Struggle and Success Go Hand In Hand: Part 1

Everyone loves a good success story, but rarely do we hear about the challenges and truths behind that success. The foundation of every thriving business or idea is persistent dedication and a lot of behind the scenes work. This series, Struggles & Success Go Hand in Hand, is my attempt to bring forward the voices of women forging their own path, and give them a space to talk about the challenges and struggles they face. Their stories remind us that our feelings are universal and that there’s no such thing as overnight success.

"What has been your biggest struggle as a business owner/creative entrepreneur? How have you dealt with it? And why do you think it's important to share stories of challenge and failure?"

Johnie Gall, Editor + Freelance Writer + Documentary Photographer & Producer


In addition to being an editor and freelance writer, I also work as a documentary photographer and producer. One of my ever-present challenges is a lack of physical community — I'm often working alone from home or out of the back of a truck. It can be incredibly isolating, both on a personal level and in terms of creative collaboration.

Projects benefit so much from collaborative input and debate, and I often find myself questioning my creative choices to the point where I'm paralyzed by them. I've sought out and built a network of people I can connect with digitally to run questions by to help remedy that, but it's still an area of my career I struggle with.

It's important to talk about challenges like these as the lines between work and our personal lives continue to blend. We're able to carve out these niche careers for ourselves thanks to our digital connectivity, but that same opportunity presents struggles we've never had to deal with before. The more we talk about them, the less nebulous and insurmountable they become. The more we humanize these challenges, the most apt we are at solving them in human ways.

Molly Fakoury, Personal Stylist + Clothes Therapy


My biggest struggle as a business owner has been the process of learning to trust myself and my decisions. I remember having a breakdown to my best friend the day before I officially launched - paralyzed with fear about putting it out into the world …

“Are you sure this is right?!” “No,” she told me, “but you have to do it anyway.”

Not having a blueprint and not having seen anyone I personally know do something like this, I was terrified of doing it wrong. I had to learn that there’s no right way of doing it. There are no right rates to charge, no right time to market, and no right way of using social media. There is just what feels true to me. Shifting my language from “What is right? ” to “What feels true? ” has helped take the pressure off for it to be a certain way and focus on what I want to create.


And while I love the idea of bringing our truth to business, it comes with its own struggles. It’s powerful to no longer feel the duality of having a ‘work self’ and my ‘real self,’ but being one in the same - makes business a lot more personal. It’s a thousand times more terrifying to share a website that feels like a translation of your soul than to share a marketing proposal. As an anxious person, I still question why I chose entrepreneurship. I struggle almost daily with feelings of fear and anxiety. I’ve had to learn how to manage it, to sit in the discomfort of the uncertainty of it all. And it’s required of me a lot more internal work as opposed to say .. a quick read through Entrepreneurship for Dummies .

Sharing our struggles feels not just important, but crucial to our success as entrepreneurs and as humans. Knowing that we all feel fucking terrified, that none of us actually know what we’re doing, and that yes, I still feel anxious every time I post on social media .. helps normalize it. We’re a lot less likely to get stuck in the fear or anxiety when we know it’s just a part of the process. I always think of John Mackey sharing how the first Whole Foods flooded - literally first store. 400,000 in losses. No insurance. Personally, I might’ve taken this as a sign that I’m on the wrong path. Thank all the organic kale he didn’t. But knowing others’ struggles shines light on the reality of entrepreneurship. It reduces the shame that comes with experiencing our own messy journey vs. seeing everyone else’s seamless journey.

And best of all, it’s helped me to reframe fear - instead of a sign that I’m not doing it ‘right’ .. but rather as a mile marker that I’m on my ‘true’ path.

Laura Hughes, Podcast Host of Women on the Road, Photographer + Content Creator


I'll be honest: I don't have many answers to how I've resolved this for any sustained period of time. I've dealt with these feelings as they come and tried to figure out what feels best as a response to those emotions in the moment. Sometimes that means calling a friend. Sometimes that means going on a walk. Sometimes it means surrounding myself with art and beautiful creations from others online, and sometimes it literally means tapping into those lost or sad emotions to create something beautiful of my own.

