Austin Church

Thriving in business as a sensitive person

When Austin Church gave himself permission to be the fully-feeling creator he is, he connected more deeply with his audience building a business helping creatives achieve their dreams.

It started with a girl; Austin Church’s first middle school crush:

I did not know how to process what I was feeling, so I wrote poetry and told no one about it.

No one.

I had enough social savvy to know it would have been social suicide to be writing poetry as a 7th grader.

But he kept writing, secretly.

He also became obsessed with choosing just the right title for his 8th grade English essays, even though no one but his English teacher would ever read them.

iaac-austin-church-notebookThough by his senior year of high school, his English teacher gave him a perfect score on his final research essay, saying, “I could not find anything wrong with this.”

In college, he started as a journalism major (“If I wanted to write I thought I had to be a journalist”) but quickly changed his major to English Literature when he realized it was the major where you got to read fiction and write papers – his two favorite things.

After college, he got a job teaching high school English:

I found my first gray hair. I said, ‘This is not for me.’ Three months in I thought, ‘Oh my, what have I done?’

He took the GRE and applied to 12 master’s programs in creative writing.

He only got into one.

He went to that one, thinking maybe he’d become a college English professor. But the more he learned about academia, the more he realized it wasn’t for him – he wanted to spend more time writing, not teaching and grading.

So after finishing a master’s in creative writing with a focus in poetry he got a writing job – at a marketing agency.

I felt so conflicted – because I loved it.

iaac-austin-church-black-and-white-standing-in-front-of-brick-background“Well, figure it out.”

Austin the poet wrote web content, press releases, white papers, social content, and brand guides.

And while Austin knew how to write, he knew nothing about marketing; he felt inadequate.

I remember being so confused. I told my boss, ‘I don't know anything.’

He was like, ‘Well, figure it out.’

His boss didn’t say it dismissively; it empowered Austin. His boss believed in who he was, not what he already knew. He could figure it out. And he did.

But six months later, he got laid off.

It was April 2009 and the country was in a recession. The kind of job he had was disappearing; agencies were hiring contractors instead.

I got laid off on a Friday. My old boss called me on Monday and said, ‘We can't actually finish the projects you were working on without help. What's your freelance rate?’

iaac-austin-church-typewriter-keysAnd I kid you not I had to look up what freelance meant.

I did not know there were writers out there who were freelancers, who worked for themselves.

I think that is when it finally clicked: One way to make a living as a writer is to write for businesses.

While the agency wasn’t hiring him for enough hours to make a living, they did pay him an hourly rate three times what his previous hourly rate worked out to be on salary; he was shocked and excited by this new possibility. What if he could make it as a freelancer?

He decided to try to find more clients and become a full-time creator.

I ask Austin if he had any fears starting out in something he’d only just learned about.

I was afraid every single day. I had $400. That number is seared into my memory. I looked at my bank account and I had $486, and that was savings, that was checking – everything.

He told people what he was trying to do and asked for a lot of help. One friend got him a meeting with a friend of hers named Andrew Gordon who owned an agency.

I brought my writing and I just remember he was thumbing through it and my chest was full of butterflies.

iaac-austin-church-dream-big-typewriterHe paused and he said, ‘Your stuff is actually really good.’

And then he said, ‘What's your rate?’

I said 40 bucks an hour. He paused. I remember thinking he is going to laugh me out of the room. But he gave the strangest piece of advice, or at least it was strange to me at the time.

He said, ‘If I were you …’

And I thought, ‘Here we go.’

‘If I were you, I would raise your rates to $75 an hour effective immediately. You will not be taken seriously in larger markets like Nashville, Atlanta, Charlotte. You're just as good, but you won't be taken seriously.’

Austin raised his rates, and “not knowing any better, I just got out there and tried any new thing.”

He made a lot of mistakes in the early days, but he didn’t mind. He was a poet, learning how to run a business, and he knew no matter what mistakes he made, he would find a way to figure it out.

But first he needed to get past his nerves.

“People refer people they like, not necessarily people who are qualified.”


In the beginning, Austin was nervous most of the time, wondering who would hire him as a freelancer with so little experience.

I think when we're getting started we tend to be self-conscious about everything we don't know.

There's the assumption that people hire other people based on expertise. To some degree that's true, but over time I noticed people who didn't know anything about my relative level of expertise would still recommend or refer me.

Eventually I connected the dots: people refer people they like, not necessarily people who are qualified.

And people liked Austin, because he listened.

It wasn’t a sales technique (he still didn’t know much about sales then). He just genuinely loved listening to people talk about their businesses and projects. A true poetic empath, he would get just as excited as they were about whatever they were working on. And as his excitement and curiosity grew, he’d ask them more questions, listening intently.

People love talking about their businesses. And so they would walk away feeling like, ‘He really gets it,’ when they didn't know anything about me, my background, my expertise.

