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.”

3 Clear Reasons You Need to Change Careers

3 Clear Reasons You Need to Change Careers

I sat in my hospital room, anxiously twirling the strings that were not securing the gown behind me, waiting for the nurses to wheel me into surgery. My husband squeezed my hand and told me we’d be okay.

Up until that moment, it certainly looked like I had it all.

I’d spent 16 years in the military, and by all accounts, had a bright future in front of me. I wasn’t on the fast track, but my boss valued my ideas and was a gifted mentor. I was engaged with my work and liked my co-workers.

I told myself again and again how lucky I was, but I still felt a kind of euphoria every time I took a day off.

Worse, I couldn’t shake the feeling that the opportunity for the life I’d always wanted was disappearing with each passing year.

It took a tragic loss, my second miscarriage in the space of twelve months, to realize what was nagging me.


Life is too short to not spend it doing what you love


Sure, sure, we’ve all heard it before. But as I awoke in the recovery room, my belly sore and my emotions crushed from the loss of my second baby, I resolved to find the work that made me feel alive.

I walked away from nearly a million dollars in pay and retirement benefits.

Crazy, right?  Certainly more than one person said so.

How I Became the Queen of Narnia (And You Can Too)

How I Became the Queen of Narnia (And You Can Too)

Sitting across from my coach, he asked me a very simple question.

“What would make this an extraordinary year for you, Jen?”

I rattled off the kinds of things that first come to mind. I’d like to make even more money in my business. I’d like to make even better memories with my family. I’d like to make a bigger impact in my coaching. Maybe this year I will (finally, for the love of all that is good in the world) write a book.

Every answer I gave, my coach countered with “What else?”

Eventually I got a little exasperated.

“Look,” I told him, “2016 was pretty much the best, most magical year of my life. I felt like I’d stumbled through the door to Narnia. If you really want to help me do something extraordinary, show me how to find the door to Narnia more regularly.”

And then, without realizing why, I added, “And become queen.”

He looked at me for a long moment, then informed me, “Jen, I’m sorry, but I can’t do that for you. You see, you’re already the Queen of Narnia. My job is to help you see that.”

I know it sounds stupid, but I started to cry.

The magic and splendor I had been searching for all my life was right in front of me all along.

And for years I’d missed it.

Do You Need Better Goals or Better Vision?


For most people, the start of the year is all about wiping the slate clean and setting new intentions. Good stuff.

But how are you going to turn those intentions into reality? What, exactly, has been holding you back up until now?

I’m not talking about creating a plan, although that’s not a bad idea. I’m talking about finding the right opportunities, the open doors to where you want to go. Because if you can do that, transformation becomes easy.

You see, once I acknowledged that I was already the queen of my own Narnia, I started to see the world very differently. Everywhere I went, every interaction I had, had an element of magic to it. And never was that more obvious than the bitterly cold day I trudged a little over a mile to the gym.

We’ve had an especially cold winter here in Seattle, and yet I noticed at least a dozen different kinds of flowers blooming. In the middle of winter. What the heck?

But this was only surprising because I’d never noticed them before. I had to wonder: what else had I been missing?

It turns out quite a lot.

When I toyed with the idea of starting a novel coaching program for CEOs and executive directors … I happened to find myself at Thanksgiving dinner seated across the table from a former CEO interested in the same thing. We’re now talking about partnering on the venture.

When I wanted to become more intentional in my charitable endeavors … a book on the topic showed up in my mailbox, apparently from a publicist hoping I would review it.

When I wanted to create a special holiday for my family … my neighbor happened to mention that the local gingerbread house exhibit had a Harry Potter theme (my Hogwarts-obsessed daughter was thrilled).


Yes, this is made out of gingerbread and candy…


Don’t misunderstand me. I don’t believe I manifested these opportunities any more than I manifested flowers in winter.

In science, this is what’s known as selective attention, illustrated by the famous Invisible Gorilla experiment. Essentially, we all have a kind of filter that predisposes us to see some things while ignoring others. We evolved that way so our brains wouldn’t get overloaded with inputs.

What does this all mean?

Most of the time, you don’t have to massively remake your life to get what you want. You just need a new way of looking at the world.

What I’m suggesting here is chewing gum simple:

You Find What You Look For


You want to find the perfect job, where you have the autonomy to create brilliant, world-changing products?

