Things I've Learned and Loved in 2008


Training in horseback archery in Nikko, Japan. (Photo: David West)

2008 has been one of the most exciting years of my life. I did more dealmaking and met more people than in the last 5 years combined. This produced many surprise insights about business and human nature, especially as I uncovered tons of my own false assumptions.

Here are some of the things I learned and loved in 2008. I’ve linked to posts that I wrote when exploring some of the concepts in more detail…

Favorite reads of 2008: Zorba the Greek and Seneca: Letters from a Stoic. These are two of the most readable books of practical philosophies I’ve ever had the fortune to encounter. If you have to choose one, get Zorba, but Lucius Seneca will take you further. Both are fast reads of 2-3 evenings.

Don’t accept large or costly favors from strangers. This karmic debt will come back to haunt you. If you can’t pass it up, immediately return to karmic neutrality with a gift of your choosing. Repay it before they set the terms for you. Exceptions: ubersuccessful mentors who are making introductions and not laboring on your behalf.

You don’t have to recoup losses the same way you lose them. I own a home in San Jose but moved almost 12 months ago. It’s been empty since, and I’m paying a large mortgage each month. The best part? I don’t care. But this wasn’t always the case. For many months, I felt demoralized as others pressured me to rent it, emphasizing how I was just flushing money away otherwise. Then I realized: you don’t have to make $ back the same way you lose it. If you lose $1,000 at the blackjack table, should you try and recoup it there? Of course not. I don’t want to deal with renters, even with a property management company. The solution: leave the house alone, use it on occasion, and just create incoming revenue elsewhere that would cover the cost of the mortgage through consulting, publishing, etc.

One of the most universal causes of self-doubt and depression: trying to impress people you don’t like. Stressing to impress is fine, but do it for the right people — those whom you want to emulate.

Slow meals = life. From Daniel Gilbert of Harvard to Martin Seligman of Princeton, the “happiness” (self-reported well-being) researchers seem to agree on one thing: meal time with friends and loved ones is a direct predictor of happiness. Have at least one 2-3-hour dinner and/or drinks per week — yes, 2-3 hours — with those who make you smile and feel good. I find the afterglow effect to be greatest and longest with groups of 5 or more. Two times that are conducive to this: Thursday dinners or after-dinner drinks and Sunday brunches.

The two blog posts whose principles I’ve practiced the most in 2008: The Art of Letting Bad Things Happen (from 2007)
; The Choice-Minimal Lifestyle: 6 Formulas for More Output and Less Overwhelm (from 2008)

Adversity doesn’t build character; it reveals it.
(Suggested reading: How to Test-Drive Friends)

Related: Money doesn’t change you; it reveals who you are when you no longer have to be nice.

Total Immersion swimming
(Suggested reading: How I Learned to Swim Effortlessly in 10 Days)

It doesn’t matter how many people don’t get it. What matters is how many people do. If you have a strong informed opinion, don’t keep it to yourself. Try and help people and make the world a better place. If you strive to do anything remotely interesting, just expect a small percentage of the population to always find a way to take it personally. F*ck ‘em. There are no statues erected to critics.

Related: You’re never as bad as they say you are. My agent used to send me every blog or media hit for The 4-Hour Workweek. Eight weeks after publication, I asked him to only forward me positive mentions in major media or factual inaccuracies I needed to respond to. An important correlate: you’re never as good as they say you are, either.

It’s not helpful get a big head or get depressed. The former makes you careless and the latter makes you lethargic. I wanted to have untainted optimism but remain hungry. Speaking of hungry…

Eat a high-protein breakfast within 30 minutes of waking and go for a 10-20-minute walk outside afterward, ideally bouncing a handball or tennis ball. This one habit is better than a handful of Prozac in the morning.
(Suggested reading: The 3-Minute Slow-Carb Breakfast, How to “Peel” Hardboiled Eggs without Peeling)

I dislike losing money about 50x more than I like making it. Why 50x? Logging time as an experiment, I concluded that I often spend at least 50x more time to prevent a hypothetical unit of $100 from being lost vs. earned. The hysterical part is that, even after becoming aware of this bias, it’s hard to prevent the latter response. Therefore, I manipulate the environmental causes of poor responses instead of depending on error-prone self-discipline:

I should not invest in public stocks where I cannot influence outcomes. Once realizing that almost no one can predict risk tolerance and response to losses, I moved all of my investments into fixed-income and cash-like instruments in July 2008 for this reason, setting aside 10% of pre-tax income for angel investments where I can contribute significant UI/design, PR, and corporate partnership help.
(Suggested reading: Rethinking Investing – Part 1, Rethinking Investing – Part 2)

A good question to revisit whenever overwhelmed: Are you having a break-down or a breakthrough?

Rehearse poverty regularly — restrict even moderate expenses for 1-2 weeks and give away 20%+ of minimally-used clothing — so you can think big and take “risks” without fear. (Seneca)

A mindset of scarcity (which breeds jealousy and unethical behavior) is due to a disdain for those things easily obtained. (Seneca)

A small cup of black Kenyan AA coffee with cinnamon on top, no milk or sweeteners.

It’s usually better to keep old resolutions than to make new ones.

Chloe Sevigny. ‘Nuff said.

To bring in a wonderful 2009, I’d like to quote from an email I received today from a mentor of more than a decade:

While many are wringing their hands, I recall the 1970s when we were suffering from an oil shock causing long lines at gas stations, rationing, and 55 MPH speed limits on Federal highways, a recession, very little venture capital ($50 million per year into VC firms), and, what President Jimmy Carter (wearing a sweater while addressing the Nation on TV because he had turned down the heat in the White House) called a “malaise”. It was during those times that two kids without any real college education, Bill Gates and Steve Jobs, started companies that did pretty well. Opportunities abound in bad times as well as good times. In fact, the opportunities are often greater when the conventional wisdom is that everything is going into the toilet.

