Fellow Riskologist,

I remember my favorite teacher in 7th grade trying to explain a little about physics and how energy works.

She told us, “When you pull the bands back on slingshot, you’ve created a lot of potential energy. But to turn that energy into something useful, you have to let go of the bands; you have to turn the potential energy into kinetic energy.”

I remember spending several weeks after that lesson looking at everything in my life as potential and kinetic energy:

• The books resting on the bookshelf were in a state of potential energy until I picked them up and started reading them (or they fell off the shelf).
• The neighbor revving his car obnoxiously was full of potential I wished would turn into kinetic energy by driving away.
• The lunch I just ate would be converted from potential to kinetic energy as I made the long trudge to class on a full stomach.

I’m not the smartest Poindexter on Earth when it comes to science and math (I still secretly do math with my fingers). The examples above do not do a great job of illustrating how potential and kinetic energy work in terms of real science.

But my understanding of it as a 7th grader has turned out to be a great way to look at life and taking great risks.

In order to do something remarkable, you must convert your thoughts and your preparation (potential energy) in to actions that produce some sort of measurable result (kinetic energy). If it’s in your head, it doesn’t count! Once it’s out in the world, it can be judged on its merits.

The difficulty is finding the courage to make the one tiny step that takes you from one to the other.

It takes no courage to read a book, but it sometimes takes a lot to put what you’ve learned into action. It takes little effort or courage to pull the bands back on the slingshot. And it takes none to watch the pellet fly away. But the moment between pulling the bands back and watching the pellet strike its target—the conversion from potential to kinetic—takes all the courage you have.

For that one moment, you are confronted with everything that could go wrong—all of your fears, uncertainties and doubts about the future right in your face as you contemplate whether or not to let go.

But the smart Riskologist knows the only way to achieve what he wants is to release the bands and let the pellet fly. He knows the books he’s read are useless until he takes the ideas learned from them and creates something tangible.

Some people spend their lives building nothing but potential. They create so much they could practically reverse the spin of the Earth if they released it. But they never do, and the world continues just as it always has.

And some never build enough. They are forever taking action before the right moment and reaping sub-par results for their (lack of) effort.

But the smart Riskologist builds just the right amount of potential and converts it to action at just the right moment. He not only pulls the bands on the slingshot all the way back, he releases as soon as the target is in sight.

When it comes to potential and kinetic energy in the life of a risk taker, one is no better than the other—both are required to take the optimal risk with the right odds of success. And neither are handed to you; you’ll work for both.

As the saying goes, “Strike while the iron is hot!” But the iron does not heat itself. That’s your job, too.

Fellow Riskologist,

With the recent unveiling that The U.S. is spying on its own citizens and a few conversations and incidents I’ve had recently, I’ve thought a lot about the concept of privacy.

For those who argue “privacy doesn’t matter when you have nothing to hide,” I would counter that everyone has something to hide.

If you think about it, we all have information—and we all do things every day—that, while not secret, we don’t really want to share publicly. Particularly with our government.

If you really do think you have nothing to hide, I’d like to ask you a question:

Is that the truth, or have you just not yet been presented with a situation that’s crossed your privacy threshold yet?

Let me illustrate with a few examples:

Are you okay with the government collecting large swaths of Internet data you’re included in because it “keeps us safe from foreign threats?” If so, continue…

Are you okay with the data of your telephone calls being kept for the public’s security? It could be saving us from terrorists. If so, continue…

Are you okay with police searching your car (and everyone else’s) on a public road to make sure no drunk drivers get through? No one wants drunk drivers on the loose, right? I don’t.

These, of course, are things that are already happening. But where, exactly does it go from there? How about a few hypotheticals:

Would you be okay with the government telling you to remove the curtains from your home so the police can monitor for illegal activity? A lot of bad stuff happens right inside of homes across the country. Should we try to catch the bad guys like this?

Would you be okay if you were asked to make a monthly report—under oath, of course—of the conversations you had with your husband or wife? Don’t forget to include pillow talk.

And since weapons are so easily concealed, what if you were asked to strip naked to prove you’re not carrying anything dangerous as you go about your day? We could be absolutely positive no one is carrying a weapon they shouldn’t be if we did this.

I say that if you close your curtains at night, if you don’t tell strangers of your most intimate conversations, and you wear clothes when you go outside, then you do care about privacy.

Somewhere along that line of hypotheticals, you probably reached a point where you said to yourself, “No, I’m not okay with that.” And that’s okay! You shouldn’t be!

Here’s something funny (read: tragic) though: The hypotheticals above aren’t (completely) made up. Each example comes from a previous assault on your privacy. For years in The U.S., the government has tried to enact laws to give them more access to your private property, to your private conversations and, in NYC, police actively perform pat down searches on anyone they like.

If you’re okay with some of these examples but not others, I’d say I’ve made my point. Please remember that everyone has their own privacy threshold that is different from yours. I live quite publicly here on Advanced Riskology, but there are other parts of my life I prefer to keep private. You probably feel the same about your own life.

Just because your line has not been crossed yet, does not mean that someone else’s hasn’t.

Whenever we’re asked to give up our privacy, it’s always for the “public good.” But this is a red herring. Our privacy (or giving it up) is not for the public good; it is for our individual good. And when you respect and protect the rights of an individual, the public good is protected by default.

As risk takers, we give up the very thing that allows us to take risks when we give up our privacy. A smart Riskologist knows that to take a great risk in public, she must be able to take many small ones in private to prepare herself.

She must feel confident that she can keep her thoughts and her actions to herself until she’s ready to reveal them. And she should feel confident that her personal life and experiments are safe from government scrutiny.

It is not up to a government to tell us when we have privacy and when we don’t. It is not even up to the people to tell their government spying and breaching personal privacy is okay because it is not up to me to decide when it’s okay to trespass on my neighbor nor he on me.

Privacy is not bestowed upon us by a government or any other person or entity, and it is not a privilege. It is a right. And just like a number of other rights we hold dear and defend fiercely, it is a natural right—one we are born with, live with, and die with. It is ours simply by the nature of our humanity. No one can grant it or take it away. It simply is.

If this message struck a chord with you, I only hope you will—as a smart Riskologist—stand up for your own right to privacy in whatever way you feel appropriate.

Remember that a right is not something that is taken away from you in one fell swoop. Instead, it’s slowly eroded over time until it is meaningless. Piece by piece, it’s dismantled while your attention is directed elsewhere.

Beware.

Fellow Riskologist,

One of the less amazing things about life is that bad things often happen to good people.

Sometimes, these are a result of your own poor decision-making. Maybe you made a bad business investment and lost a lot of money or neglected a relationship that fell a part. Maybe you simply miscalculated and made an honest mistake that hurt you or someone you care about.

Other times, bad things come to you through no fault of your own. Every day, good people get horrible diseases, loved ones pass away, and bad people do terrible things to those who’ve done nothing to deserve it.

