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A Love Note to Entrepreneurs Feeling The Fear

A Love Note to Entrepreneurs Feeling The Fear

Dear You,

I recognize the place where you’re standing right now. It feels like a precipice, or a thunderstorm, or like being crushed under the weight of too many expectations and responsibilities. You feel like maybe, just maybe, your business isn’t going to make it through this.

And you might be right. But I want to talk to you about surviving this moment, and about what comes next.

The Fear is a Liar. You’re Not Alone.

First, it’s important that you know this: we’ve all felt The Fear. Starting a business is an inherently risky move, and the risks never disappear into the sunset — they only change. But it’s easy to feel alone when The Fear comes on, because that’s fear’s superpower: making you feel alone and vulnerable. So if you’re able, remember that every entrepreneur that’s ever entrepreneur-ed has felt the way you feel right now.

I’m telling you this because I got an email from a coaching client last week that read, in part:

“Will this ever feel easier? Will there ever come a time when things are running smoothly, my future & finances don’t feel debilitatingly uncertain, and I actually feel like I know what I’m doing? In your experience of living this entrepreneurial life, does it ever feel even just a little bit easier?”

I wanted so badly to write back a sunny, “Yes! It gets so much easier.”

But that would have been a lie.

So I wrote this instead.

It’s a letter to that intelligent, soulful visionary who wrote to me, and it’s also a letter to my younger self — for all those times when my doubts clouded over all certainty and confidence.

What Are You Afraid Of?

While our culture — especially the braggadocio-fuelled culture of North American entrepreneurship—worships at the altar of “pushing through” fear and ignoring emotions, the truth is your feelings will find a way to express themselves, either directly or indirectly. I strongly prefer understanding my own emotional weather patterns so that I can engage with them consciously, rather than letting them make unconscious decisions for me.

The big secret to this is simply: feel them. Allow the feelings to rise up—and if you need to, set a timer, as Chris Dierkes suggests, so they don’t overwhelm you — and give them a chance to tell you what’s up.

Karla McLaren, author of The Language of Emotions, says that fear’s job is to wake us up to something we need to be alert to. When we feel fear, she says, our job is to ask, “What action should be taken?”

I find that when I’m deep in the midst of fearful feelings, I need to start by asking, “What am I really afraid of, here?” That helps me get to the root of it before I shift into asking “What action should be taken?”

Either way, the goal here is: feel it, engage it, and work with it to gain clarity and focus. Being “fearless” is not a good thing. (Without fear, you’d be incapable of assessing or avoiding risk.) As Mark Twain said, “Courage is resistance to fear, mastery of fear, not absence of fear.”

Will it ever feel easier?

Obviously, you’ll get a different answer from every entrepreneur you ask, but this is my experience: It doesn’t get easier, but you become more resilient. There will always be waves of difficulties that feel insurmountable and new, but the longer you stick with it, the more experience you’ll have getting over some kind of wave, and you’ll be able to trust — to some extent, anyway — in your ability to at least weather the storms, if not ride the crests.

This doesn’t mean you won’t feel, at least once every year, like you’ve failed utterly and it’s time to throw in the towel. (Again, this is my experience, and maybe not everyone’s.)

It also doesn’t mean that life as an entrepreneur is a non-stop storm of crazy proportions. There are ebbs and flows. There have been times when I felt entirely confident about how things were going. Those were the easier times that I think you’re holding out hope for. They do exist.

But I don’t want to tell you that it ever feels like that forever, or like there’s some kind of goalpost beyond which you no longer encounter dark nights of the soul.

As a friend of mine once put it, “At the end of the day, life is just the death and resurrection show.” There will be moments of intense sweetness and light. And there will be darkness. The only thing we can count on for sure is that it’s all transient, i.e. this too shall pass.

I hope this isn’t too dark. I don’t want to sugar-coat things just to cheer you up. I also don’t want you to feel alone.

Failure is Not the Whole Story.

And here’s what I really hope you don’t feel: that if you close the doors on your business, that means it was a failure.

