By the time I was 32 years old, I had created a life where I had the option of working parttime. For the most part, I got that opportunity “right” and enjoyed my freedom.

My errors came from from the thought (perhaps the lie) that spending yields happiness. That belief, shared by most my peers, pulled me back into fulltime employment twice over the last decade.

The first time I was pulled back, it was to help a friend start a business. There was huge equity upside and I loved the work. It was a good decision but I ended up over-extended financially. Thankfully, I started selling down in 2005 and, in the Great Recession of 2008, “only” lost 2/3rds of my net worth.

The scale of the losses was equal to what wiped out my grandfather’s generation. In the four generations of my family tree (that end with me), we’ve lost enough money for the entire family to never have to work a day in their lives. The bulk of my current job description (father, teacher, administrator, spouse, brother, uncle, trustee) is trying to reduce the frequency, and consequences, of these bad decisions.

When I took my big financial hit, my cost of living (2008) was 5x higher than what I spent in my first year of “freedom” post-college (2001).

Due to the bankruptcy of the business I’d been advising, I was under a tremendous amount of stress. Reflexively, I chose to cut expenses and replace income. My family’s 2009 expenditure was half of 2008, but remained 2.5x higher than what I spent in 2001. I focused on my back-up career of coaching (always have Plan B!) and managed to cover 50% of what I was spending.

At that point, 2010, I didn’t know what to do. Inside my personal business plan, I have a heuristic “if in doubt then wait.” So I repeated the year, with a couple exceptions, Axel (2011) and Bella (2012).

Gradually, across 2011 and 2012, I realized that preserving the status quo (large house, dad working to pay bills that don’t make him happy) was insane. Despite being complete insanity, I was following a path that had universal support in my peer group. As my kids popped up, I noticed that I was getting less and less fun to be around AND I was actively working to create a life outside my house.

The family readings that I shared, and my family history, show that it’s almost certain that we will wipe ourselves out (perhaps more than once) in the next seventy-five years.

What should you know about your money?

• Most of any financial legacy will be gone a couple decades after my death, or spent by people I never knew
• The greatest pressure I experience is preserving wealth that I’m unlikely to spend
• I know I can live in peace on a fraction of my current spending

What do I truly need? Easy to answer day-to-day: exercise, love, service and health.

For the long-term, I like to have a mission. Why not make the people I live with part of my mission? Then I’m surrounded by meaning, and success. If that’s the case then what does my family truly need?

Empathy – it’s easy to find people to do stuff. It’s a lot tougher to find people to listen and care.

Learn To Teach Ourselves – my writing is about sharing how I teach myself. Tools that I want to pass to my kids: write down insights and blindspots, make errors visible, replace habits that hold us back and share stories of what you’d like to become.

Cope With Loss – More by accident than design, I’ve been on a self-guided education of the major faith traditions, neuroscience and behavioral psychology. This has led me to believe that loss is an opportunity to learn by experience. Until life deals us a major setback, we will not understand impermanence and the nature of existence. Create a daily practice that let lets you process, release and recharge from the challenges we all face. Deal with loss by continuing the good that you’ve learned.

My kids weren’t around for for the first 40 years of my life. Common sense means I won’t be here for the last 40 years of their lives.

What’s your legacy?

Good memories and a skill set that let’s the student surpass the teacher.