Difficult Conversations

Over the last year, I have been travelling to learn about my friends’ lives. The trips are short, and we have the opportunity to talk a lot. By keeping the trip short, and going to my pals, the quality of the conversation is high and the inconvenience to my family is small. The trips have a large payoff for me:

  • Gratitude for the life I have
  • Learn what’s good about their lives – try to figure out the payoff from living like them
  • Make sure I see friends that I want to keep in my life
  • Learn about an aspect of their lives where they have different knowledge than me (teenagers, aging, the transition to adulthood, healthcare, performance psychology, grief & loss).
  • Do something random to generate new opportunities.

One of my favorite discussion topics is managing difficult conversations. For example, a challenging situation for doctors is telling the mirror image of themselves about the arrival of their greatest medical fear – cancer or terminal illness.

I ask questions about.. How to cope? How to be effective? What is best practice?

These skills are useful at work and are essential to create an exceptional family web. I’ll share what I’ve learned so far.

Before a difficult conversation, pause and remember:

  • This situation is not about me
  • I am part of the solution
  • Be cautious
  • Understand that I will make incorrect assumptions about everything around me

The points above get me in a relaxed frame of mind, especially when combined with my Big Meeting Protocol. The mental preparation works best when combined with an on-going process of self-reflection (that I like to do while cycling). You’ll be surprised that you can mute your emotional triggers by awareness that they exist.

Understand your hot bottons – examples might be: not caring, not doing enough, letting someone down, past mistakes where I’ve yet to ask for forgiveness, or not addressing areas in my own life where I need to make change.

Know your desired outcome – examples might be: clear communication, exit a relationship, create consensus, make better decisions.

Follow up in writing – if the conversation triggers fear, or anger, in the other person they are unlikely to remember the conversation. Even if you’re hearing each other, everyone hears a different conversation. Certainly, everyone remembers a different conversation.

Focus on helping the other person – I’m more likely to get my desired outcome if I help the other person achieve their own goals. A doctor might ask a terminally ill patient, “is there an up-coming event that we can focus on getting you to attend?” Alternatively, a family member might have concerns about public perception, confidentiality or independence.

Remembering my tendency to make incorrect assumptions – I like to gather information from the other party so I can better serve their needs. Often, a person’s needs are as straightforward as being listened to, respected and valued.

Finally, I remember that my mission isn’t to change others…

  • …because I don’t know best
  • …because I have my hands full with myself
  • …because my life is my source

28-days away from elite sport

Today is the four-week anniversary of my pause from focusing on elite sport.

For moral support, my wife’s been taking a 28-day break from Facebook . I think her break has been tougher because Facebook started an email campaign against her. I had a similar thing happen to me in 2010 and forewarned her that the spam-bots were crafty!

I’ve been Facebook free since the start of 2012 – it can be done.

My break has been 100% positive – I can’t find a single drawback to my life from pausing from professional sport.

Training – with less web usage (particularly twitter), I suddenly had time to train in the morning before my kids get up. While it was “only” one extra run per week, I felt great that entire day from the early session. It’s worth noting that 1 extra session per week, boosted 14% of my waking hours. Early training is high-return exercise.

Reading – I’ve been talking about reading at home for more than a year. I do most of my reading on airplanes and, subtly “blame” my kids for not being able to read at home. In the last month, I’ve managed to read three books at home, which is more than the previous twelve months! The books were: The Gift of Therapy; Living a Jewish Life; and Life’s Greatest Lessons. Turns out I was the issue, not my kids (who remain full of energy and a source of self-knowledge).

Patience – It could be the normal ebb and flow of parenting relationships but, as I reduce my time online, I’ve had more tolerance with my kids. Less in-bound noise seems to result in better relationships around me.

As for the outside world, Life Goes On…

My media filter isn’t complete and I heard all the major stories (and a few that haven’t hit the press yet). The difference is they filtered through gradually, rather than having to ferret them out. While I might be less informed on athletic gossip, I know enough to meet the needs of my friends, family and team. “Fresh news” is nearly always incorrect – I’m better off without it (links to my blog on improved thinking).

