Learning from a diversity of ways to live a significant life

I have plenty of role models in terms of people who’ve done wonderful things as part of regular careers and entrepreneurs who’ve created products or services. I even have a few role models who’ve explored alternative paths: simple living, writing, arts, crafts, trades… I love having such a diversity of life paths illuminated for me, with so many examples of people doing well.

I’ve been thinking about the path that I might take. The path of growing outwards – self, household, close relationships, and beyond – seems unusual, or at least harder to find information on. It feels a little feminine, I think, skewed towards domesticity. I think that’s part of the appeal for me. I want to take the skills I’ve learned in the mostly-male world of the technologies I’ve learned, and apply those skills in areas that might not be gender-balanced for a long time. This way I can maximize learning and difference-making.

2015-04-10b Reflecting on paths for living a meaningful life -- index card #experiment #evil-plans

2015-04-10b Reflecting on paths for living a meaningful life – index card #experiment #evil-plans

The impression I sometimes get from stories of startup founders is that they jump so quickly to imagining and building a service or product instead of developing deep understanding of needs, people, systems, opportunities… I know that doing things is a great way to learn things – fail fast and fail often – but I’m also curious about developing my understanding by other ways. I imagine that if I do this well, I’ll gradually develop the relationships and insights that would help me make a good difference. In the meantime, I can focus on improving myself, helping and connecting with people, and taking and sharing my notes.

2015-04-20e At peace with a small life -- index card #experiment

2015-04-20e At peace with a small life – index card #experiment

It’s getting easier and easier to not be tempted to shortcut this process. At a recent party, I was talking to a serial entrepreneur who was looking for a successor he could mentor. He seemed to derive a great deal of pride from having created a wonderful product, and it was well-deserved.

He asked me if I had created any products that could be identified with me, and if I wanted to. Reflecting on the conversation, I realized that no, I don’t particularly need to work toward that kind of significance right now. I’m happy to continue my experiment to at least the 5-year mark that I had initially set for myself, and possibly longer.

2015-04-19c 5-year plan vs 5-year experiment -- index card #experiment

2015-04-19c 5-year plan vs 5-year experiment – index card #experiment

The 5-year experiment thing boggled him too. I think he was thinking of it more as a 5-year plan: have a certain goal, get there with actions and the occasional workaround. I think of this 5-year experiment as creating a safe space for me to explore and learn, and the timeframe is there to prevent me from running back into my comfort zone too early.

I guess I could describe my aims this way: I work towards cultivating happiness/equanimity and producing understanding as my first two priorities. At this point, I’m not working towards wide impact, fame, influence, or money. I might get to that someday, but I’d like those first two things well-covered first.

2015-04-20f Experiment timeline -- index card #experiment

2015-04-20f Experiment timeline – index card #experiment

When might I move on from this phase? It’s not that I don’t think I’m ready, that I’m waiting for the stars to line up, or that I feel constrained to do this right now. I’m stacking the deck, and I’m collecting people and ideas.

2015-04-20h Conditions for considering a startup -- index card #experiment #startup

2015-04-20h Conditions for considering a startup – index card #experiment #startup

What will likely happen is that, after I figure out a little more about life, I’ll have these relationships with people I strongly want to help as a business partner or as a provider (preferably both). For example, if W- wants to start a business, or if I resonate strongly with a friend’s idea, I might dig into it more deeply. But I’d still want to see if we could build a company without making the personal health or relationship sacrifices that you often hear about in entrepreneurship circles. I’d want people to still get good sleep and spend time with other people who are important to them.

So that’s how my Evil Plans might unfold…