As a Riskologist committed to trying new things in life and continuously improving, chances are you’ve experienced both sides of this coin.

I call these my “badiversaries.” God knows I’ve collected a few.

You and I both have a string of failures lined up behind us we’d rather forget, and we can certainly remember moments from our lives we never asked for that came to us anyway.

The natural reaction, of course, is to do everything you can to forget them. In the best of times, you turn to positive psychology, your friends, family. In the worst, you turn to vices and self-harm for temporary relief.

Whichever you choose, one truth remains: your memory defies you.

Over time, you’ll begin to remember events differently. The harshest bits fade. You filter things differently. Memories change.

But, they never go away. For better or worse, these moments you’d prefer to forget are here to stay. They’re a piece of you for the rest of your life.

For that reason, a risk-taker like yourself would be wise to put them to work as an opportunity to become smarter and stronger instead of attempting to ignore them only to be haunted by them the rest of your days.

5 Ways to Properly Celebrate a Badiversary

To properly celebrate a badiversary, the only requirement is that you stop sitting around feeling sorry for yourself and start using the life experiences you have to become a stronger person. Easy!

These experiences are yours after all; you may as well do something constructive with them. Here are just a few ideas I have about how to do that.

1. Throw a private celebration.

A badiversary is rarely a time for a proper party. No guests, cake, or funny hats are a great fit here, but I find it very helpful to set aside some time during the day to at least recognize that, “Here I am on the anniversary of something that went terribly wrong.”

I try not to dwell on it too much, but if I don’t take the time to at least recognize the day, I’ll end up feeling sad or anxious, and I can’t shake it. Nowadays, I’m far too busy with amazing things to lose a whole day to unexplainable anxiety.

By scheduling a piece of my day and dedicating it to just “letting the shit flow,” as I like to put it, I can deal with any weird feelings I’m having all at once, put them behind me, and get back to being awesome again.

To become a more intelligent risk-taker, I recommend finding a way to compartmentalize failures and bad memories so they don’t consume more time than they deserve.

2. Recognize how amazing life actually is.

Even the most unlucky of us can take some solace in the fact that if you count up your life to date, you’ve had far more incredible things happen to you than you have terrible things.

This should not go unnoticed on a badiversary. Be sure to set aside time to remember all the good things going on in your life.

The normal reaction on a badiversary is to dwell on the fact that something has screwed up your utopia. But don’t forget all the things you’ve done and had happen to you that built a utopia to be screwed up in the first place!

Without being flippant about the very real suffering that people sometimes endure, at the end of the day life is still pretty damn good for most of us! And if you’re able to read this article, I’d say that rule applies to you.

3. Reinforce the lessons you’ve learned.

What sets a smart Riskologist apart from your every day risk-taker is that a Riskologist thinks carefully about his life and makes changes to it based on the lessons learned.

While many people wander through life taking risks they don’t even realize they’re taking and learning nothing along the way, you’ve been bestowed with the gift of analysis and the ability to take lessons from less than perfect circumstances.

Not everyone makes use of this gift, but I hope you will. Those that make it the furthest in life and are the happiest tend to be the people who see opportunities where others see only problems.

As you spend some time on your badiversary thinking about the things that went wrong, think of the lessons it provided that have served you well since then.

4. Make a resolution to change something and get started.

Oftentimes, a badiversary will align perfectly with another thing I like to call a Life Altering Event—a moment in time where you’re presented with both the opportunity and the motivation to change something significant about yourself.

When a LAE comes your way, you have to act fast—the effects don’t necessarily last and motivation will fade if left untapped.

If this has ever been the case for you, the proper celebration of a badiversary should include a resolution to do something important for your life. And more than just resolving to it, it’s the perfect opportunity to get started.

When the memories and the lessons learned from a tough time in life come back to you on that fateful day, harness the energy into something productive.

Getting started really is half the battle, and you have a unique opportunity right in front of you.

5. End with a stiff drink.

There are two ways to use alcohol: to numb yourself from pain and forget your problems or to celebrate the victory of a hard-fought battle.

There is something uniquely satisfying about sitting down at the end of a long day of work, looking back on all that you’ve accomplished, and toasting a job well done.

If you’ve done the hard but necessary task of turning your badiversary into a productive piece of your life, you’ve taken quite the stride. Celebrate it. Invite a friend over and pour yourself a stiff drink to toast the day.

Of course, if your badiversary is drug or alcohol related, you might substitute the stiff drink for… umm… a nice falafel or something. Either way, don’t forget to give yourself a pat on the back.

Your Homework Today

Just like a holiday, your badiversary rarely sneaks up on you out of the blue. Instead, you can see it coming. Whether you dread it or welcome it is up to you. Today, take a minute to look at your calendar and find your next badiversary.

Make a plan: When the day arrives, what are you going to do to turn it into a productive part of your life? How will you harness your energy to become a smarter and stronger Riskologist?

Share your answer in the comments if you like.

Fellow Riskologist,

Last year, I wrote an article titled 13 Rules for Being Alone and Being Happy About It. I questioned the conventional wisdom that we all have to be outgoing extroverts to get anywhere in life.

That piece has quietly become the most popular article on Advanced Riskology with nearly 200 comments and many thousands of views.

Wow, so many of us are introverts! We’re a quiet bunch that mostly keep to ourselves, so I’m glad to know you’re all here with me.

On that note: Today, I’d like to invite you to join myself and some friends in a very simple challenge that, quite frankly, could change all of our lives.

But first, I’d like to tell you the story behind it all.

My Coffee Date with a Fortune 500 CEO

“You did what?”

That was the sentiment around the office when I told everyone I emailed the CEO to ask if he wanted to go for lunch.

“You’re fired. That’s what Johan is going to write back when he sees an email from some intern.” That’s what they all joked. We had a laugh about how he might respond—if he responded at all.

I played along, pretending I was a little nervous. Actually, though, I had a hunch back then about what has only been proven to me over and over these last few years:

No matter how popular you are, how much money you have, or how much power you yield, at the end of the day, we’re all pretty similar and it’s nice to get an email from someone who likes you.

That’s why—despite being painfully shy in large groups of people (I am an extreme introvert at heart)—I wasn’t worried about the email I’d just sent.

It was 2008, and I was finishing up my internship with Skanska, one of the largest construction companies in the world. I’d been hired on full-time, but had negotiated a 3-month break so that my girlfriend and I could go explore Europe a bit before settling down for what I thought would be the next 40 years as a construction manager.

The first stop of the trip was Stockholm—Skanska Headquarters—and I thought to myself, “Johan (CEO) always sends me these nice newsletters every month. I should really send him something!”

So I did. The email, while I don’t remember it exactly, went something like this:

Hi Johan,

It’s Tyler; remember me? Just kidding. You don’t know me, but I’m an intern for you in The U.S.

