Tag Archives: family planning

The #1 Mistake Financial Professionals Make

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…is not leaving

Living!

Let’s start with the best money advice I’ve seen in 2022:

Don’t build a plan that requires your death to succeed.

Yes.

Rather, create a life that supports how you want to live.

How are we going to do that?

Get some money off the table.

How much?

5x “last year’s cost of living”

This is Core Capital – it is a function of your spending as well as your savings.

Once you have Core Capital, protect it.

The return on Core Capital doesn’t matter. Keeping it does!

It’s the most valuable money you will ever have, there are rapidly diminishing returns beyond this point.

Core capital doesn’t free you from the ability to stop working.

That’s OK.

You don’t want to stop, ever.

That’s another mistake the financial services industry makes => selling you a dream that you won’t enjoy.

You want the freedom to choose, to take chances with your time, to stay in the game.

You want this freedom to choose as soon as possible. Not late in life.

INVERT: You want the freedom to choose “not to.”

Not to deal with:

  • other people’s BS
  • fast money schemes
  • worry
  • golden handcuffs
  • creeps & crooks

Two weeks ago, in asking five questions, I gave you a nudge to start thinking about life.

  • Learning & Peers
  • Travel & Exploration
  • Values

That article introduced the concept of Lifestyle Sustainable => a low-cost base of operations where, ideally, you can live for free. The idea is to remove cost-of-housing from your financial concerns.

That’s the core financial asset for your portfolio. It cost me US$110,000 in 2000.

This is a great place to park your Core Capital.

Removing housing from your list of concerns gives you more than a financial return.

Alongside your key financial asset, I hope you have a loving, lifelong partner. This person is the most important decision, financial or otherwise, you’ll be making.

The highest return investments I made in my 30s & 40s, were not financial in nature. With a low-cost base of operations, & marketable skills, I was in a good place.

Many high-earners fail to see the value of what I just pointed out.

  • Low-cost base of operations
  • Marketable skills

Beyond that, most everything is lifestyle enhancement and ego.

Thankfully, I had a major setback in my early-30s (divorce) which gave me pause.

In 2000, I saw my future in front of me… lifestyle enhancement and ego… and I made a change.

A big one.

I became a world-class athlete. With (athletic) success came the realization that something was lacking.

So much success, still lacking!

  • If you’re good at making money…
  • If you’re good at playing the game of “career”…
  • If you are nearing the top of your field…

…then you’ll be tempted to keep doing what you are good at.

I’d encourage you to establish that low-cost base of operations, then try something really challenging…

The highest return investments I made were improving my suitability for marriage and learning how to parent. Most of my learning happened after I was married and my kids were born.

It is never too late to invest in the human capital of your family.

If you get these investments right then you might not notice the benefits. Honestly, a big driver in my life has been a fear of getting divorced again (not-divorced, winning)

Fear that drives positive action is useful.

I’ve been paid by less drama, and less problems (we don’t see all our wins).

I’ve also de-risked some of the challenges my future self will face (companionship, engagement, dementia). Study (the problems of) who you are likely to become.

You’ll notice my portfolio advice (still) doesn’t talk about asset allocation.

This is deliberate!

Asset selection is not the differentiating factor for a life well lived.

  • Marketable skills
  • Low-cost base of operations
  • Fixed-rate mortgage, if you like
  • Target date fund for your future self

Then focus on living your life and creating the friends/family with whom you’d like to share it.

Generational Transitions

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There’s a straightforward way through the headwall – just take it one step at a time

Last week, Mark Spitznagel’s book came out (Safe Haven). Don’t expect any specific strategies for constructing Safe Haven insurance. Do expect to (re)learn useful concepts:

  • a reminder of the central role of time in our lives – the capacity to sustain action, cognizant of time, is extremely rare
  • a reminder that we think in terms of arithmetic averages but experience geometric averages (COVID, portfolio compounding, fitness, nutrition, body composition)
  • a reminder that downward moves (in %age terms) have the same impact, regardless of their position in the time series – the counter to this => absolute dollar losses are best taken later in the time series (down $100,000 wipes me out at 25 y.o. – not so at 60) // by the way, creating negative net worth early (via education loans) is a very nasty geometric headwind.
  • a reminder to consider the cost of your insurance strategy, including the decision not to insure. Health, accidents, portfolios, relationships, nutrition => “insurance” comes in many forms.

