When You’ve Made Your Money

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.

Financial Karma

Having been raised in a Judeo-Christian household, I used to define karma with reference to “sin.” For example, karma is my sins coming back to haunt me. 

Over the last year, I’ve learned a wider definition that goes like this… historical and current choices result in the life I have right now. I prefer that definition as it reminds me that I change the future with decisions today. At 43, our family’s balance sheet is an expression of my financial karma. 

I grew up in Canada, a country where there’s a social contract. The system isn’t perfect but it works for many Canadians. Living in the US, most prefer a model with greater self-reliance. Both systems have their strengths and create different incentives.

The book I referenced last week, makes the point that, historically, people relied on family, rather than government. What are the areas where family support can assist, without screwing up incentives?

As a young man, being an aggressive saver made me happy. I have no idea why, likely a habit that was built from a very young age. With three kids in my house, my desire to sacrifice today, to enable security tomorrow, remains strong. At a deep level, it feels like the right thing to do.

Boulder is an environment with a lot of financial wealth. The focus in Colorado isn’t as consumption-centric, as my previous homes in London and Hong Kong, but my reality is a far more expensive life than what I had created in New Zealand. 

Part of my annual review is asking myself the question, “Am I getting value for money within my current life?” Being honest with myself, the answer is “not yet.”

A key part of this year’s review has been completing a five-year plan to get my family to cash flow breakeven. When I became unemployed at the end of 2008, I gave myself a pass for five years to take stock and see what happened. The four year anniversary of that decision is approaching and I have a good idea where I want to take the family.

Long term, I have been considering the life I want to live in front of my kids. A parent’s life choices are powerful lessons on effort, consumption and strategic management.

I see a benefit to the kids of taking my consumption down. Expectations management is something the Kiwis do very well. All my pals in Christchurch understand the relationship between work-results-satisfaction. It is a very grounded society and I enjoyed my time there.


  • What are the most useful elements of financial wealth?
  • What does my life say about my attitudes towards wealth?
  • Are my current choices aligned with my family values?
  • How best to give my kids a chance to be successful: in their own terms, relative to their peers and relative to myself?

I’ll end with book recommendation: Wealth in Families by Collier. Another title that is valuable regardless of your net worth – the sections on anchors and family management contain a lot of good questions for parents to consider.

I measure true wealth in freedom.

A Life’s Work

Last week, I was on retreat, cycling daily in the mountains. Getting outside my normal life, offers me an opportunity to reflect on three questions.

  1. What will be my life’s work?
  2. How did I do, today?
  3. Am I aligned?

As a young person, my first realizations were not-to-dos. I’m still best at telling myself what to avoid (excess booze, sloth, late afternoon naps, overeating, anger, holding my breath, fatigue). It is easier to see where I don’t want to take myself than to consider my purpose and what I want to leave behind.

Various lightning bolts from my past…

  • Not to be unhealthy (mid-20s)
  • Not to be inactive (late-20s)
  • Not to gain satisfaction from a lifetime of accumulation of wealth (early-30s)
  • Not to spend my life dragging boxes across a screen (early-40s)

Each realization struck me quickly, and powerfully. It was obvious that my current life didn’t fit. Following that realization, I would redirect myself.

When we think about “legacy”, most of us consider financial wealth. I’ve considered my family tree.

I’m the first-born of the first-born of the first-born – everyone upstream being quite young when they had kids. So I have been fortunate to watch, and learn about, many generations. In looking up my own family tree, there have been a few members that hit-it-big over the last century. Regardless of their financial success, nothing material passed more than two generations. When I die, everything in my family tree from the last 150 years will pass. This brings context to my question, how did I do today?

Being 40+ years older than my kids, they are an obvious target for having an impact or, at least, building a relationship so I might be able to have an impact. I ask myself, “what can I do that might prove useful to my great-grand kids?”

Have you considered what continues?