This post originally appeared on July 19th, 2013.

I spent last week in Manhattan; detached from my regular day-to-day context in London. When I’m in travel mode, I find it way easier to spontaneously zoom out on what it is that I’m actually doing with my life. Like, long-term. One specific debate I’ve been having with myself is whether or not to go to graduate school.

I’ve been flirting with the idea for awhile, but recently shelved it as an option because of an argument with my Dad during which he made some annoyingly excellent points loosely mirroring those of blogger Penelope Trunk. (In a nutshell: she thinks that advanced degrees can be a colossal waste of time and money.)

Since I designed and run Escape the City’s Startup MBA program, it’s pretty obvious that I too am a big believer of traditional graduate degrees having specific limitations when it comes to navigating certain industries. I totally buy into what Penelope Trunk (and my Dad) are saying.

However, over a Thai meal in the West Village, I unexpectedly found myself strangely jealous of my friend Stu as he told me about his PhD studies in computer science at Columbia. Envy is a powerful tool in pointing us towards what may be missing in our own lives and hanging out with Stu reignited the graduate school debate in my head.

I often talk to Escape the City members about this topic because many of them are considering doing MBAs. When it comes to making pivotal decisions, I really don’t think that anyone else can give you the answers that only you are best placed to address, but I do think that there are three helpful questions that can help when wrestling with a major career decision.

1. Will this help me to stay upwind?

When Paul Graham (the founder of the Silicon Valley startup incubator Y Combinator which birthed Airbnb and Dropbox) talks about what he wishes he had known in high school, he talks about staying upwind. He rallies against the “don’t give up on your dreams” advice that is so often touted at commencement speeches:

In the graduation-speech approach, you decide where you want to be in twenty years, and then ask: what should I do now to get there? I propose instead that you don’t commit to anything in the future, but just look at the options available now, and choose those that will give you the most promising range of options afterward.

Instead of trying to predict what you’re going to want in twenty years, he talks about giving yourself the best skill-set possible by always selecting the more difficult problems to work on. Those tougher projects sharpen your skills and therefore inherently equip you best for whatever you work on next (which you can’t necessarily predict from here in the present).

To continue reading, check out the original article here on the Huffington Post UK

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