Turns out I was fooling myself about my need for constant input on, and criticism of, the choices of others. Not the first time.

Another debt of gratitude to my wife (links to my gratitude list).

The cost of the status quo is always hidden. I’m glad I was willing to try a change.

What’s Your Gifting Strategy

I love riding my bike with friends. To create more opportunities for that to happen, I give away a lot of cycling gear each year. When my friends wear the gear, I hope they think of me – even if they don’t think of me, it makes me happy to give gear away.

Here’s what I’ve learned about gifting…

It is an essential and effective way to influence behavior.

At some level, most of us feel that we deserve gifts. I need to be cautious about reinforcing entitlement in recipients.

The best gifts are items we can use while doing a favorite activity. An athlete-buddy of mine gave me a set of nordic ski underwear and gloves. I think she wanted me to learn to ski! I use her gift weekly and think about what a considerate person she is. The shirt makes me so happy (it’s my favorite color) that I wear it as casual wear. It’s not surprising that my pal scored a homerun with her gift, she’s a psychiatrist.

Gift frequency is better than size – for example 4 gifts of $250 generates more happiness than one gift of $1000. However, see habituation below.

Random is better than scheduled – I like random gifts. If I see something somebody will like, I get it and send it over to them.

Value is highest at point of award, not receipt – important to remember this for children, employees, heirs and other important people that you gift towards.

Consider my piece last week about Class Dojo, earning the ten points my daughter needs for a treat gives her more pleasure than the treat itself.

An example from the corporate world… At the private equity firm where I worked, the partners would award annual profit sharing points – there were 10,000 points available for each investment fund and we’d earn our share of 1,000 points annually. This system spread the allocation across many years, rather than having it back-end loaded when the investments were sold.

Things that people will use often, and associate with you are excellent – think about my friend’s gift of a shirt and gloves. To give me the same amount of pleasure she would have had to send me $5,000! A well-selected gift is worth far more than its monetary value.

Gifting to people’s children, ie via education, is deeply appreciated – parents have a sense of obligation towards their kids.

People (employees, spouses, kids, yourself) adapt very quickly to changes in standard of living, and forget how they got there. I avoid gifts that eliminate the self-esteem that comes from taking care of one’s self.

Be wary of reinforcing feelings of entitlement – for example, beautiful people and skilled athletes are trained that the world will take care of them. As they age, they experience pain when their gifts of chance (beauty and athletic prowess) fade.


Some people gift publicly for reasons of family, or corporate, strategy. Others prefer to gift anonymously. Considerations:

  • Be wary of the motivation of recognition.
  • If you ask your pals to support your causes then you will feel an overwhelming need to reciprocate (and you might not feel the same desire to support their causes). Of course, remember that it is OK to say “no.”
  • Most of us have small budgets for gifting – pay particular attention to situations where a little time and money can have a big impact.

If you need more of something then have a strategy to gift some of what you need.

A Tale of Two Brothers

A story that’s true across cultures and time.

Consider two brothers…

If, under pain of death, you were given a week to get a task done then you’d be wise to call the older brother.

However, if you were told that you only had a week to live, irrespective of what you did, then you’d be wise to call the younger brother.

Two brothers, two different sets of skills.

It’s important to learn from all aspects of our families and respect our differences. There’s much to learn from people that are different from ourselves.

Love you bro.

Antifragile Thinking – Nothing and Waiting

How can I use volatility to improve my investment decisions?

When I read Taleb, I’m tempted to go for the big bet using options with skewed payoffs. I think the real lesson is more straightforward than using out-of-the-money options, which is good because I’m not trained in derivatives pricing!

I have a favorite game that I play with any purchase. Determine value before I find out price. In the context of real estate (or buying companies), value the asset before you find out the asking price.

In 2009, I saw a “for sale” sign come up in my neighborhood. I played my game and priced the property in my head. Unfortunately, the property was listed at 25% over my valuation. So nothing happened, I waited, watched the property and the sign came down.

