One month without a job

I'm planning to write up monthly updates on my progress on my path. Here's my first update, one month in. I don't really have a format for this, I just kind of sat down and started writing. If there's something you thought was interesting and you'd like to hear more of, let me know! Same if there's something that you thought was not so interesting. Just hit reply and I'll see it.

So I quit my job a month ago. I was inspired to do it after reading The Pathless Path by Paul Millerd. There are so many thought experiments I took away from reading that book and they became household (and work!) conversations for many weeks after.

Starting my own pathless path

But once I realized it was time for me to leave my job, and that I wasn't interested in finding a different job, that left me with "well now what"?

Paul brings up this in the book:

How do you begin to figure out what you want to do when there are not many limits?

If I quit my job and don't have another job, what will I do with my time? And how do I make sure I don't just end up in another situation where I'm equally as unhappy as before.

Paul offers this advice:

Instead of asking what makes up an amazing life, we first define the worst‑case scenario and then work backward. What does a miserable life entail? What actions would make achieving such a life more likely? Then figure out how you can avoid these things from becoming true.

So with that in mind, here's the rough outline I sketched for myself (along with my wife) to start on my own pathless path.

For me, a miserable life entails:

  • spending the majority of any given day working
  • spending the majority of any given week working on something that is not interesting to me or is energy-draining rather than energy giving
  • not learning new things
  • having to say "no" to my kids wanting to show me something or talk to me because I am in a meeting or am too busy at work
  • only seeing my kids during transition times (ie, getting ready for school, coming home from school, getting ready for bed)
  • not having time or energy to do "non-work" activities that I enjoy
    • DIY projects around the house or yard
    • gardening
    • baking / cooking
    • camping

Ok I could probably go on and on with this list. But that's probably enough for now :).

So what I started thinking about was how could I avoid getting to those points - especially given that there would essentially be no limits to how I could choose to work going forward.

I decided that I would need to impose my own limits. I chose 20 hours a week as how much I wanted to work. Completely arbitrary? Yes. But I think a good starting point. Here's why:

I've worked on projects on the side of my job in the past, and I've felt I could be very productive in 4 hours a week, but that honestly just wasn't enough time to make meaningful progress. I also realized that a lot of the work week at a given job is less about getting stuff done and more about convincing other people that something is worth doing or otherwise managing interpersonal conflict. Since I'm working on my own, I won't have to do a lot of that, and will try to avoid as many meetings as possible. So if I work 5x the amount of time I have put in on side projects before, that should be a real meaningful investment for me to move the needle. And if I think about any given work week at recent jobs, strip out 20 hours a week of meetings and I'd still be able to get a lot of work done. That's my hypothesis anyway.

20 hours a week is roughly about the amount of time that my 2 older kids are in school each week. So basically I can work while they are at school, and be available to the entire family when everyone is home.

That's a long winded way of saying this: Time is the primary limit I am putting on myself.

A secondary limit is how I make money (or rather right now, don't make money). I'm pretty sure I could cover the family expenses by freelancing or consulting, and I've done a bit of that in the past. But I want to avoid trading my time for money in this new stage as well, so my focus is on software businesses, info products and/or e-commerce products where how much I make is not limited by how many hours I work in a given week.

How it's going

So a month in, how is it going?

The Good Stuff

  • Along with my 3 year old daughter, I started a sourdough culture in our kitchen and have baked 3 delicious loaves of bread
  • We resurrected our abandoned compost pile, so we can start feeding our own garden with our food waste
  • I cooked some delicious tonkatsu with my 3 year old.
  • We cleaned out and resurrected our abandoned garden, and planted some lettuce, carrots, kale, and peas. (It's struggling a bit because we don't have much compost, only the lettuce and some surprise potato plants are coming in.)
  • I got my first paying customer on! This is the first time someone has every paid me to use software I built, a huge win (even if they are only paying me $5).
  • I built and launched You can use it to generate custom coloring pages. If you're reading this, here's a coupon code for 50% off image credits: OTLWPFEW.

The Hard Stuff


I read the [[Resources/Readwise/Books/Burnout|Burnout]] book, and hey, it turns out I was burned out. And it affected my family. It's taken a few weeks to rebuild our relationships, but having time to move slow as a family has helped everyone so much.


Finding a new anchor for everyone's schedule has been a challenge. Since my job was the least flexible part of our life over the past year and is now gone, suddenly the whole family schedule is up in the air. It's been fun to reimagine things, but taken a lot of effort to figure out how we want to spend our time, how and when to prioritize each adult getting some time for themself. We started weekly grown up family meetings to work out our schedule for the week in advance to make sure that everyone's needs are taken into account. We can be more flexible which is great, it just takes a lot more coordination, and if we don't put in the coordination work, we get frustrated with each other.


We are on a more strict budget now, and we didn't eat out at all this month. Mostly everyone has been ok with it, but now that we are 30 days in we are all itching for it a bit.

Other stuff you might be interested in

  • I wrote an update on the last few months of progress (or lack thereof) on [[Month 10 Summary - Front End Remote Jobs]].
  • A more detailed write up on my plans for ColorBliss at [[Launching]]

That's all for this month I think. Thanks for reading my rambling. I'd love to hear from you! If there's anything you're interested in hearing more about, please just hit reply and let me know.

Your friend,