Most career-advice today deals with matching—trying to pair people’s aptitudes and passions with specific jobs. So, the advice goes, if you’re friendly, maybe you should go in sales. Good at math? Consider engineering or science.
The matching paradigm here strikes me as too optimistically egalitarian. It somehow assumes that all jobs are equally desirable, but that they fit with different people. That’s ridiculous—some jobs are clearly more desirable than others. Otherwise, why wouldn’t we talk about people having a “passion” for stoop labor or janitorial work?
Another place I often see the “match” paradigm is in relationships. We talk about soulmates, connections and finding the right chemistry. While that’s also partially true, not all people are equally attractive. All else being equal, I’d rather date the volunteering, med student who looks like a model, and I’m guessing you would too.
It’s considered taboo to suggest that some people are simply better than others as relationship candidates. But just because it’s unfair, it doesn’t make it untrue. Yes “match” matters, particularly in a competitive environment , but let’s not kid ourselves that everything and everyone were created equal.
Beyond “Fit”: Jobs in Terms of Navigating Opportunities
Some careers are simply more desirable than others, irrespective of match. I have friends that can live anywhere in the world, work on any project they choose, have ample vacation time, love their work and also have incomes in the high six-figure range. Who wouldn’t want that?
Because of the huge spread of general desirability of jobs (not just the specific match), even though it’s important to find passionate work, it’s even more important to accumulate what Cal Newport  calls “career capital” which is a measure of the power you have to gain access to more desirable work.
Earning career capital seems to have two broad components:
- Ambition and building skill.
- Navigating opportunities to make your career path harder to replicate.
The first part is fairly obvious—if you have more skill or more ambition, you’ll be more able to gain one of the more desirable jobs out there. This is why parents pressure their kids to get good educations in high-paying fields, because with more career capital, the better chance you have of finding a job you really like.
The problem with raw ambition and work ethic is that there will always be people who can outwork you. I consider myself an ambitious person, but I know many people who outwork me. Unfortunately this effect is exacerbated as you move up the ladder and basically everyone is already trying their hardest.
That’s where the second part comes in. The people I know who have the best jobs with the least stress often earned their career capital from a series of unusual opportunities. Those opportunities are hard to replicate, so the person manages to build career capital while simultaneously making it extremely hard to compete against them.
Ben Casnocha  is a perfect example. He started by taking a junior-high school computer project and turning it into a website. From that opportunity, he started his first company at 15, which led to a book deal a few years later, and finally coauthoring another book with a giant of Silicon Valley in his early twenties.
Hard work, certainly, but not exactly the traditional career path that you’re taught by a guidance counselor.
Benny Lewis  has another great story. His background is in engineering, but after spending several years travelling and learning languages, he managed to become a full-time traveler, through freelance engineering translation. From there he further honed his language learning abilities until he was able to launch a business teaching his method to other people.
The power of his career capital here isn’t just the effort he put in. It’s also on the uniqueness of his path that would make it harder for people to replicate his expertise.
(Note: This principle of navigating opportunities to build career capital, comes from Cal Newport’s book . Don’t let the title put you off, it’s invaluable advice for everyone)
How to Navigate Opportunities to Build Success
Taking Cal’s insights about career capital in mind, I’ve begun to follow a manta when it comes to making decisions about my life, which is:
“Do what others won’t or can’t do.”
Doing What Others Won’t Do
This is the first part about ambition and hard work. If you want things in life (and this applies to way more than just careers) you need to be willing to work harder than the average person.
An example of this is in my own career as a blogger. Most bloggers aren’t willing to put in at least 12 months of continuous posting. If you’re willing to that, you immediately increase your odds of success.
I have the same attitude with my MIT Challenge . Sure having the right learning and productivity hacks helps. But I’m also willing to wake up early every morning and put in the effort, every single day. There’s less “me too” competition since I know most people aren’t willing to do that.
Doing What Others Can’t Do
The other part is about taking advantage of the opportunities that are exclusive to you. When you do this, you form a career path that is extremely hard to replicate, and as a result, making it easier to secure larger amounts of career capital for the same amount of effort.
Taking on this MIT Challenge was a decision based on that mantra. Anybody can learn from MIT’s open courseware, but not everyone has a business based on learning or a platform to benefit from the attention. I’m in an unusual, if not unique, position to take advantage of that opportunity.
I could have attempted a similar challenge with my fitness, travel or dating, but I’m not really in a unique position to do anything with those. There are already way better fitness and travel experts who can take advantage of that.
How Do You Find Unique Opportunities?
This sounds great in theory, you might be saying, but how do I find opportunities that I have exclusive access to?
My feeling is that you can’t know where opportunities are going to come from in advance. If you can plan them out easily, then they wouldn’t be the type of opportunities that are hard to follow. By definition, the opportunities have to come somewhat as a surprise, otherwise everyone would be competing for them.
The key to finding those random opportunities seems to be just exposing yourself to a lot of randomness. Meet tons of people, take on unusual projects, learn interesting subjects and skills.
The effect of opportunities compound, so the more unusual opportunities you take on, the more unique your position is in the career landscape. That allows you to further negotiate getting on even more unusual opportunities.
When I wrote the last update  to my MIT Challenge, I said that I’m taking on the challenge for mostly intrinsic reasons. A lot of people interpreted that as being that I have no real reason for doing anything, and that I’m somehow able to work really hard just on enthusiasm alone.
It would be nice if that were true, but it’s not. Anything that takes work requires at least some effort. My point about intrinsic motivation is simply that the project fits my criteria of “weird, interesting, semi-exclusive opportunities”, and I’m willing to pursue it to completion even though I have no idea what opportunities might arise from it.