This Is What a Fear of Success Looks Like

This Is What a Fear of Success Looks Like

I’m ashamed to admit I was a skeptic.

Whenever I’d hear that Marianne Williamson quote about how “Our deepest fear is not that we are inadequate. Our deepest fear is that we are powerful beyond measure,” I would just roll my eyes.

She doesn’t know me, I thought.

I’m a pretty ambitious woman. I enjoy challenging myself and others. My husband always jokes, “Never compete with Jen Gresham.” I’m not even sure why that’s funny. Then my daughter starts imitating me at this one mastermind, as if that explains everything.


If there was anything I was sure of, it’s that my deepest fear had nothing to do with being powerful.

And then, surprise! Something happened to make me realize how wrong I was (sorry for doubting you, Marianne).


But I’m getting ahead of myself. Let me start at the beginning.


About a year ago, I learned about the concept of moonshots by reading Peter Diamandis’ book, Bold. A moonshot can mean many things (let’s face it, it’s a concept he borrowed from Google and a concept Google borrowed from John F. Kennedy). Generally speaking though, a moonshot refers to a near impossible goal that has the potential for exponential, positive impact.

I was instantly smitten with the idea.

So I started helping clients to define and execute personal moonshots. I helped one client become the director of a major research center that gave her both the funding and collaborators to extend her work from the academic to practical policy. I helped another break into the professional video game industry (yes, it’s a thing), giving him a massive new platform to introduce health and wellness programs to young people.

In fact, the initial results were so extraordinary, both my husband and I decided we wanted moonshots ourselves. Because the family that does impossible things together is definitely a good litmus test for your marriage.

My moonshot is to help people leverage technology to create more value for their employers/clients and more meaning for themselves in an increasingly dynamic and unpredictable world. While many people are crying about robot overloads, I happen to think this is a historic opportunity to align the interests of employers and employees in ways that historically haven’t been possible.

Now, if you look closely, I’ve actually signed up for something like three moonshots in one: 1) create more value and meaning for people at work, 2) leverage technological change to do it, and 3) help humans better cope with uncertainty and complexity.


They don’t call it a moonshot for nothing, am I right?!


Here’s the thing: although I’ve led research efforts in human performance enhancement for the military and have coached hundreds of people around the world on career change, I felt massively inadequate to do this work. I still do. My amygdala basically exploded. (Side note: it’s messy)

Feeling inadequate may sound like a fear of failure, not success. The difference is that a fear of failure often prevents you from moving forward all together—you procrastinate or find a reason to quit soon after starting.


A fear of success looks like a committed effort that you hide from the world.


Which is why I felt so helpless to respond every time someone asked, “What happened to you? I never hear from you anymore.” It’s why I haven’t written a blog post in nearly a year. It’s why I decided to skip Christmas cards this year.

What happened to me? I’ve spent the last 10 or so months reading and thinking and trying to write my way to clarity. I’ve interviewed experts across dozens of different fields. I’ve dissected the ideas from different books, and then stitched them together into some semblance of a new framework. I’ve cried. I’ve questioned my sanity. I asked my husband (who, remember, was now working on his own moonshot, thanks to his “inspirational” wife) to make me a lot of tea.

And in those times he would say to me, “Let me get this straight. Elon Musk has basically decided that building a spaceship to Mars is an easier problem to solve, and you’re feeling inadequate that you don’t have a solution after working on it in isolation for a few months?”

Like I said, a litmus test for your marriage.


That’s when I had my big a-ha.


It has to do with the difference between complicated and complex problems.

Complicated problems are difficult, but both the problem and solution are generally agreed on and understood. You break the problem down into a bunch of component parts, and as long as you can solve those and put all the solutions back together, you’ll be successful. An example, ironically enough, is sending a man to the moon (or hey, Mars). There were many physics, engineering, and human challenges that needed to be solved, and those solutions all needed to work together. But everyone agreed on the laws of physics and what putting a man on the moon looked like. Complicated problems may be incredibly difficult, but they are predictable.

Complex problems are a set of interconnected problems which often evolve over time and in response to manipulation. In my case, the future of work can be described as an economics problem and an education problem and a psychology problem and a human/machine teaming problem … all of which are related to one another in ways we don’t really understand and the problems themselves change over time. The experts in all of these fields can’t agree on what the rules of the system are or what success looks like. Thus, there cannot be just one genius solution that can be engineered, but a set of solutions may emerge. However, what those solutions may be is unpredictable.