Also some great parables/examples to help explain mathematical concepts that I’d previously failed to grasp, most importantly, the negative waterfall of financial ruin in a geometric environment.

Related to geometric returns, some useful illustrations of how/when diversification fails, despite its enduring appeal.

Finally, using Eternal Return when assessing risk. With any important choices assume you’ll be stuck repeating that choice over-and-over. I’m not sure I would have been capable of applying this advice as a young man. At 52, my life continues to benefit from this mindset (health, accidents, portfolios, relationships, nutrition…).

++

Today, I want you to think about the past, present and future.

Specifically, I want you to look backwards 10-15 years, as well as forwards 10-15 years. This will give you a 20-30 year time span in which to consider family strategy.

We call 20-30 years a generation. For family leaders, it’s the shortest period we should be considering. Let me illustrate:

  • 2004 – met my wife
  • 2008 – birth of first child
  • 2032 – youngest child graduates high school
  • 2037 – youngest child self-sufficient financially

For our family finances, a generation will be closer to 40 years than 20.

Act with 25+ year time horizons => the Eternal Return is a useful mindset for multigenerational family systems.

++

Family Earning Capacity Over Time

The biggest change of the last 15 years, for us, has been the quasi-retirement of the two largest earners in our family system. Looking forward 15 years, the biggest change will be the addition of new earners into our family system.

The shift in earning capacity every 30 years, or so.

If you are the prime earner, today, then here is a question for you. Does your family system have the assets, earning power and desire to continue to run the overheads you have built over the last five years?

Current choices can create a “geometric” headwind for the next generation.

++

Family Risk Management Over Time

The demographic that seems to worry the most about financial risk is the Top 2%. Makes sense, they own most of the assets and, therefore, have the most to lose.

The easiest way to manage family financial risk is to create a cash flow statement with many different inflows, while having the capacity to painlessly chop outflows. I’ve been working on this for 20+ years, covering fixed overhead categories with a mix of inflows.

The option to shrink cash spending is valuable. Specifically, looking at your cash flow statement and seeing how much of it you could chop, at will.

For example, there are excellent reasons to borrow right now (inflation hedge, low nominal rates, negative real rates). However, the costs and negative-optionality of debt are hidden and difficult to price – particularly in a near-zero rate environment.

  • What is the correct way to price the ability for a lender, or my fixed overheads, to force me out at the bottom?
  • How do I price the capacity to invest during the next credit crisis?
  • What’s it worth to not have a boss?
  • How much is a lack of financial stress worth?

In my memory, all the remains from the 2008/2009 crisis is a note I wrote to myself to NEVER DO THAT AGAIN. Ten years along, there is no “pain scar” from the stress I endured.

With our next generation a decade out from starting to earn, we’re debt free, and happy to be there. It’s worth more than I can prove mathematically. I do not have the capacity to think in terms of negative optionality. I can’t price ruin.

I’ll finish with another note I wrote to myself:

Moderation is easier when the prime directive is simply staying in the game.

This applies to my appetite for risk, further wealth, spending choices and personal fitness => interestingly, my greed focuses on various forms of external winning, while my quality of experience is internal.

Limits of Knowledge

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A online physics course reminded me of the ways we get ourselves in trouble. I tried to explain this to a buddy and he replied, “there’s simply too much to worry about.”

I’ll give the explanation another shot.

Better thinking is not building the capacity to worry constantly, about more things. Better thinking is about training ourselves to focus on making a limited number of excellent choices, given imperfect information.

  • When to worry?
  • Where to focus?

Limits to Knowledge

Snowflakes: even if a human mind could know everything there is to know about water molecules, it would not be possible to predict a snowflake’s structure.

Mobs: understanding individuals, in isolation, tells us very little about the actions of mobs, or markets, or cities, or nations.

Lots of other examples: DNA to elephants; Neurons to consciousness; the patterns of a sandbar; the shape of a cloud, politics, wars, life sciences.

Clouds are a current favorite of mine – a reminder to stay humble with any bet that requires me to be correct about outcome.

I’m currently debt-free. As a result, I’m able to make more mistakes, be less correct and less impacted by outside factors. The value of this position doesn’t show up in conventional analysis.

