I’ve taken very few vacations in my life and hated most of them. I’ve alway just said “I don’t vacation well” and settled for weekends away. Now we are in Hawaii for 2 weeks. A week in my mind began to settle, body relax and I began to love vacation. I have never experienced this

I have lived in the same town my entire life. @sweatystartup I married my high school girlfriend. She has always lived in the same town. We’ve been married 21 years and worked hard to achieve what society and piers deemed a successful life.

I have never dreamed there could be more, be different, be better, be new. I never dream I could design a life vs accepting what has naturally occurred. I've never dreamed of a life outside of the one I have. What I have is amazing, but feels small now.

As my mind has wandered I began to dream. I am asking questions for the first time. What is the life I want? Why do I live where I live? Is it possible to live in Hawaii? Do I love my work? Can my work be done remote or anywhere? Will my business run while I am gone?

I am reflecting on my entire life, challenging decisions I have accepted as “its what we are supposed to do” The best decision I have made is being married to my high school girlfriend and doing the hard work to be married.

The biggest question has been, what does my dream life, lifestyle look like? I feel like I’ve discovered a short answer with room to expand.
1. Work: A recurring revenue service business that can be manager run. Prefer B2B not B2C.

2. Living: June-Sept Bend Oregon. Sept-Jan my hometown (SoCal) Jan-June North Shore Hawaii.
3. I would continue to buy rental properties in areas I love with the goal of cashflow greater than the life above.

4. Special Projects: I love building houses, new developments and flipping houses… I’d still do that on a project basis via a solo 401k or Roth IRA. As @girdley says "project based income is hard"

I am only 7 days in… let see what else I can dream up. The next big question… what am I going to do about it? Or will I settle into the same routine and life post vacation?

To close... I am a person of faith, a christian and believe in prayer. These questions are my private prayers this week.