A great deal of self-help emphasizes overcoming your fears. Our fears, we’re told, are the reason we aren’t sky-diving millionaires with supermodel spouses right now.

A quick Google search shows over 3.2 million entries for “how to overcome fear.” The book, Feel the Fear and Do It Anyways was a major best-seller. Clearly there is a demand from people wanting to overcome their fears and the army of authors and pundits is there to supply the solution.

Fear Isn’t the Biggest Problem

First, I want to claim that overcoming your fears is not the #1 obstacle to living the ideal life. I prefer Cal Newport’s suggestion that skill trumps courage. As I’ve written about here, the reason you aren’t a millionaire probably has more to do with not having the skills to earn a million dollars, and less to do with your fears.

However, even if fears aren’t the most important obstacle to overcome, they can still matter. Just as laziness, guilt, insecurity or any other psychological block can prevent you from making good decisions to improve your situation, your fears can hold you back.

You’re Afraid of Failure Because Failure Sucks

Sometimes your fears are legitimate.

If you’re afraid of quitting your job or dropping out of college to start a business, the fear of failure may be real. No, failing won’t kill you, but you may spin yourself into thousands of dollars of debt with nothing to show for it. Worse, you could have missed better opportunities to further your career.

If you’re afraid of asking a friend for a date, that fear may be real. The damage may be temporary, but you may sense that success isn’t likely and you may create awkwardness in your social group.

If you’re afraid to live in a foreign country, there may be some basis to that. If you don’t speak the language or don’t have an adaptable personality, the challenges of living abroad and being alone could be overwhelming.

Does this mean I think you shouldn’t pursue your ideal career, tell people how you feel about them or live abroad? Definitely not. I’ve done all those things. But that doesn’t mean I haven’t failed, or even that my fears were completely unjustified.

Being lost, broke or rejected are genuine consequences of real fears. The reason your fears are so difficult to overcome isn’t that they are irrational. The real reason is that, often, they are at least partially true.

Conquering Fears Requires More than Just Courage

To me telling someone to use courage to overcome fears is like telling a fat person to “stop eating so much.”

Sure, it’s true. Almost all weight-loss boils down to caloric restriction with exercise at some point. But is that helpful?

A better recommendation wouldn’t just use willpower, but emphasize on creating a system for reducing the desire to overeat. Keep less junk food in the house, stick to a pre-defined meal plan, learn to cook healthier foods. All of these are more practical suggestions.

Similarly, the “use courage” mantra isn’t very practical.

An Alternative: Engineer a Low Cost of Failure

If you accept that fears haunt us because they often have at least a partial basis in reality–and you accept that courage is often impractical advice, then there is another solution: reduce the cost of failure.

Engineering the situation so it has a lower cost of failure will make overcoming your fears a lot easier. Not because you’ll have more courage, but because a lot of your fears will go away, or at least reduce in intensity.

Take the fear of quitting your job. If, instead of quitting, you started your business part-time, that would drastically reduce the cost of failure. The worst-case scenario would be some lost time or less aggressive career growth at your current job.

Or what about the fear of asking someone on a date? If you can’t summon up the courage to go further, maybe make a smaller step forward. Spend more time with the person, make smaller moves and see if he or she reciprocates.

Flirting as a social practice may have developed primarily to engineer a lower cost of failure in dating. Linguist Steven Pinker devotes a chapter of his book using game theory to explain how ambiguous wording can save face if the other person isn’t interested.

How about living abroad? Even that is something that can be engineered to a lower cost of failure. Reduce the length of your trip. Travel to the region before deciding to live there. Maybe make a shorter stay away from your home environment to see if you can handle it.

Engineering Low Failure Costs Works Where Courage Can’t

The idea for this article came to me yesterday when I was cooking in my kitchen. I was trying a new recipe, and I was thinking about how the cost of failure often prevented me from experimenting with different cooking techniques. Often the win from discovering a new dish was outweighed by going hungry if it turned out poorly.

However, by making sure I had a quick backup meal if the first one failed, that made it far easier to experiment with new dishes. Also, allocating more time for cooking in my daily routine made the price of a ruined meal considerably lower.

Because I reduced the cost of failure, I’ve been experimenting with a lot more dishes. Last night I made kushari and before that I was making baba ghanoush. I’ve probably improved my cooking skill more in the last six months than I had in the six years prior to that.

The idea of using courage to improve my cooking skill seemed ridiculous. I wasn’t afraid of cooking new dishes, or if I was, I certainly wasn’t conscious of that fear. However, engineering a lower failure cost allowed me to tackle a problem that I had never considered before.

A common piece of advice is that perfectionism is bad. At least, that’s what you’d believe if you read an online article on the topic.

However, I feel the situation is more complex. Certainly some perfectionism is bad–it causes us to procrastinate, leave projects unfinished and become mired in self-criticism.