You can come in and sort of bludgeon people – hit them upside the head with your expertise – and they're like, ‘He totally knows what he's talking about. I just don't like him. I don't want to spend time with him.’

iaac-austin-church-working-in-officeThey didn’t care about how much experience he had – they wanted to work with someone who truly cared about their mission, their project. And Austin did. (“Then I would work really hard to do a great job and never give people a reason to doubt my ability to deliver.”)

Of course if he did a terrible job word would have quickly spread – but, because of his old boss, he’d learned to figure it out. When he didn’t know how to do something a client needed, he would either take a course and learn it or hire someone else who was great at that thing and be the liaison.

Above all, what Austin had (and still does, from what I can tell) was “a real eagerness to serve.”

iaac-austin-church-notebookSo much so that he could genuinely feel enthusiasm for any client’s project, problem, or product.

And I worked on some of the most mind-numbing stuff. I'm talking concrete polishing. I wrote web content for a concrete company.

But as excited as he truly got for every project and every new creator he helped, there was still a whisper he couldn’t ignore – he really wanted to make something of his own again.

“They just forgot about you.”

He started with mobile apps – a mustache-themed photo booth app he called Mustache Bash, to be exact – inspired by what he’d learned about apps at a recent conference he’d attended.

iaac-austin-church-with-hat-brick-white-backgroundHe didn’t develop the app himself, but hired a developer, something he’d learned how to do from hiring help for his clients’ projects.

And after a conversation with a friend he decided to create his first digital product, one that would share the source code he used for his app along with a step-by-step written tutorial that others could use to create their own app.

Next Austin reconnected with a friend he’d met at one of the events he’d attended (Austin never stopped attending events and meeting people) to ask for advice. That friend, Carter Thomas, a thought leader in the mobile app space, agreed to be an affiliate for Austin’s product and promote it to his large email list.

Austin made $20,000 in one weekend from his very first digital product. He remembers thinking:

Well, this changes everything.

That’s when he started an email list. He had to: “I had to deliver the download link for the files.”

iaac-austin-church-using-convertkitHe made a few more similar products and made over $250,000 from his list of 1,000 people.

He was amazed, and afraid: “That set the bar really high. I hope I didn't peak early.” But he couldn’t help but want to explore his new world of selling digital products even further: “I was hooked.”

He started blogging, teaching people who didn’t know code how to hire developers and create their app, collecting even more email addresses along the way, knowing what a difference they made in his own life:

Every email address you get is an asset.

I watched folks build up these huge Facebook groups and then didn't have an effective way to monetize them. If there is one asset you can carry with you from platform to platform, it is an email list.

Austin grew his list by creating custom and simple lead magnets for his blog posts, like a hiring checklist or a job description template: “Give them the thing that will help them solve the very next sort of micro problem.”

iaac-austin-church-website-screenshot He also still sends an email every week, which has been beneficial to his freelancing business too – something most freelancers don’t think about since email is typically associated with selling products, not services. I ask him what advice he has for freelancers who are on the fence about email:

Most of your growth will come from repeat business, referrals, and new relationships. The best way to stay top of mind with clients is to send them new value every single week.

“Make it impossible for people who already trust you to forget about you.”

I've had this phenomenon, and every service provider out there has too, where you bump into an old client and they're like, ‘Great to see you.’ And then you find out they hired somebody else.

And you're like, ‘They were always pleased with my work.’

They just forgot about you.

So I think the single best way to get referrals, repeat business, and introductions from the clients you've already got is to stay top of mind, and the best way to do that is to send them an email once a week.

Make it impossible for people who already trust you to forget about you.

But of course it’s not about sending emails just for the sake of sending emails. Austin also takes time to step away once in a while to journal and reflect on what he’s doing with email and why.

I never want to be that person standing at the elevator thinking if I press the button over and over the elevator is going to move faster.

What he comes back to, again and again, is enjoying the writing.

As soon as I started treating my email marketing as a sandbox, where if I'm having fun other people are too, that’s when email became something I looked forward to.

And he’s received amazing replies from people saying they look forward to seeing his name in their inbox.

But there was still something holding him down. The very thing that made people love Austin’s emails (and want to hire him) was also his greatest obstacle.

“What happens when those parts of yourself get crushed?”

When I ask Austin about the biggest obstacle he’s overcome in his 10 years of being a creator so far, he says:

I'm probably going to start crying.

And then he tells me his answer: “Chronic anxiety.”

I think a lot of creative people are set up to fail in business because you have this passion and you have this sensitivity and those are the things that enable you to do the work.

But passion, when it bumps into barriers, starts to stagnate and becomes resentment and bitterness.

And sensitivity, this sort of hyper vigilance, having this antenna out, makes it easy to get trampled.

So it’s needing to show up with all the feelings, emotion, and intuition, but then what happens when those parts of yourself get crushed

His poetic nature and big heart drew clients to him – but it also meant he was more sensitive to the harshness of the business side.

How, I ask him, did he manage not to get the poet kicked out of him by the business world?