Properties that emerge, at scale, make prediction impossible. Joe Norman’s presentation at RWRI helped open my eyes to this aspect of our reality.

I don’t need to become a complexity expert to apply this knowledge. What is essential is understanding the nature of the system in which we find ourselves.

  • Are we in a complex system?
  • Are we in a system subject to extreme events?

To answer my friend’s question, “when to worry?”

Complex systems, subject to extreme events… exposures here are worth the time to carefully consider.

You don’t need to be the CEO of AIG to get bitten on the butt by complexity. If you’ll get fired for the mistakes of one of your direct reports then, given enough time, you’re fired.

Sudden unemployment is one way the nature of universe can come home to roost. Happened to me in 90-days at the end of the last boom.

Here’s another… if you woke up and discovered an undisclosed $20 billion dollar loss in an important counterparty then what would that mean to your life?

What about your family, your employer and your portfolio?

Concentration is a risk we can mitigate. It’s why I have unrelated jobs and several cash flow sources. Here again, conventional analysis fails to capture the value of this position.

In 2021, in a very benign financial environment, we’ve seen multi-billion dollar losses pop up in a week, or less. Rapidly emerging, massive losses are a feature of our system.

Things, that have been stable for a very long time, can disappear quickly.

Prediction: our minds love to predict, to assign causation and to tell stories about the world around us.

Grasping for a “why” is a waste of time.

When operating in complex environments, most importantly when surprises can bite me in the butt, I need to constantly remind myself NOT to make predictions.

For myself, I actually need to go further, I need to implement a policy of NEVER making predictions and NOTING surprises. There is useful information contained in every surprise.

Even further, I shun input from individuals (especially smooth talkers) who make predictions. A reason why I try to never watch videos — too persuasive.

I’ve found that even a little prediction, it leads me down a path of wasting thought.

  • What’s likely to happen – what happens to me if the opposite happens?
  • What’s the worst that can happen – can I mitigate?
  • Does the situation appear reasonable – given the above
  • There are games, investments, relationships and opinions… I don’t need to play, make, engage or have

There are a lot of business where “the burden of the worst” falls outside of the beneficiary class (government, general partners, VC, private equity, OPM, CEO-class, banking).

We can waste a lot of energy railing against the system, I’ve found it much more useful to make sure I understand…

My family cannot afford to take the same risks as my employers, my shareholders and my government.

This is a lesson I learned through, rather expensive, experience when I left Private Equity.

Families…

No Prediction => focus on getting rid of ruin => subject to not becoming a casualty myself… education of youth “buys” more than portfolio returns, or my personal savings rate.

Conventional analysis fails to capture the present value of teaching how to avoid future mistakes.

Risks => practices that make sense for large entities, given time, will wipe out my family

So my point was…

There is more to reality than we are capable of comprehending.

Stable situations can become fragile at scale.

There are certain domains where acting “irrationally conservative” can make rational sense.

We are going to be surprised over, and over, and over, again.

Philosophically, one could say reality is pointing towards a deeper form of intelligence.

From a more linear point of view… the next time you are on an airplane, write a list of your concentrations and counterparty risks. Blow them up, one-by-one, and carefully consider if you need to mitigate.

Ski Math

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The tiny dot in the middle of the frame is my son hiking up from a yard sale, in a gale, at the top of Pali Chair. FIVE minutes later he said, “Dad, I’m glad you’re as good a skier as me.” I’d kept my skis during the traverse! They have such short memories.

Our family ski experience is like my Pandemic Predictions => I got a lot wrong.

When I was shelling out for childcare/preschool, skiing struck me as a very expensive way to do a lot of driving, without much cardio.

Not interested.

A friend, with four kids (and a jet), made the observation… “you gotta be able to do something as a family.” Given his role, as the smartest guy I know, we decided to give it a try.

My wife didn’t believe me when I said, in advance, “We’re making a million dollar decision here.”

Frankly, I took it easy on her. The math is daunting…

But wait, there’s more.

Add-in the inflationary effect of surrounding yourself with the largest spenders in our society.

And… have a look around the parking area, with the smell of legal weed wafting across the empty beer cans… Is this an environment where I’d like to leave my teenaged kid unsupervised?

Still… “you gotta be able to do something as a family”.

$175,000 worth of opportunity cost later, I can ski any run, with any member of my family. This makes me happy during a time of year I used to dread.

