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

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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What smart people are saying about this...

  1. Congrats on the “official” launch Tyler.

    I’m starting to do some IM consulting. It’s scary to value your opinion & expertise to the point where you charge people for it. I’ll enjoy the freedom it does provide and the possibility to live, work and travel anywhere =)

    joel [at] joelrunyon.com

  2. Tyler, congratulations on the launch!

    The risk – grow a small business to the point that it begins to rival my current “stable job’s” income. Then take the leap and break into full employment independence.

    I’m starting a small business that will allow me to help more people during their job search. I’m doing this as a side revenue project to start as I can’t quite afford to leave my day job just yet… baby numero uno on the way in NOV! YIKES!

    The Frequent Flyer Master guide would be an awesome tool. The wife and I have traveled to 9 different countries in the past 18 months and need to get smarter about it.

    Thanks for another great source of inspiration and information.


    Michael [at] thewurkshop.com

  3. Joel – Thanks for the well wishes. I know how scary it can be putting a real dollar value to your skills, but consider this: the scarier, it is, the more important it is that you do it. :)

    Michael – Great plan. It’s a tough road building something on the side, but when you know what you want, you go after it. Congrats to you and your wife on the baby!

  4. Nice article, Tyler. : )

    Starting my own business isn’t really in my near future but I do want to find a way to go back to school so I can either be a speech pathologist or a special ed teacher. Since my puny education salary isn’t going to make that a reality, I’m going out on a limb and starting a paper/web content editing business. My goal is to get to school within the next year and still have enough money to travel to the south of France, Greece, and Turkey.

  5. Hey Tyler!

    The big risk I want to take is to start my own business empire! I don’t want an evil empire, but simply a group of businesses I’ve started that I can potentially I can give to kids. I also want to relocate, although I’m not sure where to yet. Where I currently live has a ton of opportunities, but I know it isn’t what I want long term.

    How will starting a business help? Well it will be the first step on a long path in the right direction! I’ve been considering starting a personal finance blog, as that would likely be the first thing I would like to get into. I currently am awaiting my work experience requirement to get my Certified Public Accountant license, but I think I would rather help people in a personal sense rather than working for my current firm. All of this is coming, but I need to figure out how to set up all of this blog stuff first!

    Oh, I also am following you on twitter now!


  6. Congratulations on the launch of Riskology.co, and thanks to J.D. for the Twitter link! I’ll be following your progress with interest.

    The most immediate big risk that I want to take is not pursuing traditional employment after I graduate in 11 1/2 months, instead using the time I would have spent searching for a job start a business to fund a delayed, 3-month honeymoon for my Fiancee and me next summer and then support us thereafter. My degree is in accounting, but I don’t want to work in a traditional public accounting position–the more I think about 60+ hour busy seasons the less I like that idea.

    Starting my own business will allow my Fiancee and me to actually see each other year round rather than being virtually separated three months out of the year. A non-location specific business will also allow us to fulfill our dream of traveling for extended stretches of time.

    I’m 19 now, started a summer internship and, much like Chris, am already tired of life as an employee. I’m in the process now of trying to find an idea–those that I’ve had have, upon further research, not been targeted enough to be practical. While this is a big risk, I want to minimize it as much as possible–being in college we don’t have much extra money to throw at ideas that don’t pan out.

  7. Hey there Risk-taker!

    These are all very true points. Having my own small business, I can very well say they are valid points. Although, I think having a business that keeps you rooted in one spot isn’t necessarilly a bnegative for all businesses/business types. I hope and try everyday to make my business flourish into it’s own retail location in Portland. For me, my business is inherently tied to Portland in a positive, wonderful way.

    Though, at some point I think it’s good to reach a certain capacity where you can be mobile with your business and figure out how it can reach more of the world. And who wouldn’t love to be able to manage their business in Aruba with a cocktail and an ocean breeze?

  8. Just popping in again to say thanks to everyone commenting.

    These are some great answers so far! Whitney with the web/paper editing service, Lance with the personal finance aspirations, Philip getting started at only 19 and Jessie pointing out that you definitely don’t have to work online or be location independent to have an awesome life or biz.

    Keep ’em coming folks.

  9. Hey Tyler! Great Articles, I am embarking on a huge risk! Moving to Europe in a few months to take a job to really get to doing what I love in a bigger role! I see that someday advancing into starting a business, but really think I have some growing to do before I find my true passion. Seeing intra-preneurial opportunities is feeding my risk for now!

  10. Isn’t starting your own business a big risk in itself??

    One big risk I took was to quit my job (actually, they fired me a month before I was going to quit. eff the man!) and live in/travel Asia for a year (plus?) with no plans or return ticket. I’m currently at a Zen monastery having an excellent career break/sabbatical! It’s truly living through uncertainty as I have no idea what I want to do… Planning just isn’t my style (I’m horrible at it). I’d love to start some kind of location independent business (I guess this constitutes as having SOME idea. A very general one.) but at this point, the “see what sticks” strategy is more my style. I’m pretty terrified of this new (for me) entrepreneur/business thing because I never saw myself as a self starter EVER (well, kind of, but more in that dreamer sort of way, not reality. I mean, I’m way too unconfident for this, right? That’s what I said THEN and in many ways I am still scared but the ‘calling’ is getting stronger and stronger lately!). I am just fed up with the corporation (I’m a big fan of magazines like Adbusters) and want to help change the world. I don’t know if it’s activism or humanitarianism or what.. I’d like to thank the recession for inspiring this shift in me (and it looks like I’m not the only one!). It makes me happy to know that creatives and artists really look like they’re going to be the modern day movers and shakers!

    I have a graphic design degree so my business venture would probably revolve around service… Would love to be more of a professional blogger but authority blogging really intimidates me. I think I could benefit a lot from the e-books!