I don’t know if that’s going through your head, but again, this is my experience. Any time I faced the possibility of closing down my business, I felt like doing so would mean admitting failure. And if I could go back in time and talk to that younger self, I would say: look, you do what you need to do to get through to the other side of this. That’s not failure. That’s survival. That’s reinvention. That’s creative problem-solving. And if the business has to close down now, so be it. It had many successes, and its ending does not define its impact — or yours.

I’m not trying to put a feel-good spin on failure in the pat way that Silicon Valley bros talk jauntily about “failing up” and “failing fast” and “I’m super privileged so I can afford to ‘fail’ and then blog about it to prove how cool I am with failure.” Failure is awful. It’s really, really hard. Closing the doors to your business would feel like failure, and yet —that’s only part of the story.

Calling it “failure” carries with it a strong suggestion that you have failed. That you could have done something to fix it. My hope is that you not feel defeated, or like you’re doing something wrong. There are way too many variables in this game to pinpoint any one thing that could be causing your business to falter.

Welcome Your Tears.

Finally, if you find yourself crying: that means you’re letting go of something that needs to be released.

Now’s a good time to ask yourself what that thing is, and how you can help it move along.

It might be a dream. It might be an image of yourself. It might be a relationship (or several).

Let it go, let it go, let it go.

I can’t promise you what the future holds for your business, but I can promise you this: pushing the fear away will only guarantee it will come back with a vengeance. Asking it in, and letting it show you what you need to attend to, will allow you to take your next step with wisdom and integrity.

Love and courage,

This post was originally published on Medium.

Inner and Outer Critics: the Power Dynamics of Imposter Syndrome

Inner and Outer Critics: the Power Dynamics of Imposter Syndrome

I don’t have an inner critic.

I have at least ten of them.

Their voices are shrill, thundering, hissing quietly. They say things I’d never say to another human being. Frankly, they’re a bunch of verbally abusive jerks.

They tell me all kinds of things – things that mostly aren’t true, though they’re laced with enough truthiness that they often get to me. At their heart, my inner critics are fear embodied. Fear embedded within my mind, nervous system, muscle memory. Disdain internalized.

I’ve written before on how I work with my inner critics – how to work with imposter syndrome when it crops up, minimize its hold, move past the obstacles it has set in my path. I’ve taught others how to do the same.

What I haven’t written about before, but have been thinking about a lot, is where the inner critics come from.

They don’t come purely from within. Not everyone has inner critics – at least, not the obnoxious, and frequently paralyzing kind I’m talking about here.

Inner critics come from outer critics, seen and unseen.

They might come from your father. (He’s never satisfied. Oh man, Prince is on repeat in my head right now, but I’m gonna forge ahead here.) Your big sister. A shitty teacher. You might hear echoes of their voices in your mind when you’re working on stuff that matters, or just going about your day.

But they might also come from the environment you grew up in – and here, I mean the water you swam in, almost invisible to you:

  • The educational system that rewarded privileged kids and punished the ones who came to school hungry, tired, or distracted by the chaos at home.
  • An economic system that might not show you a whole lot of people like you rising to the top of the financial heap.
  • A culture that uplifts “normalcy,” whatever that might be, and tells you that any part of you that doesn’t fit the mainstream mold should be hidden, reshaped or disowned.
  • A society that has demonstrated again and again that you are not safe – that your body, your voice, the work of your hands can be used and stolen from you at any moment, for the pleasure, profit, and amusement of others.

These are the outer critics. They are as real as real can get.

The outer critics say: You are worthless. (Or at least, worth less.) Your idea would be more valuable if it were spoken by someone whiter, straighter, able-bodied, male. You could sell more books if you had a Ph.D. after your name, no matter that you can’t afford grad school. 

The outer critics are sometimes very, very quiet. They can afford to be, because they are everywhere. They don’t need to be loud because they are The Way It Is: indisputable, seemingly monolithic, nigh impossible to topple.

And sometimes they’re loud and proud: the trolls online who threaten you for daring to work in a male-dominated field. The music professor who told me, with no trace of irony, that the reason her syllabus featured not a single woman composer was because there were no great women composers. Justice systems that repeatedly perpetrate violence against people and communities of colour without facing repercussions.