But, in some ways perfectionism is necessary. Stopping at “good enough” is an easy way to ensure you’ll never accomplish anything remarkable.

Good Perfectionism, Bad Perfectionism

There are two types of perfectionism:

1. Short-term perfectionism on a particular project, task or goal.
2. Long-term perfectionism on projects, tasks and goals, in general.

When most people rally against the threat of perfectionism, they are really attacking short-term perfectionism. This is the crippling form that says you must perfect something before you can finish.

Short-term perfectionism occurs when you spend weeks unemployed, polishing your resume without mailing it to any potential employers. Or spending eighteen months on a new Web 2.0 platform without releasing anything to see if there is actually a market. Or devoting half your exam time to finishing your first essay response–when you need to complete another five.

Short-term perfectionism is almost certainly bad. If these perfectionists just mailed their resumes, released earlier builds or completed question one, they would waste less time and accomplish more.

But just as short-term perfectionism is bad, long-term perfectionism can be crucial.

Good Enough for Now, Never Good Enough Forever

A long-term perfectionist isn’t held back by releasing. In fact, she probably finishes aggressively since finishing allows her to get feedback. Instead, she channels her perfectionism into an attitude that good enough is never a permanent state.

This breed of perfectionist embodies the attitude I believe is necessary to become insanely good at something. Because their drive to improve extends far beyond what is “good enough”, as declared by society, they often become a lot better than good enough.

Example #1: Perfectionist Bloggers

Ramit Sethi, is one of my favorite personal finance bloggers on the internet. But most people wouldn’t guess that he spends upwards of 15-17 hours writing an article.

Tim Ferriss, speaks here about the lengths he goes to in optimizing his webpage. He tracks data ruthlessly, analyzing what are the most popular posts, what are the best days to publish and split tests his website layout over geography to reveal cultural differences in his readership.

I recently had a conversation with Cal Newport. Even though he isn’t a full-time blogger (being an author and MIT postdoc take most of his time) he still uses embodies my view of the long-term perfectionist. Cal uses each article as a chance to deliberately practice specific writing techniques he has identified beforehand.

All these three people have gone well beyond “good enough”. They’ve probably gone beyond “great enough” as well, but that’s a different story. There lesson is twofold:

1. They publish regularly and frequently (so they are definitely not short-term perfectionists)
2. Even after success, they remain dedicated to the unending path of mastery.

Example #2: Being Funny is Hard Work

Jerry Seinfeld delivers a hilarious acceptance speech for a lifetime achievement in comedy. (Click here if the player won’t load)

Midway through the speech he comments:

“The truth is, the comedians should be the only ones getting awards. We’re the only ones that actually have to think of something original. Something funny, or interesting.

Do you know how hard that is? Do you know how hard it was to write what I am saying to you right now? It was really hard. This took a long time.”

Chances are, the joke you hear a successful stand-up say has been told for live audiences hundreds of times beforehand. Each repetition perfects the timing, word-choice, delivery and body language making even a seemingly effortless off-the-cuff remark a perfected product.

The lesson of comedians like Seinfeld is twofold again. They get up and practice frequently in-front of live audiences, so there is no short-term perfectionism crippling their progress. But also, many of them endlessly refine their approach so that they can anticipate every facet of an audiences reaction before a joke is told.

My Personal Example

Recently I launched a new learning tactics subscription. On the short-term I wasn’t a perfectionist. The program didn’t have a forum, I did the design for all the content myself and I didn’t even use a website–all the content was delivered via email. Instead of delaying, I launched with less to make sure there was actually a demand for the concept.

However, once I did confirm there was a demand, my long-term desire for perfection kicked in. I’m now putting in many hours to add the features initially missing from the program. I’ve also started taking surveys and maintaining spreadsheets to help test and improve the results people can see within the program.

I definitely don’t embody the split between long and short-term perfectionism ideally. But, it has been an attitude I’ve worked to add into the way I approach life.

There is No “Good Enough”…

…in the big picture, at least. And if the desire to finish isn’t coupled with a drive to go beyond “good enough” you probably won’t get either good or enough.

I’m Canadian, but I’m currently living in the south of France. And, for the last five months, I’ve been doing something I never would have considered back home.

I’m not talking about drinking wine, eating baguettes or speaking French (although I’ve been doing plenty of those things).

No, I’m talking about riding a bicycle.

For the last 5 months I’ve commuted with my bike practically everywhere. I’d guess I bike at least 5-10km every day. And, while I’ve occasionally had a bike in Canada, that becomes agonizingly impractical when there is several feet of snow.

Location as an Underrated Factor in Pursuing the Ideal Life

I believe location is an underrated factor in pursuing the ideal life, but not in the obvious way people assume.

The obvious assumption is usually spoken in stereotypes. New York is fast paced. Paris is romantic. And if you want to start a technology company, you have to move to San Francisco.

