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I’ve been writing down my thoughts my whole life, although they were never very organized until recently. Often I’d write down an epiphany I had, in the middle of my science notebook or in the margins of a handout, unsure if I would still find it profound later.

I was always afraid of people finding these thoughts, I guess because then they’d know whether I was smart or just thought I was smart. So I’d put them in quotes, and attribute them to a fake name, circa a fake date. If anyone found it at least it would look like it wasn’t my thought. If an entry struck me as especially profound I might attribute it to a real person who was known for being smart. Oscar Wilde or the Dalai Lama.

This secretiveness was a persistent theme all the way through childhood and into my twenties. It gave me a sense of control over how others saw me. I was embarrassed to want certain things. I was embarrassed for other people’s desires for certain things, like whenever I’d see old men checking out young women, or overweight people ordering coffee with four sugars and four creams. I felt like people’s wants should be extremely private because they reveal so much, and so I didn’t want to let other people in on mine. I didn’t want other people to know what was motivating me at any particular moment.

My parents were always very helpful people to have in the house, and they were sensitive to my sensitivities, even though I had a hard time being candid with them about my intentions and motivations. If I was dealing with something tough they’d always be willing to sit down at the dinner table with me and help think up solutions. But I hated hearing their advice, because they thought of my problem very logically and I knew they were right. The answers to my problems were always simpler than I wanted them to be.

More than any other aspect of life, I found the job-hunting process demeaning and embarrassing. The prospect of pavement-pounding alone always overwhelmed me, and so I sought the wisdom of my parents. Job hunting had always made me feel like a beggar. I hated asking people with jobs to give me a job. My Dad’s suggested approach was rational — decide how many businesses to apply at every day, then go do that every day until you have a job. It’s simple and it will inevitably put an end to your problem.

The thought of actually doing this terrified me though, as it almost guaranteed the occasional moment of stark embarrassment that I would do anything to avoid. So my approach always involved sidling around the most challenging part, and trying to land a job with emails and job websites. This isn’t very effective and made the problem last months instead of weeks, creating many times more pain than necessary, even though the whole reason I was doing it that way was because I wanted to avoid pain.

This is a theme I keep noticing in life. My problems are always simpler in the eyes of others, just like other people’s problems seem simpler to me than they make them out to be. If a friend came to me today with a dilemma and he didn’t know what to do, I’d have no problem telling him “What I’d do.”

Strangely, it’s almost always obvious what others should do, and less obvious what we should do ourselves. I’ve become increasingly aware of this phenomenon, both on the giving end and receiving end of advice.

The question is, who’s mistaken? Is it that others are always oversimplifying your problems, or is it that you’re always overcomplicating them?

I think there is, almost always, at least a bit of both going on. But I know that in my case, I’m normally the one with the more distorted view of my problem and I’d bet most people are that way too. It’s easier to be rational about other people’s problems than your own, because you’re much less emotionally invested in other people’s problems, so you can stay more rational about it.

When you go to another person to help you with a problem you’re having, often you’re not putting two heads together towards addressing the same issue. The other person is trying to come up with a way to solve the problem, and you’re trying to come up with a way of protecting yourself from your fears surrounding that problem. Often this means your solution is more comfortable for you in the short term, yet it prolongs the problem, and overall, creates a worse experience for you.

The most effective solution usually resembles a straight line between where you are and where you want to be, and this path necessarily ignores the emotional landscape that path must cross. If the straight line brings me to a steep slope overgrown with brambles, then so be it — it might hurt a bit but the directness of the route ensures that it will be over soon.

When I think of my own problems, I tend to look for the easiest path from here, emotionally speaking, which almost always makes for a more circuitous route, and often that route doesn’t even go to where I’m trying to get.

I think this is a normal human tendency. We make problems harder and more complex when they are ours.

From Steve Pavlina:

I don’t think I’ve ever met someone that claimed they didn’t know what to do who wasn’t butt up against the most obvious solution, staring them right in the face the whole time. They claim ignorance in order to prevent themselves from having to face that solution, which is often quite clear to everyone around them. They think that other people are actually buying their excuse, but the reality is that there’s a whole gossip network around the person where friends and family keep asking, “Why won’t s/he just do X?”

I want to be clear that this isn’t always true, although I believe it is a strong human tendency. Sometimes others simply don’t understand what the problem feels like from the inside, or even what the problem is to begin with. Telling an anorexic woman that she just needs eat something is not indicative of a clearer, more rational view of the problem, it’s a fundamental misunderstanding of what the problem is.