I’m coming to visit Stockholm in a few weeks and I thought it would be great to have lunch if you can make the time. I’d really like your job some day, so maybe you can tell me how to run the company.

Hope you’re well and finding plenty of time to ride your bike (he always talked about biking). The weather here is incredible; I’ve been out for a ride almost every day.

Best,
Tyler the Intern

My co-workers teased me endlessly about this. It spread around the office and, pretty soon, I was known office-wide as “That Guy.” It was a little embarassing—I wished I hadn’t told anyone—but the odds were actually quite good for me.

In reality, what’s the worst that would happen? He just wouldn’t write back and I’d forever be “that one guy that sent a stupid email to the CEO.”

Of course, a few days later Johan did write back. And while he didn’t have time for lunch, he invited me to his office for coffee. When I arrived in Sweden, I took him up on it.

Best cup of coffee I ever had.

The Power of Networking for Intelligent Introverts

Why bother with networking? Especially when you’re an introvert who’d rather be doing anything else (I feel ya’…)? Simple: because it will change your life for the better, and there are lots of very “feel good” ways to do it that can enrich your life as an introvert instead of cause you stress.

Until recently, I hated the word “networking.” I could only think of it as something smarmy people did. The picture in my head was of a slimy salesman going to networking event after networking event filled with other slimy salesmen handing out business cards to people they don’t care about hoping to sell more garbage they don’t believe in.

But when I was hired at Skanska, I had a realization. I noticed that, despite my sometimes painful introversion, every job I had ever gotten in my entire life depended a lot more on who I knew than on what I knew or could do.

• I got my very first job in middle school at a car lot because my dad had built a relationship with the guy who owned it (Admittedly, I get no credit for this. Thanks, Dad!).
• In high school, I got lots of jobs doing yard and farm work because I’d built friendships with other kids at school who had parents with a lot of property to maintain. I never even got a callback the times I dropped off a résumé at local stores.
• My first job in college came through a connection I’d made with the school’s wrestling coach.
• Later, I became a resident assistant thanks to a recommendation from my own resident assistant, Matt, who I’d made friends with. Hundreds of people applied and I had no previous experience to set me apart. Matt and I are still friends today. I even climbed Mt. Kilimanjaro with him a couple of years ago.
• As an architecture student, I made it a point to get to know the campus housing director because he had money to dole out for small projects. I wanted a shot at designing some of them. I never did design anything for him, but he was the one who recommended me to Skanska, the job that paid me more than any 23-year-old should have made and gave me an opportunity to send that email to meet Johan.
• Today, running Advanced Riskology, I can attribute most of the success its experienced to simply getting to know the right people—the people I looked up to and wanted to connect with anyway.

I hated “networking” until I realized I’d been doing it all along. I just wasn’t doing it the way I thought it was meant to be done. But I had been successful, so apparently I was doing something right.

Opportunities to make great connections abound even for the painfully shy and introverted like me. And developing them has made a world of difference.

Introducing the 5-Email Challenge<–Scanners, this is your cue to start reading again

I was having a beer the other day while catching up with my friend Mike Pacchione. He’s a speaking coach who works with the über-famous Nancy Duarte. I hang out around him when I want to feel self-conscious about how often I say “um” and “like” when I talk.

Over a drink, he told me how his entire career started with one ridiculous email to Nancy—who he’d never met or talked to before—a few years ago. I told him about my Johan story.

We both said, “Wow, I haven’t done anything like that in a while.” I said, “We should have a challenge.” He said, “Definitely!” I said, “I’m going to invite the AR community to join us.”

And here we are. Today, I’m challenging you to send some emails just like Mike and I did. If you accept the challenge, here’s how it works:

1. Make a list of people you respect or admire and would like to get to know.
2. Send each of them an email like Mike and I did.
3. Collect 5 meaningful responses. No simple “yes/no” answers or form letters from assistants.
4. Bask in your improved social abilities.

I’ll be doing this right along side you, and I can’t wait to share my results. (I’ll also be coercing Mike to share his.)

For Mike and I, the challenge will end in a month on Sunday, July 7th, but you’re welcome to keep doing it for as long as you like—even the rest of your life!

At the end of the challenge, I’ll write a follow-up article with results from myself as well as stories from those of you who participated. Get on my email list if you don’t want to miss it.

A Few Tips on Writing Successful Emails

You don’t have to be a rocket doctor to take part in this. Sending an email is pretty darn simple. But, there are a few things you can do to lower your risk of rejection/being ignored. Consider each carefully as you begin your campaign:

• You don’t have to go after über-celebrities. Just think of people who you look up to and would like to get to know. Starting with this makes things a lot easier.
• Finding someone’s email address when it’s not publicly displayed is easy. Think about all the common variations you see on a daily basis, try them out, and you’ll probably strike gold with one of them.
• Your email should be short. People are busy and don’t have time or energy for a life story. Keep it under five sentences if you want a reply.
• The P.S. always gets read. This is an old copywriting trick. Even if the rest of your email gets ignored, everyone reads the P.S. line, so always include one and make it the catchy. Questions work best.
• Don’t ask for anything in your first email. Much better is to just express your gratitude and ask for advice or a question you’re pondering. If you do ask for something more significant, though, you’d better make it extremely easy for them to say yes to. Nothing they have to think about or work too hard to provide or you’ll just get ignored.
• Offering help of some kind is a good relationship builder, but never ask “Is there anything I can help you with.” The answer will always be, “Umm, I don’t know,” and it will be expressed in the form of ignoring you.
• It’s going to take more than 5 emails. Unless you’re the greatest email writer in the history of the universe or you’re not stretching yourself, you’ll have to write more than 5 emails to more than 5 different people to get 5 responses back.

Will you join us? If so, leave a comment letting us know you’re in.

I can’t wait to share more stories and updates throughout the challenge.

Fellow Riskologist,

Last night, as the clock ticked over to midnight, Advanced Riskology turned three years old. Hooray!

I was drinking a glass of wine and thinking to myself, “How did I get here, and what have I learned along the way?”

Over the last three years, AR has become a resource for risk takers the world over. I’m incredibly grateful for what it’s become and to everyone that shows up here day after day. But more than just what it’s become for you, I’m grateful for what its become for me.

This site was born in the throes of a very turbulent time in my life. I’d just been laid off from a cushy desk job. I was a little lost, and I was looking for something to bring meaning back into my life.

I knew I couldn’t stay on the track I was on, but I also didn’t know what the next one was going to be.

I saw some of my friends like Chris and Sean and Corbett and Adam (and many, many others) doing amazing things with their blogs, and I decided to follow suit.

I didn’t know what I was getting myself into, but I assumed—like most things I do with my life—I’d figure it out as I went. At the very least, it would lend some credibility to the message I was trying to spread: that life is better when you take smart, calculated risks and you don’t have to spend your life doing things you don’t like so that later you can switch to something you do.