I won’t argue with the specifics of these stereotypes, since I’ve never lived in New York, Paris or San Francisco. Maybe all the things said about these types of places is completely true.

What I will argue is that your location can have an unexpected impact on your lifestyle beyond the details that are most obvious when choosing a place to live.

The Unexpected Impact of Geography

Bike riding is a perfect example. The idea of biking everywhere I go wasn’t something I thought of when imagining life in France. Indeed, if I had chosen to live in a larger city like Paris or Lyon, the metro stations would more probably be my major source of travel.

Despite this, I think bike riding has had a major impact on my day-to-day lifestyle. For one, by biking 5-10km per day out of necessity, I’ve been getting a lot of exercise. Second, I’ve spent more time outdoors, which if you’ve ever experienced a winter in Winnipeg, is definitely a plus.

Location Independence and Choosing the Perfect City to Live

For most people, location is simply a matter of opportunity. My parents had moved to find jobs, and many other people will locate themselves wherever makes sense for their career.

However, there are a growing number of people who are drawing the majority of their income from location independent sources. Freelancers, web entrepreneurs or even at-home workers could theoretically live anywhere.

I think once you remove the job demand criteria as the #1 factor for where to live, a whole new area opens up, namely, picking the perfect city for your ideal lifestyle.

And, I believe this decision becomes more complicated for the reason I previously mentioned. Most of the salient details of choosing the perfect city are hidden, or at least obscured by popular stereotypes.

Finding the Perfect City

I’ve just started this journey, so I can’t weigh opinions about which cities are best. However, I think there are a couple factors worth mentioning, that are guiding my process of finding it:

1. Perfect is time sensitive. The ideal city, I believe, will be different when you’re 25 to when you’re 55.
2. Perfect won’t be obvious. I can’t be sure, but I’d guess that the ideal cities for most people are probably places they haven’t heard of yet. Or at least given serious thought to. The most popular destinations are also the most expensive and crowded.
3. Perfect needs defining. The size, weather and infrastructure that makes Montpellier an ideal city for biking is part of my definition of a great city. It will be different for every individual.

Of course, I’m not ruling out the importance of building relationships within a particular location over time. My argument isn’t that the ideal way to live means being a perpetual traveler. There are benefits to just picking a spot and then getting to know your neighbors.

However, just as the person you marry will have a major impact on your life, I believe the same is true of the city you live in. And, for a growing number, that decision will no longer be based on job openings.

If you need guilt to motivate yourself, your productivity system is broken.

“Are you procrastinating?” my roommate asks me. Three exams the next day and I wasn’t studying.

“No, I laugh, procrastination means I intended to do some work. I never planned on working tonight, so technically it isn’t procrastination,” I respond.

This was a conversation I had last week, during an exam period. Although my review schedule before exams tends to be a lot lighter than most, the biggest difference isn’t the time. It’s that I refuse to use guilt as a motivation tactic.

Stress-Cases VS Relaxed Achievers

Here’s the process a typical stressed-out student or worker uses to motivate himself:

1. Worry.
2. Be unsure where to start.
3. Take a break.
4. Take another break.
5. Feel guilty about breaking for so long.
6. Do 15 minutes of work.
7. Chat on Facebook.
8. Repeat.

Although there are probably a lot of problems in this situation, I think the worst is step #5. When you use guilt as a motivation tool you increase your stress without accomplishing anything.

Worse, guilt tends to be a lousy motivator, resulting in a little bit of effort but nowhere near the effort needed to succeed with your plan.

Now contrast this approach to the way a relaxed, effective student motivates herself:

1. Worry. (Hey, sometimes you can’t help it)
2. Stop and form an action plan with specific tasks.
3. Create a list of the tasks to be done.
4. Break the list down to a daily basis.
5. Work hard to complete the tasks.
6. Relax guilt-free.

Instead of guilt, there is a system. It’s this system that not only creates the results, but eliminates the wasted stress and time.

The System Doesn’t Need to be Complicated

If I’m making it seem like the second approach requires a black-belt level of mastery in GTD, that’s not my intention. A system doesn’t need to be hard or complicated to still work extremely well in 95% of cases.

Here’s the system I’ve used for the last few years of relatively guilt-free work:

1. Make a to-do list.
2. Chunk that to-do list into a list just for today.
3. Complete the list, without adding new items when you finish it.

Now, this may sound too easy. Sure, this might work for some people, but my work is too difficult, my academic program too intensive and the competition too fierce to limit myself in this way.

Wrong on both counts.

First, that attitude is wrong because this system works even better the more difficult your program is. The systematic approach to productivity, with pre-established limits, excels when your workload is hellish.

I’ve used this approach when managing full-time classes, international competitions, two volunteer positions and a part-time business simultaneously. Cal Newport has used a similar restrictions-first approach to get a PhD at MIT, build a wildly successful blog and publish several books.