Start looking for it.

You want to start a side business that allows you pay off your credit card debt?

Start looking for problems you can solve for people.

You want to go on a safari in South Africa?

Start looking for a way to get there.

I’m not suggesting that anything you want will magically turn up the moment you look for it (although sometimes it nicely works out that way). More often what you find is a trail of breadcrumbs, each taking you one step closer.

At times, the pace will be frustratingly slow.

But finding something has to be an active process.

Too many people are waiting for their dreams to happen rather than taking responsibility for creating them. I love it when opportunities drop in my lap, too. But if that’s your only source of magic in life, the haphazardness can make you feel a little helpless.

In the end, what makes you a king or queen is not castles or the crown on your head.

It’s being willing to own the power you already have—and not be afraid to use it.

How “No-Brainer” Pricing Ruins Your Business (And What to Do Instead)

How “No-Brainer” Pricing Ruins Your Business (And What to Do Instead)

Much of the marketing advice out there encourages you to set prices that are a “no brainer.”

That is, a price that is so low, compared to the value you are offering, it would be silly for customers not to buy from you.

Sounds like a smart strategy, doesn’t it? But if you’re a coach, consultant, or freelancer, there are two big problems with this approach:

1) It works: you get a ton of clients, but your prices aren’t high enough to create the revenue you want. The result is you look successful but feel like an overwhelmed failure.

2) It doesn’t work: few people buy because your low price positions you as a beginner or someone who isn’t very good. The result is you both look and feel like a failure.

I know how much these two outcomes suck because I’ve experienced both of them. And yes, they nearly ruined my business because I either believed I wasn’t good enough to make it or I couldn’t keep up the pace necessary to make it.

Both conclusions turned out to be completely untrue.

By learning how to catapult my own income as well as a wide variety of clients over the last 3 years, I’ve found a smarter strategy that works in nearly every kind of business or niche.



Set a reasonable capacity for your services and then make sure your price per client adds up to the revenue you want for your business.

To make the math easy, let’s say you want to earn $100,000 in revenue and you can comfortably handle 10 clients per year. This means, on average, you’d need to price your services at $10,000 per client.



It’s not the math that holds people back. The REAL problem is that you don’t think you can charge that much. You don’t see a path from the “no brainer” price model to the premium price model.

I get it. To go from say $1,000 to $10,000 for the same service feels, well, uncomfortable.

How in the world do you justify such a radical change? Won’t everyone be shocked and angry at your arrogance? The voice in your head almost invariably starts yelling, “Who the hell do you think you are, anyway?

But here’s what you probably haven’t considered.



Making a big leap in prices is often easier than small, incremental changes.

I know it doesn’t feel intuitively right, but I’ve done this so many times now, I can assure you it’s true.

Small, incremental prices are hard to justify. It says nothing has really changed about your business, you just want more. And, in fact, this is often how entrepreneurs try to explain such price changes. They argue they haven’t raised prices in years. Or that it’s in line with what their competitors charge.

But your customers don’t care about any of that. Incremental price changes often feel like you’re trying to squeeze more out of your customers. And they don’t like it.

Big jumps in pricing, on the other hand, require quite a bit more boldness and creativity. You can’t keep to the status quo. You (and your customers) will require a perspective shift to wrap your mind around this new number.



I use about a half a dozen strategies to help my clients earn previously unthinkable prices in their business, but here’s one you can use after just a couple hours worth of work.

Change the way you frame your business.

There’s no doubt that how you describe your services establishes a point of comparison and sets the ceiling for what you think you can charge. If you’re already at the high end of your industry, here are two ways around that issue:

1) Give yourself a new title. There are two main reasons to change what you call yourself: you either want to put yourself in a profession with a higher perceived value or you want to get out of an oversaturated market. For example, the term “virtual assistant” suffers from a relatively low perceived value whereas a website developer, marketing consultant, or online business manager can easily command much higher prices. A life coach suffers from low perceived value and is also a saturated market. Better descriptions might be an executive or career coach.

2) Increase your specialization. Specialization is an easy way to essentially double the expertise you get paid for. For example, I worked with a client who called herself a freelance editor. But much of her experience was helping professors edit technical research grants and papers. Emphasizing this specialization helped her to increase her prices 20% overnight within that sub-community of clients.

