Three Realizations from a Having, Being, Doing Approach to Lifestyle Design

I often re-read The Four Hour Work Week by Tim Ferriss. It’s not a literary masterpiece, but I like that it challenges the conventional wisdom of “find a career, buy a big house, and retire.”

An exercise in the book has the reader create a Dreamline: a list of “Having”, “Being”, and “Doing” goals. I had a hard time assembling one at first. I searched online for “bucket list ideas” and found list after list of generic life goals. My mental breakthrough came when I bound the problem. I started asking specific questions like:

  • Where do I want to travel?
  • What do I want to learn?
  • What do I want to see in the world?

Using this approach, creating my lifetime Dreamline became easier:


Being in a relationship with things.

  • A condo
  • One performance car in my lifetime
  • A hand-made Japanese Go board


Having qualities, traits, or skills.

  • A better cook (take cooking classes)
  • Fluent in design (take self-directed design studies)


Things I would like to do and experiences I would like to have.

  • Start a tech company. Sell or IPO for $1B+
  • Invest in 25 companies to help others get their start.
  • Race the Nurburgring Nordschleife.
  • Drive an F1 car.
  • Attend the Monaco Grand Prix.
  • Go into space (Virgin Galactic or other).
  • Fly a fighter jet.
  • Race in a rally/targa.
  • Visit Japan (Tokyo, Kyoto, Fukuoka).
  • Visit Hong Kong.
  • Visit Singapore.
  • Tour Thailand (Bangkok, Chiang Mai, Phuket, Ko Phi Phi).
  • Visit Germany (Berlin, Munich).
  • Tour Italy (Florence, Venice, Rome).
  • Visit Spain (Barcelona, Madrid).
  • Visit London
  • Visit Paris.
  • Visit Vienna.
  • etc…

What started as a menial exercise turned into life changing event. It lead me to three important realizations that I’m lucky occurred early in my life:

1. Consider what you need to “have” to be happy. Many things that seem important in our daily lives (designer clothes, new technology, etc) don’t make the list. Others that do can be borrowed instead of bought.

2. Your “doing” list is likely 5x longer and 5x cheaper than your “having” list.

3. ROI on experiences is non-monetary, but critically important. As an analytical person, I found investing in experiences harder to justify than investing in assets. To come to terms with this, I developed a simple heuristic: Are the most interesting people I know the ones with the best experiences, or the biggest houses?