right now if it brings me more enjoyment of the process.

Publishing my progress (successes and failures!)

In addition to this mission statement, you’re currently reading my first monthly review, hopefully of many. I think there’s a lot of value in transparency when creating something. Selfishly, it can drive attention to anything I create, which will help me get feedback as early in the process as possible. I’ve also long been a fan of reading similar accounts of people Building in Public, so it seems like a great opportunity to add something to that community.

For anyone else that loves reading these, a few of my favorites are:

Logging time for self accountability

Since the core hypothesis of this experiment is that I’ll be more productive when working on passion projects, I’d really like to avoid this becoming an extended vacation. With that in mind, I’ve decided to track my time spent working to keep myself accountable. I believe pretty firmly that my best work gets done when I allow for natural periods of motivation and relaxation, so the point is not to mandate eight hours of butt-in-seat every day. Instead, I’d like to keep myself aware of trends in my working habits, and make sure that my level of productivity is up to my standards. Additionally, time makes a helpful metric for telling you all what I’ve been working on (see below for more there!).

What Am I Not Doing?

In addition to the priorities listed above, I think there are some anti-goals to call out that I could unintentionally fall into if I’m not careful. These include:

Putting all of my energy into one idea

I currently have a few different ideas for projects/businesses that I’m passionate about and believe others would find value in too. Common sense might dictate that I pick the best one and focus on it with all my working hours until it either succeeds or dies, but I don’t think that’s what I’m going to do.

I’ve always valued variety in work and leisure, and find that some of my best ideas are influenced by something completely unrelated. As part of this experience, I’m going to try to harness that cross-pollination by forcing myself to diversify.

I’ve seen other solo developers encourage this behavior by taking on the 12 Startups in 12 Months Challenge, and I think that captures the ethos of what I’m going for. In practice, I don’t think I’ll be that rigid, but will instead set goals that encourage me to experiment and try new things.

Prioritizing making money

This is easily the anti-goal that could (will) most come back to bite me with respect to the long-term feasibility of this lifestyle, but I want to resist it as much as possible. I’m not going to be taking on any projects just because they seem like someone would pay for them. I’ve had ten years of work experience show me that economic rewards aren’t motivating enough for me on their own, and I plan to take that lesson to heart.

Instead, I plan to ask two questions before starting anything new:

Do I think it’s cool?
Do I believe that anyone else might think it’s cool?

If those are both a yes, I’ll dive in and figure out any economic feasibility questions later.

How I Spent My Time This Month

With all that out of the way, let’s get to the month in review! This was an awkward short month, with my last week of work at the beginning and Thanksgiving at the end, but I’m still going to write this up to start the habit. Here’s the raw data (encapsulating about 10 working days):

I’ll highlight two of these in more detail:

This site

Truly, my only goal for this month was to write this blog post and get danwaters.org to a state in which I won’t be embarrassed to send it out to people when they ask me what I’m up to (Thanks, Sab, for the design help!). I’m definitely going to continue tinkering with it, but I’m reasonably happy with where I’ve ended up. Hope everyone else likes orange as much as I do!

Trivianight.fun

(No link since there’s nothing there yet)

As many of the current readers of this website will already know, I spent a lot of time during 2020 and 2021 hosting a weekly trivia night for my friends and family. I’ve always loved trivia and found the routine of writing questions and hosting to be a good distraction from doomscrolling every day.

As of this post, I’ve written about 2,400 questions in the last eighteen months, in topics ranging from College Teams with Food as Mascots to the Etymology of Entomology to Obscure Units of Measurement. While I’m thrilled to have shared this effort with my faithful group of ~50 players, I’d love to spread trivia to the masses by letting others use my questions to run trivia nights with their own friends/coworkers/strangers.

My initial vision for the site is that it will provide tools (answer submission, question presentation, scoring) to run a trivia game for a group of teams, as well as access to all the categories I’ve written so far.

In the few hours I’ve spent on it already, I’ve added some of the basic functionality, but I’ve also identified one unexpected obstacle: I had assumed all of the hard work of writing the questions was done, but it turns out that aggregating thousands of questions across 60 different Google docs into a form acceptable for public use isn’t as simple as I thought. I’ve written a few automated tools to standardize the format and pull out all the relevant pieces of info, but I still expect lots of manual review will be required before it's in a state I feel comfortable publishing.

Sounds like a job for next month! Speaking of…

Goals For Next Month

I’m going to try to set some simple, high-level goals for myself each month as a way of staying on task and keeping track of my progress. Here’s what I’ve got planned for December:

Finish the MVP of trivianight.fun in time to host trivia next week

I’m currently hosting trivia during the first week of every month, which gives me a good opportunity to dogfood my product. For the first iteration, I’m punting on any sort of account functionality, and will hard-code a number of important pieces, but I want to be able to present questions and accept answers through the new site.

Get trivianight.fun to an external MVP level

After hosting myself with the internal MVP next week, I’d like to spend the rest of the month getting the site to a point where someone else can host a trivia night by the end of the month. This will still only entail a minimal set of features (and, as discussed above, will likely not support anywhere close to 2,400 questions), but is the next step towards getting things ready for public consumption.

Build something silly

With a nod to my anti-goals discussed above, I’m going to try to start on the right foot by forcing myself to spend a few days this month building something completely unrelated to trivianight. Sub-goals here include learning something new and coming up with other ideas to explore later.

Thanks for reading!