How Do You Make Big Decisions?

19/07/2013 11:51 | Updated 17 September 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).

Most importantly, choosing to tackle tough problems brings you in contact with others aching for challenge: "Look for smart people and hard problems. Smart people tend to clump together, and if you can find such a clump, it's probably worthwhile to join it. But it's not straightforward to find these, because there is a lot of faking going on."

2. Will this introduce me to supermodels?

Rob Fitzpatrick, who leads the teaching for our Startup MBA, spent time learning from Paul Graham at Y Combinator. In one of his blog posts, he came up with a twist on Woody Allen's oft-repeated quote: "90% of success is showing up (to the right place and possibly creating that place if it doesn't yet exist and also talking to people while you're there)."

In that post, Fitzpatrick is talking about meeting co-founders and getting deal flow, but it applies to any situation where you are trying to engineer a desired outcome. He uses the analogy of meeting a supermodel and how the likelihood of the episode happening rests less on your having a six-pack and more on hanging out where the supermodels actually are.

Any outcome has a pipeline and often we can place too much weight on an imagined entry price instead of just showing up. When it comes to making pivotal decisions, it's tempting to try and predict beyond what we can actually know. Fitzpatrick suggests that sometimes the most productive first step is making yourself both familiar and valuable within relevant environments.

3. Will this bring me closer to my wizards?

When I told Stu how jealous I was of his license to spend the day simply reading and researching, he suggested that I look into graduate school myself. I told him how happy I was in my current role and how much I was learning from where I already stood.

He pointed out what I had suspected all along: "At this stage in life, in your twenties, you're still an apprentice in anything you do." He said, "The important thing is to find your wizards, the masters in your field. Sometimes they're in industry, sometimes they're in academia." These are the people whose wisdom and knowledge you want to absorb, he said; whose paths you somehow want to partly emulate.

To be able to recognise your wizards, you need to first figure out what your deepest values are, what you're trying to learn more about - what excites and interests you, what you could read about all day long, what you could spend your whole life exploring and contributing towards. While those answers are not for sale, they seem to be the ones we end up spending the most on trying to find.

I spent the rest of my week in New York talking to other graduate students and entrepreneurs and friends and realising that while Penelope Trunk and my Dad and my inner cynic make some great points, the debate over graduate school isn't simple. It often intersects with what Graham describes here: "If you want to do good work, what you need is a great curiosity about a promising question. It can take years to zero in on a productive question, because it can take years to figure out what a subject is really about."

Some things can only be learned in hindsight and it can be overwhelming trying to figure out the best path forward; yet those three questions have always helped me to separate clarity from clutter on my own road to zeroing in on a productive question.