In 2010, the sign came back up and I checked the price. It was listed at a 40% reduction. Yay! I immediately put in an offer slightly below listing price. The owner countered my offer and we agreed a deal that everyone was happy with.

In 2009, I followed my investment mantras:

  • I don’t need to do a deal, I need to do a good deal
  • Let volatility do its work and create a situation to buy at an attractive price
  • My work is to build core capital, educate myself and be patient

My family needs one deal like the above per decade. Putting that in context, If the family is changing strategy more than one month in a hundred then we might be taking too much action. An “active” strategy would be anything that requires strategic change more than one month in fifty.

I don’t need advisers that earn fees when I take action. I need systems that prevent me from tinkering for no gain.

So the game is: deciding what I want, educating myself and waiting. Eventually, volatility will bring a great opportunity my way – at that point, I need to be willing to commit in size.

I tell my wife that was my strategy with our marriage – I also admit that I got lucky with her being better than I imagined. Elite swimmers have hidden options (loyalty, persistence, patience, internal motivation) and being OK with long term incremental progress.

To cope with the amount of “no action” inherent in the above strategy, I work on case studies, study history and, especially in relationships, improve myself.

One deal per decade.

Antifragile Thinking – New Old Ancient Nature

How can we use volatility to improve our thinking?

Rank the incoming information according to age – New Old Ancient Nature – if in doubt then choose the older option.

Remember that time will kill most ideas and concepts. Be willing to miss out on the latest/greatest – pay attention to concepts that are proven by time.

I coach a surgeon and his Dad was also a doctor. Now retired, the older doctor noted that “everything I learned in med school turned out to be incorrect.” Now clearly, everything wasn’t wrong! I would love to ask the doc, out of everything you learned, what was right?

We might get a list like:

  • Hygiene – do it
  • Blood pressure as leading indicator of a need for lifestyle change
  • Smoking – avoid it

Thinking back to my own education (economics and finance). What proved to be correct?

  • Track the cash
  • Interest rate trends
  • Mean reversion
  • Compounding

Another field that interests is endurance sport:

  • Consistency
  • Variable Stimuli
  • Strength and Stamina
  • Specific Preparation


  • Restrict the “new” – refined, processed, modified, engineered
  • Focus on the “old”  – ingredients your great-grandmother could have eaten

In a field that interests you, what are the three concepts that have stood the test of time? Focus on those concepts.

As you discover the power of this concept, you’ll benefit from reducing the fire hose of noise that reaches you daily via the media, advertising and social networks. These sources of info are “new” and. therefore, useless at best. More likely, they are misleading and reduce the quality of our thinking.

To improve my thinking, I need less noise in my head. “Not-thought” is what makes “good thought” clear to me.

Turning this on it’s head… if I can increase the amount of “no-thought” then the depth of my insight will increase and I’ll be able to see the useful info contained in what gets through. Implications:

  • Reduce email – a favorite from Taleb’s AMA is limit to 15 messages per day
  • Restrict media and eliminate the most noisy sources – television, chat forums, Facebook, reality TV, talk radio
  • Schedule breaks to settle mind (exercise, mediation)
  • Replace mental habits that clutter thinking
    • envy replaced by being happy for others
    • over-correction replaced by finding the good
    • Tinkering replaced by letting it ride
    • anger/fear/sorrow replaced by gratitude

I find that I don’t need to be charitable for the above to work. 

“Thank God, I’m free to act differently than that person.” triggers gratitude and let’s me move on.

Class Dojo – Promoting Good Behavior


One of our friends is a school teacher and set Lex up on Class Dojo. She created a class “Lexi” and shared the log-in with Monica and me.

It’s a simple system of positives/negatives. Each time Lex hits “10” she gets a treat. With the same log-in ID, we can access from all our our phones.

I got a little carried away with the negatives at the beginning and had to change my scoring focus. I target nine positives for each negative.

