Four Ways to Cultivate Good Luck

Luck plays a major role in the outcome of a company and of one’s life. Part of luck is just pure chance, completely out of your hands but luckily luck can be cultivated as well. Here’s how:

1. Show Up and Make Motion

“Eighty percent of being successful in life is showing up” Woody Allen

A lot of opportunities that are seemingly random, are at least partly the result of showing up and/or making motion. People often say that an opportunity was the result of being in the right place at the right time. That sounds like pure chance (uncontrollable chance) but you can maximize your chances of being in the right place at the right time by visiting many good places many times. While you cannot know for sure what will be the exact right place, you can make sure to get out there and find ways to meet high quality people. Life is like a sales funnel, you have to take as many shots as possible and stuff the top of the funnel with as many potential “leads” as possible. Looking forward, it is impossible to know what will come of this but what is for sure is that you are opening up more potential possibilities and you are bound to get lucky at some point. This motion will introduce you to new ideas and opportunities.

There is a reason why being persistent is so important for startups. You will have to keep trying things and deal with failure over and over again but you will have to keep going and making motion. This motion maximizes the chance that something will work out. Yes, it will be partially luck when things go well but usually it takes a lot of work and stirring the pot to get there.

2. Be Prepared

“Chance favors the prepared mind.” Louis Pasteur

Great opportunities are rare. One needs to be prepared to seize them when they come. Having a deep expertise in at least one field and diverse knowledge in many areas will help prepare you. On top of the knowledge, you need work experience in order to prove yourself and further develop your skills. Being prepared is partially skills and knowledge based, but it is also part mentality and world view. The prepared mind is constantly putting its feelers out for opportunity. Being prepared is the readiness to pounce when an opportunity is presented.

It was widely known fairly early on that Google was on its way up like a rocket ship but it was also extremely difficult to land a position there. Yes, the early Google employees got lucky, but they had the high-quality and rare skill-set that allowed them to have the ability to join Google. While it is unlikely that you will be an early employee at the next Google, being prepared will open up a whole new set of possibilities.

3. Be Distinctive
Have a unique skill set and set of interests. This will allow you to have a different view of the world and way of looking at problems. This often leads to the ability to solve problems that others can’t see the solution to and foresight into concepts before others can understand them. Marc Pincus had to have a deep experience in social networking ( and a deep interest in gaming to have seen the potential of Zynga. Dennis Crowley had a deep interest and a ton of experience in mobile way before the space became hot, helping him make foursquare. Jack Dorsey’s understanding of real-time and the importance of location through his experience trying to build a taxi dispatch company helped him formulate the idea for twitter. In the words of Steve Jobs “You can’t connect the dots looking forward; you can only connect them looking backwards.” That being said, fostering a set of distinctive dots and searching for unique ways of connecting them can only help one identify and understand opportunities as they arise.

4. Take Chances

“Fortune Favors the Bold” Virgil, Aeneid X.284 and one of Mark Zuckerberg’s favorite quotes

Choose high-risk, high-reward paths when it is possible. While this approach can potentially lead to failure (which is a learning experience), it can also lead to great outcomes. People will debate whether such an outcome was luck or skill, but what is for sure is that such an extremely positive outcome would not be possible without taking the risk. While it is still important to weigh opportunity cost and taking big risks may not fit some personality types, it is definitely one way you can increase your chances of being lucky. Especially when you are willing to take chance after chance and can learn from each risk you make. The media loves to share the story of the lucky overnight success. Though in reality, most overnight successes are really ten years in the making.

This post was inspired by this post by Marc Andreeson and the work of Dr. James Austin.

Beware of Local Maxima

Site owners often A/B test the design of their websites with the goal of increasing the conversion rate of sign ups or sales or some other metric. Site owners often can encounter local maxima. Local maxima are, as the photo demonstrates, like the peaks of small mountains when there are larger mountains surrounding the point that you are at. One interesting feature about local maxima are that in order to leave one, you have to make steps backwards for the chance to get to a better point. In the real world, you can not be sure whether a local maxima is also a global maxima (the highest of all possible points) or not. Even with the possibility that a local maxima is also a global maxima, it is often still worth testing a handful of divergent design ideas and then trying to refine them so that you may discover a higher peak and increase the conversion rate for your site.

This concept is metaphorical to many things in life. We may be stuck at local maxima and will need to explore to potentially find higher maxima. Unfortunately unlike in the world of A/B testing web designs, it takes a serious amount of time and effort to test different possibilities in your life. While it does take significant resources to test out different directions in your life, I think it is well worthwhile to do so. The experience of testing out different options can be an adventure in itself and life is long and you will have the opportunity to seriously pursue many things in your life.

