Risk•ol•ogist (noun): A practitioner of smart risks who thrives in an uncertain world. Join us.

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

Published on

Thanks for reading the whole thing. Here's a gift.

Start the free Smart Riskologist Test

Wow, you made it all the way to the bottom. You must have enjoyed reading this article.

I'm grateful for your attention, so here's something I think you'll find useful.

I've created a test to help you find your strengths and weaknesses as a risk-taker based on psychological research and the habits of highly successful risk-takers. It comes with personalized recommendations for how to improve your life, work, and personal projects.

Enter your email below to join our newsletter and you can start the test immediately.

What smart people are saying about this...

  1. Hey Tyler,

    Completely agree. I think we’re conditioned by school to be afraid of failure and trying new things. There is often only one correct way to do things and only one right answer.

    It teaches us to be afraid of failure and worst of all wasting our time. Nothing sucks more than having to start all over again.

    Like you I’ve learned that in some areas of life you can take advantage of the randomness of the world. But you have to get out there (or do it virually) and start doing things. Anything.

    Put yourself in as many random situations and give yourself as many random experiences as you can.

    I think I might have seen you reference Taleb on this blog somewhere. His ideas are a big influence on me that I’d like to write more about in the future. But here’s one about Tinkering / Trial and Error vs Planning. I’ve been living this idea for a few years but it’s power and profundity has become a lot more clear to me recently:


    • Creating order from randomness is the name of the game, right? It takes some getting used to—when you first start, it’s like feeling around in the dark. But, over time, the pieces start to fit together and you start to see which tests are worth trying and which aren’t the best fit for you.

    • Nomadic,

      I have to agree with your idea that we are conditioned by school to fear failure. If you try something in school that stretches you, you might not make an “A”. If you are like me and you have big goals that involve the need to make those “A”s in order to have the opportunity to pursue your goals, then you stop trying to do things that stretch you. Scary thought. I hope I can break this mindset in myself and start to pursue things that stretch me, even if I experience failure in the process.

    • Totally agree that were conditioned by school to be afraid of failure. Actually, I wanted to prepare a further maths exam on my own this year and can you believe what my teacher said to it, before I conviced her to lend me a book: “Are you sure you want to try this? You might fail!” How can she possibly say something like that? I had 6 months to prepare for it and it wasn’t that difficult!

  2. This quote:

    “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.”

    is so incredibly powerful, it probably deserves a blog of its own :)

    We all start on the same page. No one is ever born with the inherent ability to run a marathon, climb mountains or run wildly successful blog empires.

    And yet, some people manage to make these things happen – probably because they’re the ones who aren’t willing to be overwhelmed by the sheer enormity of the task.

    Start small, leave what doesn’t work and build on what does :)

    • Well, some people are born with inherent ability to do those things, but you can’t look at someone like that and expect to find the same success as they did with the same amount of work; you have to put in a lot more effort.

      I believe that, over time, persistence beats natural talent. If you can find what you’re naturally talented at and match that with persistence, you can’t be beat.

      And how do you do that? Just like you said – start small, take what works, and leave the rest.

  3. Yes!

    I have been bloody afraid of taking risks all my life. Then came the time when either I accepted the life-that-one-is-supposed-to-live and die inside, or I did something about it.
    I started yoga teacher training a few months ago. Then I took an online course that taught me to listen to my guts and let my brain take a back seat. Then I said yes a friend’s request to have private sessions with her. I said yes not because I wasn’t scared anymore, I said yes because she visibly needed some me-time and self care, and I could do something about it.

    And I’m not mentioning the freelance gigs I’ve been saying yes to.

    I’m still in my day job, but slowly I’m learning to go with what my guts tell me. I try, make mistakes, then try something else. But at least I’m doing something.

  4. You know, I’ve had reacurring thoughts a couple times reading your blog but haven’t yet voiced them. Until now.

    I really admire your “educated-hunch and plunge” lifestyle. :) I think there’s a payoff a lot of us have missed in life by following the Road of Expecations too closely. So, on one hand, I find your articles inspiring, refreshing and they make me smile with all the possibility your paradigm of life offers you.

    The other thought I have is how much easier a lot of your ideas are to put into practice when the only person you have to “care for” is yourself. As soon as you decide to have children and accept that responsibility, life’s road does take a little twist and suddenly actions, decisions and educated-hunches have a much deeper impact and broader repercussions. They’re not impossible or even unadvisable, but they’re just not as care-free.

    Or at least that’s my take on all this as I prepare to take my own educated-hunch leap :).

    • Hey Julie,

      I don’t have a family to care for, so I can’t speak to that concern very well. I like what Sarah said above:

      “Start small, leave what doesn’t work and build on what does.”