When you grow up in a world where the outer critics have power – and let’s be clear: the outer critics are the power. If they didn’t have power over us, we could brush them off, twirl on them haters, and move on – it is a completely rational response to internalize their criticism. Because the consequences of ignoring it are real.

As Cate Huston writes:

What we call imposter syndrome often reflects the reality of an environment that tells marginalized groups that we shouldn’t be confident, that our skills aren’t enough, that we won’t succeed—and when we do, our accomplishments won’t even be attributed to us. Yet imposter syndrome is treated as a personal problem to be overcome, a distortion in processing rather than a realistic reflection of the hostility, discrimination, and stereotyping that pervades tech culture.

(I would add that this is true everywhere, not just in tech culture.)

So we internalize the outer critics, turn them into inner ones, thereby doubling down on the forces standing between us and our chosen paths.


I’ve been reading some excellent writing on what imposter syndrome is, and is not. Alexis Hancock argues that we dedicate way more time and energy to talking about imposter syndrome than we do to addressing the structural inequities that are at the root of it, and to that I say Amen. And it’s no surprise that we lean that way. The powers that be will always be happier paying for imposter syndrome workshops for all their marginalized employees than facing up to their own privilege and biases. And at least here in North America, where individualism is the altar at which we worship, most of us would rather take on a self-help project than join a social movement. We’d rather tackle the problem we think we can fix within ourselves, than the one that’s systemic.

It’s simpler (or so we believe). It’s smaller. And in the case of the corporate workshop, it’s something we can buy once, and then feel good about ourselves. We’ve done that work, we can say. We feel more empowered.

Changing our collective mindsets, addressing our biases and prejudices, addressing inequities – these are hard tasks. They’re deeply uncomfortable, and they’re endless. They resist a simple line in the budget, a date on a calendar, or a metric on a quarterly report. But to quiet our inner critics when the outer ones are still raging has limited value. Even I, who have written and taught and coached on imposter syndrome, freely admit that.

Don’t get me wrong: it’s wildly liberating to learn to outsmart your fears. I still believe it’s meaningful work. But I never supposed it was the whole picture, or a complete solution.


There’s also a fabulous piece by Alicia Liu outlining the differences between imposter syndrome and simply recognizing your limitations.

Before jumping to self-diagnosing with Impostor Syndrome, get objective evidence of whether you are really valuing yourself too low, or whether it’s a more or less accurate assessment of where you are right now. It’s okay to be a beginner, and feel inadequate. Keep learning and growing, and the circle of what you know will naturally grow.

In a related post, she writes, “Impostor Syndrome instilled in me a deep fear of failing. I was afraid to speak up or ask questions for fear of saying something stupid, and people would find out I didn’t really know my stuff… I quietly avoided doing things I didn’t think I’d be good at, even though the only way to get better is to do them.” Here, she connects the dots between imposter syndrome and a fixed mindset, as defined by Carol Dweck.

Fear of failure, coupled with a belief that aptitudes are innate rather than learned – which is, of course, exacerbated by stereotype threat – is a recipe for stopping yourself from stretching. And if you don’t stretch, you’re never going to feel fulfilled by your successes.

So this is the piece I’ve been trying to tackle with my work on imposter syndrome. Not to suggest that it gets at the root of the problem, but that where we have internalized structural inequities, fear of failure, and fixed mindsets, we can intervene and change our internal narratives. We can choose to act differently, choose differently, than we might if we choose to believe the defaults our culture dishes out to us.

This is not a perfect solution. It is, in some ways, a band-aid. But a band-aid has its uses. It can help you heal in the places that hurt, even if it doesn’t shield you from ever getting hurt again.


I don’t take back my work on imposter syndrome. I stand by its value for addressing the inner dimension of this work: managing one’s inner critics. But I do believe that, as with everything, there is also an outer dimension to this phenomenon. There is a reason you experience imposter syndrome, and it’s not all your fault.

And there is deep and wide structural work to be done, here.

I have said before that imposter syndrome affects people who are both “ambitious and conscientious.That is, they want to do great work in the world, and they care greatly about that work being done with integrity.”

Ambitious people focus on the outer world; conscientious people, on the inner. The solution to feelings of being an imposter is both an outside and inside job.

Let’s roll up our sleeves.


