Less Misery, More Efficiency

It’s been over 1,000 days since I realized that my relationship with email had to change. Not only was my inbox making me miserable, it was consuming my life.

What follows is a summary of how I spent three years changing my workflow and improving my life.

#1 – Reduce the fire hose of inbound flow by:

  • Using inbox-zero techniques
  • Making your default reply not more than two words long. For example, “got it” or “ok” work well. What works even better is my preferred response – “can I delete this message now.” Delete, delete, delete, delete, delete
  • If you’re in management at company that doesn’t use a threaded email client then you should be fired. If you don’t know what I’m talking about then switch yourself, and your company, to gmail.
  • Let others reply for you – wait a day before you dive into mass email threads.
  • Unsubscribe as much as possible – if it’s important then you’ll track it down. Once you unsubscribe to everything, you’ll realized that most of the internet is waste and noise.

Recognize that your subconscious mind is terrified of being out of the loop!

Until you remove it, you won’t see how the noise in your life is ruining your capacity for effective thought AND making you miserable.

If you can’t see it in yourself then look around. Most people are not informed – they are filled with useless, and ever changing, noise.

If you find that describes everyone around you then what makes you think you’re different? This was a powerful, and painful, realization for me. Email, social networks and constant connectivity were making me miserable AND clueless.

Once you’ve created the space to think…

2 – Improve your ability to retain information by:

  • Take one slow breath (in and out) before reading any email that you can’t delete, or unsubscribe.
  • Take two slow breaths before any reply that will extend beyond one line – you’ll find your composition is better.
  • Give the sender what they need and no more.
  • Take one slow breath and re-read every reply before you send it. You’ll be amazed at the number of type-os you catch.
  • Take an honest inventory of your productivity across an entire week. At best, you’ll be productive for three hours per day (broken up into 2-4 segments). Once you realize that you’re spinning your wheels go for a walk.

If you think the above sounds hokey then pay attention to how much you hold your breath when working, driving and waiting in line.

Walking is useful to consider, and compose, your best work.

3 – When you must do your best work:

  • Exercise early
  • Eat a healthy meal
  • Wear earplugs
  • Close the door
  • Shut the internet browser
  • Write it out by hand
  • Review when you transcribe it into your computer

Let’s review…

A – reduce the fire hose of inbound to create space for thoughts that matter and reduce the misery you’re experiencing with email

B – stop holding your breath and triggering irritation with your current habits

C – with a less cluttered mind, create a routine for producing high-quality work

The above will make you FAR more happy with your work life and this will make you a better employee, spouse, parent and person.

Living behind a screen, and the back-and-forth nature of email, reinforces habits of inefficiency. Once you start to increase your own free time, be proactive about not wasting other people’s time.

  • Schedule a telephone call for any email that will require more than three replies
  • When you set a call, specify two choices and a preference
  • In advance, send a written agenda
  • Take notes
  • Write (or review) a summary of the call

What I tell myself:

  • It’s incredibly hard to say no and reduce the background noise in our lives.
  • Keep chipping away.
  • Change is difficult but worth it.

Start to pay attention how your current work habits are making you feel.

Even if you are the only person that changes, it’s still worth it.

Be grateful that you had the courage to change!

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.

Working In Corrupt Societies

Two weeks ago I shared a list of questions that I’ve used consciously, and unconsciously, to make decisions when my surroundings didn’t make sense anymore.

Until I turned 30, corruption was something that happened to other people. Looking back, either I was the problem, or I was far too self-absorbed to take a look around. Probably a mix of both.


Cycling (today) is providing a case study of what happens when multi-generational corruption comes into the public domain.

We are reading frequent insider references to cycling being a corrupt society (Hamilton, Millar, Vaughters). Against this background, it is useful to remember that most elite athletes are good people. Within my own circle, I don’t know any evil cheaters – they are simply cheaters. 

How do good people create, sustain and cope with life in a corrupt society? Deciding that there isn’t a problem (triathlon) is one way. Another way to cope is to become part of a “solution.” Activists working to change a corrupt society are given a pass because we balance their good deeds against their continued participation in corruption. I’d point out that anyone cashing a check at the top of cycling is part of that society. Best to be honest with one’s self.