Don’t tell me you’re too busy. You’re too busy not to have a system.

Second, this attitude is wrong because it assumes guilt is even remotely effective. It’s not. Guilt may be used in the 5% of situations where your system breaks down. But when you’re using it on a regular basis, it wears out and becomes useless.

Studies have shown that willpower is an internal resource. If you use it up on one task, you have less of it for the next task. So if willpower is this scarce, why force 100% of your work to rely on it?

Martyrs of Busyness

The real reason a lot of people like using guilt is for a secondary benefit that has nothing to do with accomplishing anything: social status.

When you tell people you have a killer workload, you aren’t just complaining. You’re also trying to tell people you’re important enough to have a killer workload.

Some tribes put discs in their lips or brand tattoos. Ours walks around telling everyone how “busy” we are, grinding away hours of our life in half-productive work. Whose is more destructive?

Guilt Free and Accomplished

January 2010 was the second best month for income I’ve ever had on the website. It was the number one for direct income. My health and fitness are nearing a personal best, last week I was able to complete 10 one-arm pushups with each arm in a row. Academically my grades will likely be staying high during my year abroad, and I’ve made significant progress learning to speak French.

Despite this progress, I’ve been more relaxed this year than perhaps any in my life. Tonight will be my forth night out in a row, in a series of going-away parties for friends leaving France. I’ve enjoyed enough free time to practice my cooking, read more books and enjoy the weather, women and wine in the south of France.

I’m not saying this to brag, but to point out a contrast. In other years I’ve had considerably more stress, a lot of it being self-inflicted. Also, during those years I arguably accomplished less towards my main goals.

I think that’s evidence that the burnout, guilt-soaked approach to work not only isn’t sustainable, it often doesn’t even get the most done.

Imagine that your main goal in life was to have as much fun as possible. What would your life look like?

I’m asking this question because I reject the idea that the pursuit of fun, in its maximum, would result in a life of non-stop television, fast-food binging or substance abuse.

Instead I’d argue that, even if putting fun as the highest goal wouldn’t lead to the ideal life, there is still a considerable overlap. I want to make the case for two points:

1. That serious fun requires effort. Giving up all discipline and effort results in a local maxima of fun which is far lower than the maximum possible enjoyment.
2. That fun supports work-related and nobler goals, rather than distract from them.

Why People Don’t Like to Think About Fun

What if I told you that you weren’t maximally productive. That is, your current behaviors don’t accomplish the most for the time you invest, you probably wouldn’t require much persuading. After all, we all sense our deficiencies when it comes to procrastination or laziness.

But, if I told you that you weren’t getting the most fun, you might require more convincing. Somehow we feel that work is something that can be enhanced by analysis and introspection, but fun is not. Fun is something magical and trying to think about how to have more, destroys the very enjoyment we seek to create.

I’m not going to disagree with you. The act of trying to figure out how to have more fun, when you’re playing a game or socializing, usually makes the activity less fun. Fun is spontaneous, so thinking about it too much can undermine it.

However, while I believe a mindless, go-with-the-flow approach works best in the moment, that same logic doesn’t apply when structuring your life to have more fun.

Serious Fun Requires Sweat

Take travel as an example. You might feel that going on a trip will be more fun than staying at home and playing video games. But, the video games don’t require any advanced planning, whereas the travel might. So if you don’t apply any thought, you’ll end up staying at home.

Look at sports. Sports are a classic example of the frustration barrier. When you are lousy at a sport, it isn’t much fun to play. But as you gain skill, the sport can become almost obsessively interesting. If you didn’t apply the foresight to practice through the frustrating phase, you would never experience the intensely fun phase of mastery.

Being a connoisseur of fun doesn’t mean all your leisure time needs to require years of practice or planning. Instead it means that, as far as having fun is a worthy goal, there are benefits to putting some thought into designing a more entertaining life.

I’d rather live an adventurous life, which has richer fun experiences, than a merely entertaining one, which occupies itself with shallower fun.

Mindless Fun vs Serious Fun

I don’t want to categorize certain activities as always being mindless fun and others as being serious fun. I’m not going to say Shakespeare is inherently better than South Park, simply because I feel those comparisons are so corrupted by people using high art to signal status.

The difference isn’t the activity, it’s the way you pursue it.

Imagine one person watches television for six hours straight, because he has nothing better to do on a Friday night. Compare that to a person who, spends the same six hours watching television, but it’s in the deep appreciation of a favorite story. Reveling in the character details, completely fascinated by the broader themes of the work.

The difference is between being an aficionado and a drone.

Why Serious Fun Supports Serious Work

I don’t believe that fun is the ultimate aim in life. However, I do think it’s useful to think about because I feel fun supports other goals. If you’re saturated in adventures and enjoyment, those experiences enhance the other aspects of your life, rather than detract from them.

