Tell HN: I have the perfect job, why is it not enough?

I used to be exactly the same, word for word.

Then I did my own thing, sold a business, work only on projects that interest me etc as you are aspiring to do.

Now I’m back in exactly the same situation, wanting more and being unsettled despite having a dream life on paper.

It never ends. Think it’s just the way some of us are wired!

I've had those feelings before and here is what helps me.

Everyday I make a point of being thankful for something or someone. Maybe someone put extra effort in at work, maybe my kids were really well behaved, maybe I really enjoyed dinner, maybe my wife told me a really funny story. Whatever it is, big or small, I try to show my gratitude to people around me and to myself. At first I started by writing them down in a log, then at the end of the week I would look through them. This turned out to be really important to me, seeing the concrete instead of the abstract really changed my outlook.

Remembering and referencing Maslow's Hierarchy of Needs just now ... this is the top of the pyramid - Self Actualization - achieving full potential including creative activities. Maybe this vision/desire becomes more prevalent in SW Engineers (in US at least) in their 30's or 40's because you've got the bottom tiers completed (I know its not like a video game skill tree) and possibly have Esteem met with being accomplished in comparison to many other careers. Tech is a sought after field, known to have high income and requires a certain mindset to be good at it. Being good, not even great, at Tech in the US gets you thru the bottom 4 pretty well.

If your job lacks any avenue towards creativity or path towards self-actualization professionally (like being "known" in tech, building a widely used thing, writing a tech book, etc.) then you seek out other avenues towards self-actualization.

My problem is having these ideas of things that I want to do, like an idea for a novel as an example, but not knowing how/where to start or just plain ignoring the sheer amount of work that is required and day-dreaming about it. That's not at the top of my list but that idea keeps percolating up at times. I like your approach about writing down a plan to fulfill those self-actualization types of things.

An example where I've realized its a lot more work is building a desk top out of walnut for a sit/stand desk. From roughly cut boards to a finished top looks easy on youtube videos. Squaring a board to join with other boards without pro tools is a lot of work. So much work, much more than I thought. Some of the work is part of the process of learning.

The most meaningful thing I've found in the world is to help others. But I think good intentions are not enough - it is important to care about how effectively you help others. So I recommend Effective Altruism - a community of people working on making the world a better place while focusing on effectiveness of their actions.

https://www.effectivealtruism.org/

For over 10 years I've been giving at least 10% of my income to cost-effective charities (see GiveWell for recommendations https://www.givewell.org ). There are thousands of people doing the same, you should join in:

https://www.givingwhatwecan.org/

Finally, on the topic of happiness, read up on Positive Psychology to learn how to extract more enjoyment / eudaemonia out of life. Start by reading books by Ph.D. researchers (e.g. The How of Happiness, Stumbling on Happiness, etc).

My situation is fairly similar.

I picked up a side project which has been a bit of a double-edged sword. Something that as yet has no value consistently tugs at my attention throughout the day.