Wouldn’t it be fabulous if the most wonderful and unlikely thing happened to you?
If your novel got published
or your start-up got funded
or Keanu Reeves blew you a kiss through his car window?
That’d be a good day.
But what are the odds? How likely are you to hit a moonshot? Is it ever worth trying?
I’m glad you asked. In this essay, we’ll use probability to develop a strategy for taking moonshots that you can apply to your relationships, career and craft.
I’ve loosely structured my life around these ideas. They won’t turn your galaxy upside down tomorrow. But given time, these ideas will change your life.
Perhaps it’ll work out so well that you feel your life needs no changing at all.
Let’s get started.
The Numbers
In this section I’ll use probability to generate the odds of succeeding at various levels of moonshots. In the next section, I’ll use these estimates to create three key criteria for building a life around moonshots.
Let’s start by establishing three levels of difficulty—the difficult moonshot, the somewhat easier balloon shot, and the outrageous mars shot.
I define moonshots as any attempt with a 1% probability of success.
Given that, you would have to take 161 moonshots to have an 80% chance of succeeding at least once. In this essay, I consider 80% to be the threshold for significantly good odds.
Now let’s define a balloon-shot as any attempt with a 5% chance of success. You would need 32 balloon shots to have an 80% chance of succeeding at least once.
Finally, say a mars shot is an attempt with a 0.1% chance of success (1 in a 1000). You would need to take 1609 mars shots to have an 80% chance of succeeding at least once.
If you’re interested in the math behind these calculations, see endnote 1[i].
You might also be wondering how to determine the probability of success for a particular event. There’s no exact science but see endnote 2 for my suggestions[ii].
How to Shoot for the Moon and Win
Seeing the numbers behind moonshots gives us three important criteria for the designing a life around moonshots.
Criteria 1: Platinum Shots Only
Moonshots are extremely hard.
If all your college applications were moonshots, you’d have to apply to 161 colleges to have a very good chance of getting in.
And even 161 attempts only make it likely that you will succeed one or two times.
Taking 161 moonshot attempts gives you a 32% chance of succeeding once, a 26% chance of succeeding twice, and a 13.9% chance of succeeding thrice. Put together, that’s a 72% chance that you’ll succeed one to three times in your 161 attempts.
You don’t get to pick which one out of your hundreds of moonshots succeeds. So, you should be extremely selective about which moonshots you exert effort on.
Roughly, any moonshot you make should be worth the effort of taking one hundred moonshots[iii].
Not all moonshots are created equal. Only exert yourself on those that could genuinely change your life.
Criteria 2: Choose Your Time Horizon Wisely
If you were taking moonshots, you’d need 161 attempts to have good odds, if you were taking balloon shots, you’d need only 32 attempts.
Choose a difficulty level where you are likely to succeed at least once before you burn out.
If you think you can make one attempt a week for over 3 years without success, then you’re qualified to attempt moonshots.
If each attempts takes you one month, or you think you’d need some initial success within the first year, then consider taking balloon shots (that is, easier challenges with a 5% chance of success.)
If attempts are cheap, say something that’s digitally generated, then you might be able to plan for the 1609 attempts needed to have good odds of success even for Mars shots (challenges with a 0.1% chance of success).
Initial successes make the process easier to follow, so there’s no harm starting with easier challenges and going on from there.
Criteria 3: Get Better Trying or Get Better Early
Point 2 suggests one way of succeeding quickly: lower your ambitions temporarily.
But there is another way: raise your ability. A moonshot for one person may be only a balloon shot for someone with greater ability.
Sometimes taking moonshots is one of the best ways to get better. If this is the case, keep going—you will get better trying.
But sometimes there is a much quicker path to getting better than taking moonshots.
If that is the case for you, then first grab the low-hanging fruit to improvement. Do the work to improve before or alongside taking moonshots.
A Sample Strategy
I’ll put this together in one example. Skip this section if you’re in a rush.
Let’s say you’re an aspiring writing who wants to get a non-fiction essay published at a well-known magazine like the Atlantic, the Guardian, etc.
First, you should ask yourself two questions:
- How often can you make attempts?
- For how long can you try without succeeding at least once?
In this example, let’s say you can write one essay every two weeks on the side of your regular job. And you can pitch that essay to eight different magazine outlets.
That gives you eight attempts every two weeks, or four attempts a week.
For question 2, you suppose that if you don’t succeed in the first year, you’re unlikely to continue. Work could get busier, your motivation might weaken, other hobbies may come in the way.
These two questions can help you determine whether to take moonshots (1% chance), balloon shots (5% chance) or nothing at all.
In this case, if you made four attempts a week for all 52 weeks in a year, you would have 208 attempts. Even missing a few weeks, this gives you well over the 161 attempts needed to have good odds of succeeding at a moonshot (1% chance).
