Solution: I started volunteering at my kids’ small, independent school, and eventually was appointed as an advisor to the school board. I took on the marketing responsibility (volunteer), not because I’d ever created a single marketing plan before in my life, but because they needed someone to run point on it, and I needed the mental stimulation.

You’re learning Spanish, which is great, but you also seem to have mastered the basics. It may not be that challenging for you anymore.

I suggest finding a new challenge that really stretches you mentally – and don’t do it for pay. You’re a “real world” finance wizard. Much of what you’ve chosen to challenge yourself with involves highly logical cognitive function – learning a new language, maxing out the household garden, etc.

You may need to do something else with your mind that exercises the creative part. Something like, say, painting houses with habitat for humanity. As someone else suggested, travel someplace you’ve never considered as a “vacation” spot before and just go exploring.

Give your logical brain a rest for a while, and you’ll get your mental energy back.

I’m sure you will figure it all out and enjoy yourself along the way!

Now for the random advice from a total stranger: maybe pick up a real sport? I’ve done Crossfit and run too, but tennis is exponentially more interesting/challenging (to me) both mentally and physically. Plus, it’s social and always inspirational/aspiration; I dare you to watch 80 year olds on a Saturday morning playing doubles and not grin and think, “I hope that’s me!”.

For the self-employed I think it’s a little harder. I don’t know any self-employed person who works a steady schedule, and most I know don’t keep any kind of track of the time they put into scheduling, accounts, and paperwork. They only keep track of number of hours they are serving clients (in J.D.’s case, this would be the research & writing).

So once the expenses are covered, I’d guess it takes an extra level of attention and analysis to determine the full cost/benefit of extra work.

I appreciate that he’s learning and evolving, and that he’s willing to write about the process, because so many people seem to be ashamed of the process, or only want to talk about results.

While Margot’s comment in theory would seem to be valid, it can be very difficult to find someone as committed as J.D. in reality.

I do think that some of this is burnout. In the corporate world, you might have the opportunity to “take a break” with a bit of cross-training, or switch departments, or take a sabbatical, etc. You’ve been doing this job for 6 or so years, and hitting that same sort of note, even in something you love, for so long gets old. JD, have you thought about using some of that energy you feel for the projects you love and maybe include a money angle afterwards? I mean, you had the awesomepeople.com thing going, so maybe you could do something like you intended there, and then ask their money philosophy? Like your reader stories, you should get some pretty varied answers. It may revive you a bit.

You were able to tie the garden project in with a financial angle (for mixed results, admittedly), so why not some other project you are passionate about?

Anyway, enough with the long comment.

Ps. JD, if it is a mid-life crisis feel free to join me for the base jump whenever you’re back in the UK.

Also, I work at a job where I easily could have moved up to manager by now. The stress I see among managers coupled with the domination of your free time is not worth the modest bump in pay. I will stay in the sweet spot of good pay + my time is mine – until circumstances change, because they always do.

Currently looking for a new personal currency, ideally in the $20-$40 range. It really did help me keep things in perspective and I often think about how I now make purchase decisions without properly weighing them out.

That said, likely some did fall into such positions due to political/family/who-knows-what connections. I don’t think it is ever black and white, but I would not generalize that all of the people in those positions are simply there out of privilege.

Yes. It is work. A lot of work. That is, if you want to do it well.

Again, I have no idea, but it ‘seems’ to me that dropping down to one article a week on this website and adding two articles a week for the mentioned job is still less than when you were running the website full time on your own.

I’m not saying that you do it because you need the money (you can always add to the travel fund) but if you are doing something you love, is it really work?

Regardless, I think the information is valid for a wider audience than you think. We’re definitely not in the same league as JD, but still use many of the same ideas he does. We’ve set our lives up so that only one of us has to work part-time to support a family of four; we too get to be picky about what we do and where we go to do it. Last year my wife worked full-time for 6 months in Fairbanks Alaska (and had the other 6 months off to spend at home with the kids, visiting family, etc.). This year we’re in Australia and she’s working part-time all year. We could be making a lot more money elsewhere, but we’ve decided this is the best thing for us to be doing right now. Ties in with the theme of this blog post.