Total immersion (5 million vertical feet, in three seasons) let me achieve my goal quickly… Something outside, at a high level, with any member of my family.

Unexpectedly worth it… but only after I figured out our family’s cash burn.

I cope with the “demographic” by focusing my energy on seeking to ski like an instructor, with the fitness of a ski patroller. These goals provide structure for my athletic year.

Like much of my outdoor life, my participation is conditional and always one major crash away from ending.

Stay variable.

Creating A Better Reality

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Ask a good looking tennis pro to offer their view on the sanctity of marriage and you might be surprised. Away from prying eyes, there is a fair amount of “but we never hooked up” going on.

At it’s core, this post is about keeping your home life a mile away from an unfortunate outcome.

Circa 2014… My phone buzzed when I was out-of-town. You can see my son hiding from his sister. She was bleeding a minute later… smashed her face when she fell off the couch. My memory of this moment was thinking how great my wife looked.

About the time our first child was born (2008), I found my financial life under pressure. The approach we took was unconventional.

We downsized and, effectively, spent half the proceeds from the sale of our home on childcare. I did this with the full knowledge of the annuity math underlying our financial lives. Over a decade, our childcare bill was the equivalent of ~5 years worth of current living expenses.

Most financial advisers would advise against selling a house to pay for childcare. Many families go the other direction => up-sizing: (a) complexity, (b) bills and (c) financial stress… when the kids arrive.

Downsizing was one of my best decisions of the last 20 years. It enabled me: (a) to get help to directly improve the quality of my marriage, (b) to give my wife some space, and (c) to maintain some form of personal life, at a time of great change.

This is fine – I was out of town for this one as well. Check out the baby, she’s purple.

This next one was a happy accident – I just wanted the kids out of the house.

My wife found an outstanding preschool. The lesson: socialize your kids as early as possible.

While my kids don’t always get along with each other, they are experts at getting along with others. Not spending this money would have been a false economy.

=> Total here was equivalent to another year of current living expenses.

Unexpected bonus from this choice => spending time with outstanding preschool teachers made me a better parent AND give me a deep respect for the quiet achievers in childhood education.

Because we focused on socialization, all three of my kids started Kindergarten behind their peers. We didn’t panic and this worked itself out by the middle of Grade Two. We gave a big push in Grade One to support our son learning to read – lots of little lessons at home and at school.

So it worked out to ~50% increase in Core Cost of Living for a dozen years.

Another way to quantify for you… finish college debt free, save $1,000 a month for 20 years, roll the capital into a good real estate deal… Gone by my 50th birthday.

The Lesson: the skills required to accumulate Financial Capital are different from what it takes to develop Human Capital (kids and marriages).

I don’t miss the “half a house” – it was an excellent trade.

Childcare, early education and health insurance => if you want to bring something to your adult kids, without creating incentives for consumption, then these items could be a good place to start.

It’s easy for a well-intentioned, conventionally successful family member to create lifestyle inflation for their entire family system.

Helping pay for preschool seems a pretty safe bet for help-without-harm.

PS: If you spend your weekends out of the house then remember my warning about your spouse “not hooking up” => most bad things done to me, have a seed in choices made by me.

Family Financial Structuring

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Following on from my Estate Planning Docs post.

Trust vehicles can be useful to your family and I will illustrate with a couple of stories.

First thing to remember => trusts work best if you set them up long before you “need” them.

Grantor Trust

Part One: Around the time I turned 40, I found myself in a situation where I had joint & several liability with a business partner who’d made poor choices. As fate would have it, these choices were made inside an insolvent group with over $100 million of borrowings.

Now, the banks were not going to be getting their money back by suing me but (even the remote possibility of) being wiped out late in life was highly unattractive.

Part Two: Long time readers will remember that I used to do bike-focused training camps with top age-group athletes. I would ride, on open roads, with doctors and CEOs who were completely exhausted. If an athlete was killed, or permanently disabled, then it would be easy to prove a large financial cost to their family.

As a business, we dealt with this risk through waivers, event-specific insurance and a family-level umbrella insurance policy.

When I added up the cost/time/worry of this approach it was expensive, even more so once I had my own family to protect.

Take the two parts together => I was working in two fields. The first field was similar to being a director/fiduciary of a company. The second field is similar to being a professional exposed to allegations of malpractice.

