What Would You Do If You Knew You WOULD Fail?

If you read this post’s title quickly, you might think it asked that common question: “What would you do if you knew you couldn’t fail?” And yes, in spite of being a cliché, this would have been a good question to ask. Like its spin-offs (e.g., “What would you do if you had a million dollars?” or “…if money were no object?”), it removes obstacles such as doubt, insecurity, or external limitations.

So, what would you do if success were guaranteed? Write a book? Start a business? Run for office? Pursue a career in art, music, dancing, or some other passion? Start a foundation to help animals, the environment, or homeless people?

The point of this hypothetical question, obviously, is to think about what you really want to do — without triggering the all-too-common reaction of immediately arguing for your limitations (namely, launching into all the reasons why you can’t pursue — or can’t reach –your dreams). When you put aside those excuses, doubts, and limitations, all that’s left is passion, love, and success.

But that’s not the way the world works.

In the real world, there’s almost never a guarantee of success. Almost everything you can imagine doing carries a degree of risk. And although it’s not always the case, it often feels like the greater the risk, the greater the potential reward.

When you think realistically about what you might want to do, you need to factor in the very real risks. So a more realistic question might be: “What would you do if you knew you could fail?”

In other words, what do you feel so passionate about that it would be worth taking a risk in order to pursue it? What matters so much to you that you’re willing to face the very real chance of failure — because the possibility of success compels you to at least try?

If you really want to follow that dream of devoting your life to creative expression, politics, entrepreneurial ventures, or philanthropy, you’ll do it anyway, even though you know that the dream might not come true.

(For instance, Jodi and I just started watching a TV series called Inside Jokes, which follows aspiring stand-up comedians auditioning for the Just for Laughs festival. As they pursue their dreams, they know all too well that they might fail. [In fact, the vast majority of aspiring comics don’t make it big in this world.] Yet they love what they do so much that they’re willing to risk it for the chance of spending their life sharing their thoughts, expressing their true selves, and making people laugh.)

So it’s great to consider what dreams and ambitions you’d pursue if success were guaranteed, but it’s more realistic to consider the possibility of failure and see what you’d still pursue anyway.

But now let’s take these hypothetical questions one step further by asking a question at the pessimistic end of the spectrum: “What would you do if you knew you WOULD fail?”

This might seem like a negative question, bound to lead you into depressing territory: thoughts of failure, shattered dreams, and a wasted life. But I think that just the opposite is true: This question encourages you to think of something you love so much that you’d do it no matter what — not simply because you might “make it big” but because the activity itself is inherently rewarding. This question encourages you to pursue the things that make life worthwhile, the things that feel as essential as breathing, the things that you never want to live without. It encourages you to do what you love.

So, think about this question for yourself: What would you do even if you knew you’d never “succeed” (at least not by society’s definition)? What brings the most joy into your life? What makes you feel the most alive, the most fully you? What are you passionate about…not because it might lead to something “bigger and better,” but because the activity itself is a life-affirming expression of your true self?

The good news is that when you pursue what you love, you’ve got a much better chance of making it big in terms of worldly success. But the even better news is that when you pursue what you love, regardless of the risks involved, you have the innate joy, satisfaction, and fulfillment of knowing that you’re living your calling — no matter where it does or doesn’t lead you. This way, even if you “fail” at your calling, you’ll be living a full, rich, authentic life.

And that is true success.

The Two Best (and Worst) Magic Words

The two most powerful magic words I know aren’t open sesame, presto chango, or even por favor. They’re two words that have the power to open your heart and mind to limitless possibilities and innovations: what if.

Just like Ali Baba used open sesame to reveal treasure by opening what had appeared to be solid rock, what if has the power to crack open seemingly impassable (or impossible) obstacles, revealing the treasure within them.

And just like magicians might say presto chango to change one thing into another, what if can transform a roadblock into an opportunity.

For instance, if you encounter a roadblock in your business, you […] Continue Reading…

I Just Did Something Totally Stupid

I like to think of myself as a reasonably intelligent guy, but today I did something that was just plain stupid. It didn’t make any sense. It wasn’t a good thing to do. And my timing was absolutely terrible.