Neuroses and chronic conditions aren’t the discrete problems I’m referring to here. I’m talking about situational dilemmas. Most of the time, a peer or friend is more likely to come up with a better solution than you are, but chances are it will require you to do something that makes you at least slightly afraid. We should be using this to our advantage.

In the 90s, bracelets that said “WWJD” became popular among Christian teenagers in America. It stands for “What Would Jesus Do?” and although I’ve never been a Christian I think it’s an excellent question to ask on a regular basis. It makes it easy to come up with an idea that’s probably healthier and more useful than you would have had otherwise.

And why limit this thought experiment to Jesus? There must be a hundred minds you admire, and it’s not that hard to at least guess how they’d deal with your current problem if they had woken up with it. What would your grandmother do? What would Gandhi do? What would Emerson do? MacGyver?

These are all ways of stepping outside your own, emotionally-derived view of the problem, in order to assess it again as if it’s still out there in the distance, isolated and finite. From the inside, problems tend to look interconnected to all of our other problems, and therefore they look endless. It is remarkably helpful to have someone else think about your problem, or even just to think about how someone else would think about your problem.

Readers who know me in person know that I don’t always take my own advice. I may know what the right thing to do is, and I might tell other people to do that, but when the sole hits the sidewalk I go and do it in some dumber way just because that’s how I’m used to doing it.

I am at peace with this apparent hypocrisy. I write about issues that affect me or have affected me in the past, and often I don’t realize what I know about something until I get it into words. Quite often I’ll break down a problem in a blog post, and suggest a solution, just so that the issue becomes clear to me for the first time. This is one more way of stepping outside oneself to get a longer view of something that’s too close to you to see clearly. Writers have been doing it as long as anyone’s been writing anything.

As I’m writing about this phenomenon right now, I feel that distance the clarity that comes with it, and so here’s what makes sense to me. I think we should ask our friends and loved ones what to do more often, and we should remember that their emotional distance from the problem gives them a kind of clarity about the problem that we often can’t achieve on our own.

There is a paradox to beware when it comes to rationality. We often feel more conviction about our actions when we’re riled up emotionally, but that’s when we’re least capable of being rational. In other words, we often feel more headstrong about a bad approach than we do a good approach. While you’re being swept away by something, other people are standing on the banks, where they can see where you are and where you’re trying to get to — something you can’t often see from your position — and if you ask them what to do they can tell you.

Try with a little help from your friends.


College graduation: lofty commencement speeches are given, bright futures anticipated and, for some lucky college graduates, new jobs await. While commencement addresses may be inspiring, I wish someone would take the opportunity to deliver a more practical message to new college graduates who are about to enter the work force. It would go something like this:

“Congratulations. You’ve just earned your college degree. I’m glad to be here as the first person to speak to you as college graduates. I have good news and bad news. First, the bad news: Despite your newly obtained degree, you don’t know anything. You have no skills. If you are really lucky, you will soon land your first job. You are not entitled to that job. Quite the contrary, there are many people just like you who would love to have that job. If you get it, you should be grateful for your good fortune and make the most of it. It will be hard work, sometimes backbreaking work, and you may feel that the work is beneath you. But the reality is that nothing is beneath you, because you don’t know anything — yet.

Now, the good news: You live in the United States of America, the greatest country in the world. If you work really, really hard, if you are happy to start at the bottom and work your way up, if you are ready to grind and scratch and claw, and if you catch a bit of luck, anything is possible. Anybody can be anything in America. You just have to be willing to learn fast from those around you and work really hard.”

Unfortunately, I was not invited to deliver any commencement speeches this year. So I’m doing the next best thing and reflecting in this post on my first job. I hope that it can provide a bit of help and guidance.

I’ll start with a summary: I totally whiffed on my first job experience. When I graduated from college, I knew nothing, had no skills and was not owed anything. But that’s not how I felt at the time.

I had just graduated from the Wharton School, the country’s oldest undergraduate business school and one that consistently lands the top slot in college rankings. I studied entrepreneurial management and tried to drop out of school to start a business during the winter break of my junior year. (Thankfully, my parents forced me to stay in school.) I finished my studies early in my senior year and spent the remaining weeks waking up early to read The New York Times and The Wall Street Journal, and then using the rest of the day to consume voluminous amounts of coffee while devouring Ayn Rand’s “Atlas Shrugged.” I was biding my time until I left academia to do what I thought I was meant to do: run a business.