The obvious caveat is that your new title or specialization has to be accurate. You shouldn’t call yourself an executive coach if you’ve never worked with executives before.

And of course, beyond your title and specialization, how you describe what you do and the value it produces matters tremendously as well.

Unfortunately, most people get this wrong, even if they’re whizzes at marketing, because they’re just too close to their own story. I’ve seen brilliant entrepreneurs vastly undersell themselves because they simply can’t see the true value of their work.

How much of a difference does changing the way you frame your value make? The proof is in your bank account. One of my clients used these exact techniques and got mind-blowing results, such as:

  • A new offer that even her existing clients want to buy, earning her an additional $4400 in the first two weeks of pitching it
  • A better way to package and price her monthly services, so one new client paid her as much as all her previous clients combined
  • A monthly revenue increase from $1906 to $9766 (after working together just two months)

Most people think leaving a stable job to start a business is a huge risk.

But the biggest risk is that you’ll stand in the way of your own success.

Many people hold themselves and their businesses back because they think they have to stay competitive.

Today, I’m giving you permission to charge for your value, not someone else’s.

4 Decision Making Strategies That Will Give You Instant Peace of Mind

4 Decision Making Strategies That Will Give You Instant Peace of Mind

Editor’s note: this is a guest post from Stephen Roe

It’s maddening, isn’t it?

When friends or family have a big decision in front of them, they nearly always come to you for advice. You’re clear-headed, objective, and decisive. The way forward always seems so clear.

But when it’s YOUR life? You constantly second-guess yourself, agonize about every possibility, and spend your days worrying you’ve made the wrong choice.

It doesn’t have to be that way.

Research has shown that analyzing data leads to easier and better decision-making. Data requires you to stay attuned to your feelings, weigh them against other factors, and ultimately makes the decision simpler.

I should know. I left my job, changed my living situation, started a business, ended a work commitment I’ve had for eight summers, began a new relationship and revamped my diet and exercise routine—all within the last nine months.

Without data-driven decision making, I would have been a basket case. But data helped me feel confident about my decisions, and I came out the other side happier than ever.

When it comes time to make a tough decision, these steps will reduce stress, bring peace, and allow you to make the best choice possible.

Strategy #1: Use the power of a coin flip


One of the greatest barriers to simple decision-making is ignoring its complexity.

Too often, we think a question like moving to a new house is simple. But while we only think we’re weighing two options (stay in the old house or move), our minds are actually racing between half a dozen—put an offer on that house, stay in the old one, invest in a renovation, build an addition, look for other real estate options, or finally design our dream home?

Instead, we need to recognize the complexity, and then simplify.

To find the complexity, write down every option you are considering. Compose the list over the course of a day or two–you’ll be surprised how many options are actually on your mind.

For example, you might be considering these choices in a career change:

Career Change Options

Recognizing the complexity helps, but we aren’t finished. Next, we’ll divide our options into a series of two choices, or what I call a “coin-flip choice.” Of course, you shouldn’t use random chance to make your decision, but the analogy of a two-sided coin describes it perfectly.

We are not creating a false either-or choice, but simplifying an overwhelming number of options into a series of smaller ones.

To start, break each choice down into categories and subcategories.

Now we’re going to reduce these choices into a binary decision tree–each choice will only have two options. It might take some wrangling, but any decision can be worked into a coin-flip choice.

You will end up with a tree like this:

Career Change

When we break a complex decision down, we make it easier to eliminate options and select the right option. The next step will show exactly how to do that.

Strategy #2: Predict the future (yes, really)


Wouldn’t it be nice to predict the future?

By combining probability with the coin-flip technique, you can get frighteningly close.

Using the above example of a career change, we’ll start with the first coin-flip choice—should we work shorter hours, or work fewer days?

Brainstorm factors involved. I can think of two—the possibility of unexpected overtime and the stress of the job. If your ultimate goal is to transition into working from home, be sure to include the difficulty of that change as well.

Put into a table, it might look like this:

Predict the Future 1

Now it’s time to populate the calculations with data. Use estimates in 5% increments. Don’t use 100% for any data point—nothing is certain!