He didn’t.

iaac-austin-church-recording-podcastHe tells me the business world crushed him – but it didn’t destroy him. Because who he was was stronger. The poet in him survived, and when it did, he decided he would do things differently.

I burned out and then I decided I was never going to let that happen again.

I realized certain types of success do not matter if you lose yourself.

One of the changes he made was giving himself more time to process the emotions of his creator's life: “For example, I don't respond to emails right away. I might say, ‘Thanks for the email, I need some time to think about this and I'll respond in detail tomorrow.’”

For sensitive people, a lot of us go through life thinking there's something wrong with us and that we don't have what it takes to thrive in the business world.

But I have come to recognize that my sensitivity is an incredible gift, and like most gifts – it is a sword that cuts both ways.

Austin is still prone to anxiety and discouragement, he shares, but he helps fight it by reaching out for help, and remembering that “vulnerability and sensitivity are my two best tools for making an impact.”

“So I'm not going to be the early success story.”

But that sensitivity still morphes into self-doubt once in a while.
Like when he started dreaming about making his first full online course but felt totally out of his league.

“The only thing left is the work of being who you are.”

I'm 37 and it's interesting to be like, ‘Okay, so I'm not going to be the early success story.

I'm not going to be the 22 year old YouTuber that has 10 million subscribers.

That story and the identity was all tangled up for me.

But once early success is off the table, the only thing left is the work of being who you are.

Austin – still always showing up to every event he can – attended our Craft + Commerce conference in Boise in 2019.

And sitting at a local coffee shop during a break after one session, he wrote the entire outline for his course.

And after putting in 250 hours of work over the next few months, he launched the course: Freelance Cake.

I don't think that ever would have happened if I hadn't given up on some fake story about who I ought to be, and instead just gave myself permission to be a father of three who has a lot of gray you can't see, who’s not going to be an overnight success but has been successful in so many other ways.


I realized if you're okay with being who you are and know the next thing you want to accomplish, the only way to get there is one step, one hour, at a time.

And if you're committed, no matter how long it takes – even if all you can do is offer up 30 minutes or an hour a day. If you make enough of those offerings, it becomes inevitable.

The course did well, and Austin loved creating and selling it, even though it took him a while to get there.

I think a lot of artists feel guilty about making money with their gifts.

What helps me is to look back at artists over time. Michelangelo was afraid the Pope was going to die before he got paid. Michelangelo needed to get paid.

And some of my favorite poets had day jobs. Ted Kooser was an insurance executive. T. S. Eliot worked at a bank. B. H. Fairchild worked in a machine shop.

So, this idea that business is somehow antithetical, or at odds with creativity, I think is total garbage.

It took me a little while to figure out there is honor and there is beauty in helping other people's dreams come true by using my gifts to serve them.

iaac-austin-church-stats“Flecks of gold.”

And he’s found his freelancing and digital product work actually feeds his creativity and gives him more time and energy to create his own projects.

The more efficient I get at running my for-profit business, the more time freedom I have. And then I can spend that time however I want.

He’s written books as part of NaNoWriMo and still writes poems.

But the creative project closest to his heart is Grabbling, a children’s book he wrote inspired by a story his grandmother used to always tell him, about a type of fishing done with your hands.


iaac-austin-church-with-photo-albumiaac-austin-church-holding-book-with-grandmas-photoHe did a successful Kickstarter for the book and he and his grandmother did a book signing together at the book party they held in Nashville at his parent’s home. The party was also one of the Kickstarter prizes: “We had a ton of people come by the house, eat cupcakes, get the book signed, and hang out with my grandmother.”

iaac-austin-church-book-singingBut what Austin remembers most is when his grandmother, sitting next to him at the signing table, turned to him and said:

‘Austin, I just feel so honored by you.’

He’s especially thankful to have created something he can pass on to his kids and beyond.

He mailed me a copy of the book a few weeks after our interview.

Inside there were a few bookmarks and quote cards. One featured the book’s theme (“Always be three times brave”), another alluded to the next book he wants to write (“It’s okay to be odd”), and the third featured a piece of a poem by Walt Whitman (“Day by day and night by night we were together – all else has long been forgotten by me”).

No matter how many app tutorials Austin wrote or how many websites he created about concrete polishing, he never stopped being a poet.

Rough draft (bottom) to final version (top).

And now his work gives him even more time to create (he has more book ideas in the works); but for him, it all shares the same purpose – to do for others what his grandmother did for him, as he shares in the dedication of Grabbling:

‘For Jeannie, a.ka., Grandmother, whose love, joy, and stories added flecks of gold to my ordinary days.’


iaac-austin-church-book-promotion-close-upYou can connect with Austin on Instagram or subscribe to his email list at

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Isa Adney

Isa is an author and writer and has profiled incredible creators and artists, including Oscar, Grammy, Emmy, and Tony winners. When she’s not writing or interviewing creators, she’s probably walking her dog Stanley, working on her next book, or listening to the Hamilton soundtrack for the 300th time.

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