Three years later, I’m happy to say that while—in some ways—I still haven’t a clue what I’m doing, in other ways I really have figured some things out.

I still don’t make as much money as I did back in the corporate world, but I don’t need as much either. And I’ve created a respectable full-time income for myself. To know that I am in complete control of my destiny is something I could have barely even imagined just three years ago when this all started.

I’ve learned how to build and connect with an audience. This is probably one of the most useful skills I’ll ever develop for myself. After three years, I’ve learned that no matter what direction I take my life, I’ll be able to rally a team of amazing people around it that are as passionate as I am.

Most importantly, though, I’ve learned (the very hard way) the importance of consistency.

When I started Advanced Riskology, I promised readers I would publish two articles every week. For more than two years, I did just that. It wasn’t easy. There were times I wanted to give up. There were times I was publishing from airports or from coffee shops on the side of dirt roads in rural Africa just to meet the deadlines I’d given myself. But I always made it.

Then, last year, I decided to try something different. I was feeling a bit down. I was feeling like I needed something more.

I quit publishing as often, and I went off to build a coffee company (random, I know). I’m incredibly grateful for that experience and I’m very proud of what we built, but I also couldn’t shake the feeling of guilt that I’d  had to trade my regular publishing schedule here to do it.

Now, the coffee business is up and running and I’m back to my old self here on AR. It feels great, but I learned a hard lesson about consistency along the way. Many of you stuck around and supported AR during the slow times. Thank you! But also, many chose not to. And how can I blame them? My attention was elsewhere. I slipped on my promise.

Now that I’m back, everything is falling into place again (a testament to the value of this community), and the power of consistency rings truer to me now than it ever has before:

If you have something great, don’t give up on it! You can change a million things about it along the way, but don’t stop doing it. Advanced Riskology is a blog, and I’m a writer. If I want to keep calling myself that, I’d better be writing pretty damn often!

A writer writes. The key to doing something big is to do something little over and over.

So, here we are three years and 266 articles later. In terms of the Internet, three years kind of feels like a dinosaur. But I’m happy to say this is but the beginning of our journey.

We’ve only scratched the surface of the world of smart risk taking. I’m glad you’re here with me, and I can’t wait to explore so much more with you as we dive into Year Four.

Now what about you? What risk are you looking forward to exploring?

All the best,

P.S. Confession time: Some people will look at the archive and argue that AR started on April 29th, 2010 based on the date of the first published article. The truth is that AR was not live to the world until June 2nd, 2010, and all the articles dated before then were actually written and published the night before the launch and back dated so as not to interfere with the launch post. Now you know…

For the last few weeks, we’ve focused on finding and addressing fear so you can move forward with big projects in your life. Before you clear away underlying fears, getting started on a big project can feel like pushing a boulder up a hill while breathing through a straw.

But once they’re dealt with, you start see the way forward. You see the things you must to-do to succeed, and that’s where the next problem strikes: overwhelm.

If you’ve read AR for a while, you know how I feel about overwhelm: It’s a gift.

But left unchecked, it’s still a problem. And the solution is a system to organize all your to-do items—something to manage the overwhelm and keep you on track.

That’s why I felt our little series needed one last installment: How to manage your massive to-do list.

I’m not much of a productivity nut. In fact, I get a little annoyed around people who can’t seem to do anything but talk about how to do boring work even faster. But I love what I do and, I must admit, the idea of doing a better job at it is appealing. I’m always optimizing how I work to get to all the fun stuff I wouldn’t be able to otherwise.

There are dozens of productivity tools out there to help you manage your endless to-do list, but few have ever worked for me.

Over the years, I’ve learned whatever tool it is I’m using to manage my life, it absolutely must meet these requirements:

• It must be simple. If it takes more than a few seconds to input and update the system on a daily/weekly basis, it’s a waste of time I could be spending actually doing stuff.
• It must be flexible. Reality changes all the time, so it’s critical that any tool I’m using makes it easy to change the plan—reorganize tasks, change deadlines, etc.—when necessary.
• It must be able to rank tasks. Any Riskologist who’s taken on a big project knows a mile long checklist is terribly overwhelming and useless. A good project management tool allows you to easily see which tasks are most important right now and work on just those.
• It must support deadlines. Face it: If you don’t give yourself a deadline, you’re probably never going to finish. Giving yourself hard and fast dates to complete the milestones of your project is critical.

Introducing Trello: The Smart Riskologist’s To-Do List System

First thing’s first: Trello is free, and I have no relationship with the company nor am I compensated in any way for recommending it. I just think it’s great.

I’ve tested many different project management apps over the years and abandoned most of them because they didn’t work the way I wanted them to. I’d spend hours setting everything up and then get frustrated with the workflow and give up just days later when it wouldn’t accommodate the way I wanted to work.

That finally changed when I tested Trello last year as my business partner Jonathan and I started building BrewPony. It was perfect. We were able to run the entire project through the app. Any time something needed to be done, we’d just create a “Card” in Trello, and assign it to one or both of us.

The reason Trello works so well is because, at its core, it’s very simple: a series of to-do lists. But if you want, just a few clicks will allow you to use it many ways.

You can test out Trello over here.

How I Use Trello

I’ve used Trello in different ways for different projects (which is a testament to its flexibility), but the standard workflow I use for most projects looks something like this:

First, I set up a new “Board.” This is where everything for any specific project lives. Then, I set up four specific “Lists” inside that board:

• To-Do
• Doing
• Blocked
• Done

Those lists are pretty self-explanatory. When a project is beginning, I’ll load every task I can think of into a Card  what holds an individual to-do item) on the To-Do list.

Once I start a task, I’ll move it to the Doing List if it’s something that’ll take a little time to complete. Once it’s complete, I move it to the Done List. For short tasks that I can finish quickly, I don’t bother using the Doing List. I just move it straight from To-Do to Done.

If I run into a roadblock while working on a task, I’ll move the card to Blocked if I get frustrated and want to move on. This way, I never get bogged down or lose track of what I’ve done. If I need to leave things unfinished at the end of a day, I can come back to Trello any time and see exactly what I’ve already started and where I’m blocked. Then, I get to work on those things first.

How I Organize Trello Cards

The Trello Card is extremely simple, but also versatile. At it’s most basic, you can just type a task into one and call it a day. Or, you can open the card and use it’s more robust features to do a lot of organization.

Trello Labels

The first thing I’ll do when I create a new card is assign a “Label” to it. Trello allows you to assign up to 6 different color coded Labels to a card. Here’s how I typically handle this:

• Red = Urgent
• Yellow = Important But Not Urgent
• Green = I’ll Get to it “Someday”

Whenever I log into Trello and I’m in a hurry, I’ll immediately filter the cards so that I only see the urgent ones (Trello has an incredible filtering system that allows you to see only what you want at any give time). That way I don’t have to wade through a lot of stuff that’s important but I don’t have time for at the moment.