With truly good people, their goodness will drive them from corruption. Reading the cycling autobiographies, I was struck by how the lying drains the joy from cyclists’ hearts.

I don’t blame others for taking the money. As a young man, I had my price.

When I have set my price (via wins, money or recognition), I knew it was time to leave.


Identifying Corruption

Taleb writes that to see fraud, yet remain silent, makes us a fraud. It’s a powerful argument but, before speaking up, I like to think things through.

What should you do when you realize that your spouse, your boss, your business partner or your peers might be corrupt? Before taking action, I have some questions that I ask myself:

Look around and ask… Am I sure? – this question has saved me from many mistakes. Most of what I see in others in generated by something inside of me.

Look around and invert by asking… What is the likelihood that all these people are not corrupt? This method brings me clarity when faced with white lies and circumstantial evidence.

Consider the implications of no-action… If they turn out to be crooks, and I stick around, then what’s likely to happen to me?

Consider the breadth of corruption: is it local; is it in the leadership; or is it through the entire organization?

When I’ve been faced with difficult decisions, these questions have been extremely useful. I’ll share case studies over the next few weeks.

Skin In The Game

Sticking with the Antifragile theme, Taleb (and Gordon Livingston) write that honor flows from demonstrating courage when exposed to risk due to one’s beliefs. Taleb uses the example of enduring ridicule, and financial risk, for being true to his beliefs. 

Last summer, I listened to elites hammer on about the underclass not having skin in the game. This discussion seemed to lack justice but I wasn’t able to put my finger on an exact reason.

Having worked alongside the wealthy, I have experience with the problems of the rich. My move to the US gave me a chance to dig deeper into tax policy and I’ll be sharing some observations about that in future articles.

At the top of society, what does an honest person risk?

  • Size of main residence
  • Frequency, location and duration of vacations 
  • Number of years until retirement
  • Proportion of personal budget dedicated to luxury spending
  • Amount of capital passed to the next generation

Facing the above doesn’t require courage – no wonder extreme activities become popular in societies with wide income differentials.


In Taleb’s worldview, meaning comes from exercising courage with regard to one’s beliefs. I tend to derive meaning from the pursuit of excellence, working on my goals and meeting my obligations to my family. There’s not much personal risk in the way I roll through life, but it seems to work for me.

I enjoyed the Antifragile book, so I’ve been considering how I might be fooling myself. I’ve come up with a few areas.

As a 4th generation, first born, white male… the world has been skewed in my favor since birth. Listening, to my peers complain about the burdens of sharing society with their fellow citizens, demonstrates an ignorance of my reality. Seeing older versions of myself complain offends something inside me – my time in Asia taught me that I rarely have anything to complain about.

There is a disconnect between my reality and what the public is told about people like me. My effective (US) tax rate is similar to what I paid in Hong Kong. Having lived in Europe, Oceania and Asia – America is a low-cost, and very attractive, place to live and work.

Taleb makes the point that seeking to change the human condition is folly and warns against seeking to remove greed. He advises regulation to protect our societies from the effects of greed. Examples would be getting rid of banks that are too big to fail and applying criminal sanctions for white collar criminals. There have been a lot of examples in the news recently. HSBC banking drug cartels and Barclays fixing global interest rates. If a small institution took these actions then their directors would be going to jail, or at least losing their banking license.

Remember that we only see a portion of the corruption in our societies.

  • What do the financial scandals tell us about that society?
  • What does the USADA report tell us about endurance sport?
  • What lessons can we learn from these real-life dramas to make better decisions in our own lives?
  • When faced with an ethical choice, do we take the money or remain true to ourselves? 
  • Is it possible to do both?

I’ve spent a lot of time considering the above and my latest book shared a road map for how I live.

Before we publish on Amazon, my editor asked me to include the human side of how I arrived at my framework. Over the next few months, I’ll be sharing the stories that created my way of living.