In retrospect, I can see that it was stupid. What makes it even worse, though, is that I realized that it was stupid before I started doing it — and even while I was doing it — yet I kept on doing it anyway.

Just to set the scene: this is one of the busiest times of the year for me. I’m launching two […] Continue Reading…

Idle Time Is the Angels’ Playground

I just read the words “Idle time is the devil’s workshop” for about the thousandth time, but it just now struck me how cynical, fear-based, and diametrically opposed to my own worldview this proverb is. Maybe it’s because I recently took almost a week off — five days filled (or not filled) with lots of idle time…and no sign of the devil!
Those days off were wonderful. My wife and I relaxed, took afternoon naps, went to the beach, explored a nearby town we’d never visited, played tennis (for the first time in about 16 years!), went on a real date, ate yummy […] Continue Reading…

5 Life Lessons from Bird by Bird

As part of the Your Soulful Book writing program, I recently re-read Anne Lamott’s modern classic, Bird by Bird: Some Instructions on Writing and Life.

The first time I read this book — over a decade ago — I was primarily focused on learning to write better. This time around, however, I was struck by the subtitle’s truth: so many of these “instructions” really do apply equally to life beyond the page.

Of the book’s many profound life lessons, here are five of my favorites:

“It is so much easier to embrace absolutes than to suffer reality. Reality is unforgivingly complex.”

I’m not sure […] Continue Reading…

No Pain, No Pain

Sometimes we learn from people who model what we want. Other times, we learn from those who model what we don’t want!

In my previous post, I discussed someone who falls into the latter category: a guest on the TV show This Time Next Year who justified her inability to find love by claiming that “Men don’t want to commit” (Once again, using myself as counter-exhibit A, I’ll borrow Amy Poehler and Seth Meyers’ one-word catchphrase: Really!?!) This time, I’m using another counter-example from the same show (which really is a great, inspiring show 99% of the time — I promise!) to address one of the most pernicious attitudes out […] Continue Reading…

1 DO + 1 DON’T of Romantic Relationships

If you’re looking for love or would like to improve the romantic relationship you’re already in, Valentine’s Day can be the best time of year…or the worst! It seems like everyone is talking (and frequently giving advice) about love and romance. And while much of this is wonderful — a celebration of love — a lot of it is negative, self-defeating, and untrue (or at least not necessarily true).

Everyone’s experience of love (and everything else) is different, so I’d never want to dismiss or downplay what someone else has been through. But over the last 16 years of being in […] Continue Reading…

A Timeless Message of Hope

I wasn’t planning on writing a timely post for Martin Luther King day this year, but I saw something yesterday that inspired me to do so: I watched David Letterman’s recent interview with Barack Obama, and when the far-ranging conversation turned to civil rights, Letterman recalled walking with John Lewis across the Edmund Pettus Bridge in Selma, Alabama, 50 years after the Selma-to-Montgomery marches of 1965.

As you may already know, during the first march (a legal, nonviolent protest against discriminatory voting regulations), state troopers attacked the unarmed marchers with nightsticks and tear gas, and even beat Amelia Boynton (one of […] Continue Reading…

David Cassidy’s Last Words

Last month, former teen idol David Cassidy died at the age of 67.

The world has lost some pretty big rock stars recently — including Tom Petty, Walter Becker of Steely Dan, Malcolm Young of AC/DC, and Pat DiNizio of The Smithereens (not as well known as the others, but one of my all-time favorites) — but none of their deaths haunt me as much as Cassidy’s.

This might seem odd since I wasn’t even a fan of his. I never watched The Partridge Family, and I don’t really know his music. (I only vaguely remember hearing “I Think I Love You” as a kid, but that’s […] Continue Reading…

Inspiration from a Young Mother

The stories in our new book, Goodness Abounds, follow two basic guidelines:

They have to be true stories about goodness.
The “good-doer” has to be someone other than the author.

Because of guideline #2, these stories aren’t about authors “tooting their own horn” (which is fine in many contexts — but that simply isn’t the focus of this book). Sometimes, though, even while they were shining a spotlight on other people’s goodness, I couldn’t help but admire the authors themselves. This was definitely the case with Jerri Eddington’s story, “The Baby and the Bus Driver.”

In this piece, Jerri pays tribute to a bus driver who […] Continue Reading…