One day, I was talking to a tax accountant about what was going on in my life, and the changes that were expected in Estate Taxation. He recommended I speak with a local trust attorney.

An initial meeting showed me that the cost to set up a new structure would be the same as one year’s insurance bill. Because I have the skills to run the fiduciary aspects, the ongoing cost would be a fraction of what I was paying my insurance company.

Step One was setting up something called an Intentionally Defective Grantor Trust. From a layman’s perspective, I put my share of my house and rental property into a trust that benefits my spouse and kids. I retain the tax liability for the trust, for my life.

From my point of view, the main asset I am left with is my earning capacity, balanced against future tax liabilities. I’m a much less attractive target to any potential litigant.

From my family’s point of view, the trust is similar to an annuity, tied to my life. When I die, they can sell assets and/or move into a small rental property, while living off the rental income produced by the larger rental property.

The specifics are technical, there’s a bunch of tax considerations and you should take expert local advice.

This change gave me a more secure feeling than the insurance policies.

Over time, I exited the disaster-prone aspects of my life and that helped too.

Irrevocable Family Trust

I’ll illustrate with a recent example – my brother-in-law died and his balance sheet will flow into my wife’s family.

What follows isn’t what is going to happen, but it could have => check with an expert in your jurisdiction if this seems useful.

Here’s a story… assume Andy had a brother called “Dude” (he didn’t).

Andy had planned ahead and wanted to leave assets to Dude. However, Dude didn’t need the money, or Andy didn’t like Dude’s wife, or any number of reasons Andy might not want to support Dude’s personal balance sheet.

So Andy set up an Irrevocable Trust. Let’s call it The Dude’s Trust => Dude, and Dude’s descendants are the beneficiaries.

Andy then drafted his will, or his Living Trust, to leave everything to Dude, but gave Dude a specific power of appointment to nominate The Dude’s Trust in his place.

Before Andy dies, he would also have the ability to make gifts to The Dude’s Trust.

Did you see what happened? Andy was able to achieve what he wanted => money to Dude. Dude is left with a choice to inherit directly, or into a family trust.

In a world with an unknowable future, this is a valuable option.

The current Estate Tax Threshold is $11.58 million per individual, double for married couples. I’m far, far below that threshold.

However, that limit sunsets in 2025 and who knows what tax regime will be in place when I turn 75 (some time after 2040), or beyond 2080 when my kids age up.

I can imagine we shift to a regime I’ve worked with outside the US => deemed sale at death, zero personal exemption, no step-up in basis, the estate pays capital gains tax and the net flows to the beneficiaries of the estate. It’s simple and I like tax simplification.

In that scenario, trusts that were established prior to the change in rules could be grandfathered, particularly if they already own assets. To get around assets sitting in a trust “forever,” the IRS might create a rule for the deemed sale of trust assets, this rule exists in jurisdictions outside the US.

Even if everything stays the same… given the asset protection benefits of a trust, and the ability to “finance” the structure through reduced insurance payments, it made sense for my family.

This is not legal, tax or accounting advice – seek local experts.

Combination article, with chart, from 2013 is here.

Basic Estate Documents

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Recently, a local lawyer advised a friend, “Sorting these documents, now, will save you a multiple of time, money and hassle – later.”

I would add… it is best to make end of life plans when stress is low.

With Andy’s death, I re-read my stuff last week. I was surprised how little needed to change.

Indeed, a good attorney saved my family time, money and hassle.

General Durable Power of Attorney – this lets someone I nominate act as “me” while I am alive – I do not need to be disabled.

The POA does not enable anyone of act on my behalf after I die. This limbo period (immediately after death) should be considered by you and your family.

The POA does not enable anyone to step into my work roles, say, as a fiduciary. This needs to be considered.

If you execute a POA then place the original in a fire safe where you can run it through a shredder (not joking) in case there’s an issue with the person you appointed – I’ve seen a lot of wacky stuff in my life, things change and this is a very powerful document.

Living Will – this covers how I’d like to be treated when I’m dying. Very useful for your family, who will be blasted if you’re in any sort of condition to need to dust off this document. Also useful for your medical representatives, who may be reluctant to deny you treatment.