This led to two very important insights about where my fear of success was coming from.


I had never in my life taken on a complex problem.

Few of us do really. I wasn’t even sure how to get started.

And that not knowing turned out to be, shall we say, uncomfortable for me.

I couldn’t tell people, “I’m building a school in Africa!” or “I’m teaching coal miners how to code!” I underestimated how much of my confidence came from having lots of knowledge, and by trickle down theory, answers.

When I couldn’t immediately tell people HOW I was going to make my desired impact or heck, even exactly what impact I wanted to make, well, I wanted to hide.

Ironic in light of my desire to help people cope with uncertainty and complexity, right?

I realized that the biggest mistake people make is trying to apply complicated thinking to complex problems. I might well spend a year or more just trying to understand and frame my problem in a new way—and that would be time well spent.

The biggest innovations often come from asking a better question (there’s a whole book on that idea called The More Beautiful Question—I highly recommend it). We’re not used to thinking of questions as contributions, but then again, we’re not used to grappling with complex problems.


You can’t tackle a moonshot alone.


This realization was initially a relief. Thank goodness I didn’t have to figure everything out myself.

Unfortunately, sharing an incomplete vision and then asking for help are not natural for me. I like to have everything figured out and polished before I go public.

I was a bundle of nerves.

Would they think me naive? Would I sound dumb without a proposed solution in hand? Would the people I was reaching out to reject me and never take another one of my calls?

This is what a fear of failure looks like—procrastination and perfectionism. No kidding, it took me months to write a single email to someone I already knew professionally to see if he would partner with me on this idea (if we can call my vague notion about the future of work an “idea”).

It was on a family vacation where I was decidedly moody that my husband begged me to stop re-writing the pitch and just hit send.

That’s when I remembered: it wasn’t about me.

As I explain in this conversation with my coach, Rich Litvin, the good that needed doing was just too important to wait any longer (spoiler alert: I cry and yes, it’s embarrassing).

It was my why that motivated me to start reaching out, one phone call or email at a time.

The response was extraordinary. You know you’ve got a moonshot when you tell people what you’re up to, and instead of getting a polite, “That’s neat,” people very often say, “How can I help you?”

And help me they did. One connection led to the next. Each conversation broadened my understanding of the issue and the potential solutions I might pursue. I got commitments from some of the most brilliant minds in tech, business, and the nonprofit world to attend a meeting in June to develop a way forward.

I was creating momentum. My ideas were coalescing into something people wanted to be a part of.


And that’s when I got really scared.


Scared I wouldn’t measure up to the bar I was setting for myself. Scared people would question my leadership. Scared my life would change in ways I couldn’t control and maybe wouldn’t even like as the project gained partners and champions.

This is what a fear of success looks like—and I’m not sure it’s such a bad thing in the initial stages of a moonshot.

Your big, crazy ideas need time and space to grow without getting squished under the collective boot of pessimism.

Choose your initial partners and confidants wisely. You don’t need encouragement so much as constructive criticism. People who see your passion and want to see you succeed so badly, they will tell you the truth, the whole truth, but nothing more.

Then, once you’ve got a bit of traction for your idea, once you can see the wheels in motion, you can and should tell the whole world about it.

You’ll still be scared. You’ll worry everyone will think you a braggart or arrogant for thinking you (you!) can do something so big.

This is what a fear of success looks like.

This is also what it looks like when you say, “Screw it. I’m not hiding anymore.”

How to Stop Your Insecurities from Hijacking Your Aspirations

How to Stop Your Insecurities from Hijacking Your Aspirations

Editor’s note: guest post by Scott L. Sind

Ever feel like your professional life is a constant roller coaster ride?

Some days you experience huge wins, but others leave you languishing in emotional despair, questioning your competence and wondering if you’re on the verge of being outed as an utter fraud.

Sound familiar? I’m willing to bet that most of you have felt this way at one time or another. I certainly have, and I still do when something doesn’t go quite as expected.

Even worse than suffering these moments of insecurity is that it’s far too easy for negative thoughts to become etched in your psyche as limiting beliefs. Once that happens, your reality is then defined by those beliefs—you now have a view of the world as unfriendly, uncaring, and rife with barriers.

