Explore broad with a view of your downside drivers

#careertransition – #2 of 8 | I recently went through a process of career exploration and made a significant career switch. This series of 8 posts is a synthesis of the lessons I’ve learnt.


Once you have a starting hypothesis of what you’re solving for, break down the kinds of paths available to you. Big company. Small company. Starting your own. A certain kind of industry. Lay them all out – and even if you have strong hypotheses on what you want, validate them against what you’re solving for.

The reason it’s important to go broad is simple. We regret the shots we didn’t take the most.

The process of exploring will sharpen your thesis and give you better clarity on what’s right for you and what’s not. That matters – because it’s easy to lose sight of your internal compass with so much external noise.

Every place has an inherent value system that adds noise. In Silicon Valley for example, it’s cool to be a founder. Does that mean it’s the right decision for you? Maybe. Maybe not. It’s extremely cool right now to work for a hot AI company. Before that, it was something else. No matter what captures the zeitgeist, that doesn’t mean it’s the right answer for you.

The way out is simple – speak to as many people as possible. Go down as many rabbit holes as possible. And then make a decision based on what works for you.

But while you explore broad, be mindful of the downside drivers. The most important part of this game is the ability to keep playing – you don’t want to get kicked out of the game.

For immigrants, the most pertinent downside is any decision that impacts your visa or permanent residency. Nobody who isn’t an immigrant can fully understand the angst of a tricky visa situation – the fear of getting kicked out of a place you call home, or not being able to get back in.

For everyone, anything that impacts your health or your wealth is a downside driver. If you decide to go to a small company, you don’t want to go in with the pressure of needing a financial exit – that’s completely out of your control. You’re much better off going to a bigger company if that kind of pressure exists. This is why common advice is to take risks when you’re younger – you don’t have those kinds of pressures yet.

Once you get past the major sources of downside, it’s a lot easier to make decisions based on upside. But it’s important not to confuse the two.