The Power of Moonshot Thinking

Authors note: Anything you see in any of my blog posts that is underlined is either a cool external link to help you learn more or internal links to my own related content.


Last year, I read a fascinating book called How Google Works (2014) co-written by Google's Executive Chairman and ex-CEO Eric Schmidt and former SVP of Products Jonathan Rosenberg. While the book credited many factors to Google's unbelievable success, the one big idea that stood out to me was their concept of Moonshot Thinking.


Moonshot Thinking is about ideas that aren't merely 10% better than what already exists, but 10X better than what already exists. Rather than small incremental improvement, Moonshots are about massive improvement.

The best Moonshots tend to also be what I call Positive Asymmetric Bets - bets where the potential payoff if the idea/project succeeds is magnitudes greater than the cost if the idea/project fails. Imagine rolling a dice with six sides. Every time you roll the dice and roll 1-5 you'll be charged $10, but every time you roll a 6, you'll get $80. Even though 5/6 individual throws will lose money, if you roll the dice enough times, you'll eventually average $5 in winnings per dice throw. Throw the die long enough, and you'll be richer than Bill Gates. That's powerful.

If you keep your eyes and mind open, you'll start to see that life is full of these happily lopsided opportunities. Finding and attempting your own Moonshots is a fantastic way to improve your life.

Here are five quick, real-world examples to get our mental juices flowing:

1) Emailing a famous person and asking for advice

2) Applying for a job way above your current pay grade

3) Starting your own podcast, blog, or other "side hustle"

4) Asking out a guy/girl who is "way out of your league"

5) Applying to an Ivy League school when you don't exactly have the grades or pedigree.

These five ideas/projects, individually, all are more likely to fail than to succeed. However, like the dice example, the payoff is so high compared to the relatively minimal downside if the idea/project fails that it still makes sense to take a chance on the idea/project because the expected value is still positive.

The secret to making moonshots work for you in the long run is making sure you're able to roll that moonshot dice with relatively high frequency. Because most moonshots will fail, it's generally pretty stupid to put most or all of your "eggs" into a single Moonshot bet. The trick is to carefully consider both the magnitude of the asymmetry and the proportion of your overall resources (time and money) that you are willing to allocate to each of your Moonshots bets. I've found that allocating 1-3 years worth of time and money to each moonshot seems to work quite well. That gives you about 12-30 good moonshots over your working life, and maybe even 50-100 moonshots over the course of a long, full life.

Famous investor Mohnish Pabrai (author of the Dhando Investor) has summed up the entire Moonshot concept in one pithy sentence: 

"Heads I win big; Tails I don't lose much."

You can watch Pabrai's great talk regarding this concept (at Google, ironically) here:

Although I didn't realize it until after I read How Google Works, I've actually been using Moonshot Thinking to vastly improve my life over the past 5-7 years. Here are some personal examples from my own experience:

MOONSHOT #1 - Applying to better Grad Schools after already being rejected by a "worse" grad school.

Low Downside: I was likely to lose $200 (and an afternoon) filling out applications. 

Huge Upside: Potentially vastly improving my career prospects, if accepted.

  • In 2013, I was getting tired of working in a call center, so I began considering my options. I worked out the upside/downside of going to business school and getting an MBA. Despite already having over $70,000 in undergraduate student debt, I applied to two business schools. School A, which was traditionally much less prestigious and easier to get into than school B, rejected me. I knew that the odds were very low that someone rejected from School A could get into the more prestigious and selective School B. However, the Moonshot reward here was vastly improved career prospects and the cost was a $200 application fee and a day spent filling out an application. I took the unlikely bet, applied to School B, and got accepted. This one moonshot seriously improved my life.

MOONSHOT #2 - Volunteering in my local community

Low Downside: I'd be "giving up" a few hours a month to do whatever volunteer work my local community needed.

Huge Upside: I could potentially connect with and befriend many of my neighbors and maybe even improving the community a tiny bit.

  • In late 2016, after 4 years of working intensely, and almost exclusively, on improving my career trajectory, I decided it was time to start spending more of my time and energy on other people. I sent an email to my local government asking if they had any volunteer opportunities available. I told them, quite literally, i'd do anything that would get me involved and contributing to the community. Like my previous Moonshots, I saw local community service as an opportunity to get to know my neighbors and maybe do some good in the process (high potential reward) for the price of just a few hours of my time per month (low potential risk). I expected to be planting flowers, or helping with the historical society, or something boring like that. Instead, I was appointed to a seat on the Board of Directors of my local library! Holy cow, what an awesome opportunity for a bibliophile like myself. I eventually was elevated to Treasurer in 2018 where I now combine 1) my love of books/libraries 2) my love of finance and 3) my goal/duty to give back to my community. That is some serious Ikigai right there! And it all started with one tiny email that took 30 seconds to write.

MOONSHOT #3 - Launching my own podcast in 2017, and blog in 2018.

Low Downside: Spending $250 on microphones and a website, and having awesome conversations about books and big ideas over delicious alcoholic beverages with my friends, but having zero listeners. (Talk about a worst case scenario!)

Huge Upside: Possibly having a successful podcast/blog that are both fun, allows me to meet and interact with cool new people, and possibly even build a small platform for myself.

  • In 2017, I started a Podcast. The podcast/blog has acted as a force multiplier for me because it gives me an excuse to have deep, 1-on-1 conversations with people that otherwise wouldn't wouldn't occur. This is both super-fun for me, but also helps me be more social. (Which is something I really struggled with growing up)
  • Inspired by the success of my podcast, I launched this blog in 2018. (Yes, the one you're reading right now!) Again, a similar asymmetry: I was already going to read constantly, take a lot of notes, collect and big ideas just for myself. Why not SHARE those good books and big ideas with the world? I have virtually nothing to lose, and potentially a TON of people on line who might gain something from my blog ideas or books reviews and vice versa.

My life has been vastly improved by consciously (and unconsciously) Moonshot Thinking and pursuing positive asymmetric opportunities, especially over the past 6 years. Moonshots are a key feature of Google's incredible success, and this mental model can REALLY help YOU in your own life. 

So keep you eyes and your mind open for Moonshots in your career, your community, and among your relationships. Say yes to Positive Asymmetries whenever you can, and good things will happen to you. 

Good luck with your Moonshots!