For nearly a year, General Ulysses S. Grant tried to crack the defenses of Vicksburg, a city
perched high on the cliffs of the Mississippi, critical to the Confederacy’s stranglehold on the
most important river in the country. He tried attacking head-on. He tried to go around. He spent
months digging a new canal that would change the course of the river. He blew the levees upstream
and literally tried to float boats down into the city over flooded land.
None of it worked. All the while, the newspapers chattered. It’d been months without progress.
Lincoln had sent a replacement, and the man was waiting in the wings. But Grant refused to be
rattled, refused to rush or cease. He knew there was a weak spot somewhere. He’d find it or he’d
His next move ran contrary to nearly all conventional military theory. He decided to run his boats
past the gun batteries guarding the river—a considerable risk, because once down, they could not
come back up. Despite an unprecedented nighttime firefight, nearly all the boats made the run
unharmed. A few days later, Grant crossed the river about thirty miles downstream at the
appropriately named Hard Times, Louisiana.
Grant’s plan was bold: Leaving most of their supplies behind, his troops had to live off the land
and make their way up the river, taking town after town along the way. By the time Grant laid siege
to Vicksburg itself, the message to his men and his enemies was clear: He would never give up. The
defenses would eventually crack. Grant was unstoppable. His victory wouldn’t be pretty, but it was
If we’re to overcome our obstacles, this is the message to broadcast—internally and externally.
We will not be stopped by failure, we will not be rushed or distracted by external noise. We will
chisel and peg away at the obstacle until it is gone. Resistance is futile.
At Vicksburg, Grant learned two things. First, persistence and pertinacity were incredible assets
and probably his main assets as a leader. Second, as often is the result from such dedication, in
exhausting all the other traditional options, he’d been forced to try something new. That option—
cutting loose from his supply trains and living off the spoils of hostile territory—was a previously
untested strategy that the North could now use to slowly deplete the South of its resources and will
In persistence, he’d not only broken through: In trying it all the wrong ways, Grant discovered a
totally new way—the way that would eventually win the war.
Grant’s story is not the exception to the rule. It is the rule. This is how innovation works.
In 1878, Thomas Edison wasn’t the only person experimenting with incandescent lights. But he
was the only man willing to test six thousand different filaments—including one made from the
beard hair of one of his men—inching closer each time to the one that would finally work.
And, of course, he eventually found it—proving that genius often really is just persistence in
disguise. In applying the entirety of his physical and mental energy—in never growing weary or
giving up—Edison had outlasted impatient competitors, investors, and the press to discover, in a
piece of bamboo, of all things, the power to illuminate the world.
Nikola Tesla, who spent a frustrated year in Edison’s lab during the invention of the lightbulb,
once sneered that if Edison needed to find a needle in a haystack, he would “proceed at once” to
simply “examine straw after straw until he found the object of his search.” Well, sometimes that’s
exactly the right method.
As we butt up against obstacles, it is helpful to picture Grant and Edison. Grant with a cigar
clenched in his mouth. Edison on his hands and knees in the laboratory for days straight. Both
unceasing, embodying cool persistence and the spirit of the line from the Alfred Lord Tennyson
poem about that other Ulysses, “to strive, to seek, to find.” Both, refusing to give up. Turning over
in their minds option after option, and trying each one with equal enthusiasm. Knowing that
eventually—inevitably—one will work. Welcoming the opportunity to test and test and test, grateful
for the priceless knowledge this reveals.
The thing standing in your way isn’t going anywhere. You’re not going to outthink it or outcreate
it with some world-changing epiphany. You’ve got to look at it and the people around you, who have
begun their inevitable chorus of doubts and excuses, and say, as Margaret Thatcher famously did:
“You turn if you want to. The lady’s not for turning.”
Too many people think that great victories like Grant’s and Edison’s came from a flash of insight.
That they cracked the problem with pure genius. In fact, it was the slow pressure, repeated from
many different angles, the elimination of so many other more promising options, that slowly and
surely churned the solution to the top of the pile. Their genius was unity of purpose, deafness to
doubt, and the desire to stay at it.
So what if this method isn’t as “scientific” or “proper” as others? The important part is that it
Working at it works. It’s that simple. (But again, not easy.)
For most of what we attempt in life, chops are not the issue. We’re usually skilled and
knowledgeable and capable enough. But do we have the patience to refine our idea? The energy to
beat on enough doors until we find investors or supporters? The persistence to slog through the
politics and drama of working with a group?
Once you start attacking an obstacle, quitting is not an option. It cannot enter your head.
Abandoning one path for another that might be more promising? Sure, but that’s a far cry from
giving up. Once you can envision yourself quitting altogether, you might as well ring the bell. It’s
Consider this mind-set.
never in a hurry
never stopping short
Remember and remind yourself of a phrase favored by Epictetus: “persist and resist.” Persist in
your efforts. Resist giving in to distraction, discouragement, or disorder.
There’s no need to sweat this or feel rushed. No need to get upset or despair. You’re not going
anywhere—you’re not going to be counted out. You’re in this for the long haul.
Because when you play all the way to the whistle, there’s no reason to worry about the clock. You
know you won’t stop until it’s over—that every second available is yours to use. So temporary
setbacks aren’t discouraging. They are just bumps along a long road that you intend to travel all the
Doing new things invariably means obstacles. A new path is, by definition, uncleared. Only with
persistence and time can we cut away debris and remove impediments. Only in struggling with the
impediments that made others quit can we find ourselves on untrodden territory—only by persisting
and resisting can we learn what others were too impatient to be taught.
It’s okay to be discouraged. It’s not okay to quit. To know you want to quit but to plant your feet
and keep inching closer until you take the impenetrable fortress you’ve decided to lay siege to in
your own life—that’s persistence.