If you are completely satisfied with your current path, by all means, stay the course. Though, if you are not sure, do not be afraid to explore. While exploring, it may be best to focus on one thing at a time so you can really delve deep in a subject rather than merely reaching the foothills of many subjects. Part of the adventure is to explore many different possibilities and who knows, you may reach new heights.

The Flaw of The “I can turn it on whenever I want” Excuse

“The best time to plant a tree is 20 years ago. The second best is now.” Chinese proverb

There are many excuses that people have for not doing what they know they should and what they really want to do. One especially dangerous excuse I call the “I can turn it on whenever I want” excuse. I know, the name needs work but it gets the message across. Whether it is starting to exercise and eat healthy, learning to program or whatever other activity/habit, many people delay taking action thinking that they can just start whenever they want. The good news is it is not too late, you can start whenever you really want to if can muster up the will power and apportion the time to do so. The bad news is that most people will never start, let alone keep it up.

Of course the best time to have started something would have been in the distant past but unfortunately the past can not be changed. Duh. Thus, the best realistic option is to start now. If you can keep up the desired activity for a decent amount of time, the activity can turn into an automatic habit and it will be easier to keep up after that point. Depending on the activity, there may also be a steep learning curve in the beginning and being in the middle of a steep learning curve is oh so frustrating. Therefore, the hardest part is to start the activity and keep going for a long enough period of time so that it becomes habituated and that you can conquer the beginning of the learning curve. But once you conquer the learning curve, you can begin to see results and your work can begin to feel like play.

Yes, starting is hard. Yes, you can think of many excuses. Yes, you can keep putting off action. Though if you do not start now, time will pass you by and no progress will be made. You will one day look back at the past (the current present) and will wish that you started then (now). So what are you waiting for, start now and go and get yours.

P.S. Even though this blog post is written in the second person view (the you view), I am the intended audience of this post. I have had trouble starting things and keeping them going but I am trying to change that. I decided to share this post because I think it is possible that some other people could possibly benefit from this message as well. Thanks for reading.

Don’t Eat The Marshmallow

In the 1960s a series of experiments were conducted on young children, now known as the “marshmallow test”. The young children were each offered a marshmallow and told that if they could wait a few minutes they would be given another marshmallow. The videos of the experiments make for great entertainment and the results have had a large impact on the success of peoples’ lives. For more information on the experiment, read this delightful New Yorker piece by Jonah Lehrer. In brief, the reason why this experiment is able to predict so much of one’s future success is because it conveys whether one has the ability to delay gratification, the ability to focus on greater future gains at the expense of immediate gratification.

I never took the “marshmallow test” when I was young so I am not sure whether I have an in-built nature to delay gratification, but now having the conscious knowledge of the importance of delayed gratification I plan to further cultivate this ability and to apply the concept to my life.

In the real world, the test is not of delaying the eating of delicious desserts(1) but of ignoring the abundant distractions that surround all of us so that we can focus and accomplish meaningful work. Paul graham describes how distractions have evolved and have become more addictive then ever. The challenge is to overcome these distractions and in the words of Mark Suster, to JFDI.

I am not advising one to never goof off or relax, focusing on enjoying the present is important too. Though if you want to accomplish great things, it is important to on some level to sacrifice the present for the future. Or sacrifice may not be the right word because that word signifies giving something up and in a way, it is more of an exchange. I have experienced the fulfillment of accomplishing good work and the state of flow while doing so and I have also experienced the hedonistic enjoyment of lounging by a tropical beach during the day and partying at night. Both are enjoyable in their own way, but I prefer to focus more on the former. Of course hard work is not just a state of flow and a feeling of accomplishment. It is hard work. It is struggle. It is finding ways to continue when you may not feel like it. But in the end, I think it is well worth it.

For a while I was focused on living the 4HWW ideally designed lifestyle(2). I tried out living abroad briefly and backpacking around Costa Rica and Nicaragua. While I thoroughly enjoyed the experience and plan on doing a lot of traveling throughout my life, I want my work to more than finding out how to spend the minimum amount of time to bankroll my lifestyle. I want my work to be meaningful and engaging to me. I want to swing for the fences and to repeat the Silicon Valley cliche, I want to change the world. Maybe at some point in the future I will change my mind but at the very least, putting in the hard work now is the way to stay upwind and to keep my opportunities open.

So remember, don’t eat the marshmallow.


(1)Though eating healthy is another test of will power

(2) I am still a big fan of many of the concepts in the 4HWW and have applied the work principles to be more productive in learning and at my former jobs. The problem in my view is that it implies that the goal of a “lifestyle business” is to minimize work and in doing so, maximizing free time and then recommending that that time should be used primarily for traveling and living abroad. I think Tim’s own choice of how to spend his time is a better example, working hard to write quality content and engaging in advising innovative startups. THe other problem is that Tim down plays the importance of working hard, especially in the beginning of a business. He worked 80 hour weeks to build BrainQuicken and only afterwards did he find a way to decrease his weekly work load. It may be possible to only spend the mythical four hours a week but it may be better to rather think in the mindset of what you can accomplish with hard work.

