Things That Keep Us Up At Night: Entrepreneur Anxiety


Each year, I invite my clients to participate in the Lucky Break client survey. I ask you all sorts of things: about your business, about where you turn for advice, about how confident you feel in various aspects of your business, and about what biggest piece of entrepreneur anxiety is keeping you awake at night.


Several hundred people rose to the occasion this year (thank you!) and I wanted to share some of the responses with you. Why? Because so very many of us are lying awake with worry/ fear/ overwhelm at night, and there’s a surprising amount of commonality in what plagues us. Entrepreneurship is damn hard and sometimes I don’t think we talk about that enough.  In my entrepreneurial journey, I’ve often taken comfort in community, talking about the “hard stuff” and realizing that my worries and failures are well-tilled ground among the small business set. In fact, that’s the reason that I started a consulting company- to help us connect to one another, pull back the curtain on running a product-centered brand, dish “no b.s.” business advice, and help others benefit from the 3,719 mistakes I’ve made as an entrepreneur.


Entrepreneur Anxiety


I sifted through hundreds of survey answers to discover that the vast majority of replies fell under one of five main “umbrellas.” Below you’ll find some direct-from-our-mouths answers about what’s rumbling across the brain waves at 1am. The responses are purposefully provided without any identifying information, because the replies could easily have come from any of us!



  • Fear holding me back every step of the way. Worried that I’ll waste my family’s money on a failed attempt at entrepreneurship.
  • Every-frigging-thing.
  • Worrying that I’ll fail.
  • Not getting this company I’ve worked so hard for off the ground and where I want it to be.
  • Wondering if it’s all worth it.
  • Are my products good enough?
  • Family balance.
  • Should I continue this business or shut it down? Is it adding to or taking away from my life?
  • Managing anxiety, and managing unfounded doubts about potential success and failure when taking risks.
  • Imposter syndrome.

Mercy… that’s is a heavy list, isn’t it? I put it forward because I think these are the anxieties that constantly dance through our heads, but so rarely roll forth from our mouths. But there is comfort in the commonality… you aren’t alone. You’re not the only one facing that fear, white-knuckling it, and sweating it out.  In my experience (and in the experience of the majority of my consulting clients), struggle is at the very core of entrepreneurship.  But there’s a tremendous beauty in challenging ourselves, pushing outside our comfort zones, and taking a risk. It’s never easy and rarely boring, but there’s almost nothing else I’d rather do with my life at this point.


Here’s my advice…


Nervous energy isn’t your friend. And I say that as someone whose first grade teacher gave her a book about anxiety at the ripe old age of 6. I’ve ultimately realized that all energy is either productive or destructive, and anxiety is massively destructive energy. That doesn’t mean that we should go running off of cliffs blindfolded in the name of courage. We shouldn’t ignore our gut, but it’s wise to be aware of (and attuned to) our nervous energy. Once we’ve made a decision, stand confidently in those decisions.  Don’t give into panic or stagnation or the negative narrative that your mind wants to produce. Becoming more self-aware is an essential building block of business success.

One of my favorite books to read to steady myself and help me pay attention to the negative narratives that run on a loop in my head is Rising Strong by Brene Brown.  It’s a good read and I hope you might find some value in it, too.




Impostor syndrome is real.  And we all suffer from it. I don’t think there’s any level of success that’s immune from this beast. But the key- I think- is to hear that narrative when it pops up. Be attuned of it, but don’t indulge it. Two things that help me:

  • Keeping a journal of my accomplishments.  Progress is hard to see when it’s incremental and we’re standing so very close to it. But if I keep a notebook nearby (or even a digital note on my smartphone), then I can casually jot down the wins- both large and small- in the moment.  When I feel stagnant and like I’m up against the impossible, I leaf back through those notes and I’m continually reminded of just how far I’ve come.



Guest Post: A Meditation on Fear with Melyssa Griffin


Melyssa and I originally met during my Girl Friday search. I’m all kinds of love drunk on her positive energy and have enjoyed reading her blog every single day since we first met. Since she’s currently working in Tokyo, there are a few oceans between us,  which means that no matter how hard I’m crushing on her, that Girl Friday gig would have had some serious challenges. But all hope is not lost! Melyssa graciously agreed to pitch in at the blog while I’m in Africa and the post she submitted made me swoon. There’s so much kickass in this one post that it makes me dizzy, but I hope you’ll inhale deeply and drink it all in! Take it away Melyssa…