Inevitably you settle into a state of inertia. It’s comfortable there, where you aren’t exposed to the notion of failure.

But what about your dreams? Your lifelong desire to do great things? Sadly, many of us have created mental models that abundance is for the lucky and achievement is reserved for others who are better, smarter or more deserving than we are.

The good news is that you don’t have to accept this as truth. (more…)

On Vulnerability, Going Carless, and Having a List of People You Can Call

On Vulnerability, Going Carless, and Having a List of People You Can Call

One of the things I like the most about not having a car is that it forces you to be a little bit vulnerable.

Sure, in this day and age, you can take advantage of ride-sharing or just rent a car. If you’re lucky enough to live in a city with public transportation, that’s another option. But there comes a time when you’ll wish you could borrow someone’s car.

Why is it so hard to ask?

If the number of cars that line our street during the day is any indication, there are certainly plenty available. The truth is I’ve always avoided asking for help unless it was an emergency. For example, if I slipped on a rock after a long stroll down the beach, I would, most likely, ask for a stranger’s help in the long hobble back.

I wouldn’t like how vulnerable that made me feel. And I know I am not alone. (more…)

You Don’t Have to Prove Yourself to Others–Love Yourself Instead

You Don’t Have to Prove Yourself to Others–Love Yourself Instead

“The girl has to kill the rabbit.”

E veryone stared at me. It was my second day of Survival Training, a program that’s meant to teach you how to stay alive in case you’re shot down behind enemy lines.

I had resisted peer pressure before. In high school, I refused to style my hair or wear make-up, despite classmates who told me I could be so pretty if I just tried. I stuck to my guns, even when my mother had to beg her colleagues to offer their sons as dates to dances.

This shouldn’t have been any different. I am a huge animal lover. I have nothing against hunting for food, especially in a survival scenario. But this wasn’t a wild rabbit we’d caught. It was supplied. It was trusting and tame.

And I absolutely did not want to swing a stick like a baseball bat to break the creature’s neck.

This time, however, I felt a need to prove myself, to show those boys I was every bit as qualified to be a military officer as they were. I wanted them to know I was brave and tough. I accepted the gauntlet as the natural fate of a woman in the armed services.

They had found my weakness.  (more…)

If You Love Someone, Set Them Free (Starting With Yourself)

If You Love Someone, Set Them Free (Starting With Yourself)

P ETA thinks I’m cruel.

According to them, all cats should be indoor cats. They call on owners to protect their loved ones from the “not-so-great outdoors.”

Why? They might get kitty AIDS. There are bad people who will sell them to laboratories or light them on fire. There are even other cats, and make no mistake, those cats are mean.

It’s not that these things aren’t true, even if the selling them to laboratories sounds a bit like an urban myth. It’s a dangerous world out there and you will likely extend your cat’s life span by keeping them inside.

But it’s also a pretty one-sided story. Yes, it can be a big, bad world, but there are plenty of insidious dangers inside the house: boredom, aggression, depression.

Just because your pet can’t vocalize what they’re feeling doesn’t mean they aren’t suffering. When a heat wave hit London and we were desperate to at least crack open some windows, one of our cats wouldn’t stop making escape attempts. No matter how clever we tried to be, she would find a way to wriggle out, forcing me to track her down and drag her back to her prison cell, I mean, loving home.

Until one day I looked in her eyes and I just couldn’t do it anymore. I love this animal like a part of my family and here I was denying her the one thing she wanted, and all I could think about was keeping her safe.

So I opened the window and let her go. (more…)

The Price of Freedom

The Price of Freedom

A lot of people tell me they’re looking for freedom.

I completely understand, because much of my life has been a crazy courtship of the concept. I just didn’t understand the cost until recently.

After high school, I joined the military to escape a totalitarian father, which even I have to admit is funny. It’s true that, by comparison, the military was a picnic. The upperclassmen at the Air Force Academy nicknamed me Cadet Happy Camper because even when they were yelling in my face or making me do iron mikes, I couldn’t help but smile.

The military culture convinced me I was willing to die for freedom, the kind that belonged to someone else. But I struggled to take even the tiniest risks to grant me my own. (more…)