Well…we’re nearing the end of another great year, and, despite what we read about the outlook for 2009, we can look forward to a New Year filled with opportunities as well as stimulating challenges.

Happy New Year everyone!

Goofing around at a maid cafe in Akihabara, Tokyo. (Photo: David West)

Posted on: December 31, 2008.

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181 comments on “Things I've Learned and Loved in 2008

  1. I started swimming again last year and find it an excellent exercises.
    Really profound comments right there about not having to be nice.

    Regarding a walk outside – I do that during the summer and spring and its a fantastic way to start the day off.

    Happy Belated New Year


  2. This is late and probably one of the last posts but I had to say that I have found Seneca and understand why you have quoted him regularly in your book and on this site. Very good.

    After coming to the realization that I need to change some things in my outlook, reading Seneca and The Magic of Thinking Big has been like a big slap in the face. A great wake up call. There are so many great things to look forward to and start today.

    Thank you so much for the recommendations.


  3. Tim,

    You are wrong about leaving the house, unrented. Just sell the house or rent it out. I will greatly increase your energy, you spend in thinking consciously/unconsciously about the house unused.

    Also, it voilates all your earlier principles of having less clutter.


  4. Tim, as always thank you for the great motivational insights. I too reflect back on 2008 with many lessons learned, both good and bad, and yet each contributing to my overall growth. I keep up reading your blog and have read through your book more than 3 times, good stuff, especially about theory of time, money & foreign economic strategies. I also signed up for a new virtual assistant service called Red Butler to help me outsource my tasks. They’re based in the US and take care of a lot of my day to day tasks. I look forward to seeing what you have planned in 2009, and please keep posting pics. The picture of you and the maids in Japan rocks!

    KP -


  5. Hey Tim
    I find you interesting.
    Ive read your book and found it stretching and liked that.

    I was thinking – with your energy, intelligence, amount of spare time etc what an incredible amount of value you could add to an agency that helps people.
    Why not volunteer for some worthwhile cause – I think you and many more people will benefit from it than a very well put together chair review.

    It would be incredible to see what you could accomplish if you fell in love with helping people.
    Saying that – you have definitely encouraged me to work smart and free up time so that i can contribute to lives that need.

    All the best


    • @James from S. Africa,

      Hi James! I have fallen in love with helping people, specifically with education. Just search “Donorschoose” “litliberation” or “karmic capitalist” on this blog to see what I mean.

      All the best,



  6. Hi James,

    I think it’s possible that you don’t see the true value of “a very well put together chair review”. Let’s suppose that Tim would like to help all mankind as much as possible. And we know that he has a brain. It might even be the “best” brain.

    So does that mean his talents should be used to directly help every person in need? Or would they be better used to help other “powerful brains” or potentially PBs get into the position of being as capable of helping others as he is?

    To be as capable as he is, he has had to solve problems that any human might face in a similar situation. The importance of these solutions in allowing any of us to become super productive should not be underestimated, and I personally appreciate his sharing deeply.

    How about you? Wouldn’t your time be better spent increasing your power/brainpower to the point where YOU would have the “energy, intelligence, amount of spare time etc” to add “an incredible amount of value” … “to an agency that helps people.” rather than thinking about what Tim should do?


  7. Tim, I’d get overwhelmed by the stuff I have to do then I’d remember your site… it puts me back on track by reminding me that life and work don’t have to be such a drag if you are conscious about having other things besides work.

    Thanks again.

    By the way, please answer Kristie Wolfe’s question! :)


  8. From very powerful takeaways in the post. I especially liked your mention of Slow meals = life. I have found that I tend to feel better when I take at least once a week to do this.


  9. Hi Tim, hi All!

    Short question: is it OK to play with the Rubik’s cube during the morning walk? Does it replace the ball bouncing sufficiently?

    All the best to everyone!



  10. Tim,

    I am preparing for an extended trip to Sri Lanka as I asked the magic question from my employer – can I work remote? Yes – Great – sell everything and taking off in 28 days. – Thanks and Have a great life.



  11. I’ll be in China/Japan Japan this summer and I’m dying to do the horseback archery in Nikko. Is this something they offer or did you pull some strings to try it? Thanks!


  12. Hi Tim,

    I had to run away from domestic violence with my 3 month-old baby girl. I had to start again from zero. I have just finished reading your book and it gave me so much motivation and strength to do anything I want and take care of my little one. I´m already working on my business idea, I´m going to implement automation so that we can finally start enjoying life and start smiling again. Thank you for great ideas and inspiration…


    • Best of luck to you, Monika :) There are many like-minded people here, so I hope you stay part of the community! Definitely also visit the forum, where a lot of people share their successes and advice.


  13. Tim,
    Love your thinquing, and writing style… but then I love to laugh as I learn :)
    Especially loved this one: “You don’t have to recoup losses the same way you lose them.” It’s typical of your ‘outside the box insights’ that makes so much sense once you recognize it. Now off to check out the two blog posts whose principles you practiced the most in 2008… as I’m sure they’ll be as timely for me as this was (2 years after you wrote it!).


  14. I have learned some essential things through your website post. One other stuff I would like to talk about is that there are lots of games out there designed mainly for preschool age young children. They incorporate pattern acknowledgement, colors, animals, and forms. These generally focus on familiarization as an alternative to memorization. This keeps little children engaged without having a sensation like they are studying. Thanks