There are many choices we make in our life that┬ájust don’t matter.

Which flavor of ice cream do you want?
Do you want to go to the movies before or after dinner?
What outfit do you want to wear today?

The outcome is nearly the same no matter what you choose, excluding serendipitous opportunities. These questions often use the word “want” in them, because none of the choices are necessary.

However, there are some decisions that we make slowly and have a more permanent effect. You can usually spot a “should” in their question:

Should I take this job or that one?
Which city should I move to?
What should be my major?

I have a mantra:

If you’re not sure, take a mulligan.

When you have an important decision, you have to be certain about the answer. If you’re not confident, then it likely is the wrong one. The safest course of action is to do whatever keeps your options open, look for different solutions, and wait until you can make a sure choice.

When my 1-year lease was ending for my apartment in San Francisco, I was presented with the option to move somewhere else. There were many things that I hated about that apartment:

  • Living in the crowded city.
  • Renting instead of buying.
  • The floor creaked everywhere you walked.
  • The social effort required for interacting with neighbors.
  • I could hear my neighbors and I assume they could hear me.
  • Nowhere to park my car nearby.
  • Terribly small laundromat with limited hours.
  • I could never see the sky.

The problem was that anywhere I could move in the city had nearly the same problems. Anywhere outside of the city was expensive and required a long commute. In either case, I would have to sign another 1-year lease and provide an insane security deposit.


Previously, I had the fortune of staying a night in a 2-bedroom motor yacht, used as a primary residence by the owner. I was able to see how space-efficient living worked and I loved it. There are two problems for me to live on a boat, however: I wouldn’t be able to drive a boat to Austin, and I can’t swim.

Discussing the idea with co-workers, we joked about living in a trailer instead, so I started to research. I found two fantastic resources of people following that lifestyle and I was hooked:
Gone with the Wynns

With that, there was no turning back. The decision was made.