Getting My Affairs In Order

In March, I shared a family legal structure. Even with that structure in place, there will be significant admin for your family to sort when you pass. This admin will hit your spouse and children when they are least equipped to deal with it.

Given that people are useless at administration when they are grieving, how can you make life easier for your family? 

Simplify possessions, portfolios and personal legal structure. Almost everything we have will be sold, donated or disposed. Streamlining yourself, in advance, is an act of love that will save your kids days and weeks of effort. If you have mementos that are special to you then sit down your kids, and grandkids, for storytime. Use the pictures and personal effects to make your history, their history. Without this effort, your memories will end with your passing. Your kids will treasure their memories when you pass. 

Brief your successor(s) – consider the roles that you play in your family (financial, administrative, emotional), who’s backing you up? Do they know it? Have you explained their role to them? Do your successor(s) have written plans and checklists to work through? It’s far easier to update an existing plan than to create one when you’re under the stress of an unexpected event.

Establish A Joint Operating Account – Start with a joint operating account with your spouse. As you age, consider a joint account with your most reliable adult child. In my family, at least half of us have bodies that outlive our minds. It’s very likely that I’ll need to hand off to one of my kids at some stage.

Consider Medical and Financial Powers of Attorney – These roles require different skill sets – consider splitting. Have an honest conversation with the individual you’re considering to help you out. Are they willing, and able, to fulfil their role.

Consider Probate – If you died today then would your estate require probate? What are the costs, and disclosure requirements, associated with probate in your locale? Are you OK with that? What are the steps necessary to avoid probate?

Clear Instructions – make your Will crystal clear, simple and easily available when you pass. Brief your executor, and personal representative, well in advance.

Proactive Disclosure – Hold meetings with your financial/admin attorney, your medical representative and your spouse. I’m 44 and have a quarterly state-of-the-family meeting with my succession team. Not because I expect to die anytime soon, rather as an insurance policy to lessen the blow on my loved ones if I’m taken out at short notice.

Sorting the above doesn’t make coping with death easy, but it does go a long way towards reducing the chance that your survivors are overwhelmed, or ripped off.

Be very careful with financial powers of attorney and signing rights over your assets. I’ve seen fraud within families and between lifelong friends. Establish structures that limit the ability to one corrupt individual to hurt your family. Remember that even competent people make mistakes.

When you think you’ve got everything sorted – try explaining it to a trusted friend. Once you’ve explained it to your pal, have them explain it back to you. I guarantee you’ll learn something.

Three tips for estate planning:

  1. Say what needs to be said, today.
  2. Be a hero now, not when you pass.
  3. You’ll get the greatest satisfaction from sharing gifts (in person) with the people you love.


Denver Bar Association: what to do when someone dies

Colorado Bar Association: personal representative and trustee under probate

Two Luxury Vacations

In each of April and May, my wife and I left the US (and our three kids) for about a week.

While it is cheaper to leave the kids at home, our childcare bill for a week away is massive – roughly equal to what we spend on all other aspects of the trip, combined.

A friend jokes that spending money to strengthen your marriage is cheaper than a divorce but it’s still a heck of a lot of cash to have flow out the door.

Given my primal, subconscious, and frequent urge to flee, I know that I’m likely to keep fooling myself about the need to “get away.” 20 hours of planes, trains and automobiles on the return leg from Italy gave me a chance to take some notes.

What Is A Luxury Experience?

Early in the vacation, I was trying to put my finger on what made the hotel feel luxurious. I came up with:

Ease of exercise (swim, bike, run) – the hotel where we stayed had multiple scheduled rides each day, all seeded by ability, all guided.

Ease of laundry – the hotel offered overnight laundry service (included in room rate) for all our training gear.

Ease of eating – the hotel catered three meals per day with a wide selection of healthy foods, and a ton of veggies.

Coffee – high quality Italian coffee for breakfast and one (or more!) cappuccino stops on every single ride!

People – Marina and her staff are extremely friendly and enjoy helping guests have a good time. They care about the little things and are genuinely happy to see the guests.