I get a lot of emails from people wanting to give up online gaming or partying so they can focus on working more. That’s fine, if in their honest assessment, they’ve decided that there are more satisfying ways to use their spare time.

However, in most cases, I feel people want to abandon these pursuits, not because they’ve found something better to replace it, but because they feel they should. That watching television, playing World of Warcraft or going to a club is working against their bigger goals.

I’ve fallen into this reasoning trap myself. I’ve previously written about giving up television, and while I enjoyed the challenge (I still don’t have a television), I think I pursued the goal for the wrong reasons.

Instead of trying to eliminate all those distracting sources of low productivity, I should have been embracing them. Embracing serious fun.

How Fun Improves Productivity

The truth is, for almost all my goals, if you asked me whether I’m more productive now or years earlier when I had a more obsessive focus on work, I wouldn’t have to think about it. I’m definitely more productive now.

I believe a big reason for this is that seriously pursuing fun, making sure life is as fun as possible, gives you the energy to put back into your more focused pursuits.

Again, however, I want to draw a distinction between mindless fun, which is usually done just to occupy time, and serious fun, which is the conscious effort to make your life as adventurous and entertaining as possible.

Making my life more fun has occurred on many levels:

• Improving my business, so that the creative work I find incredibly fun is something I can get paid for.
• Living abroad, so even acts like going to buy groceries are interesting challenges.
• Building my social network, so I’m connected to other people’s adventures.

Even more, it’s been accepting that the serious pursuit of fun is productive. And that the ideal life not only accomplished but thoroughly enjoyed.

Being good at things is the key to success. Painfully obvious, right?

That means being good, having mastered skills, ranks far higher than other commonly touted “keys” to success, such as:

• Overcoming fears
• Just getting started
• Rejecting societal norms
• Having the best attitude

Sure, being a terrified, procrastinating, peer-pressured, pessimist probably won’t help you master skills. But that doesn’t remove the fact that mastery, both in your career and in your personal life, is the most important element.

Why Being Skilled Matters

For your career, the argument is simple: we live in a capitalistic world where, all else being equal, the people with the rarest and most valuable skills get the biggest rewards. Assuming you can convert those rewards to what you desire in life (do you want a big house or location independence?), mastery leads to career success.

For your personal life, the argument is subtler but I believe the same logic applies. If you have skill, achieving success becomes easier in almost any area of life:

1. Health - mastering a sport or exercise routine will keep you healthy, while mastering your own habits and willpower can ensure that they stick.
2. Relationships - mastering your interpersonal communication helps, whether you’re trying to find a new relationship or sustain an existing one.
3. Learning - improving the way you learn has a ripple effect, where ideas you pick up can be integrated into any other area of life.

Even if you disagree that mastery is the most important element, I think most people can agree it is at least a very important part of living a successful life.

What Encourages Being Skilled?

The biggest gains in skill come when you are situated on edge of your current competence. If you stay with what you’re already good at, you won’t improve much.

Being way outside your level of skill isn’t conducive to mastery either. Unless you can receive positive feedback, or regular wins amidst failures, it is difficult to learn from your mistakes. The best way to train as a sprinter isn’t to run against Olympic athletes from day one. It’s to race against someone just a bit faster than you, so you’ll know when you make improvements.

Therefore, practicing for improvement should always be at the edge of incompetence. Where you have enough skill for positive reinforcement, but not enough skill to be considered good–yet.

Living on the Edge of Incompetence

If you accept the first premise: that mastery is an essential ingredient to successful living. And, you accept the second premise: that mastery requires an environment of being on the edge of your incompetence. Then the conclusion is difficult to escape: successful living requires living on the edge of incompetence.

For the last several years I’ve made a deliberate effort to live on my edge of incompetence. I make an effort to choose goals and projects that are not just difficult, but require skills I don’t currently possess.

In the business projects I’ve undertake with this blog and website, I’ve always chosen ones that were slightly outside my skill level. I wrote and designed a free ebook, then created one for sale, then created one with an affiliate program, finally now I finished a hybrid between an information product and a monthly coaching service.

Successfully executing the latest project would have been a certain failure a few years ago, but I slowly advanced my edge of incompetence. And I did that by living on it.

My other goals have also put me on the edge of incompetence. From learning French, taking salsa classes, practicing to cook more elaborate dishes or training to do a pistol squat and handstand pushups. The goals weren’t just difficult (although challenge is important) they also pushed me beyond my current skills.

Hard Goals vs Skill-Acquiring Goals

It’s possible to set a difficult goal that doesn’t explicitly require gaining new skills. For example, let’s say I set a goal to give up junk food. This might be a difficult goal, but after having done 30-Day Trials as a method for changing habits for years, it probably wouldn’t improve my skills significantly.

Similarly, I could set business goals that don’t really express what skills are going to improve. I have a goal to increase my business income to a minimum of $3000 per month. That will be a challenging goal to meet, but it doesn’t make it clear what skills I’ll need to improve and where I’ll be sitting on the edge of my incompetency.