      If something I say doesn’t sit well with you, I think the best thing to do is to ignore it and try to just focus on the parts that you can work with. Good luck with your big leap!

  5. For some reason you seem to know exactly what I need to read each day… I found out Tuesday that tomorrow (Friday) is my last day at my current job. I wasn’t happy anyway. Now it’s really time to throw some noodles!

    One of my problems, however, is that I’m not just afraid of failing. I’m also afraid of success. I’m afraid I’ll be successful at something I end up not liking and get sucked into it. A lot of that fear has to do with debt. I’ve been paying off debt for awhile now but still have a lot to pay down. I don’t feel like I’m in a place where I can risk too much. Debt sucks. It closes doors and limits the risk you can take. Get rid of it!

    But your posts give me hope and ideas I can still put to use when I’m not at a hated desk job. I’ve got some ideas I’ve started on that may help me pay off that hated debt quicker. And if they fail, it’s only a little wasted time that isn’t really wasted because I’ll learn from it and still have fun.


  6. Hey Beowuff,

    The way I try to think of it is that it really doesn’t matter if I “succeed” my way into something I don’t like. Every step is, in one way or another, a step forward. So, if I get where I aim for and decide I don’t like it, big deal, onto the next place.

    For me, this all comes down to the idea that success is always fleeting. I’ll never get to one place and say, “A ha, I’ve arrived,” and then kick off my shoes and relax. The only way to stay successful is to constantly change and innovate.

    By embracing that mindset, it’s a lot easier to get past that fear of success mentality – at least for me.

  7. Last year I threw some spaghetti and now I am in a roller derby league, so that gave me the confidence to start applying for grad school this year. Who knows, maybe I’ll be able to focus on derby and school full time next year! I think its worth a shot. If that doesn’t work out, maybe at least my “find a job that you might actually like” spaghetti will. I’m generally a pretty confident person, but sometimes, reading posts like this is what I really need. Thank you.

  8. You write that you think you learn more from success than from failure, and this post, maybe your best so far, contradicts that. Isn’t this all about what didn’t work? It’s brilliant and kind and so illustrative.

    Thank you for your candor and showing how you sorted through all this. Stories of success without the background are useless, and to me, demoralizing. Thanks again for your tender heart and fierce dedication.

    • Hey Billy,

      I don’t think there’s really a contradiction — just a choice to emphasize success over failure. Yes, you have to fail and fail a lot to figure out what works, but focusing on the failure isn’t important to me. I’d rather spend my energy focusing on what went right because, ultimately, that’s where I want to spend the bulk of my time.

  9. So here are some thoughts from another generation about “guesses”. You and I know each other from a previous life but never took time to explore philosophies. I am a new viewer to your site but enjoy very much your sense of humor and your poetic timing.
    Today there are many of us facing similar challenges to life and taking different approaches as to how to navigate the murky waters. It appears from the responses to your blog thoughts that many young people are looking for opportunities to experience what they wouldn’t otherwise do. Taking risks and following hunches is what life is suppossed to be about. People of my generation facing the same issues have forgotten what it was like when they were carefree and they could follow their dreams. If more of us, accross all generations, would re-evaluate ourselves and act on that similar to what you describe…WOW!! I am just 52 years young but have followed my hunches leading me half way around the world and back. I have faced miserable uncertanty twice in my chosen career and taken the unknown path each time, coming out the otherside richly rewarded!
    I like where you are going and think all of us should continue to dream big and take a stab at what feels right.

    • Hey Bob, thanks so much for sharing that. I think it’s important to remember that an idea, a philosophy, will apply differently to everyone depending on their life experiences and current situation.

      It’s best not to get bogged down in the details; if you like an idea but it’s not presented in a way that works for you, find a way to alter it so you can still get the benefit.

      Thanks for sharing your perspective.

    • Bob– As a reader from “another generation”, as well, I’m encouraged to read your post and hear from a “been there, done and and am doing that” voice. Thanks for sharing this.


  10. Excellent read, and it feels like it came at the right time for me…Thanks.

    I can definitely relate to that time. I graduated college last August, felt a little “over-qualified” for the current job market. Not to toot my own horn, but every single thing was an entry sales job, and I had already dabbled in affiliate marketing, so if I was going to do sales, I would stay online and do it there.

    I passed up higher income opportunities, to start my blog and take the big risks that pay off.

    Right now, if I do NOT take any risks….Then I feel like things are out of control. I take risks, for the control I get in life!

    Thanks Tyler

  11. “… 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?”

    Tyler, this quote made my day and is exactly what I needed to hear. I’m just coming off a meeting with my Stir the Embers partners about what direction we’re heading next and I was seriously feeling overwhelmed and a little nervous about getting started. Thanks for the gentle nudge. 😎

    • Well, I find it incredibly hard to get something started, but once it’s rolling, I have an even harder time stopping it. I like to look for any opportunity I have take the energy I have and spin it into something bigger.

