
Someday my kids will move out. This is a summary of what I hope they take with them.
Here’s what’s most important to remember:
- We’ve already won
- It’s ok to say no
- We can handle the truth
- We can do difficult things

There’s a great book out there called Winning The Loser’s Game – a “loser’s game” is one where you win by not beating yourself. The book has an investment angle but, in many ways, a successful family is created with a similar approach of avoiding error.
Errors such as… financial ruin, substance abuse, fractured relationships and emotional upheaval.
Many unforced errors occur, and repeat, because their causes are deeply programmed into our consciousness, and family culture.
To avoid errors, we need to think slower and whittle away at the habits that hold us back.
So how do we slow down our thinking?
We take away feelings of obligation, feelings which can lead to blame and lack of personal ownership => All family is optional
We don’t let pressure build up… Everyone can speak, about whatever they’d like to discuss, and we commit to a “no secrets” policy.
Secrets, taboos, not being able to speak => these habits make it easier for evil doers to do bad things.
Ask child abuse survivors to describe their family culture and you will find a consistent pattern, of repression and secrecy, that enabled their abusers.

I got the next tip from a four-generational family, where the patriarch was deeply successful (work, family, financial, community). The family has multi-generational quarterly meetings and has successfully managed two transitions between generations.
Close but not too close – via staying in your own space – via sorting your own food – with a respect for differences.
Take the above and invert them…
…a feeling of obligation, never being able to say what’s on my mind, staying in close quarters, eating different food…
then… add alcohol, relentless toddler noise, politics or any emotional trigger..
and… BOOM!
Not winning!

What does winning look like?
We enjoy sharing experiences with each other, usually in nature.
It is about shared experience and, frankly, it need not be all that fun. My son and I find meaning enduring difficulties together.
Each generation, each household, each adult needs to affirm its own set of values and define winning on its own terms.
If there isn’t a consensus then we remember… it’s OK to say “no” and all family is optional.
Also… we don’t need to agree to be buddies and I’ll respect your right to not have an opinion.
Some multigenerational thoughts…
Seek to connect not correct. Do not put a spotlight on people, just ask an easy, “how are you doing.”
Down, and up, the generational chain remember our goal is shared experience, not optimization.
Joys, and disappointments, with founders/followers/descendants are best used to motivate positive personal change in myself.
The most powerful form of teaching is living an open life where people see us modeling the best we have to offer.
Pay attention to those who bring out your best.

What about money and finances?
The fundamental point is everyone pays their own way and we do not create incentives to consume more. By the way, COVID gives you a useful opportunity to make changes in your family spending choices.
Any capital that become multigenerational is managed in a custodial capacity.
What does that mean?
It means you take care of things you didn’t create so others can enjoy them.
When financial decisions need to be made, we remember we are less likely to make errors if we keep it…
- Simple
- Low cost to hold
- Focused on long term capital gain
- Tax effective
- If it won’t make a difference then wait
I use the above as a checklist because it slows my decision making.
For me, the three most important factors to remember are: cost to hold, leverage/borrowings and wait if it doesn’t matter. Together they nudge me to avoid the most common errors of investing => fees, tinkering, borrowing leading to ruin, cost to hold resulting in cash crisis….
After I’ve taught the above, I will hand it off and focus on modeling grace through what remains of my life.
Take what’s useful and make it your own.
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