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I'm Tyler, and I created Riskology to be a community where introverts master their psychology and make a dent in their universe—little steps every day to build something great. Join 25,000+ others just like you on our (totally free) email newsletter and I'll send you our Leadership for Introverts test to build your skills.

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The Riskology.co World Debut (Complete with Free Stuff!) - (Archived)

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Hello there! Welcome to the world debut of Riskology.co. Please allow me to say hello in this little video I made just for you:

If you’re not able to watch the video, here’s the important stuff:

My mission statement for Riskology.co is to help as many people as I can learn to find happiness by doing really scary shit. (Learn more about the site.)

You see, as much as your body and your mind try to reject it, you can learn, grow, and succeed so much better and so much faster by taking risks in your life. Not just taking risks, ya know, but really embracing them – learning how to take comfort in things that are completely uncomfortable.

As simple as it is, this was a realization that was a long time in coming to me. Once it was here, though, I knew I had to do something about it. Better late than never. So twice a week I write articles about taking bigger and better risks in your work and other parts of life.

I also talk about the risks I’m taking myself in the 1% club. I call it that because most of the challenges I’m attempting are deeply meaningful to me and less than 1% of the world will ever do them.

It’s also a challenge to you to create your own meaningful list and share it with everyone here. As the old saying goes, “If you want to go fast, go alone. If you want to go far, go together.”

I want to go far. How about you?


In addition to a big hello, I also have an interview with Chris Guillebeau, everybody’s favorite non-conformist, talking about unconventional business building and big, scary goals as well as a special giveaway where one person will win these 3 awesome prizes:

  • A copy of Chris’ Unconventional Guide to Working for Yourself because a huge part of taking bigger, better risks in life is setting up a work/life situation that fosters and encourages it.
  • A copy of Chris’ Frequent Flyer Master Guide because if you’re going to work for yourself and become location independent, you might as well take full advantage of it.
  • One month of email start-up help from yours truly because that first month can be a big hurdle when you’re trying to build inertia and I want to make sure you get all the help you need to start things off on the right foot.

How to Win

Check out the interview with Chris below, and then leave a comment telling us about a big risk that you want to take in your own life.

A panel of esteemed judges and trained chimpanzees will evaluate all the responses (so make ’em good!) and I’ll announce the winner on Saturday, June 5 during my very first site update.

Important: You must leave a valid email address in the email field of the comments in order to win as it’s the only way I’ll have to contact you.

Update: The contest is over. Thanks to everyone that participated.


Chris, you’ve been self employed for you’re whole adult life. When did you decide that life as an employee wasn’t going to fit into your plans? Can you point to a specific event or was it a slow realization?

Life as an employee ended at age 20. I was slinging boxes on the FedEx third shift in Memphis, Tennessee while going to grad school during the day. The job was fairly exhausting and I kept falling asleep during class due to working until 4am.

At the time, eBay was a new business and I learned to buy and sell in a way that made $25 an hour. The FedEx gig paid $8 an hour, so that was an easy choice.

Then, over the course of the next decade, I grew more and more appreciative of the power of entrepreneurship as a force for good and an important way to change the world. But in the beginning it wasn’t very strategic—I just didn’t want to work for the man.

You didn’t start off as a “full-time” entrepreneur. For awhile, you were working for an aid organization in Africa while running a business on the side. What was that like?

Well, I’ve never been full-time in terms of a regular schedule, but I’ve always been responsible for my own income. So in Africa I volunteered throughout the day for a medical charity, and then at night I went into my small office with a satellite internet connection and worked with business clients in the U.S.

For me it was actually a lot of fun to combine both worlds, but it was also stressful at points when a lot of things were happening in both worlds.

People who’ve bought your guides have learned all kinds of incredible things from you. What’s the most important thing you’ve learned from them?

I learn from customers (and also readers in general) every day. Overall, they have made the business and overall mission much better than it would be if it were just me.

In terms of the biz learning, probably the most interesting thing was talking to so many entrepreneurs during the recent production of the Empire Building Kit. I heard a range of fun stories about building a lifestyle business in all kinds of unusual industries like dog-walking and murder mystery hosting.

It proved that you don’t have to be an “internet marketer” or star blogger to create your own little project that has an impact on the world while also providing a good income for the business owner.

That’s really great – a testament to how many ways there are to make a difference. Starting your own business can be quite a challenge, though. A lot of people never do because they’re afraid to fail. You’re on a mission to visit every country in the world by your 35th birthday. What if you don’t make it?

Good question. The short answer is that I’d be disappointed, but I’d keep working on it. Age 35 is a deadline, but the more important part of it is making it to every country.

With any big goal, there are factors that are within your control (most of them) and others that are out of your control (fewer, but some can be crucial). It’s kind of like your goal of running marathons: you have to make sure you train well, prepare well, rest well, and so on. Those are the most important factors to ensure success. But you could also have an injury comes along and isn’t your fault but still prevents you from achieving the goal.

So my perspective is that we should do everything we can to max out the factors that are within our control, and therefore reduce the risk of failure. In my case, I have to make sure I can get visas sorted, which gets progressively more difficult as I start working on countries like Iran, Libya, and North Korea. I have to make sure I block off enough time in the calendar to cover inevitable delays. And so on.

So the point is that it’s more important to get it done than to get it done perfectly. I definitely agree with that. What’s one thing anyone can do – right now with no experience – to take a step towards starting a business they truly care about?

Two different approaches to this:

1) I always ask people to think big-picture about what they care about that other people also care about.

This is important because despite what you may hear, you can’t build a business strictly around yourself. It has to be an intersection or convergence between yourself and a big enough group of prospects/customers/supporters/clients to support you. Ultimately, that is the best path to starting a business oriented about someone’s passion.

2) That said, you can also just get out there and start doing things.

The “throw stuff against the wall and see what sticks” strategy can work very well, especially in the beginning when you’re not sure what you want to do. Can you list something for sale on eBay or etsy today? Create a website in a day? Offer some kind of service on a blog and see who’s interested?

There are all kinds of interesting business models out there just waiting to be discovered. Look at this guy who wears company t-shirts every day for a living. Look at the infamous million dollar home page. Those ideas are taken already, so what’s yours?

Thanks for the interview, Chris. And thanks for offering up your guides for the launch day giveaway. I’m going to make sure they help change someone’s life.


Alright, folks. If you want to win a copy of Chris’ guides and a month of email support from me, you know what to do:

Update: The contest is over. Thanks so much to all that participated.


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