      Resting usually just leaves me with a more difficult job to start once I’m done.

  12. Love your idea of following that first tiny step with an enormous one! Get a taste of what your new endeavor’s all about, then full-on jump in the fire . . . certainly an M.O. that I see you adhere to time and time again. Rock on, Tyler!

  13. Hi Tyler,

    Thanks so much for that post. I think its awesome what you’re doing with Riskology.co – even if you are guessing : ). Your candid and honest style comes through, and it is always helpful. Especially this post, risks, baby steps, “where’s the meat” really resonated with me as I am just starting to jump into my own projects now, and really want a plan, direction, as to which project is best and fits best. “Where’s the meat” will hopefully help me answer that. Thanks again Tyler!

  14. Oh, and in terms of “throw spaghetti”? I just bought my first domain for a UV proof beach coverup, and have recieved my first samples of cloth… also about to move (back) to the other side of the world (US from Australia) so need to throw some more spaghetti at the opportunities there.. Boulder CO, San Fran, Seattle, Salt Lake, Boston, so many possibilities! Time for a Riskology.co Biography I think..

  15. Hi, Tyler. This was a great post. I really liked the part about changing your mind so often. It’s nice to know that there are other successful people out there who aren’t afraid to try new things. I feel like I get labeled as fickle when I try something and it turns out to be a bad fit for me. Thanks for sharing this experience.

  16. I would rather try and abandon a half a dozen concepts than stick with one that doesn’t fit right. Luckily I’ve had a few pan out well over the years. :)

    I just ran into a post the other day from someone talking about the abandonment rate of blogs and websites. He viewed it as a failure and later told me he’s never dropped a domain once starting it.

    I on the other hand have abandoned several half started websites before finding a good fit. Then I found a second good fit, etc. :)

    I love to experiment and risks are part of that. I like your idea of dipping your toe in the water “small” and then going big later on if you like where it leads. Awesome!


  17. Tyler,

    I can’t think of a better way to make decisions than this. The thing about it is that no matter how much you research something, you’ll never really know what it’s like until you actually experience it, and you therefore can’t make the best decision. Not only that, but many times, if I haven’t actually experienced something, I can’t help but wonder later on if I made the right decision—if I would have liked this or that better.

  18. Thanks so much for this! Lately I’ve been taking this approach, though not consciously, and it feels exactly right—even though it’s not the safety net I always thought I wanted. Who knew?

  19. Wow! Great thoughts. :)
    I came across this post via Lifehacker, and I knew this is one idea I want to read in entirety. The first half was great; it got me hooked and I’m going to come back when I’m not dead tired.

    And hey, great phasis idea! :)


  20. U R the man! K, IM a young person wan-a-B…I turn 60 next month! Truth, though, seems to be ageless, and you speak great truth. Now the problem for my people (old that is), is how to do all this changing when you’ve already changed (several times in your life), and now you have a lot of baggage (not to mention co-habiants that don’t want change). Dude (forgive me), love to help you in your endeavors.


  21. It’s the same way with picking profitable ideas online. You have to test all your ideas knowing that most of them will be losers. If you aren’t willing to put in the work and be willing to fail, you probably won’t ever last long enough to succeed.

  22. I love this post. It keeps resonating with me at the most important points in my life. Thanks for providing clarity in what is otherwise a tiresome and confusing process.

  23. […] It’s not a grand step that I needed to take, but it still required action. Research and planning is important but every plan has a point when you have to act or that plan isn’t worth anything. To quote Tyler Tervooren from Riskology.co, “start with a tiny step and then, if it works, follow it up immediately with an enormous one” (read it here). […]

  24. Hey Tyler, thank you so much for pointing this out. I maybe halway around the world but your blog speaks to me like it’s somewhere close. I’ve been learning about making guesses and how I could be more in control of my life and what I’m going to be doing. Anyways, your articles have inspired me and has given me ideas on how I can control of my own thinking.

    Ps. I’ve subscribed to your newsletter. Hope to hear more from you soon. All the best bro!

  25. Hey Tyler, once again I have to say I’m impressed by what you’re writing about. It’s fairly in line with the way I think. I’ve been doing the same thing this year. Building ideas, pumping out prototype products, seeing what works and what doesn’t. Now I have an idea that feels right and I’m ready to start executing it.

Founded with love by Tyler Tervooren

  • Are you a smart risk-taker? Find out in 2 minutes.

    Where do you excel? Where are you vulnerable? Get your free, personalized analysis now by signing up for our newsletter.

  • This field is for validation purposes and should be left unchanged.