I’m sure you’ll agree with me when I say we are short on time.

So where should we allocate our finite time? What projects should we work on? Should we create a startup, or should we go down a more traditional route?

Making these decisions can be difficult. But often the most difficult decisions are the most important. In fact, difficulty is often a signal that a decision is important.

So here it goes – two rules for career success:

Rule 1: Do not plan your career

Rule 2: Instead of planning your career, focus on developing skills and pursuing opportunities

Do Not Plan Your Career

Huh? A careers advice newsletter is telling you not to plan your career?

Yep, that’s right. But don’t take it from me. I’m no good at this. I’m still caught up in the stress of trying to work out exactly what my career will look like. Hypocritical, I know, but I’m working on it.

Instead, take it from billionaire and legendary VC, Marc Andreessen:

You can’t plan your career because you have no idea what’s going to happen in the future. You have no idea what industries you’ll enter, what companies you’ll work for, what roles you’ll have, where you’ll live, or what you will ultimately contribute to the world. You’ll change, industries will change, the world will change, and you can’t possibly predict any of it.

Okay sure, there is a bit of nuance here. You want to be driven and know what your next steps are. But it is futile trying to plan your career all the way from year 1 to year 50. Sure, you want to have a sense of where you might go, but if you steadfastly fixate on one path and one path only, then you close yourself off to better opportunities, and to serendipity.

So if rigid career planning = career limiting, what then is the solution?

Optimise for Skills and Opportunities

I’ll talk about the four most important skills next week. But for this article, let’s put the spotlight on opportunities.

There are two kinds of opportunities:

1. Those that come to you
2. Those that you go out and create

1. Opportunities that come to you

A huge part of ‘career planning’ is being continuously alert to opportunities that come to you. This is often the matter of being in the right place at the right time. Opportunities tend to present themselves when you’re not expecting it.

To quote Nassim Nicholas Taleb in his insightful book 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.

When you’re just out of school is when you should take income risks to seize opportunities. You should take the job or say yes to the opportunity that will best develop your skills or give you invaluable experiences and connections, irrespective of the salary. This is not a time play it safe.

So, how do you spot these opportunities?

There is no cut and dry answer. But sometimes opportunities can be hidden in plain sight:

• A senior person at your company is looking for someone to help on an important project, in addition to your day job
• A small group of friends invite you to the pub at 11PM to discuss an idea for a startup
• Your manager jumps ship to a hot growth company, and calls you a few months later asking you to join

2. Opportunities that you go out and create

We’ve spoken at length about pursuing a personal project, networking through coffee meetings, reaching out to have lunch with strangers. And really, this is the key to creating opportunities.

To repeat what we’ve said before:

If I made you a bet where you had a 0.4% chance of winning, would you take it? On average open roles get ~250 applicants. 4-6 of those applicants typically get invited for an interview, and one of those people gets hired. One in 250. The odds are stacked against you.

So instead, you need to create your own opportunities.

The world is a malleable place. If you know what you want, and you go for it with drive and energy and passion, the world will often reconfigure to help you reach your goals.

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