Fear, crisis, failure: How the best entrepreneurs confront ‘the struggle’, and bounce back stronger

Business books are crammed full of success stories, heroics and winners, but the reality is often very different — and it needs to be confronted. Coping with adversity is probably the most important reality of all for almost every entrepreneur.

This expert’s playbook draws on the wisdom of Ben Horowitz, Arianna Huffington, Safra Catz, Jim Collins and more. Learn how they think about — and confront — fear, and turn setbacks or problems into something good.

The struggle is real

“Every entrepreneur starts her company with a clear vision for success. Then, after working night and day to make your vision a reality, you wake up to find that things did not go as planned.

“The walls start closing in.

“Where did you go wrong?

“Why didn’t your company perform as envisioned?

“Are you good enough to do this?

“As your dreams turn into nightmares, you find yourself in the Struggle.”

That’s how Ben Horowitz, cofounder and general partner of venture capital firm Andreessen Horowitz, describes what he calls ‘the Struggle’ — “the deep, dark pit that confronts almost every entrepreneur at some stage” — in his book, The Hard Thing About Hard Things.

“The Struggle is when your employees think you are lying and you think they may be right. The Struggle is when food loses its taste. The Struggle is when you don’t believe you should be CEO of your company. The Struggle is when you know that you are in over your head and you know that you cannot be replaced. The Struggle is when everybody thinks you are an idiot, but nobody will fire you. The Struggle is where self-doubt becomes self-hatred. The Struggle is when you are having a conversation with someone and you can’t hear a word that they are saying because all you can hear is the Struggle. The Struggle is when you want the pain to stop. The Struggle is unhappiness. The Struggle is when you go on vacation to feel better and you feel worse. The Struggle is when you are surrounded by people and you are all alone. The Struggle has no mercy. The Struggle is the land of broken promises and crushed dreams. The Struggle is a cold sweat. The Struggle is where your guts boil so much that you feel like you are going to spit blood. The Struggle is not failure, but it causes failure. Especially if you are weak. Always if you are weak. Most people are not strong enough. Every great entrepreneur from Steve Jobs to Mark Zuckerberg went through the Struggle and struggle they did, so you are not alone.” 

“The Struggle is where greatness comes from. There is no answer to the Struggle, but here are some things that helped me: Don’t put it all on your shoulders. It is easy to think that the things that bother you will upset your people more. That’s not true. The opposite is true. Nobody takes the losses harder than the person most responsible. Nobody feels it more than you. You won’t be able to share every burden, but share every burden that you can. Get the maximum number of brains on the problems even if the problems represent existential threats …

“There is always a move. Play long enough and you might get lucky … If you survive long enough to see tomorrow, it may bring you the answer that seems so impossible today. Don’t take it personally. The predicament that you are in is probably all your fault. You hired the people. You made the decisions. But you knew the job was dangerous when you took it. Everybody makes mistakes. Every CEO makes thousands of mistakes. Evaluating yourself and giving yourself an F doesn’t help … If you want to be great, this is the challenge. If you don’t want to be great, then you never should have started a company.”

Don’t be afraid of shame

“Fear runs deep. Fear used to keep our ancestors alive. Fear keeps you from taunting a saber tooth tiger,” writes Seth Godin on his management and strategy blog.

“The thing is, most of us don’t have to deal with tigers any longer. But the fear still runs deep. We still feel the same feelings when we face possible failure, but now those feelings revolve around shame. Losing a video game in private is fine, but asking a stupid question in a meeting is not. Shame is the dream killer, because shame (or the possibility of shame) amplifies our fear of fear, keeps us from contributing and short circuits our willingness to explore. As soon as we give it a name, though, as soon as we call it out, we can begin to move forward. Fear of shame unspoken is fear of shame amplified. Be afraid of significant failure if you can quantify the downsides. But fear of shame is a waste and a trap.”

Don’t self-sabotage

“If our fears were easy to conquer, we would have already done it,” writes Holly Ransom in her leadership tome, The Leading Edge. “They’re really not. The point is, they’re important enough for us to feel the fear and do the frightening thing anyway. 

“To help ourselves, we’ve got to catch the ways in which we stop ourselves … We continually get in the way of our own aspirations with our habits. We can’t unleash creativity if we’re fearful of being vulnerable and sharing new ideas. We can’t be entrepreneurial if we won’t take a risk on our ideas or if we demand results by tomorrow. We’re also not going to make progress if we let ourselves think about all the reasons ‘why not’ before we give ourselves permission to try.”

Holly Ransom. Source: Supplied

You don’t need to know all the answers

“It’s not fear that gets in the way of daring leadership; it’s armour,” argues Brené Brown on her blog. “When things get tough, do we lean in to vulnerability and get curious, or do we self-protect in ways that move us away from our values?

“Having to be the ‘knower’ or always being right is heavy armor. It’s defensiveness, it’s posturing, and, worst of all, it’s a huge driver of bullshit. It’s also very common — most of us have some degree of knower in us. Unfortunately, needing to know everything is pretty miserable for the knowers and everyone around them. It leads to distrust, bad decisions, and unnecessary, unproductive conflict.” 