During the main transitions that I manage (drive to school and bedtime) I run through the positives that she has earned recently. I’m trying to remind her of those behaviors. Getting dressed, seat belts, pajamas, playroom clean up, kind to brother…

I also put myself into her class so she can “beat me” with her behavior. Perhaps we need to loosen the standards for Daddy Byrn. I’ve been at one point for over a week…

Towards An Antifragile Life – Living With Volatility

I’d encourage you to read Taleb to experience the hero, and anti-hero, directly. Acting on his books saved me from personal bankruptcy. I owe him much of my personal freedom.

Separate from his tips for financial living, what are the lessons that I can bring into my larger life?

Don’t Tinker, Let My Winners Run, As Much Nothing As Possible – I blow at least $10,000 a year forgetting these points. My sin is neglecting the benefit of “no action.” Every year:

  • I cost myself money by tinkering with my winners
  • I waste emotional energy by getting involved in situations that will work themselves out with my help
  • I spend goodwill via over-correcting the people close to me

The tip about letting my winners run is so persistent in my investing errors that I’ve sent myself an email that I see every time I log into gmail. The other email is designed to make me a better man.

Inbox Almost Zero

Inbox Almost Zero

Maintain Personal Freedom – Taleb’s style is about freedom. Freedom to do what he wants. Freedom to say what he wants. I get that. I need to be cautious with choices that restrict freedom.

Debt – my family has one loan, a mortgage on a house that I could leave and rent for more than my mortgage/insurance/taxes.

Taleb, and others, challenge conventional wisdom about the use of debt, particularly with regard to College. My wife and I left college debt free and that colors our judgement. Friends of mine, that are doctors, talk about debt-free doctors being able to “do medicine right.” Statements like that, bring home Taleb’s advice to use as little medicine as possible.

Pay For Optionality & Avoid Open Ended Commitments – I’ve made both necessary, and ill-considered, commitments in my life. I pride myself on reliability so feel pain when I’m falling short on a commitment, or need to exit. As a result, I’m willing to pay a premium for flexibility and accept less success to avoid long-term attachment. The pain I feel is an Anglo-Saxon cultural phenomenon, in some Asian cultures, it is expected that relationships will change with circumstances. I smile when I think about Northern Europeans doing business in China and India.

Relationships – Taleb is big on parties, especially ones with lots of different interesting people. My goal at a party, if you can get me to go, is simple. Avoid being the most boring person there! I’m selling myself short. While it would help, the solution isn’t to liven up. The solution is to understand that exposure to many different people is helps create a life with meaning and opportunities to use our skills to help others. Networking is about using volatility to our advantage and the most valuable form of networking is having fun while sharing a mutual interest. I’ll go a far out of my way to share a bike tour with a buddy! I’ve made most of my best friends while exercising!

Insurance & Legal Structuring – insulate yourself from the improbable via insurance and appropriate legal structuring (links to blogs that tell you what I actually do).

Toxic People – have you considered the emotional payoff profile of the people that are close to you? Taleb talks about asymmetric outcomes in the financial sphere but far more common is the downside associated with certain individuals. Some people have a poor payoff profile and others consistently make me feel fantastic.

Think about the people you spend time with – how do they make you feel about yourself? Create space for great people by ditching the toxic folks.

By the way, if you’re truly courageous then think about how you make other people feel about themselves – especially people that have no recourse against you. Too often, I come up short here! When I’m tempted to criticize, I ask myself three questions:

  • What are my goals here?
  • Will criticism serve my goals
  • How am I making this person feel?

Taleb rails against bankers and senior management. Speaking as an insider, he is 100% right about how those sectors operate. The deck is stacked, and will remain stacked, in favor of the insiders.

If you find yourself in senior management, or finance, then think back to what was “enough” when you started.

Too often, the compromises associated with success are the seeds that create Black Swans in our personal lives.

Should I Sell My House

Spring has seen a surge in the Boulder property market. As a result of the surge, many locals are considering selling their homes, or investment properties. I am going to share how I try to make better decisions with real estate.