Edison once explained that in inventing, “the first step is an intuition—and comes with a burst
—then difficulties arise.” What set Edison apart from other inventors is tolerance for these
difficulties, and the steady dedication with which he applied himself toward solving them.
In other words: It’s supposed to be hard. Your first attempts aren’t going to work. It’s goings to
take a lot out of you—but energy is an asset we can always find more of. It’s a renewable resource.
Stop looking for an epiphany, and start looking for weak points. Stop looking for angels, and start
looking for angles. There are options. Settle in for the long haul and then try each and every
possibility, and you’ll get there.
When people ask where we are, what we’re doing, how that “situation” is coming along, the
answer should be clear: We’re working on it. We’re getting closer. When setbacks come, we respond
by working twice as hard.
What is defeat? Nothing but education; nothing but the first steps to something better.
n Silicon Valley, start-ups don’t launch with polished, finished businesses. Instead, they release
their “Minimum Viable Product” (MVP)—the most basic version of their core idea with only one
or two essential features.
The point is to immediately see how customers respond. And, if that response is poor, to be able
to fail cheaply and quickly. To avoid making or investing in a product customers do not want.
As engineers now like to quip: Failure is a Feature.
But it’s no joke. Failure really can be an asset if what you’re trying to do is improve, learn, or do
something new. It’s the preceding feature of nearly all successes. There’s nothing shameful about
being wrong, about changing course. Each time it happens we have new options. Problems become
The old way of business—where companies guess what customers want from research and then
produce those products in a lab, isolated and insulated from feedback—reflects a fear of failure and
is deeply fragile in relation to it. If the highly produced product flops on launch day, all that effort
was wasted. If it succeeds, no one really knows why or what was responsible for that success. The
MVP model, on the other hand, embraces failure and feedback. It gets stronger by failure, dropping
the features that don’t work, that customers don’t find interesting, and then focusing the
developers’ limited resources on improving the features that do.
In a world where we increasingly work for ourselves, are responsible for ourselves, it makes
sense to view ourselves like a start-up—a start-up of one.
And that means changing the relationship with failure. It means iterating, failing, and improving.
Our capacity to try, try, try is inextricably linked with our ability and tolerance to fail, fail, fail.
On the path to successful action, we will fail—possibly many times. And that’s okay. It can be a
good thing, even. Action and failure are two sides of the same coin. One doesn’t come without the
other. What breaks this critical connection down is when people stop acting—because they’ve taken
failure the wrong way.
When failure does come, ask: What went wrong here? What can be improved? What am I
missing? This helps birth alternative ways of doing what needs to be done, ways that are often
much better than what we started with. Failure puts you in corners you have to think your way out
of. It is a source of breakthroughs.
This is why stories of great success are often preceded by epic failure—because the people in
them went back to the drawing board. They weren’t ashamed to fail, but spurred on, piqued by it.
Sometimes in sports it takes a close loss to finally convince an underdog that they’ve got the ability
to compete that competitor that had intimidated (and beat) them for so long. The loss might be
painful, but as Franklin put it, it can also instruct.
With a business, we take most failures less personally and understand they’re part of the process.
If an investment or a new product pays off, great. If it fails, we’re fine because we’re prepared for it
—we didn’t invest every penny in that option.
Great entrepreneurs are:
never wedded to a position
never afraid to lose a little of their investment
never bitter or embarrassed
never out of the game for long
They slip many times, but they don’t fall.
Even though we know that there are great lessons from failure—lessons we’ve seen with our own
two eyes—we repeatedly shrink from it. We do everything we can to avoid it, thinking it’s
embarrassing or shameful. We fail, kicking and screaming.
Well why would I want to fail? It hurts.
I would never claim it doesn’t. But can we acknowledge that anticipated, temporary failure
certainly hurts less than catastrophic, permanent failure? Like any good school, learning from
failure isn’t free. The tuition is paid in discomfort or loss and having to start over.
Be glad to pay the cost. There will be no better teacher for your career, for your book, for your
new venture. There’s a saying about how the Irish ship captain located all the rocks in the harbor—
using the bottom of his boat. Whatever works, right?
Remember Erwin Rommel and the quick work he made of the British and American forces in
North Africa? There’s another part to that story. The Allied forces actually chose that
disadvantageous battlefield on purpose. Churchill knew that they would have to take their first
stand against the Germans somewhere, but to do that and lose in Europe would be disastrous for
In North Africa, the British learned how to fight the Germans—and early on they learned mostly
by failure. But that was acceptable, because they’d anticipated a learning curve and planned for it.
They welcomed it because they knew, like Grant and Edison did, what it meant: victory further
down the road. As a result, the Allied troops Hitler faced in Italy were far better than those he’d
faced in Africa and the ones he ultimately faced in France and Germany were better still.
The one way to guarantee we don’t benefit from failure—to ensure it is a bad thing—is to not
learn from it. To continue to try the same thing over and over (which is the definition of insanity for
a reason). People fail in small ways all the time. But they don’t learn. They don’t listen. They don’t
see the problems that failure exposes. It doesn’t make them better.
Thickheaded and resistant to change, these are the types who are too self-absorbed to realize
that the world doesn’t have time to plead, argue, and convince them of their errors. Soft bodied and
hardheaded, they have too much armor and ego to fail well.
It’s time you understand that the world is telling you something with each and every failure and
action. It’s feedback—giving you precise instructions on how to improve, it’s trying to wake you up
from your cluelessness. It’s trying to teach you something. Listen.
Lessons come hard only if you’re deaf to them. Don’t be.
Being able to see and understand the world this way is part and parcel of overturning obstacles.
Here, a negative becomes a positive. We turn what would otherwise be disappointment into
opportunity. Failure shows us the way—by showing us what isn’t the way.