Deciding exactly how a particular project will push you to learn new skills is an often neglected step. It’s the difference between aimless and deliberate practice.

Setting up Camp at the Edge of Incompetence

I feel, for many people, they want to get out of their edge of incompetence as soon as possible. It’s cold, painful and irritating outside. Far nicer to be safe and warm within your existing skills.

So when they live their life, the venture to the edge of their skills only lasts as long as it needs to be. When they need to pass a test, they study really hard. However, when the exam no longer threatens their security, they don’t bother reading a book on a difficult subject.

Not only do I feel this is suboptimal, since these people will only increase their skills when forced to, it is also a lousy way to live.

If you set up camp on the edge of your incompetency, you get used to scaling your frustrations and learn to tolerate the uncertainty. So when most people are complaining about being outside the comfortable home of their skills, you feel fine because you never closed the door.

Everyone procrastinates. Heck, you might be procrastinating right now by reading this, instead of doing something that should be done. That isn’t news.

What I feel is more interesting is where people procrastinate when we do. Even the most productive people have Achilles’ heels, types of tasks which they procrastinate on. Similarly, even the people who claim they have no willpower still have some work they always do on time.

Why is that? And how can you use that knowledge to fix the problem?

I’m a Productive… Except When I’m Not

I’m not superhuman. I have bouts of laziness, procrastination and every other typical human failing.

But, when it comes to my normal work, whether it is assignments for university, tasks for running my business or personal goals, I usually show up. I’ve written according to my 2-3x weekly schedule for this blog almost without exception for nearly 2 years.

I’ve also exercised for nearly 6 years 3-5x per week. I’d guess that in those past six years, I’ve never missed more than 2-3 weeks in a row, and only then because of travel or illness.

Despite that, I have my own Achilles’ heel. Certain types of tasks I’m no better than average at getting them done on time. Others, I forget to do, delay them when I remember and generally fare poorly at getting them done.

What’s my Achilles’ Heel? (And How That Can Help You Fix Yours)

In looking over my weekly/daily goals for the past few years, I would say there are two types of tasks I’m most likely to procrastinate on:

1. Maintenance tasks.
2. Non-routine errands.

Maintenance tasks are things like backing up my computer or website, reorganizing my filing system, tidying or doing laundry. For example, on that last point, I pushed doing laundry off my daily goals list for about 5 days before finally getting it done.

Non-routine errands are another weak-point for me. Things such as calling a support line to cancel a subscription or renewing a driver’s license. Especially if these things have no clear deadline (a subscription could renew indefinitely, unless I stop it).

Why do I procrastinate on these things? Also, how can the self-knowledge of your weak points allow you to improve on yours?

Two Reasons: One in the System, the Other in Motivation

The first reason certain tasks are procrastination trouble spots is that the system you use to organize your life doesn’t accommodate them well.

Obviously, if you used a system like GTD to the exact specifications, keeping every list and folder and using it perfectly, there wouldn’t be any tasks that don’t fit. But nobody uses those systems perfectly, and even if they do follow it closely there are certain types of work that will more easily slip through the cracks.

This seems to be a major reason errands occasionally are sources of procrastination for me. Because they don’t take much time, or have any significant advantage for completing them early, they don’t get much weight in my weekly/daily goals system. I do use a calendar to funnel date-sensitive tasks into the system, but if the errand has no deadline, W/D Goals tends to ignore it.

This is especially true with errands which may not get finished just because you invest time in them. Last year I continually procrastinated on making phone calls to difficult-to-reach people. The reason was simply that my productivity system didn’t manage those types of tasks well. If I call and get a busy signal, am I finished?

Correcting Systemic Errors

Fixing problems in your system usually isn’t too difficult. The solution is just to create a way of elegantly capturing those tasks so that you don’t forget about them. Defining deadlines for errands without deadlines will probably go a long way to solving my procrastination problem with these kinds of tasks.

The difficulty is sometimes in fixing a system problem, you make your life more complicated. Now instead of just having one to-do list, you have three. The bulkier your system, the less it pushes you to work. I’d rather have a 95% successful system that was ruthlessly simple, than a 99.5% system which was horrendously complex.

The Other Problem is Motivation

The other reason for an Achilles’ heel is psychological. There are certain types of tasks that you just don’t like to do.

I think maintenance tasks fall into this category for me. In theory, they shouldn’t be procrastinated in my W/D Goals system. Exercise and blogging are similar tasks in terms of work, frequency and consistency, but I rarely have procrastination issues with them.

Somehow, backing up my website or reorganizing my filing system just feels a lot less satisfying than finishing a blog article or going to the gym.

I could give up and claim that the situation is intractable. That blog writing and exercising are just naturally more fun, so I’ll always be doomed to procrastinate on the other items. But that isn’t really my style.

