What do you think I can do next? What “career move” do you recommend? How can I land that fantastic CEO job at company (or bank) XYZ?

Again, those are some of the questions I am faced with daily.

As simple as they are, they cannot be answered seriously.

Let’s see how we can take a different angle, open up a different perspective, by combining a few separate thoughts: that of a “Black Swan“, that of “Obliquity“, and that of a “much smaller, yet more precious list” I have discussed separately.

Black Swans (…) are large-scale unpredictable and irregular events of massive consequence—unpredicted by a certain observer.

Nassim N. Taleb, “Antifragile, Things that Gain from Disorder, Prologue, 2012.

Black Swans can be negative as well as thy can be positive. Limiting the exposure to negative Black Swans and increasing our exposure to positive Black Swans is the challenge, then.

John Kay describes obliquity as follows:

If you want to go in one direction, the best route may involve going in another. This is the concept of ‘obliquity’: paradoxical as it sounds, many goals are more likely to be achieved when pursued indirectly. Whether overcoming geographical obstacles, winning decisive battles or meeting sales targets, history shows us that oblique approaches are the most successful, especially in difficult terrain.

Obliquity implies that future opportunities can best be pursued indirectly. Black Swans imply that the only safe thing we know about our next move is that we don’t know what it is going to be.

Remember, though, that people, not what we do, will make us happy. Finding people we like, people who inspire, is therefore as unpredictable and as uncertain as the combination of Black Swans and Obliquity. Yet, finding and nurturing relationships will give us pleasure, stimulate our thinking, open up endless possibilities.

Hence, that “much smaller and more precious list“, our path to connecting wisely, is our way forward. The wiser we are in connecting with people we like, the more will we be exposed to positive (and oblique) Black Swans. That person we like, whom we regularly talk to, seek advice and inspiration from, at a given, unexpected moment will come out with that fantastic thought, with that inspiring question, which will lead to our next opportunity, perhaps to our next job.

There’s no predictable limit to the power of relationship, the power of connecting wisely.

Tommaso Arenare

www.twitter.com/tommaso_arenare