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Part 1 of Marc Andressen’s blog series on career planning

<figcaption class="wp-caption-text">via flickr/cdevers</figcaption></figure>

The first rule of career planning: Do not plan your career

The world is an incredibly complex place and everything is changing all the time. You can’t plan your career because you have no idea what’s going to happen in the future.

Trying to plan your career is an exercise in futility that will only serve to frustrate you, and to blind you to the really significant opportunities that life will throw your way.

Career planning = career limiting.

The second rule of career planning: Instead of planning your career, focus on developing skills and pursuing opportunities.

Opportunities are key. I would argue that opportunities fall loosely into two buckets: those that present themselves to you, and those that you go out and create. Both will be hugely important to your career.

Opportunities that present themselves to you are the consequence — at least partially — of being in the right place at the right time. They tend to present themselves when you’re not expecting it — and often when you are engaged in other activities that would seem to preclude you from pursing them. And they come and go quickly — if you don’t jump all over an opportunity, someone else generally will and it will vanish.

I believe a huge part of what people would like to refer to as “career planning” is being continuously alert to opportunities that present themselves to you spontaneously, when you happen to be in the right place at the right time.

I am continually amazed at the number of people who are presented with an opportunity like one of the above, and pass.

There’s your basic dividing line between the people who shoot up in their careers like a rocket ship, and those who don’t — right there.

The second bucket of opportunities are those you seek out and create. Let me say up front that I am also continually amazed at the number of people who coast through life and don’t go and seek out opportunities even when they know in their gut what they’d really like to do. Don’t be one of those people. Life is way too short.

The world is a very malleable place. If you know what you want, and you go for it with maximum energy and drive and passion, the world will often reconfigure itself around you much more quickly and easily than you would think.

Now, I’m not proposing that you simply ping pong from opportunity to opportunity randomly. You can have a strategy. And here’s how I think that strategy should work.

I believe you should look at your career as a portfolio of jobs/roles/opportunities. Each job that you take, each role that you choose to fill, each opportunity you pursue, will have a certain potential return — the benefits you can get from taking it, whether those benefits come in the form of income, skill development, experience, geographic location, or something else. Each job will also have a certain risk profile — the things that could go wrong, from getting fired for not being able to handle the job’s demands, to having to move somewhere you don’t want to, to the company going bankrupt, to the opportunity cost of not pursuing some other attractive opportunity. Once you start thinking this way, you can think strategically about your career over it’s likely 50+ year timespan.

Most people do not think this way. They might occasionally think this way, but they don’t do it systematically. So when an opportunity pops up, they evaluate it on a standalone basis — “boy, it looks risky, I’m not sure I should do it.” What you should automatically do instead is put it in context with all the other risks you are likely to take throughout your entire career and decide whether this new opportunity fits strategically into your profile.

There are a set of potential downsides to almost any decision — but they can be analyzed, and often quantified, and thereby brought under control.

Which is important, because in life, there is generally no opportunity without risk. There are always real and legitimate reasons why people often pass on opportunities — they see the risks and they wish to avoid them. The issue is that without taking risk, you can’t exploit any opportunities.

When you are presented with an opportunity, carefully analyze its risks, but:

All that said, here are some of my opinions about the kinds of risk you should take and when:

Those are just a few examples. You will run into specific return/risk situations that nobody can predict ahead of time. When you do, just sit down and tease apart the risks — and think hard about whether, in the context of your overall career portfolio, they are really so scary that they justify passing on the return potential of a great opportunity. They often won’t.

From Nassim Nicholas Taleb in The Black Swan:

Seize any opportunity, or anything that looks like opportunity. They are rare, much rarer than you think… Many people do not realize they are getting a lucky break in life when they get it. If a big publisher (or a big art dealer or a movie executive or a hotshot banker or a big thinker) suggests an appointment, cancel anything you have planned: you may not see such a window open up again.