    PS: hi from a fellow PDXer. I’m starting to think we all rock!! :)

  11. Hey Tyler,
    I’m very happy to see your “big offical launch”.

    Here my “big risk”-story:
    I have a pretty nice job with all the perks you might want. The problem is: I don’t have the feeling that I’m really contributing to a better world.
    I’ve always been obsessed with developing AND implementing concepts and strategies that facilitate synergy, collaboration, creativity and thus democracy in places where people get together to do “work”.
    As a consultant and planner I often get at least a glimpse of what is and imagine what could be, which – with my work stopping at this level – leaves me completely unsatisfied.

    The Big Risk I want to take is to develop a sustaining business where I can make my personal obsession my daily “job”. I’m sure I won’t find peace until I take this step.

    I hope to see many more wonderful posts that inspire me on my way.


  12. I’m going to go out on a limb here (again) and speculate that quitting your job and moving across the entire continent to start your own business is a fairly sizable risk.

    The larger risk, the one this smaller risk seeks to help me satisfy, is to connect with amazing people and be location-independent with a flexible schedule.

    Congrats again on the launch, Tyler.

  13. Thank you Tyler! I was just thinking yesterday…hmmm, this risk-taking is kind of addicting. Yes? I started my blog this year- which was WAY scary. I just finished my book, and putting it out there and trying to sell it scares the shit out of me. I’m a dancer by profession- and after raising my family- I’m trying to get back out there for whatever opportunities exist. I want to share all that has been given to me. (I’ve emailed a pitch to an artist friend – I want him to paint on me. That was scary). I love the simplicity of your message and the way in which you launched it. You are great. Thanks!

  14. Thanks for the replies Matt, Floreta, Agata, Matty, and Megan.

    Ya’ll are blowin’ me away with your ideas. There’s obviously a lot of passion here. The esteemed judges have some tough deliberation to do.

    I’ve already fired the trained chimps. They were worthless.

  15. First- Thank you Tyler for doing this!
    Second- What serendipity that I am starting a small biz! http://www.whipstitchwares.com is taking over the world one handmade bicycle accessory at a time!
    Third- I’m scared shitless! Mostly about the things I HAVEN’T DONE. Like finish my undergrad degree…yeesh. The scariest things aren’t the 800 mile bike trips, the new biz, or the break ups- they are the boring day to day stuff, the looking yourself in the mirror moments…I’m ready to take some advanced risks, my friend!

  16. Hello Tyler,
    We met at last thursday , Im Jon’s little brother.
    I love the site and ideas behind A.R. .The risk I want to take is to become a web design freelancer. My biggest problem is staying focused and following through with ideas/plans. Hopefully some of your ideas will be absorbed by my mind grapes.
    Stay Classy !

  17. Hey Tyler!

    This site and philosophy guiding it are killer. Keep up the good work.

    The risk I’m currently trying to figure out how to execute is “putting myself out there” as a musician. Let me explain. I want to focus on my songs and my own voice. I’ve had some success being a supporter of other people’s projects, that is, playing drums, guitar, and singing back-up as a means for other people to realize their own visions. Although I enjoy this quite a bit, part of me feels stunted as a performer and musician. I’ve never been very good at selling myself to people and find it oddly (and frustratingly) comforting to take the role of “sideman” to other people. Isn’t it strange that being comfortable in this instance is the very thing that’s keeping me from growing in the way I want? My risk will be to put myself out there by performing my own songs SOLO on a guitar without anybody else for me to defer to. Ultimately I hope to get a band of people together who will be motivated and interested in what I want to produce musically.

  18. Hi Tyler,
    I’ve been taking risks since I was 15 and left home to move back East. I’m still taking risks but have slowed down these past few years to live a “balanced life”. Finding there is no adrenaline there..I’m a single mom with two kids and told them years ago I wanted to visit a different country every year with them until they left home – not just sightseeing, but living wherever we are like the locals. My kids are always asking when we are going to get started. I just realized today my son is starting high school in the fall and I need/want to make good on this. Scary how fast time goes by. Second risk is going to be how I am going to financially make this happen. Deep down I want to raise risk-takers who are passionate about being alive- and I need to be the example – kids learn what they live.

  19. My risk is that I want to make a difference in homes, my community and maybe even a nation. I see a serious problem in society today and that is the breakdown of it. It wasn’t perfect in past generations either but one thing there was a lot more of in previous decades was good manners. Think about it a minute. Watch some popular tv shows. Respect and etiquette are hard values to find today. I could be like the Joker and decide the world needs an enema but what I really think it needs is simply a revival of good taste. So I’m desiring to found a charm school in my area and branch out from there. I know, I’m crazy but it’s a burning desire within me nevertheless. Your blog is fantastic and I wish you much success!

  20. thanks for the imput im 57 yrs old i found my self almost broke getting closed to my retirment age with nothing save to speak abouth it except debts and young family that depends on me im try my best to follow my gut and my heart, im been working since 14 yrs of age im tired and i dont see a way out let me know what can you ofer sincerely your ted sr tedwiny@yahoo.com

  21. I started doing art professionally three years ago, straight out of school. Ignored traditional jobs despite everyone’s unwarranted advice. Didn’t start seeing any profit until last year.

    But it seems if i don’t take a bunch of little jobs to keep afloat, i can’t seem to pay my bills. I want to stop taking on little commissions and to focus on longer more extensive personal driven projects. There is a gap of undetermined time that would happen in the transition before i’d find out how to make that profitable. And i’m not sure how to make it all happen.

    Not sure how to jump a large income gap in my market base/ clientele.

    Thank you for the opportunity Chris and Tyler! <3

Founded with love by Tyler Tervooren

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