How That Vicious Inner Critic Can Be Your Closest Ally

Editor’s Note: Ken Goldstein has served as Chairman & CEO of SHOP.COM, Executive Vice President & Managing Director of Disney Online, and VP / Executive Publisher of Entertainment & Education for Broderbund Software. He is the author of This Is Rage: A Novel of Silicon Valley and Other Madness (2013) and Endless Encores (2015).

There’s something about optimism. Nothing in business is quite as powerful in motivating people to believe in a mission as a leader who undoubtedly believes. The energy that radiates from a passionate entrepreneur is engaging, uplifting, and inspiring. When we hear someone tell us he or she is following their muse, boldly pursuing a personal dream, we want to root for them. We want to become a part of it. We want to hitch our cart to their wagon. We want to step out of the ordinary and get onboard the outrageous.

A leader who won’t be deterred can bring purpose to a business enterprise.

A leader who rises above petty criticism and backstabbing naysayers can turn a hundred dollars into a hundred million dollars.

A leader who is “all-in” and won’t be dissuaded from a cohesive, organic vision can literally change the world.

Over and over we hear the speechifying that tells us never to give up, that resilience is all that matters, that we should forget the critics and ignore the naysayers.

Already doing that? Great. But there’s a catch.

Walt Disney was told he was no good as an illustrator, that his characters would never be popular. Steve Jobs got fired from his own company for being difficult, and refusing to compromise his ambitions. They were never dissuaded. They were resilient and persevered. They could not have cared less what their critics were saying.

Walt and Steve are held up as classic examples of rejecting rejection. They maintained an uncompromised vision and carved their place in history because of it. Detractors who called out “their folly” could do them no sustained harm. Walt and Steve evidenced a form of courage that set a new high water mark for leading teams beyond the fog to unbridled innovation. They remain heroes to those who aspire to transcend the ordinary.

So what’s the catch? You want to be That Leader, right? Or maybe you just want to sign on with That Leader? What’s the missing element that is most likely to take you down?

Is it that the odds against a startup succeeding are enormous? Nope. Most entrepreneurs know this long before they quit their day jobs. Many are wacky, but few are stupid.

Is it that capital is very hard to raise, especially for a first time entrepreneur? Nope.

Most entrepreneurs discover this lesson the first time mom or dad says, “What!? Are you kidding me? You’re not a CEO… you can barely manage to get matching socks on your feet!” They secretly know that mom and dad are just negotiating their share of the deal for the seed round.

Is it that it’s nearly impossible to get super-talented people to work for deferred or limited pay for the long runway until a business is cash flow positive? Nope.

Most entrepreneurs are confident that if they articulate an exciting enough plan, the right people will get with the program no matter what, and the ones who said no just saved the entrepreneur the pain of having to fire them later for their mediocrity.

Then what is it? What is the Achilles Heel of the resilient? What is the repelling force that stands counter to the success of leaders brave enough to shake off a world that tells them No No No when all they hear in their heads is Yes Yes Yes?

Presume for a moment this entrepreneur is You. Get your highlighter ready. You’ll want to make note of this for the rest of your career.

The problem might be YOU.

Don’t highlight that. I haven’t gotten to the important part yet. The part you need to highlight is this:

If you’re not going to listen to the critics who will tell you every reason in the world why you are going to fail—and believe you absolutely must tune them out in order to be a renowned, world-class leader—you are going to have to be the hardest critic in the world on yourself.

Yes, in order to earn the privilege of ducking all the pessimists trying to steer you away from your dream, you must beat yourself up in ways they can’t even imagine. There is no luxury in resilience. There is only a level of self-critique so necessary that the pain it will cause you as a lone wolf makes child’s play of the third-party negativity you will never hear. What you hear in your head must be far more thundering—and far more impactful.

The real reason most startup leaders fail

It’s not because of a lack of devotion, or a lack of passion, or even because of a lack of talent.

They fail because of a lack of self-critique.

Does this apply to you? Have you actually established yourself as your own toughest critic? I don’t mean a little tough. I mean vicious, brutal, send yourself into a tailspin tough. Sorry to break the news, but that’s why Walt and Steve were often perceived as miserable. They were always very, very tough on themselves, an order of magnitude more thrashing than what any bleacher critic was or even could have been.

