Year One: The Year of Not Walking Away

year one Angie Webb in Sedona Arizona


When I sat down to write my recap of my first year as a full-time freelancer, I wanted to write something uplifting and beautiful. I wanted to show you all the interesting projects I’ve worked on, and leave you with an inspirational tidbit leaving you inspired and uplifted.

That’s what I wanted to do.

I scribbled out pages and pages of garbled letters and words in my signature chicken scratch  handwriting that only I can read. I looked up words in the thesaurus. And now as I read back on the garbage I spewed into my notebook, the only thing I really want to write is this one real truth: this is hard.

This work-for-yourself, be-your-own-boss, make-your-own-hours thing is really really hard.

This year revealed to me new brands of worry I never knew existed. As I’m settling into my late twenties (still very uncomfortable to say), I’m finding myself more and more unsure about my role in the world. As the no-longer significant breadwinner in our household how can I make up for what I’m not contributing? How am I going to feel significant if I’m no longer bringing in the dough? Can I be comfortable in the skin of someone whose main priority is emotionally supporting someone else? Suddenly the weight of every $2.41 tall hot Earl Grey at Starbucks becomes unbearable as the dollars and cents of every decision add up in my mind.

Entrepreneurship brings about a constant feeling of edginess that seems unshakeable. The wheels of thought never seem to stop. The inbox never seems to get to a truly manageable place. The worry, oh the worry, that you’re forgetting something, that you’re falling behind, that you’re not doing something you should, it never ceases.

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Work-life balance is not a part of my current vernacular. When everything rests on your shoulders, how could anything, how could everything ever really be enough? Over the past year I lost sunsets, meaningful conversations, joyful moments, social outings with friends, and showers…LOTS of showers because I was lost in a maze of emails and phone calls and Illustrator files.

But all that pales in comparison to the biggest struggle of all: dealing with the daily, hourly, heck, constantly present voice that tells me to put all of this down, to relent to the pull on my heart that says give it up already.

I gave myself this year to create a brand new body of work that would better speak to the ultimate direction I’m trying to drive this old train, and though I ultimately accomplished that goal, the road to getting there was full of fails. Missed deadlines, poor communication, mistakes, mistakes, mistakes, if I had a report card it would be full of shiny red F’s all the way down the page.

Where it left me was in a hotel room in Hilton Head completely alone and seriously contemplating giving up.

You are not strong enough.

You are not personable enough.

You don’t know what you’re doing.

You have made too many mistakes.

You don’t have enough clients lined up.

You should just quit while you’re behind.


Then, like it fell out of the sky, I happened upon a post on Every Bitter Thing is Sweet that stopped me in my tracks. You know when you see something in just the right space and time and you have no idea where it came from or how it got there and it leaves you feeling awestruck at the cosmic-ness and complete relevance of it all? It was like that. In her post, What Do You Say to That Voice That Wants You to Quit, Sara says:

“The accusations in your head aren’t the personal report-card you thought they were, they are arrows from an enemy who’s hounding your life and your pursuit of God. He’s found your weak spots — you know, the ones that were maybe even pre-purposed for the greatest glory of God in your life — and you’ve been duped. The enemy is, after all, a thief and destroyer of what is good.

There are closets full of half-painted canvas and electronic files of never re-opened stories and dusty dreams you once dreamt for your children that are awaiting revival from Him. ‘Cause when we shelf that boldly-vulnerable expression of ourselves because this shameful lie spoke louder, we are missing a meeting with God.”

I tried the other way already. I did the conventional thing. And one year ago I walked out on conformity, stability, and a 401K. And I didn’t do it for no reason. I felt compelled, I may have even possibly felt called to do this.

The last year has been riddled with mistakes and slip ups and messes on the road to finding my footing and figuring out my place in this big big world, and it’s my responsibility to make things right in the future. But if I could just tattoo something across my forehead to ensure I’d remember it and really believe it forever and ever, it would be my mistakes don’t define me. Because they don’t. They really really hurt. They’re embarrassing. They’re frustrating. They’re threatening. But they don’t define me. They’re just another page in the book of my life that God has written. They’re opportunities to grow and learn. And rather than leaning into the voices in my head that are telling me to quit, it’s time to see them for what they really are: utterances of my insecurities ready to kick me when I’m down and rob me of my potential, rob me of this thing I’ve been called to do.

The problem with being an entrepreneur is that this internal bloodbath happens entirely internally. There’s no one else there to put a stop to it, and that’s where the importance of community comes in. I have been blessed to know so many wonderful people in the industry. As a fix-it kinda girl with an only-child disposition, depending on others is basically impossible for me, but the more I looked to others the more I found they were just as confused as I. I took workshops and classes with creatives I idolized only to find that surprise surprise they were humans too with their own unique brands of insecurity and fear.

The truth is we’re all wandering around in the dark, and we find light not in things or learning more or trying harder or making more money, but in each other.

I found the most gratifying moments of this past year not to be those late-night lightbulb moments alone in front of the computer screen, but rather across the table over coffee, over dinner, over Skype in the eyes and words of my peers and clients and colleagues and friends.

This is really really hard. We need each other.


To any of you out there who may be thinking about trying this whole working for yourself thing, get ready for a wild and scary and gratifying ride. I have unfortunately spent the last year waiting for the other shoe to drop from the ledge upon which it has been meticulously placed. Every move cautious for fear that the slightest vibration would throw the whole operation into a tailspin and my worst fears would become my daily reality. A year later, I’m realizing what I hope you already know: when it comes to own own fates, our own lives, our own destinies, the shoe only drops if we let it, doesn’t it? Every ounce of self doubt is just another opportunity to let it all fall, but every day we wake up with the opportunity to replace those thoughts with positive ones and say no, not today.

For me, this year was really less about changing career paths and more about learning how to accept me. How to accept the peaks and the valleys. How to trust the process. How to be vulnerable and willing to fail. I didn’t always feel good, but I’m so glad I took some time to feel something. Pursuing safe routes that you know will yield successful results is a reliably safe way to life your life, but at the end of my life, I want to be able to say that I got dirty, that I lived to the core, and that I felt all of it.


Everyday when I walk out of my office, I see this quote hanging on the wall. It’s my daily reminder that tomorrow is a new day and a new opportunity to shrink back into the shell from whence I came, or to go out and create magic in this big big world. The best part is, I get to decide.