Medical Durable Power of Attorney – just what it sounds like – who is authorized to make medical decisions on my behalf. Keep the contact details up to date and available to your family.

HIPAA Releases – who can receive my medical information. There could be people you’d like to have informed, but not act on your behalf.

Living Trust – a very useful form of trust – assets can come in/out and it can be used to title financial and real property assets – a local attorney can tell you more.

These documents are not expensive to put in place.

My current will was done ~13 years ago and has seen 4 changes.

The changes were minor, inexpensive and easy to arrange. Once again, doing it right the first time saved us time, money and hassle.

The original will predates my kids. You might get a kick out how it played out.

Before my wife was pregnant, I was leaving my life to charity. At the signing meeting, my lawyer, who drafted the docs, smiled and said, “I bet I see you in a couple years to change that part.”

Sure enough, my kids arrived, I got to know them and I made some revisions. Those revisions start to get a little complex so I’ll outline them in another post.

Most people don’t need complexity. All my assets, eventually, flow into my living trust, which already holds title to most of my assets. Standard clauses are used to protect my spouse and follow the tax code.

Whatever you decide to do – double check what’s required for a will to be valid where you live. There are places where a handwritten letter, witnessed by the sole beneficiary, doesn’t work. Colorado is one of them – link is to what’s required for a will to be valid in Colorado.

A good attorney, familiar with the laws in your state, is essential. She will have you decide, in advance, on the areas where disputes happen.

Ask your attorney about something called Joint Tenancy with rights of Survivorship. It can be a useful way to hold property titles for some situations. Link from the Colorado Bar Association.

Also find out about successor beneficiaries for your assets. Certain jurisdictions will let you nominate where your assets go, separate from a will.

Your attorney will likely have a checklist of items for you to consider => 529 accounts, retirement accounts, death benefits… take time to think it through.

The US has something called Stepped-Up Basis – it is worth learning about. Basically, certain assets (like real estate) have their taxable basis reset at the date of death.

I’ll illustrate with a quick example: Grandpa G bought a house in 1980 and his taxable basis is $50,000. He dies in 2020 and the house is worth $1,000,000. If he sells the house the day before he dies the gain is $950,000. If his estate sells after his death then then gain is $0.

Be aware there are wrinkles to do with trusts and certain types of assets don’t qualify.

With all this stuff => ask an expert.

If you trust someone enough to give them a General Durable Power of Attorney then consider making them a signing officer on an “operating account.”

More than a decade before we needed it, a grandparent did this in our family. This made it easy for a trusted family member to pay bills before we were in a situation to invoke the POA.

It also removes the expectation for the wealthiest member of your family to finance everything, which can create an unnecessary distraction when you should be supporting each other.

Kids => If your kids end up orphaned then you might want to split their “care” from their “finances.” The skills of a Guardian could be very different than those a Conservator. Are you familiar with these terms? Ask your lawyer to explain.

Andy used to joke that all we needed to do was leave him with enough to cover a beach hut in Central America. With a small nest egg, he’d ensure our kids were well loved and became pro surfers…

We miss him dearly.

Final words of advice…

1/. There are good people who are useless under duress

2/. There are people who cope with grief by misusing veto power

Think carefully about who you put in charge and what you let them control.

I have a medical doctor and a military officer in my structure => individuals I trust to be compassionate, and execute my wishes, under duress.

This a quick outline – take expert advice from someone familiar with your jurisdiction.

I’m not an expert. Over the years, I have hired experts and it has proven to be money well spent.

What’s Your Filter

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Our youngest told me our cat needs a Halloween costume. I laughed while realizing that my home-school internet monitoring system might need improvement.

Most of us will be “adulting” for 50+ years.

Half a century is more than enough time for choice to impact outcome.

Here’s how I stack the deck.

Understanding three things greatly simplifies decision making:

  • Payoff function
  • Worst-case scenario
  • Who bears the worst-case scenario

In most cases, knowing the above eliminates the need to make any prediction (of an unknowable future).

In investing, you can bet big when someone else bears your downside (non-recourse leverage, other people’s money). At home, you will want to be more careful.

You are going to be tempted to spend most of your time predicting an unknowable future.

Don’t.

Instead, figure out the payoff function, what’s the worst that can happen and who bears that downside.

Previous writing touched on the payoff functions for fame, financial wealth, strength training and personal freedom.