Believe in your company, and stick with it

“Never, never, never give up.” That’s the overwhelming motto of the builders of visionary companies, writes Jim Collins in Beyond Entrepreneurship 2.0.

“But what to persist with? The company. Be prepared to kill, revise, or evolve an idea … but never give up on the company. If you equate the success of your company with the success of a specific idea — as many businesspeople do — then you’re more likely to give up on the company if that idea fails; and if that idea happens to succeed, you’re more likely to have an emotional love affair with that idea and stick with it too long, when the company should be moving vigorously on to other things. But if you see the ultimate creation as the company, not the execution of a specific idea … then you can persist beyond any specific idea — good or bad — and move toward becoming an enduring great institution.”

Failure and success are not opposites

“Very often, the difference between success and failure is perseverance,” said Thrive Global founder Arianna Huffington during a keynote address at Sarah Lawrence. “It’s how long can we keep going until success happens. It’s getting up one more time than we fall down.

“Of the many things my mother taught me … the one that’s proved most useful in my life is the understanding that failure is not the opposite of success, it’s an integral part of success.

“And that means not letting the fears in our heads get in our way. Not letting that voice of doubt, which I call the obnoxious roommates living in your heads, have the last word. Because, as Montaigne said, ‘There were many terrible things in my life, but most of them never happened’.”

The one word to deal with setbacks

“How do I deal with setbacks, failures, delays, defeat, or other disasters? I actually have a fairly simple way of dealing with these situations. There is one word to deal with all those situations, and that is: ‘good’,” says Jocko Willink, retired US Navy SEAL Commander in Tools of Titans: The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers by Tim Ferris.

“Oh, mission got cancelled? Good. We can focus on another one.

“Didn’t get the new high-speed gear we wanted? Good. We can keep it simple. 

“Didn’t get promoted? Good. More time to get better. 

“Didn’t get funded? Good. We own more of the company. 

“Didn’t get the job you wanted? Good. Go out, gain more experience, and build a better résumé. 

“Got injured? Good. Needed a break from training. 

“Got tapped out? Good. It’s better to tap out in training than to tap out on the street. 

“Got beat? Good. We learned.

“Unexpected problems? Good. We have the opportunity to figure out a solution.

“That’s it. When things are going bad, don’t get all bummed out, don’t get startled, don’t get frustrated. No. Just look at the issue and say: ‘Good’. Now. I don’t mean to say something clichéd. I’m not trying to sound like Mr. Smiley Positive Guy. That guy ignores the hard truth. That guy thinks a positive attitude will solve problems. It won’t. But neither will dwelling on the problem. No. Accept reality, but focus on the solution. Take that issue, take that setback, take that problem, and turn it into something good. Go forward. And, if you are part of a team, that attitude will spread throughout.”

Indecision is the enemy

“Don’t stand still,” said Oracle chief executive Safra Catz during a keynote speech at Wharton in 2018. 

“You can’t beat the competition by standing still and you can’t be driven by caution all the time. It is extremely easy to be lulled into inaction; we are all facing an increasingly competitive global economy. 

“Indecision really is your enemy. I am actually baffled by how much time and effort is put into standing still. I call that notion no progress. There are dozens of reasons not to do something and the easy things are often hardly worth doing. It’s really the tough decisions, the game-changing decisions, that generate the most return. That’s true in both the smallest and the largest companies. 

“It bears repeating some of Oracle’s greatest competitive successes have come simultaneously from our willingness to take risk and from our competitors inability to make decisions. And if you want to beat the competition, and you want to advance your career personally, you need to make decisions and take actions. If you make decisions quickly and you make a mistake, you very well may have a chance to fix it. If you wait too long, I tell you, the decision will make itself and any change will be impossible.

Lean into the Dip

“Most people will tell you that you need to persevere — to try harder, put in more hours, get more training, and work hard. ‘Don’t quit!’ they implore,” says Seth Godin in The Dip: The Extraordinary Benefits of Knowing When to Quit (and When to Stick).

“But if all you need to do to succeed is not quit, then why do organisations less motivated than yours succeed? Why do individuals less talented than you win? It involves understanding the architecture of quitting, and, believe it or not, it means quitting a lot more than you do now. Strategic quitting is the secret of successful organisations. Reactive quitting and serial quitting are the bane of those that strive (and fail) to get what they want. And most people do just that. They quit when it’s painful and stick when they can’t be bothered to quit.

“Almost everything in life worth doing is controlled by the Dip. It looks like this: At the beginning, when you first start something … it’s interesting, and you get plenty of good feedback from the people around you. Over the next few days and weeks, the rapid learning you experience keeps you going. Whatever your new thing is, it’s easy to stay engaged in it. And then the Dip happens. The Dip is the long slog between starting and mastery. A long slog that’s actually a shortcut, because it gets you where you want to go faster than any other path.

“IMPORTANT NOTE: Successful people don’t just ride out the Dip. They don’t just buckle down and survive it. No, they lean into the Dip. They push harder, changing the rules as they go. Just because you know you’re in the Dip doesn’t mean you have to live happily with it. Dips don’t last quite as long when you whittle at them.”