Instead, I’d like to probe into why I don’t have motivation to do these tasks, and maybe see the beginnings of how to correct it.

Looking deeper, I think the main reasons I lack motivation to work on these tasks is that:

1. Deep down, I don’t feel they accomplish anything meaningful.
2. I don’t take much pride in their completion.

Now for some maintenance tasks (polishing cutlery, for example) these two points are probably true. But that’s probably why I never put them on my to-do list in the first place.

The problem here seems to be that consciously I recognize that regular backups or reorganizations are necessary and important, but I don’t sense that on a gut level. Second, I don’t reward myself enough for sustaining these types of maintenance tasks. I congratulate myself for keeping the blog regularly updated and feel guilty if I don’t exercise, but I don’t have the same internal rewards for keeping my desk tidy.

Obviously recognition of these motivational weak spots is just the first step. The next is to start installing habits to correct it. That will take more time and effort, but it isn’t an impossible problem to solve.

However, just as I have current procrastination weak spots, I used to have even more, and patient habit adoption helped cure many (if not all) of those weak points.

How to Spot Your Motivational Weak Spots

I think just about anyone here could go through a similar process to what I went through. Starting with fixing the gaps in your productivity system and then identifying why you don’t put energy into accomplishing certain types of tasks.

Procrastination strikes unevenly. Fixing the weakest links strengthen the entire chain, so spotting these glitches in your approach can have a huge impact.

A big learning point for me over the last few months has been rejecting the common online wisdom of “passive” income. “You want to earn money while you sleep,” goes the rhetoric, “if you need to be there to earn a dollar, that work can’t scale!”

My rejection isn’t based on passive income being bad, or even undesirable. Simply that needing passive income is a good problem to have. For most people, the problem isn’t that there business doesn’t have enough “passive” income, but it doesn’t have enough income, period.

Lack of Scale is a Good Problem to Have

If your #1 problem when running a small business or doing freelance work is that your time doesn’t scale, you are probably doing very well.

Think about it. If you’re active complaint is scale, that means (usually) two things:

1. You are already well-paid for your time.
2. You have more lucrative clients, or business opportunities, than you can handle.

If these two things aren’t the case, scale shouldn’t be your #1 priority. Figure out how to earn a decent business or freelancing income before worrying about how to make it more passive.

Don’t Focus on Scale Too Early

I think a big mistake I made in the earlier running of this blog was to fall for the passive income rhetoric.

I was hesitant to let people know I responded to emails because, hey, that activity won’t scale and it will eventually reach a point where I can’t handle the volume. The thing I forgot was the word “eventually” and that, in the meantime, my ability to interact with people and respond to every email was a personal strength.

I ignored business opportunities that might not scale perfectly. Earlier, I rejected ideas of membership-based programs that involved coaching from my part because, in theory, I could only serve a certain number of people. So, instead I focused strictly on ebooks or other goods that could scale from zero to infinity.

The thing I forgot was that if you spend a month writing an ebook and only sell 30 copies, that still isn’t a lot of value for your work. Doing that same work for 100 people, even if it can’t scale to 1 million, can be more profitable and personally rewarding.

The Online World Hates Perfect Scaling

To borrow a line of reasoning from Chris Andersons’s excellent book, Free, the online world doesn’t like paying for things with perfect scale. When you do, there are forces which work against you.

So, when you decide to create an ebook, you have a product that can scale perfectly. You also have something which can be pirated easily. I once found a torrent of one of my ebooks with nearly 10,000 downloads and several highly positive reviews. Um… thanks?

With unscalable products you also have to face a higher level competition. Maybe this isn’t so much a problem in the blogosphere, but if you were starting a web 2.0 service, it might be. How can you make an excellent service that people will pay for, when Google is giving it away for free?

It’s not impossible, and I know many people who have succeeded with purely passive income business models. But I feel, for new entrepreneurs or freelancers, scale shouldn’t be a priority. Worrying about scale comes when you’re sold-out and making bank.

Early scale worries are delusions of grandeur.

How Rejecting Scale Helped My Business

It turns out, as much as the impersonal forces of the online world hate scale, they love its opposite. They love things that can’t scale.

I mentioned yesterday I sold out enrollment in a rapid learning program I was offering in 36 minutes. There were probably many reasons for this. But, I feel a big one was that I was only offering 100 spots. The program lacked theoretical scalability because I was offering feedback and coaching as part of the package.

Just as you value a handwritten thank-you card more than an automatic email, value is tied (in part) to perceptions of marginal cost.

While it may have lacked scale, in theory, in practice that means potentially adding an important revenue source to my business which will help it survive as a full-time income source. And I’d rather have full-time income with imperfect scaling, doing what I love, than a perfectly scalable business and still need a job.

If you’re a casual reader of the website, you probably noticed small announcements the last two months about a program I was working on. The program is Learning on Steroids, and the idea behind it is to implement rapid learning tactics that will make you a more effective learner.