Postscript: I realized after publishing this post that I failed to credit another article that inspired my thinking on this subject: Sarah M. Seltzer’s piece for Refinery29, which argues that imposter syndrome has its roots in systemic problems. “Once you become less insecure,” she writes, “you may end up becoming more pissed off.” And later: “Imagine waking up every day and going to work in a country with more humane policies, like paid sick and family leave, longer vacation time, universal basic incomes, occasional sabbaticals, or anything else that would allow us to pursue our intellectual and career ambitions in a healthier way — without feeling like they were the only things that mattered… In that country, which would look a lot like every other industrialized nation, I think a lot fewer of us would feel like impostors, and a lot more of us would feel like people.”

Adventure and Grief on the Road to New England

Adventure and Grief on the Road to New England

Last night, in the deep darkness that comes at this time of year, I got in the car and drove to an empty parking lot outside of a shopping mall. I circled around until I found the row of large metal donation bins in the corner farthest from the mall entrance; parked; opened the trunk of the car, lugged three heavy bags of children’s books to one of the bins, and tossed the books by handfuls into the clanging interior.

I estimate that I’ve read some of those books hundreds of times, talking to my young sons about the pictures, savouring the rhymes and alliteration, laughing at slapstick humour and hoping for the baby animals to be reunited with their mothers. (If you haven’t read children’s books lately, that’s a staggeringly common theme .)

We’ve set aside the books we’ll be shipping to Boston in a few weeks. Some are treasured gifts from family and friends; others are simply too delightful and beloved to part with.

(Kinda skipped over that move to Boston, didn’t I? I’ll get to that in a minute.)

When you’re moving across both a continent and a border, every single item gets evaluated. Is it worthy of shipping? Of packing into storage? Either way, you’ll be paying for the privilege of holding on to your possessions. So there’s a new calculus that gets invoked, beyond that wonderful KonMari question – does it spark joy? – and beyond its monetary value.

It doesn’t always matter how much you paid for it, and how much joy it sparks; if it won’t fit in the shipping container and it’s going to cost you an extra fifty bucks a month to store it, you will confront the question of how much it’s worth to you right now.

(This isn’t another ode to living minimally, by the way. It’s simply a letter from this moment in my life to this moment in yours.)


So about this move to Cambridge: my partner David has been offered a totally amazing job. He’s going to be teaching at Harvard. That’s particularly amazing because David isn’t an academic – so we didn’t see this coming. It was definitely not in the plans. But it is a what-what-omg-can’t-say-no opportunity. So we are moving, with our two young kids, to a new city.

And we’re working every day to focus on the adventure of it all, and the possibilities it presents, and not get swept away by the grief of saying a thousand goodbyes, of giving away our sons’ baby clothes, of leaving our beloved home.

I’m trying not to be swallowed by sorrow when the books our children teethed on clang into an echoing metal bin in a dark corner of an empty parking lot.

Not because I won’t allow myself to be sad. I will. But because the aching beauty of this experience is that it is bringing me face to face with the passage of time.

Face to face with the present. (This is what transition looks like. This is how not-knowing feels. This is the best use for this object right in this specific moment, no matter what it meant to me last week or six months ago. This is the sound of books falling into a bin, no matter how much my mind wants to fashion it into a leitmotiv of nostalgic farewells.)

Face to face with the transitory value of all material things. (The boys have outgrown the baby clothes. Those books will be better loved elsewhere. And still, the grief is here.)

And for that, I am thankful.


This is a letter from this moment in my life to this moment in yours. What does this moment hold for you?

What are you holding on to because it matters enough to keep investing in it?

What are you holding on to that has served its purpose and is ready to be released?

What do you need to grieve in the cold dark? What memories will keep you warm forever?

Where is the not-knowing that makes you so uncomfortable that you reach for your soothing balm of choice again and again?

I’m listening.


Photo credit: RebeccaVC1 on Flickr.

Hi. I'm Lauren.

I'm a seasoned tech entrepreneur and author who asks a lot of questions. I offer strategy and coaching for creatives, entrepreneurs, and accidental bosses who want to infuse more joy, curiosity, and ease into their lives and work – and create growth that has meaning and purpose. More about me…

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