I just launched two big new Unschool Adventures trip: a 6-week adventure in Spain for teens and a 2-week hiking trip in Spain for parents.

I put a lot of time, money, and research into these trips, and I’m super excited for them to happen.

I also know that, for any number of reasons, they might not happen:

• The itineraries I chose don’t match what prospective applicants actually want
• The price point is wrong for my demographic
• My desire to fill trips early (6-8 months ahead of time) is unreasonable
• Other excellent programs draw away prospective applicants
• I don’t spread the world about the trips well enough
• Some unforeseen world event makes travel to Spain unappealing
• and on, and on…

This is the nature of entrepreneurial ventures, and especially very small operations like Unschool Adventures. Sometimes they just don’t happen.

What do I do if these trips don’t happen? Financially, these trips represent a significant portion of my potential income for the year. I’ve got savings to fall back on, though I prefer not to. But more importantly, how would the failure to fill these trips affect my sense of purpose, contribution, and accomplishment? What else would I do with my time to feel like I’m still “moving forward” in life?

When these nagging doubts creep up on me, I take out my journal and challenge myself to write down a large number of alternative life paths and scenarios. I force myself to get out of the “one right answer” mindset (i.e., run the Spain trips) and generate “second right answers” that would make me feel like I’m still making the most of my life.

In that spirit, here’s what I wrote this morning:

(Excuse the redacted bubble, it’s something I’m not at liberty to share.)

Each of these paths would feel like a good—or at least interesting—use of my time. Some would earn money, most would not. I’d really prefer to run the Spain trips. But lists like these help me feel reassured that, if it all fell apart, my world would not in fact collapse.