It seems like the lesson is to play to your own strengths rather than try to improve your weaknesses.

Agrees with Drucker's work.

So does it ever make sense to work on your weaknesses?

Good question. I'd say when they're critical. A lot of the self-experiments I do are all on improving weaknesses not strengths and I can tell you this: it's goddamn hard. The ROI on time invested vs deliberate practice on something you are good at and are interested in just sucks. But I'd say that improving weaknesses is vital if it's in critical areas for an overarching goal (area of a job you're not good at but can't move forward without) or fundamental areas (being happy, basic people skills, etc.)

I'm noticing that two of your overall themes are:

1. Practicing to become an expert in something you're passionate about, and

2. Correcting a bad habit with the least amount of effort.

Number one is improving strengths, and number two is reprogramming weaknesses.

The main barriers to improving strengths are lack of focus, lack of knowing oneself, and lack of follow through.

The main barriers to reprogramming weaknesses are that an ossified human brain resists change.

In practice, the happiness ROI on #1 far exceeds the happiness ROI of #2, but that does not eliminate the importance of #2.

Wow. That's an excellent summary. Can I hit the props button twice? :P

I think the main barrier, more than anything else, is the line between knowing and doing. Many people have read my posts and replied, "Oh, I know that." Yeah, but do you do it? If not, all you're doing is preparing for the psychology/self-improvement category on Jeopardy.

Next would be follow up. We're all naturally terrible at it and that's why manipulating context and building good habits is vital.

It is amazing how many people KNOW what to do, but don't / cannot do it.

There's gotta be something significant in our wetware that short circuits the connection between understanding and taking action.

As far as being bad at follow up, that may be a different phenomenon attributable to poor organization skills and lack of focus.

(And though you cannot props twice I appreciate the sentiment!)

One of the issues with acquiring new habits/behaviors is basic scaling. If we could easily make ourselves consistently do new things we'd probably fill up our days very quickly and not necessarily with things that matter most. Our brains would be like a terrible government bureaucracy with rules, regulations and processes for everything.

Also, our minds inherently do not work like that. Motivation is much more emotional than cognitive which is why "wanting" to change behavior isn't enough. Some of the most effective methods for changing behavior work based on taking advantage of this emotional switch, changing defaults or taking advantage of our general passivity.

I am intensely jealous of people who get to spend most of their days in flow. Something to work on...

I think to do it you have to be working on your passion full time, obsessively so.

I had never thought of work as a flow activity before... I certainly have never experienced flow while working for someone else ! at a corporate etc... but, now that I think about it, I do have a strong sense of flow when working on Scrattch ... hmmmm... barking up the right tree ? Something to definitely think about :)

When your avocation is your vocation, you have tremendous flow in work!