I had been collecting emails of interested students, with the promise to give them priority announcements when the project launched.

Well, I did and the program sold out in just over half an hour. You guys rock!

I’ll be opening the program again in a few months after making improvements from what I’ve learned from this group. Hopefully I’ll be able to let in another 100-200 students, so if you’re interested you can join the email list and you’ll be the first to know when we reopen:

Click here to get in.

Thanks to everyone, gratitude is definitely my feeling for 2010!

I’m a fan of meta-skills. These are the skills that allow you to learn faster and master new disciplines more quickly. I love meta-skills so much that a good portion of this blog writing, and my entire upcoming program are devoted to them.

One of the most important meta-skills for becoming good at anything is being able to push through the frustration barrier. This is the early phase of skill acquisition where you suck at it. The skill isn’t fun, because you haven’t reached the level of proficiency where you can actually enjoy it.

A perfect example is learning a foreign language. When I started learning French, the process was difficult. Speaking French wasn’t enjoyable. I had difficulty understanding simple things and the effort wasn’t rewarding.

Now, I’m still not fluent, but I actually enjoy French. I’m reading my first novel in the language (The Count of Monte Cristo) and I’m currently spending my winter holidays with a Belgian family, speaking French exclusively. These are experiences I wouldn’t have enjoyed if I had got stuck at square one.

How the Frustration Barrier Cuts You Off From New Experiences

The frustration barrier doesn’t just make learning more difficult, it also cuts you off from new life experiences. When you face the barrier repeatedly in one area of skill, you may confess to yourself that you are simply not born with the talents necessary to be successful in that area.

In my life, an interesting consequence of this was dancing. When I was younger, I was a bit clumsy and introverted. Therefore I never tried dancing, and when I did I was lousy at it. I had just accepted that I might not possess the gene for uninhibited party enjoyment.

But, being the optimist that I am, I signed up for dancing classes one day. After a brief introduction (note: overcoming the frustration barrier) I found out I actually liked to dance. To the point where I love going to nightclubs and dancing.

That’s a simple example, but I think many people get in there head a false belief that, “I’m not born with the talents to do ____” simply because they never invested the initial effort to overcome the frustration barrier in that area of their life.

The Meta-Skill of Rapid Learners: Dominating the Frustration Barrier

I later discovered that most people can become good at almost anything (not necessarily spectacular, but good). The key is mastering that meta-skill of overcoming the frustration barrier. Once you defeat the early part of skill acquisition where learning is painful, you can start reaching the part where mastery and hard focus feel good.

I don’t believe there is one grand key to overcoming the frustration barrier. But I do believe there are many heuristics you can use to help yourself push through this difficult phase.

As always, practice is important. If you practice running headlong into the frustration barrier, it is easier to do it again. This is why I believe people like Tim Ferriss, Benny Lewis or other seemingly statistical anomalies in learning exist. They have mastered the meta-skill of frustration barrier ascension, so that any new skill is comparatively easier to acquire.

Here are some of my favorite heuristics for overcoming this initial phase:

#1 – Admit You Suck.

Let go of the ego. When you just flatly admit you aren’t very good, you stop trying to protect your self image and appear qualified.

This may go against the traditional confidence hypothesis, until you understand that the goal isn’t performance. It’s to embrace your awfulness and use that embrace to keep you going despite your missteps.

#2 – Surround Yourself with People Who’ve Done It

You need to believe it’s possible. The only way to do that is to be immersed in people who have succeeded in the path you are now going through.

Not only will their great ideas for success rub off on you, you will be able to face the frustration barrier knowing that, at one point, it will get easier.

#3 – Study the Mastery Process

Or, as Cal Newport would suggest, invest a non-trivial amount of time into understanding how to master your chosen skill. When you do research two things happen:

1. You expose yourself to great ideas for improvement which shorten the time to mastery.
2. You gain confidence in the process of mastery, making it less likely you’ll give up out of frustration.

#4 – Enjoy Being Awful

I’ll admit, it’s easier to enjoy things your good at. However, just like you can have fun on a cloudy day, you can have fun being lousy at a skill as well. Fun is mostly about creative perception, so if you learn to enjoy the intensity of the challenge you are under, you can surmount the frustration barrier.

#5 – Commit to Mandatory Practice

Sometimes the best way to beat the frustration barrier is just through discipline. If you commit to practicing a certain amount, every day, you can eventually defeat the beast just by putting in enough time. I’ve done this for numerous fledgling skills where my internal resistance would otherwise defeat my desire to become good at it.

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Of course, having a community of enthusiastic people and regular follow-up doesn’t hurt either. That’s the main reason I created Learning on Steroids, to create an environment to teach these sorts of meta-skills (while at the same time employing some of the tactics above to make it easier to overcome the frustration barrier).