I started 2013 as I start most years – hopeful, but with a tinge of fear. I’d been out of college for enough time, at this point, to think that I should be doing something productive. Yet, here I was, beginning my second year as an English Teacher in Japan – a job I figured I’d do for a year as a “learning experience.” My hunger for purpose, creativity, and drive wasn’t satiated and I wondered how I could pull myself out of this funk. In the midst of my wallowing (a.k.a my solitary internet surfing), I stumbled on a cute little website banner that read, “Creative Courage eCourse.” I clicked it, not knowing what I’d find, and was immediately drawn to all the things its teacher, Stephanie Levy, proclaimed she could teach me. Even though I was a teacher, I desperately missed being a student. I watched the teens in my classroom have a-ha moments, but epiphanies and I were becoming old friends – the kind you only see for Thanksgiving and Christmas. Desiring the chance to learn and let the power of creativity back into my life, I signed up immediately and spent the next six weeks soul-searching, creating, and bursting at the seams with energy, life, and passion. It.was.awesome.


It was so awesome, in fact, that I fell ridiculously behind in the eCourse work after only week two. Not because I didn’t like it, but because I liked it SO dang much. See, I turned my attention to using all the things I was learning. And boy, did I use them! I joined the class because I wanted to create, but from the start something unusual happened – I felt less afraid.


As creators, business owners, doers, I truly believe that the absolutely positively biggest obstacle standing in our way is not money, location, or a lack of ideas. It is without a doubt in my mind, fear. Fear that it will suck. Fear that you’ll be living in a cardboard box. Fear that people will see you on the street and snicker at you for even trying. Fear you don’t have the skills. Fear that people with the skills will look at you and snicker. Fear. Fear. Fear. But the biggest thing to me, is the fear that we’re not worthy enough to really follow our creative, life-altering passions.




I have some bad news. The fear never goes away. It’s like a virus that permanently dwells in you, but with the right steps, you have the chance to manage it. Your voice and your vision are so damn important that they absolutely must be heard. Since January, I have become convinced that the most successful people – our idols – are probably not more talented or intelligent than any of us. They’re just more brave. They knew their mission was more important than their ego. They knew there was wisdom in failure. And they knew they’d never learn how to do it until they, well, did it.


The first step I took after realizing all of this was to create a blog. As I love writing, photography, and graphic design, it was a small, pipe dream of mine for way too long. I never went for it because I was scared for too many silly reasons. Does my writing suck? Will people think I’m full of myself for sharing my thoughts all the goddamn time? Nope. Actually people loved it. It’s only about six months old, but already reaches about 10,000 visitors and 1,000 subscribers every month.


When I realized that to conquer fear, you had to let go of it, I also started a graphic design business, Bumble + Buzz Design. I was scared, again, and wondered what the embarrassment of putting myself out there and not getting any clients would feel like. Nope. Wrong. My design schedule is totally booked and I’ll probably be able to realize my dream of leaving my day job before winter.


I’m not any different from you. If we’re being honest, I’m probably pretty average. But I’ve seen the power of courage the way people say they’ve seen the power of God. If you believe you can do it, well little lady, I’m already convinced that you can.


I feel like I’m on a roll this year and I am certain that as long as I keep doing the things that scare the absolute crap out of me, I’ll succeed.


After feeling totally changed by the eCourse I took as a student and being an instructor in my day-to-day life, I decided to try my hand as an online teacher and create an eCourse of my own, “Everyday Happy.” It combines all the lessons I think are necessary for feeling confident, radiant, positive, and powerful. It’s also only for women, because I believe the world tends to trick us ladies into being even more afraid of our overwhelming potential. The course facilitates some deep soul-searching, inner optimism-building, and serious fear ass-kicking. It is my goal that women walk away from it with resilient, balls-to-the-walls attitudes and tools. If you want to give fear the boot and unwrap a more radiant and driven version of yourself, then I would absolutely love to see you there.

So, I want to know, in what ways has fear dictated your life? And what have you been doing to give fear the cold shoulder?


Remember, you are worthy of success and courageous enough to obtain it.


Originally from Southern California, Melyssa has spent the past two years as a Teacher in Tokyo, Japan. Aside from teaching, Melyssa also works as a graphic designer under her business, Bumble + Buzz Design. When she’s not designing blogs or teaching literature to 16-year-olds, she aims to promote positivity and self-exploration through her blog, The Nectar Collective. When Melyssa is not writing, designing, or teaching, she’s probably singing made-up show tunes to her corgi, Monja, or binging on sour gummy worms.