I think that your point about the education system is very accurate. People spend 12 to 16 of their formative years with clear direction and immediate feedback. I remember noticing a lack of immediate feedback at my first job out of college. But a 9-5 job much more closely emulates the education environment than working for yourself.

I think that you are right that it takes conscious effort to find better ways to measure progress and success for self-directed projects. The “standard” measure for success of a business or project is how much money it makes. While making extra money would be nice, it is never the primary reason that I start a project; so it is not really how I measure success. I have yet to find a method that works well for me. I should probably try Bill’s tracking spreadsheet as a way to measure and reward time committed toward goals.

For me, I think a lot of that mental model comes from the education system, where the learning process is generally very structured and the rewards are clearly defined. I was always really “good” at school, and I think that success has to do with always having a clear direction to move towards (at least in undergrad and below), understanding the definition of success (A, B, C, etc.), and always having someone who celebrates your successes and guides you along the way (the teacher). Work hard, do your homework, ace your tests => Academic Success!

However, achieving “success” with your own time in the real world is always trickier, especially when you have the opportunity (or curse) of defining your own version of successful outcomes vs time invested.

For me, I’ve been thinking that one of the keys to overcoming this for your own projects is to measure progress and success in aggregate (over weeks and months), rather than at the end of each day. It’s so easy to spend a whole day falling down a rabbit hole of debugging, or to spend hours and hours on a feature only to later abandon it. This process is always at least a little bit demoralizing (on your own or working for someone else), but at least when you work for someone else you get paid for it (success! as you so eloquently put it).

I also think it’s important to learn to celebrate yourself and your own achievements however grand or meager. Having the camraderie of coworkers, a boss, or others to approve of your work, give you a pat on the back, or otherwise give you positive feedback and direction is nice, but it’s definitely not always achieveable when working for yourself.

Alternately, measuring success in working on your own projects in terms of time committed rather than progress can also be helpful – similar to your Don’t Break the Chain / committment to practicing violin. Any one day might not yield much progress, but committment to the practice yields great progress over the long haul.

At any rates, just some traits I’d like to better internalize and break my habits of needing external structure to be successful.