Then, once a week, I’ll spend a few minutes reviewing tasks with all Labels. If something in the Important But Not Urgent Label needs attention—or if I have more time available to work on it—I’ll move it to Urgent so I can start making it a priority. I’ll do the same moving Someday cards to Important.

And just as important is taking a second to archive any cards I’ve created but realized I’m just never going to get to. This keeps the list clean and focused. I can always pull them out of the archive later if I decide I want to work on it.

How I Use Trello Due Dates

Deadlines are a critical part of actually getting anything done in life, but I admit I haven’t been the best about setting them for myself. Trello has helped me with this a lot, and the way I use them is simple and flexible.

First, only cards marked Urgent or Important get due dates. Sometimes, a due date is very clear and can easily be assigned. Other times, it’s nebulous. When this is the case, it’s easy to just ignore it or avoid giving it a deadline, but this is when it’s most important to have a deadline lest you end up with an urgent and important task that never gets done.

In these cases, I just make up a deadline that sounds good. There’s no science to it. I just pick one out of thin air.

This works because of the way I filter cards when looking at Trello. I can show myself only the cards that are “urgent and due within the next week.”

That’s my hot list that I know I need to kick it into gear on. If a task with a made up deadline  works its way into this filter that I know I don’t need to get to, I’ll simply change its deadline. Not the best, but it at least keeps me—for the most part—focused on tasks that are important and need to be done.

Due dates get the same scrutiny and adjustments during my weekly review.

How I Use Trello Checklists

The Trello Card is very versatile. It can be as simple or complex as you want it. Inside of each Card, you can also set up a Checklist. This basically allows you to create another to-do list inside of a to-do item. Very meta, I know.

I find it useful for keeping my board organized. Rather than creating a whole slew of Cards for one specific task, I’ll create one overall “to-do” Card and then set up a Checklist of tasks to complete inside of the Card that I can check off as I make progress. Trello keeps track of each Card as you make progress so you can quickly see which Checklists need to be worked on at any given time.

This is mostly a personal preference. If you’re the type of person who likes to have every task out in the open, you might opt to create a Card for every single task and not build a hierarchy using Checklists. Or, if you wanted to go all out, you might take your biggest to-dos and create a new Board just to manage that one piece of your project. The options are endless.

If at any time you realize a Checklist item needs its own card, Trello thought of that, too. With the click of a button you can convert one to the other.

How I use Trello Comments

The comments section of Trello is the most useful part of the system for me. This is especially true if you’re sharing a board with another person like a business partner or a few team members.

Each Card has its own comments thread, and you can add a note and tag other members in it (so that they’re notified) at any time. You can also attach files directly to a Card so that important assets like pdfs, images, etc. are right there for you to look at when you open a Card.

I like to use the comments system for each Card when working with other people because it’s better than email. When you work this way, conversations stay organized and on topic because there is a specific comment thread for each Card. This eliminates the frustrating headache of searching your email archive for “that one email with the thing mixed with the seven other things.”

For some reason, most people feel comfortable mixing tasks together in one email (very frustrating and difficult to track), but commenting inside Trello keeps conversations nice and organized.

I’ll also use the comments section to leave notes to myself. This is particularly useful for Cards on my Blocked list. I can leave a note explaining exactly what’s blocking me and what I’ve tried so far. When I come back to it, I have a history there so I can pick up right where I left off.

The Real Magic Behind Trello

All of Trello’s features are great but, at the end of the day, there’s one specific thing about Trello that keeps me attached to it and makes it a great project management app—the ability to move Cards from place to place.

This very simple feature—clicking and dragging a Card from one list to another—went mostly unrecognized by me at first, but when I think about why I enjoy using Trello so much it’s because I get some type of satisfaction each time I drag a card from the To-Do list to Doing or Done. It’s like a little mind trick that makes you feel like you’re getting even more done.

That bit of satisfaction is important! Staying motivated to work on your goal is what’s going to make or break everything, and Trello actively helps me stay motivated.

Now, I’d caution any smart Riskologist to never rely on a project management system as a source of motivation, but it’s good to know that Trello will never get in the way of my progress. It works just the way I want it to, when I want it to—never a source of friction.

Your To-Do List Should Actually Help You Get Things Done

At the end of the day, it doesn’t really matter what system you use or how you organize yourself so long as you have something that works. It should help you get things done and never feel like a burden.

Trello works for me, and I’m happy to recommend it with no compensation because I think a lot of Riskologists here probably have similar projects that would be a great fit for it.

Trello is completely free, and you can try it out here.

If you have a system that works for you, tell us about it in the comments because I’m sure my way won’t work for everyone. We’re all a little different!

Fellow Riskologist,

If the source of your fears remain the same throughout your life, I’d argue you’re not truly living.

Last week, I published a piece called The Risk Taker’s Boogeyman syndrome, and many brave Riskologists answered my call to arms:

Identify where your fears come from—where your boogeyman lives—and take a step towards moving them further away.

In life, most of us will never experience complete fearlessness, but it also isn’t necessary. In fact, thinking fearlessness is the goal will hold you back. Instead, I say the main ingredient to a great life is to challenge your fears—to confront your boogeyman—and move them from one place to anther (hopefully further away).

If you’re working on a big goal for your life, you’ll have to go through this process many times.

My Own, Personal Boogeyman

In my quest to join the 7 Summits Club, I have to face these kinds of fears regularly. And the fear that stands out the most for me now is climbing Mt. Everest. With some high altitude experience under my belt now, I don’t get too scared about the idea of climbing any more. But this is not true for Everest.

The idea of spending more than a month on the tallest mountain in the world still terrifies me a bit. There are so many variables involved in an expedition like this it quickly becomes overwhelming just to think about.

The more I understand about the mountain and what it takes to climb it, though, the less I fear it and the closer I get to standing on top of it.

The 5 Step Risk Analysis Plan for Any Life Goal

If there’s a project you’re trying to start, there are probably a lot of variables involved. As long as you don’t understand them and fail to plan for them, you’ll struggle to bring it to life. It’s hard to take a leap when everything feels like such a big risk.

What you need is a system to help you work out the many pieces of your big challenge so that you can take action on them.

This is the 5-step plan I use each time I take on a big challenge. Working this all out on paper is therapeutic. As we go through the steps, I’ll be using my future expedition on Mt. Everest as an example. You can do the same for your own project.

This is a repeatable process for any risk you want to take in your life, and it forces you to do these three important things:

• Identify the risks involved.
• Define and understand each important variable.
• Create a plan to reduce each risk.

Step 1: Define the variables and threats to your success.

The first thing you must do to overcome a fear and mitigate a risk is to simply make a list of all the different moving pieces that have to be planned for and things that could go wrong.