Like all Wharton undergraduates, I interviewed with companies that came calling on campus: investment banks, strategy consulting firms and technology companies. At the time (I graduated in 1997), there was a company called Trilogy, based in Austin, Tex., that was getting a lot of press. Trilogy had been started by Joe Liemandt, who dropped out of Stanford to start an enterprise software company that was selling multimillion dollar software applications to big companies like Boeing, Sun Microsystems and Hewlett-Packard. While the software seemed esoteric — who understands what product configuration software does and why another company would spend millions of dollars for it? — Joe’s success was tangible. He was on the covers of business magazines and was ranked as one of Fortune’s 40 richest under 40 in 2001. He was the type of entrepreneur from whom I could have learned a tremendous amount.

But I didn’t think there was anything I needed to learn.

I was recruited to Trilogy by Ajay Agarwal. Before joining Trilogy, Ajay had graduated from Stanford, then Harvard Business School and worked in strategy consulting at McKinsey & Company. Today, Ajay is a managing director at the venture capital firm Bain Capital Ventures. Ajay’s recruiting pitch was particularly compelling: come to Trilogy to work in an entrepreneurial environment with extremely smart people. The problem was that I believed I was ready to be the entrepreneur immediately.

Still, I accepted the job, and after a summer schedule meant to shed a wanderlust that I assume most college seniors have, I moved to Austin. I was paired with Jason Wesbecher, another Wharton undergraduate who had been working at Trilogy for about six months. (Today, Jason is the founder and chief executive of Handshakez in Austin.) Jason was the epitome of inherent intelligence, hard work and focus. He was driven to acquire customers for Trilogy, understanding that revenue was the lifeblood of a fast-growing start-up. At the time, I could not have been less impressed with that role.

I was ready to start a company. I felt it was my destiny to do so. It was what I had dreamed about since I was a child. In retrospect, I was terribly, utterly, naïve. Now, 16 years later, here are my reflections:

1. I knew nothing. Yes, it is true I studied business in college, and the college I went to is a good one (if you were to ask Donald Trump, it is without question the best). But there is a vast difference between studying business and doing business. Until I had actually done it, I knew nothing at all.

2. I didn’t know that I didn’t know anything. This is actually worse than not knowing anything. I thought that I had something to contribute. In fact, I thought that my presence at Trilogy was a real gift to the company. I was wrong.

3. I missed the opportunity to learn. Because I believed that I already knew everything, I missed the chance to learn from the incredibly smart people who did know something. Trilogy was an exceptionally good company at recruiting. It produced a Trilogy Mafia well before anyone talked about the Paypal Mafia. Former Trilogians have gone on to accomplish absolutely amazing things. And the people I had the chance to work with directly — Joe, Ajay, Jason and many others — were all truly extraordinary businessmen.

4. I thought I was entitled to something. Somehow, I arrived at Trilogy thinking that it was to their great benefit to have me as an employee. As a result, I thought I was entitled to the opportunity of doing something “strategic.” What I came to understand afterward was that many college graduates would have loved to have that job, and that it was my opportunity, but not my right, and certainly not something to take for granted.

5. I was confused about the meaning of hard work. I thought I should spend my time thinking big thoughts. I assumed that if I were in the office a lot, I must have been working hard. I didn’t know that I should have been doing what Jason was doing — the hard work of calling potential customers, learning about their problems and presenting our solutions. That was hard work and meaningful work. I didn’t realize it until after I had left.

My time at Trilogy was a missed opportunity. I realized it at the annual Trilogy Prom, where the entire company gathered at a luxurious location to celebrate the year’s success and to recognize extraordinary individual performance. Jason (deservedly) won a Trilogy Star Award based on his exceptional contribution to the company. As I watched him walk to the front of the room to accept his prize, I was of mixed emotion: proud of him but disappointed with myself. The experience proved to be a turning point.

After just over a year at the company, I decided to leave. Thankfully, I started to figure out what it took to achieve success. It was Jason’s focus and do-whatever-it-takes attitude that caused me to re-evaluate my own disposition. Once I did, I realized that I needed to start afresh. I looked for a small start-up where I could join on the ground floor. If I proved my mettle and the company grew, I might be able to take on more and more responsibility, learning essential skills to start my own company someday.