I’ve been thinking of what I want to learn more about when it comes to investing.

I’ve read stacks and stacks of personal finance books. I enjoy reading them, even though many books repeat the same uncontroversial advice. My ledger of income, expenses, and investments goes back to 2005, when I moved to Canada and started managing my own finances. We might never be absurdly wealthy, but if we continue to be frugal and hard-working, I think we’ll enjoy more flexibility and less stress than most people have.

2011 was a good year, despite the fluctuations in the stock market. Although it was occasionally discouraging to see my carefully-saved index funds dip below their book price, I kept plugging away. I figure that if businesses have managed to do fine despite past events like the Great Depression, things will be okay. If the rules of the game have changed and the stock markets no longer perform the way they used to, well, we’ll have bigger problems than the lack of a decent return on investment.

Investment-wise, we’re on a good path. I don’t have the time or interest to pick individual stocks, and I’m comfortable with a boring balanced portfolio made up of index funds and skewed towards equities. From here on, it’s more about time and persistence than sophistication.

What I’m curious about is this: what’s worth investing time and money in? What does investing in awesomeness look like?

I’m not the kind of person who chases bucket-list experiences in order to check off things I’d like to have done. I’ve tried it and it didn’t sit well with me. I like simple things and everyday activities. Fortunately, W- does too.

I thought about resuming my experiments with outsourcing. I don’t mind my chores that much, though. I’d rather save the time (money is time, after all) so that I can give myself a focused year instead of spending it on an hour here, an hour there that can be so easily absorbed into distractions of everyday life. I might pick up the experiment again someday, when I run into something that I don’t want to limit by my skills. We’ll see.

So here’s what I’m saving up for and investing in instead:

• Experimenting and learning
  • Tools for working better
  • Trying a new community-supported agriculture program, because we can
• Streamlining life
  • Multiple sets of socks that are all the same, to reduce the need for matching
  • Decluttering and the freedom to ignore sunk costs
  • Simplification and fewer frustrating things
• A year-long sabbatical in 2014, during which I plan to focus on writing and development

It’s about striking a balance between long-term goals and shorter-term ones. I don’t want to postpone enjoyment until I’m 65 or 70. I want to test ideas earlier than later, so that I can tweak and adjust.

I’m a little envious of other people who are exploring the worlds of freelancing, entrepreneurship, or lifestyle design. Envy being mostly useless, I shift that energy into analyzing my decisions and testing some of my assumptions. It looks like IBM will still provide the best stability as I build up other experiments. I’ll continue with that for now, and I’ll trust that this preparation will give me more opportunities for interestingness over the next few years. In the meantime, I guard my evenings, weekends, and holidays more closely from the temptations of work. These are excellent times to test ideas for the next step, and they shouldn’t be wasted.

What do I want to learn about investing? I want to learn how to better test my assumptions about life. I want to learn about small and simple experiments that have good ROI for knowledge. I want to learn how to make better choices. I want to get even better at ignoring what the world tells me I should want in favour of figuring out what I truly need.

Today I read a book called I Moved Your Cheese. It reminded me of Jonathan Livingston Seagull, another book I enjoyed. In I Moved Your Cheese, the author pointed out that even if you’ve absorbed the lessons from Who Moved My Cheese? on not letting change frustrate you, you’re still chasing after cheese. I don’t want to chase after money, or time, or even happiness. (The odd thing about happiness is that once you pursue it, you can’t have it.) I want to create space for interestingness and discovery.

So we’re investing in wanting less and needing less, in enjoying life more, and in experimenting with making life better. I’d love to hear about your experiences along these lines!