First Step: Gather Information

Start with a family budget that lays out expenses and revenues for the next twelve months. Once created, budgets are easy to maintain.

A technique that I use as a budget reality check is comparing cash that leaves our family bank account (for a month, or a quarter) against our projected expenses. Over the years, I’ve had some surprises by comparing “cash out” to budgeted expenses.

The next step is gathering income and expense details for your key assets. In my family, we make this easy for ourselves by having a separate “house account” which pays out everything that’s house related. In my property business we track everything by property.

To help you out, page 55 of my recent book has a list of expenses as well as detailed case studies for various types of property investments.

If you resist pulling this information together then consider if you are seeking to hide something from yourself. I’ve been known to resist gathering information when it might contain bad news!

Step Two: Pull the information together for the target property.

Here’s an example from where I used to live. I’ve adjusted the figures to reflect expenses per $100,000 of house value.

If I rent the house then I have to pay:

  • Rental Agent Commission – $321
  • Insurance – $180
  • Taxes – $677
  • Maintenance – $136
  • Furniture Removal – $85
  • Mortgage – none for this property
  • Utilities – tenant pays
  • Damage & Hassle – possibly material, property is in excellent condition and ready for sale

Against that I have a rental projection of $5,145 per annum (per $100,000 of house value). Round numbers, the property is forecast to yield 3.7% [(5,145 less 1,399) divided by 100,000].

If you have a mortgage against the property then remember to consider the return on investment with, and without, your mortgage.

  • Yield on valuation – take your net profit before interest and divide by the net value of the property (after sales commission and capital gains tax)
  • Yield on equity – take your net profit after interest (exclude the principal amount of your mortgage payment – only include interest) and divide by the net equity that you have in the property

To illustrate, if there was $40,000 of debt per $100,000 of value then the interest payment would be $1,400 at a mortgage rate of 3.5%. The net profit after interest would be $2,346 on $60,000 of equity (3.9% net yield on equity).

Step Three: Consider Big Picture Questions

What will I do with the equity if I sell? For many of us, housing is a form of forced savings. If we had the equity sitting in a bank account then we might be tempted to spend it. If you are thinking about switching to another property investment, then you’re likely to do best by staying put. Property has very high transaction, and switching, costs (due to real estate commissions).

How often can I sell this asset? Certain assets, such as vacation homes, boats, luxury goods, can only be sold in good market conditions. This creates a paradox because your best window to sell will be when you’re tempted to hang on to the assets. If I want to sell then I remind myself to leave something in the deal for the buyer.

Where will you live? If you are thinking about selling your main residence then be clear about where you will move, and the expenses associated with your new location. Generally speaking, prime markets are the first to respond to an uptick. For example, the Boulder market saw this recent surge a year after Palo Alto ticked up. Secondary Colorado markets might take another year to see improvement. What’s been happening in your next location for the last year, how does that compare to your home market?

As an example, the value of my old house now “buys” 30-35% of the square footage in Palo Alto vs Boulder – it used to buy 50-60% of the square footage. When moving between cities, states and countries, timing plays a key role with purchasing power. When moving “prime” to “secondary” – it is possible to get priced out of a market. I’ve seen examples of this in the San Francisco Bay Area, London and Vancouver. If you sell out of a prime market then values can rise and make it very tough to buy back in.

What does your current mortgage, insurance and taxes “buy” if you were to shift to a rental unit? I like to compare own vs rent. My current house would cost me $1,000 per month more to rent than to own. This is a function of the down payment I put down and covered in my article on Mortgage Debt As Inflation Insurance.

What’s your tax exposure ? Agent’s fees and realized capital gains can make moving from owning to renting less attractive. As a landlord, being able to depreciate the house (but not the land) will reduce the taxable income generated by the property.

Three final questions that I like to ask myself:

  • Can I afford to be wrong?
  • What happens if I do the opposite?
  • Under what scenarios does my preferred choice become a really lousy decision?

For now, my decision has been to continue to market my old house for sale. However, the yield from renting it out, rather than selling, is compelling.