Sometimes, when you take risks or make decisions, it helps to think about how your choices affect your story. We all tell stories. Stories are how we make sense of things. The same set of facts can support many different kinds of stories. The story you choose to tell–the perspective you pick–affects how other people see you or make sense of your life.

When I was planning this experiment with semi-retirement, thinking about the stories that I could tell helped me make that jump. How would I explain that gap in my career if I decided to work someplace where that could matter? After all, most employers want commitment, not gaps.

It helps that I’ve been able to plan ahead. Having enough savings to cover five years of expenses lets me tell a different story compared to someone who quit a job without having anything else lined up. Leaving my job on a happy note is different from leaving because I was burned out. Structuring this break as a time-limited experiment helps me make sense of it. I incorporated right away, and eventually came up with a company name that was general enough to cover a lot of different things I was interested in exploring. If I tell the story in the right way, then the five years that I’ll spend outside the easily understandable structures of work will give me a different but possibly useful perspective. If I don’t have a story to tell, it will just look like drifting.

The human brain is really good at rationalization, so you can come up with multiple stories to fit your facts. You don't even need to make things up. You can choose the parts you want to emphasize, the reasons you want to explain. Also quite handily, there are lots of stories you can pattern yours on. For example, I might be framing this as an experiment now, but I can also talk about it in terms of freelancing. People shift to freelancing, and some shift back. If we have kids, then my story could be as simple as those of many other parents who’ve taken breaks from traditional careers. The on ramp might be tricky, but it’s there. And even if I started my break a few years before having kids, people probably won’t dig into that.

Imagining one possible Sacha of five years after the experiment (with subtext or notes in parentheses), pitching a business:

Yeah! I was doing well at IBM (evidence: performance ratings, recommendation letters, testimonials), but I knew that I wanted to learn more about business, technology, and other topics. Besides, I'd saved up a lot, so I could take more risks. I gave my manager plenty of notice and transitioned all my projects neatly. (See, I'm responsible.) I experimented with different kinds of business models and found that I really enjoy helping people understand complex ideas through simple visuals, tutorials, videos, and consulting. I learned about what I can do on my own, and now I want to scale up by working with a good team. (So that's why you don't have to worry about me being all flighty.) With the skills I polished (NodeJS, more Ruby, even Emacs geekery) and the network I developed, I think I can help you make even awesomer things happen.

Another Sacha, talking about choosing alternative paths:

I had a great time in the corporate world, so I wanted to see what the other types of work were like. I have a lot of role models who have small businesses, and I was excited about learning how to build one myself. I experimented with different business models and was lucky to find immediate profitability with consulting, sketchnoting, and publishing. I re-invested those profits, and the investments grew enough to cover my needs. Since I have the time and space to explore things just because, I've decided to focus on the things I like to do: helping people learn more about Emacs or visual thinking. It's pretty cool what you can do when you challenge your assumptions.

And yet another Sacha, blending in with the crowd (assuming we have kids):

I took some time off to raise a family. Since I knew I wanted to get back into technology afterwards, I kept my skills up to date by working on open source projects and building sites. You can see my portfolio at ____. Why don't we set up a trial project so that we can find out if this is a good fit?

I think a lot about what’s going to be part of my story. I want to be able to put enough into that box, and I want it to make sense. Time moves so quickly. I’m already almost halfway through these five years. What I want to be able to say at the end of it? How am I different now compared to when I started, and how much more different do I want to become?

I’m more comfortable with business and paperwork than I used to be. I was pleasantly delighted to discover that I could create things that other people valued, and that people would buy things even if they could get them for free. I learned how to put together e-books and printed books. I got more comfortable at helping people online, and I learned that was something else that people valued. I learned how to interview people and turn that into additional resources. I got deeper into drawing, and I used that to explain ideas and explore my own reasoning.

I haven’t learned as much as I thought I would about some of the technologies I was curious about. I’m still not a super-leet developer of Emacs, Rails, Node, or Android. I spend more time on the beginner side of things, building resources and filling in gaps. That’s useful too, so I’m not too worried.

What do I want to add to this story? More coherent Emacs evangelism: guides, e-books, then maybe books – more help, more chunks that are part of a story (and that tickle my brain and that result in good karma; it’s icing on the cake that it’s part of a “worked on open source” story). Maybe Org or other Emacs contributions. More modern web development. Writing. Plenty of writing. Someday, more style and humour.

So far, my investment income covers what I need. It is always possible, however, that I’ll need to focus on more active work. Something might happen to W-, or our situation might otherwise change. I’m not entirely sure yet that I have a good plan for that, although I’ve set aside some buffer so that we can ease into it slowly. In those kinds of scenarios, I’d probably post here while I figure out my options, which will likely involve programming of some sort or another. (Then people can be part of the story too!)

Sometimes I think about alternate universe Sachas who travel in parallel along more conventional paths. It's less about “what if” or “if only” and more about “Hmm…” I can relax a little, knowing that alternate universe Sachas are exploring those trails. I check in with myself from time to time: is the story worth the divergence? Can I scent other interesting story possibilities nearby?

While I give up a little of the power of the story by actually talking about my thought processes, I’m betting that it’ll help more than hinder. At the very least, this will probably help other people think about their stories.  =)

What are the different stories you can tell about the facts of your life, and how are you working towards the stories you would like to be able to tell? Here are some tips I've picked up:

• Look for similar stories that you can pattern yours on–and that you can use to decide where you'll diverge
• Brainstorm different aspects you can emphasize about your story
• Try out the stories you want to be able to tell