Over the last few years, I’ve found myself looking at all my important relationships through the Enneagram lens…. I wish I had discovered it much earlier.
Drew Houston is CEO and co-founder of Dropbox. After graduating from MIT in 2006, he turned his frustration with carrying USB drives and emailing files to himself into a demo for what became Dropbox. In early 2007, he and co-founder Arash Ferdowsi applied to tech accelerator Y Combinator. Dropbox went on to become one of the fastest-growing startups in YC history. Dropbox now has more than 500 million registered users and employs more than 1,500 people in 13 global offices.
What is the book (or books) you’ve given most as a gift, and why? Or what are one to three books that have greatly influenced your life?
I’ve always admired Warren Buffett and Charlie Munger‘s clarity of thought and how they manage to explain complex topics in simple terms. Poor Charlie’s Almanack by Charlie Munger is one of my favorite examples.
As the CEO of a company, and in life in general, you find yourself making a dizzying variety of decisions in areas where you don’t have a lot of expertise, and your environment is constantly changing. How do you navigate this? How do you cultivate judgment and wisdom without waiting for a lifetime of experience?
Poor Charlie’s Almanack is a good start. It describes how to make good decisions in any situation with a relatively limited mental toolkit: the big, enduring ideas of the fundamental academic disciplines. Virtually everyone is exposed to these concepts by high school, but few people truly master them or apply them in everyday life. In my experience, it’s this kind of essential, first-principles thinking that enables the unusual level of insight and conviction that sets the great founders apart from the merely good ones.
In the last five years, what new belief, behavior, or habit has most improved your life?
I’ve found the Enneagram to be incredibly helpful. At first glance it’s a personality typing tool like Myers-Briggs. There are nine Enneagram “types” and every person has one dominant type. But I’ve found it to be much more useful and predictive of how people actually behave.
At first I was skeptical, but after reading the description for my type I found it spookily accurate in pinpointing what makes me tick: what motivates me, what my natural strengths are, what my blind spots tend to be, and so on. It’s helped me tailor my role and leadership style to my strengths.
It’s even better with a team—all of our senior leaders have typed themselves and we encourage everyone at Dropbox to learn about it. You can easily find (free) online tests and resources.
Over the last few years, I’ve found myself looking at all my important relationships through the Enneagram lens. It’s a great way to build deeper empathy for the people in your life and better understand why they are the way they are. I wish I had discovered it much earlier.
What advice would you give to a smart, driven college student about to enter the “real world”? What advice should They ignore?
I thought about this a lot when I gave the commencement address at MIT back in 2013. I said that if I had a cheat sheet I could give myself at 22, it would have three things on it: a tennis ball, a circle, and the number 30,000.
The tennis ball is about finding something that you can become obsessed with, like my childhood dog who would go crazy whenever anyone threw a ball for her. The most successful people I know are all obsessed with solving a problem that really matters to them.
The circle refers to the idea that you’re the average of your five closest friends. Make sure to put yourself in an environment that pulls the best out of you.
And the last is the number 30,000. When I was 24, I came across a website that says most people live for about 30,000 days—and I was shocked to find that I was already 8,000 days down. So you have to make every day count.
I’d give the same advice today, but I would clarify that it’s not just about passion or following your dreams. Make sure the problem you become obsessed with is one that needs solving and is one where your contribution can make a difference. As Y Combinator says, “Make something people want.”
In the last five years, what have you become better at saying no to? What new realizations and/or approaches helped?
This was a hard thing for me to learn; I like helping people. But realizing a couple things made a big difference: You have a lot less time than you think, and you’re not spending your time the way you think you are.
I’ve found this analogy useful. Think of your time like a jar, your priorities as “rocks,” and everything else as pebbles or sand. What’s the best way to fill your jar?
Doesn’t seem like rocket science. Ask anyone and they’ll be utterly convinced they already start with the rocks, then fill in the pebbles, then the sand. I was, too. The first time I did this exercise (when reading The Effective Executive by Peter Drucker, one of my all-time favorite management books) I was convinced that the majority of my time went into recruiting and working on our product [the “rocks”].
But once I actually created an hour-by-hour log of where my time was spent over a couple of weeks, I was shocked (along with everyone else who has ever done this exercise) that 1) my jar was mostly filled with sand and 2) really important rocks were falling on the ground.
That helped me put outside requests into perspective. My jar isn’t very big to begin with; am I going to fill it with my rocks or am I going to let other people fill it with theirs? I actually have an email label called “OPP” to remind myself that those requests are “other people’s priorities” and to think carefully before putting unsolicited requests for favors ahead of all my teammates and customers, who are quietly counting on me to do my actual job. Note that this doesn’t mean “never help people.” Just be conscious of your choices.
A couple more tips: Schedule specific blocks of time in advance for your rocks so you don’t have to think about them. Don’t rely on wishful thinking (e.g., “I’ll get that workout in when I have some downtime”); if you can’t see your rocks on your calendar, they might as well not exist. This is doubly important for things like sleep and exercise. If you don’t put those in first, no one will.
As far as actually saying no, I’ve learned you don’t owe anyone lengthy explanations, and you don’t have to respond to every email (particularly anything unsolicited). Brief, one-line responses like “I can’t make it but thank you for the invitation” or “Thanks for thinking of me—unfortunately my hands are full with [my company] so I can’t meet right now” are more than adequate.
* Source: Tribe of Mentors by Timothy Ferriss