Tim’s blog did a great job of laying out on his worst-case scenario – shot in his own home as well as a brain dump of everything that can go wrong, and right, with fame. It was an enjoyable read but life is too complex to perform cost-benefit analysis for every choice.

Sounds good, doesn’t scale.

One of my favorite shortcuts is to teach myself the areas of my life where I have a lousy track record, and defer to my expert advisor(s). I look for advisors with domain-specific experience and a temperament different from my own then… …I do what they recommend.

There’s deep wisdom in stepping outside ourselves => What Would Jesus Do, or Buffett, or your coach, or whomever you think knows better than you.

Each time I choose, I open the opportunity to make a mistake. To reduce unforced errors, there are filters I use to eliminate the need to make a choice and to make the correct choice obvious.

First level filter => repeat my choice for a decade, where’s this likely to take me?

What’s the worst that can happen? Live long enough and you’ll see it happen.

Specifically, I want to stay well away from:

  • Prison
  • Permanent Disability
  • Bankruptcy
  • Divorce
  • Violence
  • Self Harm

The first three are obvious, but that doesn’t stop many, many people from surfing close to the edge, or getting an emotional rush from having charismatic risk-seeking friends.

Sometimes I need to phase out a relationship, sometimes I need to adjust my own behaviors.

With marriage, specifically, it’s impossible to “see” just how challenging your life will become if you have kids. You’re going to be really, really stressed out for a decade. Every single one of my prior bad habits tried to make a re-appearance in my life!

There’s no easy way around it but you can significantly reduce your chance of disaster if you pay attention to how your potential mate approaches risk.

Personally, I like to drive with people. You can learn a lot about someone by chatting, and watching, while they drive in traffic.

It is difficult to let charismatic sociopaths out of our lives. These people are a lot of fun to hang around with, especially when we aren’t the target of their ire. It gets easier with a few bad experiences.

When you need to make a change, resist the urge to justify your choices.

Learn to ghost with grace.

What if we are the person that needs to change?

Owning my choices and considering where they might take me.

Mountaineering, peer choice, alcohol use, cigars, bike racing… as my life changed from “just myself” to “my young family” the following became clear to me…

The people who were bearing the downside had no choice in whether to take the risk.

To make myself feel better, I took out a long-term care policy. The insurance reduced the financial burden if I was disabled but didn’t address the mismatch between who was taking the risk and who was bearing the downside.

In my 40s, severe permanent disability could have been worse than death. In 2013, with three young kids and an impaired balance sheet, I was in a very different place than I hope to be when our youngest graduates high school (in 2030, or so).

Perhaps I’ll add back risky stuff in my 60s… right now, I doubt I’ll have the energy.

🙂

Divorce, violence and self-harm => the bottom half of the list.

  • Nobody gets married hoping for a divorce.
  • Nobody starts a drive hoping to get their car shot up in a road rage incident.
  • Nobody repeats a pattern of justified rage hoping to create a crisis.

But these things happen, and their seeds are small choices, repeated.

I try to be alert to habits that can lead me astray.

Anger remains a challenge for me.

I pay attention to situations and habits that reduce my faults.

I focus on better.

My definition of winning has changed over time. However you define it, success is more likely with a plan, a couple well chosen peers and a habit of referring to a clear filter.

Making a habit of the first-level filter, tosses all kinds of stuff into the forget-about-it pile.

Reminder about the 1st Filter => repeat for a decade, where am I likely to be?

The first filter very quickly gets rid of (most of my) bad ideas.

Then what.

Here’s how I set priorities and shape my “to do” pile.

When I was an elite athlete, every decision I made was passed through a filter of, “Will this help me win in August?” At that time, the filter worked very, very well.

August 2007, with my real 1st Place Trophy. Before kids, we took ~1,000 days for ourselves. Highly recommended!

In 2005, I married and quickly realized my filter (of winning) would, if applied over many years, make a second divorce more likely. Deeply seared from my divorce, I really, really, really didn’t want another divorce.

I wanted a different result so I needed a different approach.

I needed to change my filter to…

“How will this impact my marriage?”

Your situation is likely different, but your need to know, and direct, your filter is the same.

Baby, or COVID, arrives… “How will this impact my family?”

Allocating time week-after-week… “What’s my real priority?”

