A Little Guide to Making Better Guesses

Let’s get something out of the way that I should have cleared up a long time ago. I don’t really have any idea what I’m doing.

It’s true. I know a few things about this or that. I’ve learned a lot about what I’ve done so far, but to be completely honest, I don’t really have a clue what I’m currently doing.


  • Riskology.co is about nine months old now. I’m incredibly happy with how things have gone so far, and I feel honored every day that you’re here reading, but this whole things was just a guess. I thought people might be interested in taking more risks and maybe, just maybe, they’d stick around long enough to read what I have to say about it.
  • I’m knocking things off the 1% Club list much faster than I had anticipated when I first created it, but every time I start preparing for another challenge I can’t help but think to myself, “What are you doing? You have no idea how this is going to turn out.” Then I usually go and just do it anyway because, well, why waste the momentum?
  • Guerrilla Influence Formula, my first product for advanced riskologists, has been selling incredibly well and I’ve been getting lots of great feedback from the people using it. That makes me happy. Truth is, though, I created it on a hunch. A well developed hunch, yes, but a hunch nonetheless.

Sometimes, when I sit down to write an article, I think to myself, “Why would anybody listen to me? I’m not a guru, I don’t have a million dollars, and I get scared every time I try something new.” I even question it as I write this article.

Lately, I’ve been wondering how things seem to keep working out okay despite the fact that my whole damn life seems to be a never-ending guessing game. I think I’ve come up with a pretty good answer:

I take a lot of guesses.

I play the odds; it’s a numbers game. If you look at any given day, week, month, etc. of my life, I mean really examined it, you’d see a whole lot of failures. I don’t always write about them here because I think there’s more to learn from success than failure, but I make a lot, I mean a lot, of mistakes. But they’re small; I can recover quickly.

The Minimum Viable Risk

This is what I call the Minimum Viable Risk. The idea is that you try something big enough that it would give you a strong indication that it’s the right direction to head if it works, but wouldn’t ruin your day if it fell apart.

Essentially, it’s gambling, but not in the way that you’re used to thinking about it because there’s little downside. You don’t have to win more than you lose. You only have to win once. One little win that you can use to build momentum into something bigger erases all the previous losses. It establishes a “proof of concept” that you can turn into extraordinary success with more focus.

Let’s look at a case study.

When I decided to start AR, it was only one of about 10 other ideas I had. I thought about finding another job in construction. I seriously considered becoming a professional musician. I almost returned to ticket scalping like I’d done to pay for groceries in college. I entertained the idea of building a network of niche websites that would provide passive income.

Rather than picking one and just going with it, I went after them all. I spent a little time here and there developing each idea to see where it would take me. In this case, I wasn’t necessarily looking for which project would generate the most income the quickest (though there’s nothing wrong with using that as a criteria), I was looking for what would make me feel the best about myself and had potential to make money.

I used a couple of rapid experiments to decide which direction to go. Within a month, I could see, quite certainly, which was right. Here’s how it panned out:

  • I carpeted Portland with resumes and talked seriously with a few big firms. Lots of income potential, but I hated every second of it. There also wasn’t much of an opportunity to make an impact with the work.
  • I started playing all my random instruments again, recorded a few songs, and went to a bunch of open mics around town. I had fun, but couldn’t help but notice that it just felt out of place for me. I felt out of character and somewhat inauthentic. There was big potential for impact, but it wasn’t quite the right fit for me.
  • I only had to do about 20 minutes of research to realize that I’d definitely outgrown the ticket scalping phase of my life. Plenty of money to be made and I could set my own hours, but absolutely no impact. In fact, the impact might be a net negative.
  • I spent a month writing down all the stuff in my life that I thought was important and interesting, and then looked for a way to tie them together. I noticed I wrote about risk-taking a lot. If I started a site and people liked it, it could potentially reach millions of people and I saw others making a comfortable living doing it, so why couldn’t I? Riskology.co was born.

Keep in mind that all this occurred over the course of just a month. One week I was going to be musician, the next I was going to sell concert tickets to the moms of Justin Bieber fans (or moms who are Justin Bieber fans).

To everyone around me—friends, family, casual acquaintances—I had to have sounded like a total nutjob, changing my mind on a weekly, even daily basis. But—with the decision criteria in place—it all served a much larger purpose, and I’m glad as hell I did it because if I hadn’t, I’d probably be sitting behind a desk right now, wearing a tie, arguing with some contractor about how he installed the mirrors in a doctor’s office wrong.

I’m not the only one who works like this. Most of the people I know that love and are incredibly good at what they do work in the same fashion. They test every idea that comes across their mind, throwing away most of them as total failures and sticking with the ones that work.

So why don’t more people do this? I think it’s because it’s incredibly hard to take the first step. No one wants to fail at something, so rather than allowing yourself to test it, you settle for doing nothing. This is the default response. We all know where default gets us.

Important realization: If the very first step is incredibly scary for you, then it’s too big. Notch it down until you can visualize yourself actually doing it. Then, do it.

Ever since I started this site, I’ve struggled to decide which is better: to start something with a small step or a big one. Small steps are easy, but big steps are exciting.

I think I’ve finally found my answer, and it’s a compromise: Start with a tiny step and then, if it works, follow it up immediately with an enormous one. Take the smallest action possible to give yourself your own proof of concept, then start the shock and awe campaign.

You have to do this over and over and over again. You throw the spaghetti against the wall and see what sticks. The reason most people don’t get far is that they simply don’t throw enough spaghetti enough times before adding the sauce.

Where’s the Meat?

To tip the odds in favor of success, you have to extend the pool of possibilities and pursue each one. That takes a lot of time and energy, so how do you manage it when there’s only 24 hours in a day and you already have a lot going on?

The answer, of course, is that you have to relentlessly look for the most important piece of any experiment, and focus on it entirely at the exclusion of everything else. Before you start something, ask yourself:

Where’s the meat? What’s the one factor that will decide if this is successful or not?

Everything else is filler.

The funny thing about this is that when you do take the time to ask yourself, “Where’s the meat?,” you’re naturally inclined to focus on it, and when you focus on the important, you dramatically increase your odds of success. Most importantly, you eliminate “false negatives”—ideas that are actually good, but fail because you never hit the target that will make it succeed.

So don’t just try one thing, try a lot of them. Abandon whatever fails and build onto whatever works. It’s good to create a roadmap, but it’s difficult to find the beginning of the road until you fail your way to the starting point.

Every big success I’ve ever had has been built on the backs of countless little failures that most people never hear about. No one will hear about yours, either, so go make them.

What spaghetti are you currently throwing at the wall, and which pieces are sticking? Let me know in the comments.


Reminder: If you missed the launch of my free guide, Instant Adventure, on Tuesday, you can still download your copy over here.

Image by: Stéfan