Get in the ring

Doing something where there is a chance of failure is scary but remember in the words of Theodore Roosevelt:

“It is not the critic who counts; not the man who points out how the strong man stumbles, or where the doer of deeds could have done them better. The credit belongs to the man who is actually in the arena, whose face is marred by dust and sweat and blood; who strives valiantly; who errs, who comes short again and again, because there is no effort without error and shortcoming; but who does actually strive to do the deeds; who knows great enthusiasms, the great devotions; who spends himself in a worthy cause; who at the best knows in the end the triumph of high achievement, and who at the worst, if he fails, at least fails while daring greatly, so that his place shall never be with those cold and timid souls who neither know victory nor defeat.”

So go for it and get in the ring and give it your all. Happy new years everyone and here is to a great 2011.

An Important Question: If money was no issue, how would you spend your time?

This is a very important question. One that I ask myself more than nearly any other. You should spend some time thinking about how you would answer this question as well.

Recently Hacker News has had a series of entries on the front page about FU money. I think the real purpose of FU Money is to maintain a desired lifestyle[1]. If you can find a way to live an ideal lifestyle while making enough money to live, you circumvent the need to pursue a deferred life plan [2].

The Tricky Parts:

1. There is no easy way to measure whether the way you are spending your time is ideal.

2. Money and prestige are much easier to measure then happiness so people often pursue those goals over happiness and lifestyle.

3. It is hard to find a way to support yourself financially while also living an ideal lifestyle.

What comes to mind when you think of how you’d spend your time if money was no issue?

You might think of traveling the world, partying, jet setting… all good things but that lifestyle probably isn’t sustainable for one’s entire life. At some point, we all have a need for meaning–to be a part of something larger then ourselves. This can come from many different areas but it requires going beyond a purely hedonistic lifestyle.

I can’t prescribe one right answer to this question as each person has a different temperament and unique passions. Sorry if you were looking for the answer because there isn’t one.

Rather then prescribing one answer, the goal of this post is to encourage you to think about your personal answer to this question when making major life decisions and to take it into consideration. Hopefully good things will come from it.


[1] A desired lifestyle has two parts: 1.being able to do what you want with your time 2. to be able to buy expensive things and live a very luxurious lifestyle. I’d argue that this is a distant second in importance for achieving lasting happiness to spending your time how you would most like to. Furthermore, no matter how much you earn, if money is your main motivator, you will probably start to surround yourself by even more affluent people and will never have enough. Thus, I recommend trying to scale down the importance of great wealth in living an ideal lifestyle. Quora’s take

[2] The deferred life plan is basically doing stuff that you don’t like now in order to live your ideal lifestyle later. I borrow this term from Tim Ferriss. This plan is epitomized by people who hate being investment bankers but are anyways in order to acquire enough currency so then they can pursue something else later in their life. It seems that the ideal solution for someone in this situation is to just start doing what they really want to do. (If you are an IBanker and love it, good for you and no offense intended)

The Idea of Multiple Mental Models in Poor Charlie’s Almanack

Warren Buffet’s business partner, Charlie Munger writes Poor Charlie’s Almanack in the style of Benjamin Franklin’s Poor Richard’s Almanack. While the book has a fair amount of fluff I think it is worth working your way through it in order to find the insights on life and investing that Munger shares with great wit. The reviews on amazon can do better justice to the book than I.

Munger focuses on the importance of multiple mental models that can be gathered across academic subjects. These mental models form a latticework that provides the holder with new ways to analyze problems and look at the world. Learn more here. One of my goals of my broad liberal arts education is to develop a deep understanding of these important mental models. The sum of which Munger calls “elementary worldly wisdom.” Munger argues, “80 or 90 important models will carry about 90% of the freight in making you a worldly-wise person.” Focusing on one narrow model too much can cause what Munger calls the Man with a Hammer Syndrome: to the man with a hammer, everything looks like a nail. Adding more mental models increase the number of tools one has so the world can be viewed more accurately.

After hearing that I was eager to learn what these models were. Munger does briefly review some of them. The first ideas he shares are from math: things like compound interest and decision trees. From physics there are the ideas of breakpoints and critical mass. Psychology has many models ranging from classical and operant conditioning to the principles of influence. As I go through my education, I will place an emphasis on the mental models that I can learn and apply.

Mental models may appear rather academic in nature but they have importance beyond the academic world and can be useful when analyzing the world and investing decisions. Munger with his signature humor captures the importance of learning a multitude of mental models by saying otherwise “you go through a long life like a onelegged man in an asskicking contest.”