It’s unlikely I’ll be called into work an extra day (10%), but staying late is a real possibility (65%). Missing a few days a week and catching up will add a bit of stress (45% vs. 35%). And finally, there will be fewer barriers to start working from home if I’m taking days off (45%) than reducing hours (75%).

The final result is this:

Predict the Future 2

Yikes! This is an easy answer now. Since I know the better of those options, I can eliminate it from the decision tree:

Using the same strategies for the other options, we’ll get simpler and simpler choices, like this:

Predict the Future 3

Probabilities allows you to predict the future with uncanny accuracy. With that kind of power, making decisions becomes easy.

Strategy #3: Taste each outcome, and see which you prefer


In a perfect world, life would borrow a method from ice cream parlors: nobody would have to make a final decision without tasting a few outcomes first.

This strategy is the next best thing: create the perfect day for each choice, then use it to decide. This exercise helped me quit my job as an elementary school teacher and follow my passion for personal development writing.

For each choice facing you, make a list of activities throughout the day.

Here’s an example comparing a lateral move in a company versus a promotion. Notice the types of work you do as a boss are very different than what you do as an employee:

Taste the Outcome 1

(Note that a new house will be better reflected in a perfect week, and a car will be noticeable over the course of a month or year. Just rename the hour markers to days, weeks, or months.)

Create two new PowerPoint presentations, one for each scenario. Include a photo and description for each section of the day (for bonus points, include a relevant audio track—perhaps it’s music, coffeeshop chatter, or ambient nature sounds).

Make it as realistic as possible (no teleporting to work), but also remember this is a perfect day. If everything went exactly as you’d like, what would happen?

For inspiration, here are slides from the transfer vs. promotion scenario I mentioned above:

Taste the Outcome 2

Once you’re finished, set aside 5-10 minutes and “live through” each day. It doesn’t have to be a hokey, woo-woo exercise. Just think about what you’d do during that time. Imagine yourself in the photo, listen to the audio you’ve chosen, and estimate how you’d feel.

Once you’ve “lived” through each day, take a minute and reflect. Which day did you enjoy the most? Which was closer to how you’d like to live your life?

Strategy #4: Don’t ask for advice, start an argument


Asking for advice before a major decision is like asking about a baby’s name before he or she is born—no matter the original opinion, everyone politely agrees once the decision is made.

“Reginald Picklesworth Smith? What a beautiful name!”

If you want to get someone’s perspective on an issue, don’t seek advice. Start an argument.

Don’t argue in a frustrated way that leaves everyone angry and bitter. Not at all.

But stop trying to ask for advice with an open mind, and instead present and defend a position. Your mentor’s constructive criticism will be specific, targeted, and invaluable.

To do this, prepare a pitch before the meeting. Create an argument for the choice you’ve made. Write every reason for and against the decision, and prepare a response for each. In other words, prove to yourself that you’re correct.

When you meet with your advisor, be persuasive when you give your pitch. Convince your mentor that this is truly the right choice.

But don’t forget the critical next step: ask what concerns he or she has. These can help if you’re stuck:

  • What factors do you think I’m missing?
  • What questions do you have about my decision?
  • What else have I not considered?

The goal is to hear some form of argument against what you’ve already said. If it’s an argument you’ve already prepared for, use your response and see if it holds up to scrutiny. If it’s new, consider the feedback and decide if the reasoning changes your perspective.

Ask at least five people to listen to your pitch. Include individuals with different backgrounds, experiences, and skill sets to get an accurate picture. Record notes from the discussion as soon as possible after the meeting.

If you notice a pattern emerging, don’t be afraid to change your original stance. After all, that’s why you asked.

The solution to solving difficult decisions


Perhaps more than any other factor, tough decisions steal your control. When forced with a complex issue, it seems like the choice has power over you, not the other way around.

But that isn’t fair. You deserve to feel in control.

You deserve to have a clear mind during the process.

You deserve to wake up tomorrow, next week, or ten years from now and be content with your decision.

If you use these strategies, tough choices won’t drain your energy. They should energize you. They allow you to work hard, think carefully, and choose wisely.

And after all the confusion and chaos settles down, you’ll be at peace. Because you’ll know you’ve made the right decision.

Stephen Roe actually enjoys making decisions, but spends more time writing about data-driven personal development. Download the templates and scripts from this article (plus two bonus strategies) for more decision-making help.