What I do know is that there is a huge importance in sharing these challenges because it brings us closer together. For every handful of people reading this article, one person will resonate with what I've written here in some deeper way. And maybe they'll feel less alone because of it. Maybe they'll feel like they have permission to call their friend on an off day, or put on some listful music when they're down for the sake of creating from the heart. Maybe they'll feel more empowered to tell their own communities when they're having a tough time. Maybe they'll continue to build relationships. From this starting point. That's all I really want.

Brynne Caleda, President and CEO of Yoga Ed & Executive Producer for Omolulu Yoga

“it’s not what you are that is holding you back. it’s what you think you are not.”

“it’s not what you are that is holding you back. it’s what you think you are not.”

One of my personal struggles in 7 years of entrepreneurialism has been self-doubt, and the implications my doubt has had on my personal mental and emotional wellbeing and ultimately the performance of the company that I co-own. The mental side of doubt is when my mind is suspended between two or more contradictory propositions, unable to assent to any of them. On the emotional side, doubt is indecision between belief and disbelief. For me, it involves uncertainty, distrust, and a lack of decision on certain actions and decisions that need to be made.

Naturally, when I feel like I am in a place of self-doubt, I look to podcasts (How I Built This, a favorite!), read magazines (Fast Company, innovation high five), browse blogs (Brene Brown adore her), and scrolling social media (Alex Elle, drooling), looking for inspiration, validation, and learning opportunities from other entrepreneurs.

What I have come to realize is that while I find learning opportunities in all of their success stories, I am silently comparing myself and my company to them. As I am listening or reading I think things like "How can I be more like them?" How is my company similar to theirs? What did or are they doing that I am not?” While I think this is a normal human tendency, the constant comparing has done nothing but hold me and the company back. In fact, it has deepened my self-doubt.

I have come to realize that with all of the “success stories” I read, even woman like Brene and Alex probably have had a million setbacks, tons of failures, and dark nights, that maybe they don’t talk about that often. Like myself, I am sure all of the valleys and peaks of entrepreneurialism have taken a toll on their mental and emotional wellbeing, and ultimately I believe that this has led them to the "success" of their business.

From this awareness I am reminded, it is not what I am not, but what I am. Set aside the self-doubt Brynne and remember, just like all of the success stories you read and listen to, these woman like you are learning from their failures and darkest hours, and these teachings have brought them the success that you too have all the potential in the world to have."

Casey Callahan, Freelance Designer and Illustrator

Screen Shot 2019-03-13 at 8.35.59 AM.png

I’ve always said my favorite part about being in the creative field is that I get to create something bigger than myself every single day. But the truth is, I still wake up every morning and second guess, doubt, and deflate myself.

As someone who has always struggled with being impatient and anxious with the unknown, I’ve been known to look 20 steps forward and not focus on the step right in front of me. Especially in this world of constant comparison, it’s easy to look at others and think “damn, how did they make that jump so easily?”. But the truth is, they probably never jumped.

Because if I could tell you one thing about my own creative path, it’s slowly taking 3 steps forward, going 5 steps back, and repeating. Then one day, you take enough steps that you can physically see how far you’ve come and the unconventional path it’s taken you on. The jump is not the jump. The jump is the process, the second-guessing, the failures, the continuous progression.

I want to sit here and tell you that I have it all figured out. That my creative world is perfect and I’m happy and I make work I’m proud of every single day. But that would be a huge, raging lie. Because I would be absolutely nowhere if I believed this career was one huge “jump”. I wouldn’t have pushed myself to create every single day (even when I thought it looked like crap), I wouldn’t have been inspired to try harder, I wouldn’t have figured out how to balance my work with my personal, physical, and mental health.

There is nothing more important than letting our guard down as creatives. Than being open and honest about the struggle and how it hurts, grows, pushes, deflates, and inspires us. The continual growth is a raw, beautiful thing. Embrace the messy. Embrace the unconventional and the uncomfortable and the vulnerable. It’ll always make you a better creative and a more empathic, passionate person. Your work, your career is a living, breathing thing. Give it the time, space, and love it deserves.”