In my example of climbing Mt. Everest, here are the major pieces of the puzzle that I’ll need to contend with:

• Cost: Climbing Everest, at its cheapest, is still a very expensive endeavor.
• Transit: I’ll need to figure out how to get to and from Katmandu, Nepal. From Katmandu, I’ll need to get to and from Everest.
• Mountain Guide: I can’t climb Everest alone. I’ll need to hire a very skilled guide and at least one sherpa.
• Climbing Gear: Climbing Everest requires a class of gear above anything I’ve had to use before.
• Weather: Even in the best conditions, weather on Everest can be extremely harsh.
• Crowds: Climbing Everest is becoming a bit popular which means more people on the mountain causing traffic jams on technical slopes.
• Climbing Skills: Everest requires a level of technical climbing skills above what I have now.
• Physical Conditioning: My body must be in top shape to handle the grueling climb.
• High Altitude: Everest is the tallest mountain in the world at over 29,000 feet. Being at this altitude for any length of time can do significant damage to your health.

There are many other variables in an expedition like this, but these are the major pieces that I can start thinking about and planning for now.

Action Step: Make a list like this for your own project.

You’ll notice that, as you learn more, you’ll find new variables that you didn’t know about before. These are the “unknown unknowns,” and you always run into more of them. You can’t be expected to pre-plan for everything, but the better you do planning the pieces you do know, the less likely an unknown variable is to ruin things.

Step 2: Identify the Worst Case Scenario for each variable.

One of the biggest benefits to becoming more educated about the risks you take is that the more you understand, the better you can see and plan for Worst Case Scenarios. When you don’t understand what you’re up against, you’re more likely to commit one of these two major mistakes:

1. Overestimating the Worst Case Scenario: You may be scared of something that is unlikely to be a problem. This is the source of irrational fears that keep you from making progress on your goal. This is your personal boogeyman.
2. Underestimating the Worst Case Scenario: Without educating yourself, you may set out to do something extremely dangerous without planning for a very real and present threat.

For most of us—the cautious types—overestimating is a more likely scenario. Once you learn more about what you’re trying to do and practice at a smaller scale, you find the realistic Worst Case Scenario is usually not as bad as you once imagined. The boogeyman becomes a little less scary.

Action Step: For this step, use the variables from above and outline the realistic worst case scenarios you’ll face if each one goes terribly wrong.

Here’s my list for Everest:

• Cost: I could fall short of my fundraising goals after committing large amounts of money to people and equipment that cannot be refunded. In this case, I would lose a lot of money and the trip would never materialize.
• Transit: There aren’t many options for transport to and from the mountain. If my schedule fails, it could end or significantly delay my climb.
• Guide: I could hire a bad guide that fails to prepare properly for the expedition or doesn’t keep me safe. If this happened, my climb could be ended early or I could be lead into a dangerous situation.
• Gear: I could buy insufficient gear that gets me into a lot of trouble if I were to face extreme weather.
• Weather: Storms are a regular occurrence on Everest. If I get caught in one below 8,000 m, it could prematurely end my climb. If I get caught in one above 8,000m, I could die.
• Crowds: Getting caught in a slow-moving crowd above 8,000 meters could be deadly.
• Climbing Skills: I could fail to train properly and fall during a technical section of the mountain. This would probably result in significant injury.
• Conditioning: My body might be ill-prepared for the climb. This would force me to end the expedition early.
• Altitude: My body could react poorly to the high altitude, causing cerebral edema. If not caught early enough, the result could be permanent brain damage or death.

Wow, there are a lot of worst case scenarios on my list that realistically could end in death. That’s not the most fun thing to think about, but it’s a good thing I’ve at least identified them!

Most likely, you will not face the same level of risk for your own challenge. But I can feel secure knowing that, as I learn more about climbing Everest, I’ll find many ways to significantly lower these risks.

Step 3: Figure out which variables affect the others.

In a big project with lots of moving pieces, you’ll find not all of them are as important as others. Instead, there’s a hierarchy and certain outcomes are connected to others. Figuring out how the different pieces of your project are interconnected will help to whittle your action steps down to a manageable amount.

Overwhelm can kill a big challenge, so complete this step carefully to narrow your focus.

To decide which risks are most important for you to focus on, go through your list above and ask yourself:

How does the outcome of this variable affect the others on my list.

You’ll find some stand alone and don’t affect other parts of your project while others are highly connected and failure would prevent other variables from even coming into play.

For my Everest expedition, here are the most highly connected variables I’ll need to focus on first:

• Cost: If I don’t raise the money or find a way to lower the expense, the expedition cannot move forward. All other factors are irrelevant.
• Transit: If I don’t successfully arrive at the mountain at the right time, an attempt at the summit will be out of the question. All other factors become irrelevant.

These are the two variables I control which could make or break the trip before it ever happens. But they’re not the only risks. Once I’m on the mountain, I can see that conditioning, altitude, and climbing skills are highly correlated:

• Altitude: If I spend too much time at altitude or my body reacts poorly, it will affect my ability to use my climbing skills and conditioning. It will also impair my judgment.
• Climbing Skills: If I fail to develop the climbing skills I need, I won’t climb efficiently and I’ll waste energy. It will also cause me to climb slowly and risk spending too much time at altitude.
• Conditioning: If I don’t condition myself properly, I won’t be able to confidently execute my climbing skills and I will spend too much time at altitude.

I’ll need to make a plan to  lower the risk of these variables blowing up in my face as much as possible. I get to completely control two of them, so I’ll focus my attention there. You’ll want to look at your project with the same scrutiny.

Action Step: Find the variables in your project that could cause problems in other places if neglected.

Step 4: Determine how likely each variable is to go wrong and how much you control it.

Now you have a list of the variables for your project that are connected with the others. You know you’ll want to focus on these. But you’re not quite done. Your last step before getting down to business is to decide how likely it is that each threat to your project so far will actually come to be, and decide how much control you have over it.

This is important where there are highly connected variables that don’t pose much risk, but several threats that stand alone could take down the whole project.

Here’s how I’ve evaluated the threats to my Everest expedition:

• Cost: Low likelihood of failure because I have a high level of control. If I don’t raise the money I need, I can always delay the trip. Not ideal, but not a massive failure point.
• Transit: Low likelihood of failure because I have a lot of skill in arranging itineraries. Even if something outside my control goes wrong, I feel confident I can at least find my way to Base Camp.
• Guide: Low likelihood of hiring a bad mountain guide because I have access to people who can make excellent recommendations, and the trip budget will accommodate a skilled guide.
• Gear: Low likelihood of failure because the best gear for climbing Everest is well established. It will be important that I follow recommendations and don’t skimp on important equipment.
• Weather: High likelihood of failure, and I have no control over it. I will need to come up with a plan that lowers this risk as much as possible.
• Crowds: Moderate likelihood of failure. Crowding is a reality on Everest these days, but there are strategies that can be used to avoid climbing in a traffic jam.
• Climbing Skills: Low likelihood of failure. I have much control over the time and resources I dedicate to improving my climbing skills.
• Conditioning: Low likelihood of failure as long as I keep up my current conditioning and don’t slack off.
• Altitude: High likelihood of failure. I know my body, and it’s not the best at handling high altitude. I’ll need to carefully build a plan that allows plenty of time to acclimate to the high elevations and minimizes the amount of time spent near the summit.