This means that if you can find 8 magazine outlets with a 1%+ acceptance rate for your kind of pitches, then you can confidently choose the strategy of pitching all eight outlets every two weeks for the next year.
This would be a good strategy for you since it is a worthwhile goal (meeting criteria 1 from the previous section) in a time horizon that’s feasible (criteria 2).
It’s also meets criteria 3, because writing and pitching essays is one of the best ways to become a better writer. So you get better trying.
The Heart Behind Moonshots
Having described the math about moonshots, I’d be remiss if I didn’t mention three unquantifiable reasons for taking moonshots.
1. The School of Failure
Our mathematical model exists in a binary world. Either you fail or succeed, nothing in between.
In truth, almost no endeavor is a complete failure.
Failures teach you skills, improve your understanding of the world and yourself and connect you to other people. They also make for great stand-up comedy material.
As I put it in one of my more bombastic essays, there are good reasons Why You Should Fail More.
For more inspiration, you could go straight to the ultimate treatise on personal failure: How to Fail at Almost Everything and Still Win Big by Scott Adams. Failure ends very well for that author.
The fact that failures are worthwhile is a point in favor of moonshots.
Since even the “failures” are valuable, taking moonshots is worth more than we estimate.
2. Stretch to Stand Taller
The idea for this essay came to my mind as I was applying for the Rhodes Scholarship.
It’s a competitive scholarship and I didn’t end up getting it. It made me wonder what that long, arduous application process was worth.
One benefit stood out to me.
Simply applying to the Rhodes Scholarship raised the level at which I was thinking about my life. And the effect didn’t wear off when I didn’t win it.
For example, I realized that if I was going share my online writing on the Rhodes application, it needed to be better.
And that increased the quality of essays I expected from myself.
3. It’s Breezy at the Top
Most people self-select out of the most valuable-looking opportunities.
The most attractive people don’t get asked out as much as you’d expect, and the best jobs don’t have as many applicants.
There’s less competition for great opportunities than for good opportunities.
If it looks like a moonshot, odds are that most others have talked themselves out of trying. So why shouldn’t you give it a shot?
Real Talk
I’ve written strongly in favor of moonshots so far, but I’m see-sawing on publishing this essay. Because there is an important danger I need to make you aware of before I do.
I wrote this essay because it’s valuable to aim high without becoming discouraged by the early results.
But it’s also destructive to hang your identity on your goals.
Moonshots, if taken too seriously, encourage a binary view of the world. And they can make you brittle to change. The world is always changing, and your goals should too.
Getting attached to a singular outcome is one fantastic way to break your heart.
And even succeeding at a moonshot doesn’t guarantee freedom from the game. Spend long enough on the moon and it can start to look like one more tired rock.
Now it is possible to have the benefits of taking moonshots without the dangers of becoming attached to them. But you’ll have to be mindful to build that balance.
And this is the piece of advice I will end on:
In a perfect world, you take moonshots often. But you think about moonshots almost never.
Shoot for the moon and appreciate the rock that you’re on.
Every week, I take a moonshot by writing the best essay I can about a grand idea. I’m on a mission to build an internet for bid ideas, and I would like to do it with you.
Open the door to big ideas in your life today by joining my email community. I write twice a month, sharing insights from me and brilliant ideas from other writers.
Endnotes
[i] How to Calculate the Probability of Success:
If the probability of any attempt succeeding is A, and the number of attempts is x, then the probability of at least one (one or more) success after x attempts is:
1 – (1 – A)x
(To convert a percentage into a probability, divide by 100. So, 90% success equals a 0.90 probability of success.)
[ii] How to Estimate Your Probability of Success for a Particular Task:
A crude metric to calculate the probability of success would be to divide the number of successful attempts (e.g. jobs offered) by the number of total attempts (total applicants) for your moonshot. Both of these stats are generally available. Google your general area of interest to get some ballpark figures (e.g. “acceptance rate for entry-level jobs at venture capital firms”).
This would give Harvard University applicants a 3.5% base probability of success.
This would give you a general probability, but we ideally want your personal probability of success: how likely are you specifically to succeed? You could get close to this figure by altering the base probability of success with your estimation of how you compare to the average applicant.
Say your application looks slightly weaker than the average Harvard applicant, you might estimate your personal probability of success to be closer to 2% rather than 3.5%.
This will usually be a crude estimate. In reality, the exact numbers are unknowable. And that doesn’t matter too much. As long as you’re somewhere within the ballpark, the lessons in this essay will be applicable to you.
[iii] Benefit-to-Cost Ratio for Moonshots:
Rationally, a moonshot (1% probability event) would be worth taking if the benefit of success was worth the cost of 70 attempts. Because at 70 attempts, you’d have 50/50 odds of success. Most humans prefer better than 50/50 odds, so saying that a moonshot should be worth the cost of 100 attempts is a good rule of thumb.