I have had the privilege to lead a handful of creative companies and I have had the privilege to be a published author. In all cases I was told innumerable times why I would not be successful. I didn’t hear a word of it. I didn’t need to hear a word of it. In all cases I was already way ahead of the peanut gallery, working and reworking the scenarios of why I wouldn’t be successful.

I study product features like I study word choices. I might tell you that no one on the market has anything like this, but before you’ll hear me utter those words, I have done the homework to assure myself this is worth defending. No one else can do that as stridently as I can. I say no to a sentence a hundred times before I let you see it. I edit it, erase it, rewrite it, rework it, change it, question it, then pick it apart word by word until I have exhausted all its failures. Same with a product. Same with a service.

I can only ignore the amateur naysayers because I am my own best professional naysayer.

Let’s take it deeper, to a place you may not want to go. Here’s another reason why startup leaders fail: they doggedly champion a product that is no good. It’s not because the naysayers are right. It’s because the startup leader doesn’t embrace the radical discipline to relentlessly question themselves and, by extension, their product.

If running out of time and money don’t apply as explanations, most entrepreneurs fail for a very simple reason: their idea was not good enough to create a category defining product or service. Too often we dupe ourselves into believing the ordinary is extraordinary. We fall in love with an idea because we gave birth to it, and rather than beating that idea into something exceptional—or dumping it, learning from it, and finding the fortitude to reinvent it into something else—we tell ourselves we will not be dissuaded and we go to market with mediocrity. That’s when we get walloped.

Once again, the tough love, get out the highlighter:

The only way you can defy the odds and ignore the critics is if you have a massive built-in crap filter. If you don’t want someone else to tell you your product is crap, you better be willing to tell yourself it’s crap or you’re going to blow a lot of time and money on nothing.

Artists and inventors have a crap filter no matter how successful they are. Walt did. So did Steve. Walt was told that audiences would never want to see a feature-length animated motion picture. He didn’t hear it, because Snow White and the Seven Dwarves was already worked out in his head, after he had rejected every possible way to make it something people would never want to see.

Steve was told there would never be a market for something as intimidating as home computing. He didn’t hear it, because the Apple 2 was already worked out in his head, after he had rejected every possible way that it would intimidate people.

Both of these visionaries agonized over perfection and were never satisfied. When they were starting out they were never satisfied. When they were at the bottom they were never satisfied. When they were at the top of their game they were never satisfied. The critics failed to resonate with them because they were lightweights in comparison to their own pounding criticism.

Are you embracing this burden of innovation?

Why do I need you to hear this? Why is this so desperately important to everyone who wants to make a difference and change the world? Because too many hopeful leaders are embracing the rhetoric of “going their own way” without embracing this burden of innovation. Every single day someone shows me a derivative app and begs me to believe in them. It’s a minimum viable product, they tell me, they will build on it and make it great later.

Right, after customers have yawned.

You really think they’ll give you another chance? So yours is 12% faster than your competition? So what? So yours addresses a tiny niche with a quirky set of differentiating features that matter mostly to you for pitching on demo day… So what? Get your eyes off the IPO listings and back on the shelf where the war for customers is lost or won. Don’t be Happy. Be Grumpy.

Incrementality is toxic. Don’t tell me how all your competitors have slightly weaker products than what you’re proposing. Convince yourself you can blow my mind with something that leapfrogs the entire market if not in one product cycle then over a generation. If you don’t want me to tell you that your app is crap then be sure you’ve asked yourself a hundred times before you ignore me. If you don’t know that your app is crap because you aren’t being honest with yourself then you haven’t earned the right to ignore the naysayers.

That’s the secret sauce—knowing when you are ready to play and when the cards you hold are not worth playing. Be that critic and you’ll never need another. When you stand up onstage and tell your story of success, it will undoubtedly be preceded by the chapters of failure that led you to your day in the sun. I want to come to that speech and applaud. I want to see you do it again and again. I want to see you tell the naysayers to jump off a peer.

Are you ready to take on the responsibility of being your own toughest critic? Wield your inner critic in such a way that it allows you to do the best work of your life. Then yeah, tell us all to bugger off and let’s get to work changing the world.

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About the featured photo:

Fabio Napoleoni’s “Solid Declaration” is our feature painting this week. Many events influenced Fabio’s artwork but none more than the traumatic events that followed the birth of his second child. His daughter, born with major heart abnormalities, had to face several surgeries to correct issues that could prevent her from having a future. Through this experience, Fabio realized what was missing from his work: emotion.