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Study Hacks Blog

Do What Works, Not What’s Satisfying: Pseudo-Striving and our Fear of Reality-Based Planning

The Dune Revelation

In July 2009, I took a trip to San Francisco. At some point, I ended up hiking at a sand-duned nature preserve, not far south from Monterey on Highway 1.

What I remember about this hike is a thought that struck not long into the route. In the summer of 2009, I was two months from defending my PhD dissertation. I had arranged for a post doc after graduation but found the academic market beyond to be uncertain for me and my skills. It was in this context that I had my insight:

Why hadn’t I systematically studied the most successful senior grad students when I first arrived at MIT?

Every year, a small number of computer science students at MIT easily generate multiple job offers while the rest have to sweat the process. What do these students do differently from the others? It’s a basic question and yet almost no one arriving in Cambridge seeks an answer. We instead carve out our paths blindly, sticking our heads up only at the end to see if we’ve stumbled anywhere near our destination.

I ended up fine, landing a great tenure track position at Georgetown, but the 2009 version of myself did not have this certainty, and my failure to more systematically plan for my arrival on this market suddenly seemed a glaring omission.

The $100 Startup

This 2009 experience came back to me earlier this week as I read an advance copy of Chris Guillebeau’s new book: The $100 Startup. In this book, Chris tackles a topic made popular by Tim Ferris: how to build a lifestyle business in a digital age.

Lots of people are enamored by the idea of having a business that requires little investment and yet supports you financially while injecting flexibility into your life.

What sets Chris’s book apart, however, is that he was not content inventing a bullet-point system that simply sounds good. He instead systematically studied people who had actually made these types of businesses work. He started with a survey of 1500 such entrepreneurs which he then narrowed down to 100-200 that he interviewed in more detail. He lists them by name in his appendix.

The result is often messier than the internally-consistent, inspiration-boosting acronmyized systems of competing books and blogs, but the advice come across with an authenticity that’s rare for this topic.

Put another way: Chris did with his interest in lifestyle businesses what I should have done as a grad student with my interest in becoming a professor. The only plan he was interested in was a plan grounded in reality.

The Big Question

I’m telling these stories because they inspire an important question: Why do so few people do what Chris did? Most of us are content, it seems, to work hard and build complicated systems, but we avoid basing our efforts on a reality-based assessment of what really matters.

And I think I finally have an explanation…

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Don’t Know What To Do With Your Life? Seek Bargains.

A Career Crossroads

In the early winter of 2004, I was a senior at Dartmouth College and in the fortunate position of having two good job offers.

The first was from Microsoft. It paid, by 2004 standards, about as much as you could possibly earn right out of college (around $85,000 in cash and stock per year).

The second offer was to join the computer science PhD program at MIT. It paid considerably less (around $28,000 in stipend) but promised near complete freedom (MIT is quite unstructured and entrepreneurial).

I had no clear preference for which job to take — they both seemed exciting. But in my effort to make a decision, I stumbled on a key tool in the career craftsman toolbox.

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Can I Be Happy as an Investment Banker? The Difference Between Pursuing a Lifestyle and Following Your Passion

A Nervous Sophomore

The following question came from a sophomore finance major at a well-known state university:

I have read and heard that entry-level investment bankers have to work long hours doing meaningless grunt work assigned by bosses (sometimes portrayed as evil)…How can your career craftsman philosophy be applied to high stakes fields such as finance?

This reader believed in my career philosophy and was perfectly happy to sidestep the flawed idea that he should “follow his passion.” But the option of heading into investment banking — a popular choice for his major at his university — was making him nervous.  The requirements for standing out in this field seemed brutal and he wasn’t inspired by the rewards you can obtain for banking stardom (more respect and money in exchange for more work hours and stress).

I told him not to become an investment banker.

Here’s why…

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