I often imagine different futures, sketching them out on paper or in those moments right before or after dreaming. It’s a good way of testing an idea to see whether I’d like it, and then working backwards from there to figure out how to get there from here. I also explore mediocrity and failure so that I can get a sense of what I want to avoid and what I could do to lower the risks.

For example, how might this 5-year experiment of mine turn out?

• Awesome: My blog has plenty of detailed, open notes about trying different things. I’ve found an idea or two (or a business, even!) that fits me well, and I have the financial foundation to continue with even more experiments.
• So-so: I have a fairly conventional consulting / freelancing story. It’s okay, but I missed out on pushing myself to do a lot more because of my safety net.
• Darn: I’ve misjudged skill growth and finances. I reach the 5-year mark with little to show for it, and need to work a lot with my social network to get back into the job market.
• I can influence this by being more deliberate about my experiments.

How about my relationship with W-?

• Awesome: We consciously cultivate the relationship, sailing into our later years with plenty of stories and shared experiences.
• So-so: We settle down into normality.
• Darn: We forget to pay attention and end up drifting apart.
• I can influence this by investing time.

Family?

• Awesome: I’m close to both my family and W’s – I know people’s stories and interests, and I help out with whatever I can. I visit every other year or so, or more frequently if finances allow. I keep in touch through Skype and letters.
• So-so: We keep in touch occasionally, but tend to be peripheral to each other’s lives.
• Darn: The distance leads to miscommunication and fights.
• I can influence this by investing time and setting aside money.

Friends?

• Awesome: I’ve gotten to know a bunch of people whose company I really enjoy. I think they’re great people. I learn a lot by hanging out with them, which I do one way or another every week. I have conspirators for ideas and projects, and work with other people to make their ideas happen.
• So-so: I practise the skill of making friends with people as people drift in and out of life.
• Darn: I forget to pay attention to this and let my introvert hibernation urge take over.
• I can influence this by investing time and setting aside money.

Finances?

• Awesome: W- and I live frugally, with roughly the same level of expenses that we’re at now. We have a great safety net, though, so we don’t have to worry. I resist the potential wonkiness of irregular income (both fear and overconfidence) by stabilizing it with savings. I’ve learned how to build businesses, so I can jump on opportunities when I see them.
• So-so: I dip into my savings occasionally, replenishing it with income.
• Darn: Tax or legal issues, prolonged sickness, disability, or death chew into our savings.
• I can influence this by being deliberate about spending and earning.

Learning?

• Awesome: My learning is aligned with my goals in terms of topic and depth. I learn a little bit about random things and go deeper on a few topics, but I push myself to try things instead of being lulled by “knowing” things from books. I seek out specific learning opportunities. I’ve learned how I learn best, although I keep working on learning other ways too. I map out what I’m learning so that I can review it easily and so that I can spot gaps.
• So-so: I drift a little, but in a general direction. I back up learning by trying things out.
• Darn: I confuse reading about something or listening to something with knowing something, and spend way more time doing more of the former two. I drift a lot.
• I can influence this by examining how and what I learn.

Playing?

• Awesome: I play with things that teach me more about life, give me a new way of looking at things, help me relate better to other people, or improve the way I live.
• So-so: I play the occasionally distracting thing, and then get back to regular life.
• Darn: I get sucked in by game mechanics. W- gets annoyed with me.
• I can influence this by reflecting on what and how I play.

Good to get a sense of what good looks like.