I like planning ahead. Thinking through best-case scenarios and wild successes helps me clarify the decisions I need to make now. Planning for worst-case scenarios gives me confidence that things will work out. I have only one life to live, but with imagination and planning, I can test my ideas before committing to them.

For example, while working on the paperwork for marrying W-, I considered death, disability, divorce, relocation, family needs, and distance, at varying ages and in varying situations (kids? no kids?). I think we can make things work out – and that frees me up to focus on the best-case scenarios.

I’m considering the next steps in my career. My managers and mentors have been very supportive, and they’re helping me figure out what’s next. I’m thinking about the next three years, sure, but I’m also thinking about the next sixty. Who do I want to be? How do I want to change the world?

I think I want to have run my own business for at least ten years by the time I’m 65. Corporate life gets a bit fuzzy around then, but I like how my parents can keep doing what they love doing because they have their own business. That still gives me plenty of time to do what I want to do with IBM: illuminate work with happiness and passion, build tools and teach people to build tools, connect people and make it easier for people to do their best work from anywhere, and help shape the future of organizations.

I don’t need a plan that assumes neat, linear steps to get me from A to B. Life will happen. I’ll change my mind. But planning ahead helps me think. Considering the best, the worst, and the more realistic outcomes lets me exaggerate the tiny differences in today’s decisions so that I can get a better sense of what I really feel.

Thanks to Cate Huston for the nudge to write about this!