Action Step: Determine how likely it is that something will go wrong in each variable of your own big project. And to what extent do you control the outcome?

Step 5: Define your “next steps” and get started.

You’ve done a lot of work up to this point to prepare yourself for success, but any smart Riskologist will tell you, “No plan is complete until you take action on it.”

You can spend the rest of your life making plans, but they’re all worthless until you’ve put them to work. You must begin to test your preparations against reality.

Action Step: To get started, create a “next step” that you can take right away for each of your project’s variables. These tasks should be small enough to be completed in a day. This prevents unnecessary procrastination.

Here are the next steps I’ve created for my own Everest expedition:

• Cost: Create a rough budget that includes all major pieces of the expedition.
• Transit: Research and make a list of all transit options for each leg of the trip.
• Guide: Get in touch with three of my experienced climbing contacts to recommend a mountain guide.
• Gear: Assemble a list of gear I’ll need to buy or rent to complete the expedition.
• Weather: Research the different weather forecasting services for Mt. Everest.
• Crowds: Create reminder to discuss crowd control with the expedition guide I select.
• Climbing Skills: Study the Everest climbing route to find which skills will be the most important to develop.
• Conditioning: Continue working out as usual. Create plan to increase intensity in the months prior to the trip.
• Altitude: Create Pre-Everest climbing plan to acclimate to high altitudes before arriving in Nepal.

Your Homework Today

When it comes to making progress on your biggest life goals, things can get overwhelming quickly. Today’s article lays out more things for you to complete than you can probably accomplish today (but don’t let me keep you from trying if you’re up for it).

Your homework today is to do one thing from this lesson that will help you manage the risks involved in your own big project.

Tell us what your project is and what you’ll do in the comments below.

Fellow Riskologist,

Funny thing about running a blog: If people read it, there’s a whole world of folks who will want to give you free stuff.

An audience is a valuable thing and, if you have one, there are lots of people and businesses who will do anything they can to get their name in front of it.

There’s nothing wrong with it, but Advanced Riskology does not operate like this. Almost every day I have to tell someone no when they want to pay me to write about their “amazing” new product or service. I even have a fairly strict policy of saying no to free offers. I turn down books, products, free trials, etc. all the time—even when there are no strings attached.

Side note: When a business sends you something for free with “no strings attached,” you had better believe that there are strings attached. There are *always* strings attached.

I can say with certainty that I’ve turned down tens of thousands of dollars in cash and free offers since starting Advanced Riskology almost three years ago. Keeping my integrity and your trust is far more valuable to me than free stuff I don’t even want.

But, every so often, I’ll get an offer for something I think one of our smart Riskologists here can put to good use, so I’ll accept it and then give it away. Everyone wins!

The other day, American Airlines gave me a free day pass to their Admirals Club. The Admirals Club is a network of private lounges in 37 different airports around the world. Many airlines have a club like this, and access is limited to frequent flyers who have status with the airline or pay a ridiculous fee for a pass.

I’ve never visited an AA lounge, but I’ve visited other airlines’ lounges and, I have to say, it’s a nice experience!

Since travel is a big part of the story here at Advanced Riskology and I like to write about frequent flyer miles and airports from time to time, I thought it would be fun to give away my day pass to a reader who can put it to use.

I’m giving away a free day pass to the AA Admirals Club. If you want it, here’s what to do:

1. Sign up for my free email newsletter over here. (Only newsletter subscribers are eligible to win).
2. Ensure you’ll be traveling before July 31, 2013. This is when the pass expires.
3. Ensure you’ll be traveling to/from/through an airport that has an Admirals Club lounge in it.
4. Most important: Send me an email with the subject line “I Want the Pass!” (Be sure to use the same email address you signed up to the newsletter with.

UPDATE: The contest is now over. Thanks to everyone who entered, and congrats to Marko from Chicago who won the day pass.

See you in an airport somewhere!

Fellow Riskologist,

First, a confession: I used to be terrified of the dark (I was a little kid, gimme a break). I’m over it now, but it was a fear that terrorized me every night before I was forced to confront it. We’ll come back to this in a minute.

Each one of us spends much time every day thinking about something important to us that’s beyond our reach.

You have an idea you’d like to bring to life but seem to feel stuck on—you don’t know what to do first, and you’re afraid of everything that could go wrong in the process. So, you just put off getting started.

Chances are, you’ve done it for awhile.

This isn’t an indictment! We all struggle with this in some form. But what’s behind it? What keeps you from actually taking action on this thing that feels so urgent and important.

Maybe you want to skip town and travel the world. Maybe you want to start a non-profit that helps your local community. Maybe you just want to quit your job and try something else.

At the end of the rope, of course, is fear. And where does the fear come from? In all my experiences, it comes from not fully understanding the risk you want to take. It feels risky because you don’t actually know what’s involved. The variables feel outside your control.

This is what I call the Risk Taker’s Boogeyman Syndrome.

When I was a little tyke—not much of a Riskologist yet—I slept with the light on in my room every single night. I was terrified of the dark. There were shadows, there were noises, there were all these things happening that I didn’t understand, and they frightened me. Certainly, if I left the light off too long, the boogeyman was going to crawl out of the closet and disembowel me.

Luckily, I had a simple solution that worked every time: leave the light on!

The only flaw in the solution was that when you leave the light on all night, every night, you get horrible sleep, and you spend your days tired and unhappy.

One day, my mom got tired of  dealing with me being a Grumpy McWhineypants that couldn’t sleep through the night, so she forced me to spend the whole night in my room with the light off. In fact—if I remember right—she locked me in my bedroom and took my light bulb away. (If I don’t remember right, I’ll be getting a phone call shortly.)

I was stuck in a lightless hell! I was going to die!

I don’t remember all that happened next, but it seems I survived, no boogeyman made off with my intestines, and while I probably didn’t sleep at all that night, the exhaustion from an all night panic attack put me right to sleep—sans lightbulb—the following night.

Today, the idea of trying to fall asleep with the lights on sounds horrible. When I realized my closet is, essentially, exactly the same with or without the lights on, I no longer feared what was inside it. I knew what was inside it—my clothes and some old baseball cards. Aside from my Batman costume, pretty harmless.

Every kid goes through a realization like this growing up. Many of them, in fact. Kids have all kinds of irrational fears that go away once they’re familiar with what they were scared of. That’s just part of growing up.