Trivial irritations, the opinions of strangers… “Who gets my emotional energy?”

Every single person we meet has a filter => victory, vanity, external wealth, fame, likes, validation, please the person in front of me, attention, minimize conflict, how do I feel right now, what is the last piece of advice I heard… lots of people, lots of different filters.

Make a choice.

Iterate towards better.

All That Remains

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We finished our volcano science unit with a trip to a volcano! This was the first field expedition of Home School.

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
Lunch on top – my wife catered the kids and I made a huge error by self-catering!

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!

Carrying weight is a privilege. On the way down, I grabbed his pack and he busted out a quick hill repeat. Blood was tasted, apparently. He gave himself an introduction to “race cough.” The kid has a passion for hills!

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.

What I Talk About When I Talk About Building Wealth

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SuperGirl

When people ask me about asset allocation, I guide them towards family wealth.

Over your life, you will see things blow up.

  • Jobs will be lost
  • Divorces will happen
  • Guarantees will be called
  • Companies will fail
  • Investments will go to zero

Certain habits make us more prone to blowing up:

Debt – fixed obligations can ruin you in bad times.

Lack of emotional control – this runs deeper than, say, anger management.

People who make a habit of rationalizing a lack of control in one domain (elite sport, closing a sale, acting in a client’s best interest) rarely have the capacity to control themselves across domains. If you might get caught, then you’re fragile.

Substance Abuse – it’s more than the cost of sorting yourself out – it is the lost opportunity of a life well lived and the impact on the rest of your family, especially your kids.

Spending vs Cash Flow – personal spending, burn rate and fixed costs => the more spending you have relative to cash flow, the more fragile your finances.

The above is a long way of asking, “What aspects of your life might blow up?”

Which is a polite way of saying, “I’m not sure asset allocation is the most pressing issue in your life.”

If you work in an ethically-challenged field, have a lot of borrowings, have a high burn rate or are surrounded by peers with issues…

…then tweaking portfolio construction is a lower priority item than immediately removing what might ruin your life.

I’ve done it. You can do it. It’s better on the other side.

How large is your current portfolio when compared to your lifetime portfolio? – AKA you might have more wealth available in your career than your portfolio.

Investing is different at 25, 40 and 55 years old.

The nature of “different” depends on your personal circumstances.

#1 => Consider your Core Capital. The single best thing I did out of college was save four years of personal living expenses, $100,000 in the mid-1990s. It sat in a bank account, while I worked my ass off at my career.

Having that money enabled me to choose better and choosing better became a habit.

Very, very, very (!) few people can be professional investors – AKA can I get rich by beating the market?

Take an honest look at the people that you know in finance. How many of them “got rich” from their own money? Remember these are the experts.

In finance, most people get rich due to the rules of their game and collecting pools of other people’s money (your money, by the way).

With your portfolio, keep it safe, simple and low-cost. A target-date fund makes a nice core holding.

Having my Core Capital enabled me to take more risks in my career path, and life experience => not with my Core Capital.

Once-in-a-lifetime opportunities happen once a decade – AKA great deals happen when credit markets are shut

Here are the assets I own and why I own them:

  1. Index funds => long-term, diversified, not linked to my home real estate market
  2. US Treasuries/Core Capital => 5 to 10 years family expenses
  3. Boulder real estate => A relative value play against California, a cost-effective way to raise a family and a fantastic outdoor life. Think very carefully before locking yourself into any location. As a young man, my lack of ties enabled me to jump at great opportunities.
  4. Cash => my early retirement was funded by three deals I did coming out of the last credit crisis. Once you have your Core Capital (say, five years living expenses) then building up a pool for “great opportunities” is a consideration.

Starting out? Read this PDF.

Be wary of home bias => you can see it in my portfolio => even more risky is having your balance sheet, retirement and job reliant on the success of your employer.

Switching Costs – AKA think carefully before you sell good assets

I have assets in my portfolio that I would not buy at today’s prices. Financial theory tells me I should sell these assets.

  • I have zero confidence in my ability to predict the future.
  • If I sell assets then I pay taxes and commissions.
  • After selling, I have to figure out where to put the capital.
  • I doubt any “new” plan will be better than my current plan, which is simple and low-cost.

Release yourself from constant optimization => good enough is good enough.

Put your efforts into being a better version of yourself.