Friends – I had a chance to spend time with existing, and new, pals who enjoy living the same way as me. This was the #1 lesson for me – it is worth making an effort to meet new people and spend time with successful leaders. This is the one aspect that is tough to re-create at home, multiple days of having fun with friends.

Bedtimes – I was relieved not to have to put my kids to sleep for a week. We are going to rejig our bedtime duties so we rotate our exposure to the kids – might prove better for everyone.

Unscheduled afternoons with my wife – Monica and I rarely spend an unscheduled afternoon with each other. We should. This time together was the best part of the vacation.

When I wrote the list down, I realized that I could re-create all of the above (minus Marina and her team) at home. I simply have to get organized. Further, the money that I spent in 8 days would buy 50 similar days at home. Somehow a luxury vacation “feels” better but a ratio of 50:8 shows how I fool myself.

Until the flight back from Italy, I had been thinking that it would be nice to get away quarterly and focusing on reducing the cost of our childcare when we travel.

Much smarter to apply the lessons every-single-week at home.

Living at home makes it much more likely that I’ll maintain what’s good with my life. Being ruthlessly honest I noticed the following about my week away:

  • I drank a month’s worth of booze
  • I consumed ten weeks (!) worth of sugar, and had the headaches to prove it
  • My kids start to suffer when both of us are away for more than five days
  • Training fatigue triggers feelings of entitlement for: anger, stress, gluttony and excess

Naturally, all of the negative implications were easier to see in others than myself… another example of fooling myself.

The key lessons:

  • Make time, to spend unstructured time, as a couple
  • Consider what you really enjoy about being on vacation
  • Build “luxury” into your daily living
  • The toughest part of improving my life is creating the space for change
  • Once a week, free yourself from the self-imposed tyranny of scheduling

Upon getting home, my first restructuring act was to collapse three working trips into a single visit where everyone came to Boulder.

Let’s see if we can build these lessons into our family plans for the next 18 months.

A Death in the Family

I spend my working life with high achievers that are used to being in control. These individuals are used to getting stuff done and sorting things out. They are the doers of our society.

Because death can appear to lack a solution, it is a challenge to a high achiever’s identity. Overlay the reality, that our own time is coming, and it’s not surprising that we feel overwhelmed.

Interestingly, there’s no quicker way to pull the energy out of a room, or conversation, than talking about my experiences with death. It’s one of the strongest, deepest emotional triggers (for avoidance) that we have. Even my pals that are doctors and chaplains, become visibly uncomfortable with these topics – the well-adjusted have subtle tells, but they remain. We share a deep avoidance of the topic of death.

Here’s what I learned over the last few months of watching a family cope with the death of a parent.

Death strips our filters away – the dying person as well as their closest family. This can be terrifying to consider, the world seeing our minds laid bare. We have nothing to fear because our fears are universal.

I found it inspirational – because what lay beneath all the filters was a very accepting person. A life, well lived, brings a sense of peace at the end.

Next I was grateful, because I have the time to continue to sort myself out. I can offer my children a powerful gift by demonstrating how to cope when it’s their turn.

With the curtains pulled back, and facing an ultimate source of power, everyone trended towards their automatic, and deepest, programming.

Death, and dying, are powerful – they aren’t good, bad, angry, scared, fearful, or anything else – the emotional interpretation of their power comes from within us. If we can pause, even briefly, to consider what/how we are feeling, there is a tremendous opportunity for learning.

For example, I learned that my deepest emotional response is “flight.” Faced with the power of dying, pressure would build inside my body and I’d have an overwhelming urge to ride my bike uphill to release that energy.

By the way, I followed my urge to ride over the last two weeks and it was deeply therapeutic. I gave a spontaneous solo eulogy to myself every ride for week.

In my emotional life, breakdown, sadness, fear and anger are signs of resistance, an internal blockage that needs to be opened. Exercise provides me with a physical mantra to open myself and release energy before it solidifies into emotions.

Another member of my family lives cerebrally. She found that pressure would build in her head. To process, and release, her energy – she engaged her mind on a family-related history project.

Every member of the immediate family found their capacity to think, and remember, was impaired. For some this lasted for weeks, others for days. Don’t expect to get anything achieved when you’re grieving. Ask for help.