But then… it stops.

For some reason, it’s a parent’s job to help their kids deal with irrational fears when they’re young but once you’re an adult, it’s perfectly okay to have a whole other set of fears, and no one expects you to get over them!

For many of us, the boogeyman is still alive and well. He just doesn’t live in the closet anymore. Instead, he lives at work. He lives across the world in different cultures. He lives in the attorney’s office or at the bank.

And, for the most part, we’ve all agreed that’s okay. We don’t challenge each other on these grown-up fears.

Except at AR. You’re not getting away with that here!

I don’t think the boogeyman ever really goes away, but your job as a smart Riskologist is to continue to move him from one place to another. As long as he’s on the run, you’re doing something right; you’re overcoming fears and moving onto new ones.

Each time the boogeyman moves, he goes further away than he was before. And each time you find him, he’s a little less scary to face.

Your Homework Today

This is my favorite part of every article I write. I love giving you little homework assignments to do because it shows me who’s reading here and actually taking action to become a better risk taker.

Today, I challenge you to look at your own boogeyman. Where is he, and how long has he been hanging out there?

If he’s been in one place for a while, it’s time to take action on your fear and put him on the run again.

Share your answer in the comments.

Sidenote: I’ll be following up on this next Monday with 5 strategies a smart risk taker can use to overcome any fear and get started on a big, meaningful project. Stay tuned.

Update: I did receive a call from my mom explaining that my memory is not quite accurate. I guess I shouldn’t be surprised.

There’s a silly debate that’s been raging since, I guess, the beginning of time. One side says, “Focus on quality! Always get the very best you can!” The other side says, “No, quantity is what’s important. The more the better!”

Both sides have fair enough points, and you can see the debate rage in almost every aspect of life from saving money on groceries (read the naysayers in the comments) to doing work to making travel arrangements. You probably even debate yourself on it each day as you make decisions for your own life.

What few seem to realize, though, is that—in the end—both arguments kind of suck. And a smart Riskologist knows that to get ahead in life, you must be able to look at the decisions you make for yourself through the lens of cold, hard reality.

Let me illustrate with a few examples.

The Folly of the Rolex Watch

What’s the point of a rolex watch? It’s fancy, it’s expensive, and many people (usually those who own one) think it the best of the best in how-to-know-you’re-late technology.

But is it?

Perhaps many years ago it represented a better time piece than any other on the market, but with the technology we enjoy today, you can get all the same quality and time-telling-fanciness from a $20 Casio. It won’t look as nice, but it’ll work just as well.

And there’s the problem. The quality argument is no longer about the quality that matters: telling time.

All of a sudden, it’s about more than that. It’s about making a statement and owning a status symbol.

There is not a Rolex owner alive that can look you in the face and tell you with honesty that they bought their watch because it tells time better than any other watch on the market.

No, they bought it to show other people that they have money. Only, now that they’ve bought a Rolex, they have less of it, which makes it hard to actually have it when people expect you to.

Next thing you know, you’re spending money you don’t have to keep up an image that isn’t honest and no genuine person cares that you have or not. Whoops!

I have a family friend that ended up in this very predicament. He spent his whole life trying to prove to everyone he had money he actually didn’t. He bought the “best of the best” in everything he owned.

Of course, it was all fake. He didn’t have any money, and now he’s about to go to jail because his addiction to keeping up appearances lead him to theft and fraud. Double whoops!

Sad story for everyone involved. Let’s move on.

The Truth Behind “Free” Frequent Flyer Miles

On the other side of the debate, the quantity lovers will say, “Your dumb friend should have watched his money better! He could have had the life of his dreams if he’d found cheaper ways to own the same things!”

An example of this concept in action is alive and well in the travel hacking community. Travel hackers will spend inordinate amounts of time searching for the best deals that allow them to travel for cheap. They find glitch fares, hoard frequent flyer miles, and do all kinds of funny stuff that make the average person scratch their head in disbelief.

They travel, and they do it a lot. According to them, it’s all freeeeeeeeee!

I’m a big fan of frequent flyer miles. In fact, they’ve changed my life. I’ve flown all over the world for nearly free because of them, but I don’t try to kid myself. There’s a whole world of other expenses that comes with that lifestyle once you’ve bought into it.

First, I would never pay full price to travel to all the places I do so, without miles, I wouldn’t have the opportunity to spend money on lodging, food, and other expenses that go hand in hand with travel. The more “free” travel I take, the more I spend while traveling.

And while I have zero debt and have never paid a penny in interest to anyone for anything in my life, there are plenty of self-proclaimed “frugal travelers” who are up to their eyeballs in debt after spending more and more on their frequent flyer credit cards to get more miles. They don’t realize their free travel costs them many times more than if they’d just used cash and paid full price.

I’m nothing but grateful for all the travel experiences I get to have, but I try to be honest with myself about just how free it all really is.

The quality lovers would argue, “You could spend the same amount and just take one lavish vacation each year and not hop all over like a nomad.” And they’d be right! Sort of.

Now the Answer: Value (As Explained by My 16-Year-Old Bicycle)

What all the quality and quantity loudmouths shouting over each other fail to realize is if you look at the argument as a one-or-the-other scenario, there’s no way to win. If you simply have to pick sides, you’ll always end up worse off. The same is true for most dichotomies.

In reality, quality and quantity exist on a spectrum, and the sweet spot you ought to land on is called value. This is a lesson I learned in 6th grade when I bought my first bike from the local shop in my hometown—a good ol’ Trek 420 that, 16 years later, I still ride every single day. Yeah, it’s a little small—like a bear riding a tricycle—but it’s perfect for me.

Even at age 12, I did a painstaking amount of research to find the bike that would be the best value for me. I wanted to spend as much as I needed to get the best fit without paying for an unnecessary status symbol or a bunch of bells and whistles that don’t matter.

The bike was $600, a princely sum for a 12-year-old who earned a “living” splitting fire wood. In the end, both my parents supported me in the decision, but my mom nudged me to save a little longer for a slightly nicer bike (quality), and my dad was ready to disown me for even thinking about spending so much on something I was just going to lose or sell in a few years (quantity).

Yet here I am, 16 years later, still pedaling it around every day. I suspect the same will be true in another 16 years. When my friends ask me if I’m ready to upgrade, my answer is always, “Why mess with perfection?”

***

Don’t get lost in the dogma surrounding the quality/quantity debate. The smart Riskologist need not choose sides. Instead, he should look at every aspect of his life on a spectrum, finding the option that satisfies every reasonable need without ever wasting time or money on extras that don’t actually improve his life.

Your Homework Today

If you’re a smart Riskologist yourself, I’d like you to leave a comment below explaining how you find the sweet spot of value in your life. How do you avoid being sucked into the quality vs. quantity debate?

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