Six Failures — One Takeaway

The older I get, the more I’m convinced that success is simply a product of action -– of doing, and being willing to fail.

Sure — the motivational corner of the internet is filled with trite maxims and quotes that say just that:

“Test fast, fail fast, adjust fast.” — Tom Peters (management consultant)

“You miss 100 percent of the shots you don’t take.” — Wayne Gretzsky (hockey player)

“80 percent of success is showing up.” — Woody Allen (film director)

But to me it boils down to this — the difference between “mediocre” and “world-class” often is just a matter of attempts.

I’ve enjoyed a wonderful (albeit circuitous) career so far. 98 percent of the world would call me successful.

And yet, what sticks with me most are the failures. And the epiphany this weekend was that those failures are precisely what has enabled my success.

Because the key is I tried.

There are huge vistas of things I will never accomplish in this short life. But the key to success may just be the ability to ignore your ego and embrace failure.

Some examples:

1) Japanese

I’m not good at languages. By that I mean, I’m not naturally talented at them. Five years of Latin in junior high and high school equipped me merely to fail the AP exam in Virgil.

Similarly, I was probably the worst student in the Japanese class I took at the University of Pennsylvania my senior year of high school. My decision to then major in Japanese in college cost me the chance to graduate with honors, as my final undergraduate GPA was a mere 3.45.

The reason for this was simple — I got a “B” in every Japanese class I ever took, and I took 15 of them (including three at a Japanese university).

Was it worth it?


Because it was sufficient.

Two years out of college I landed a job working for the Japanese Embassy in Washington, DC. A year later I found myself writing speeches for the Japanese ambassador.

There’s no shame in lacking talent in something if perseverance and hard work can help you achieve the same end result.

2) Law school

Law school was the only time academically where I truly tried my best, worked my tail off for nine months, and failed. In fact, I dropped out.

I ended 1L in the bottom half of my class, having received two C plus grades (the grad school equivalent of an D).


1) Shaken confidence for the next four years.

2) I’m still paying student loans from that aborted grad school experience.

3) I learned to read and synthesize vast quantities of boring information quickly.

4) I am not intimidated by lawyers, and can speak their language (which is far simpler than Japanese).

On balance, I think the latter two outweigh the former, so I win.

3) Capitol Hill

I long held the dream of working as a staffer on Capitol Hill, the epicenter of U.S. politics. The problem? I had no connections and my only state ties were filled with representatives from the other party.

Easy solution — I arranged informational interviews with staffers, who advised me to intern. That internship led to a temporary staff position with a key senator.

But once I was in the system with a solid resume and recommendations from insiders I ultimately failed to secure a permanent staff positon for one simple reason:


I lacked the emotional fortitude to face rejection — to walk the halls and cold call each and every Congressional office until I found one that would take me. I gave up after 7 rejections. I now know that if I’d held out for 50 rejections, I likely would have secured a permanent job and had a longer and more substantive career on Capitol Hill.

4) Negotiations Class

The most valuable class of my MBA coursework was one on negotiations. And here, I received a B (the B-School equivalent of a C-). Why? Because of one simple assignment that I failed to finish: “Collect 20 no’s.”

It’s as simple as it seems — the assignment was to ask strangers a series of outlandish requests until you were rejected 20 times. The key? To track how many requests it took, and in many cases, it took more than 50 requests to receive 20 no’s.

What was notable is the yes’s I received along the way: I asked random strangers I found attractive for their phone number; I asked for free upgrades at Starbucks, I asked for free donuts — and all of these were given to me, and far more often than I expected.

I gave up at 37 attempts, having received just 14 of the 20 required no’s. So I forfeited my A in the class, lowering my final MBA GPA by 0.15 points.

But the intended lesson was clear — Show up and ask.

People say yes a lot more than you’d think.

5) The girl

There was a girl (isn’t there always?) The one who got away. She knows who she is. Better to have loved and lost? Sure, but the point is, personal failures count too.

6) Being fired

I was fired. From my first job out of school.

It was the best thing that could have happened to me.

I learned from every mistake of that year and ensured I never made them again. I succeeded wildly in my next job, and the one after that, and the cycle continues.

But had I not failed early, and brutally, I never would have corrected some things at age 22 that others still struggle with at 32.

And for that, I am grateful.

The lesson, the takeaway, in all this?

Don’t worry about failure, about embarrassing yourself or falling flat on your face.

The greater sin, by far, is to look back on your life from your deathbed and regret that you never even tried.

This was originally published on my blog,

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