To become an outstanding athlete, I needed to process my emotional history. Or perhaps it was processing my emotional history that’s enabled me to deepen my capacity for success. I’ll never know for sure, but I’m grateful for the lessons of sport.

Many high achievers use performance to mask, rather than cope with, their emotional histories. If that’s the case then you’ll find a unique opportunity for growth as you move through the process of grieving.


Recommended reading:

Grannie’s Bystander Problem

I played a central role in managing my grandmother’s care over the last two years. Here are some thoughts that might help you and your siblings.

It’s better for everyone to have ‘the conversation’ before it is required. Most families lack plans, or skills, to deal with their elders’ passing.

A – each elderly person needs a champion. By champion, I mean a leader, not an owner, of a situation.

B – the champion’s role is to co-ordinate care by the family, and outsiders. In our family, reflecting different skills, we split the financial/admin support from the emotional/medical support. This split works very well.

C – be careful not to ‘own’ an elder. Use caution with commitments that might impair your ability to meet the needs of your spouse and kids. Don’t become a casualty, emotionally or financially.

The highest achieving, or most emotionally giving, can be tempted to move the elder into their house. This can be great, or a disaster, we’ve seen both outcomes in our family. Often from the same situation, but different perspectives (grand kids vs spouse).

D – be open with what needs to be done and ask everyone to contribute a little bit.

E – geographical spread costs time and money. My family lives all over the world, there is a large, mostly hidden, potential liability due to our spread.

Because the problems of the elderly (health, loneliness, death) are difficult to resolve, many people don’t bother to try. That’s a shame because you’ll never regret a small kindness but you might regret not making any effort at all.

A friend shared with me that, in death, she didn’t have anything to offer her parent. The earlier relationship had been unhealthy and she’d decided to end the cycle of pain in her family. She was getting push back from her family to engage but couldn’t bring herself to do something that lacked authenticity.

It reminded me that sometimes our role might be to take the blame as others deal with their grief. Being a father gives me many opportunities to chose what I think is best, rather than expedient.

As a parent, I hope to teach my kids to improve a little bit on the legacy I pass to them.

With powerful emotions, write down how you’re feeling. Time will reshape your memory and you may want a record of why you made your decisions, especially if you have a habit of regret.

The following were central lessons:

As the end nears, small kindnesses have large impacts.

Everyone contributes based on their own capacity.

Don’t keep score.

Your community likely has resources to help you manage. Ask for help.

Our actions train our families to manage our own decline.

Preserve dignity as long as possible.

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.

Mentors and Peers

How can I stack the deck in favor of being a good guy?

First, I try as much as possible to get positive influences to visit me.

Second, I’m willing to travel to hang out with people that are what I’d like to become. Back when I was an elite athlete, this drove my travel schedule. These days I travel less but it remains a big chunk of my year.

My family allocates 14 weeks per annum for my travel.

  • 4 weeks of that is my wife and me
  • 2 weeks is used for continuing education
  • 8 weeks is for my own uses – these days split between non-Boulder family visits and personal trips, mainly to ride.

My daughter joins me for two weeks of the above and we do another two weeks worth of in-state travel together.

Pulling it together, I have a job description that gives me 16 weeks per annum of variation from my normal routine.

Before my daughter was 2 years old, this allocation would roll between 30 and 40 weeks per annum. As I’ve simplified my life, and released my expectations for triathlon greatness, I feel more free with less travel.

In considering a trip, I ask myself three questions…

  1. Are the people that I will see infused with goodness?
  2. How do the people make me feel?
  3. If I turned out like these folks, would I be ok with it?

There are plenty of people, and companies, who pass the test. Make a note when you meet these people and keep them in your life. 

While its tempting to vacation in, say, Vegas, we are more likely to generate success by keeping the goodness in our lives. For the key relationships (bosses, mentors, clients, peers) visiting on their home ground will broaden your understanding, and keep you humble with your capacity to predict. The on-the-ground situation is nearly always different than I imagine.

The focus on “the good” is an ethical litmus test. I’ve caught myself valuing winning over kindness, an occupational hazard if you’ve spent time in a field (sport) that values relative performance. I’m also prone to errors of judgement due to wealth and beauty.

Choose Wisely.