<img height="1" width="1" style="display:none" src="https://www.facebook.com/tr?id=658263587654409&ev=PageView&noscript=1" />

Tune In:


last updated:
December 12, 2018


Use the same library of tools I use

Browse resources, book recs, aI tools & more tailored for creative entrepreneurs

Get my free, 5 min. 2x week newsletter—used by 51,700+ to be wittier, clearer copywriters

take the quiz

what's your voice vibe & selling style?

let me write your next sales email:

psychology nerd
j-school grad
conversion copywriter
business mentor
pencil affeciando
old-school ad hoarder

Hey! Ashlyn here, OG copywriter for creatives—reporting for duty. 

Let's get you a message so tight you can bounce a quarter off of it. Around here, we serve up science-based storytelling strategies the creative set.  Even while raking in more than 1.26M in agency work since I've been at it, I firmly believe working from a place of rest (not hustle) IS possible—and I want the same for you. Words matter. Best be sure they work (and oui, with math) ... and know how to party while they're at it. 

My Story

Download Now

Load up your copy bank with instant access to email copy templates, web copy snippets, swipe copy, subject line ideas, & more—my gift to you.

Get 1-month bundle of sales copy swipes & templates—free


shop all

Reading time: 10 min.

I’m going there—today, I want to talk about small business investment tips that have worked for me.

My friend Stacey (a side-hustling stationer buddy with a sweet day-job as a campaign manager at a major non-profit fundraising agency) and I crunched over leaves after work yesterday in sneaks on a walk around our neighborhood.

“I mean, the saying’s true,” she said. “You’ve gotta spend money to make money after all.”

Where to spend your money as you build a creative biz_Ashlyn Writes Copywriting and Calligraphy
There’s a phrase “never go into debt for your business.”

And according to Georgia state records, I’ve only been a business owner for 17 months, but I did fulfill midnight oil orders for brides for about 5 years before that and probably need to get that on some books somewhere.

I’ll be honest.

I’ve not seen that phrase work out, at least for me.

But I’m also not talking about JUST a line of credit debt.Sure, that’s one way to have smart debt, but my big sister business coach reminded me that not everyone wields a credit card well. I’m first to say that I’ve made MAJOR mistakes in the personal category of owning a credit card in my lifetime. #college

Borrowing against yourself and your cash savings counts as a risky investment, too.

Put a penny-pincher like me in business, I’m suddenly Shark Tank-like in my investments. I borrow against myself and the cash I’ve saved up in my business all the time. Will it make the business more money? Ok. Maybe not? Then no.

Business is about well-wielded risk.

And I think, as a creative community, we need to make sure to define the line between hobbyist and professionals. Not that there’s anything wrong with being a hobbyist, truly. Art for art’s sake is part of God’s design for us, I think. Running a business isn’t for everyone, and sometimes I wonder if the online world has glamorized something that takes a lot of blood, sweat, tears, spreadsheets, and strategy.

[bctt tweet=”Business is about well-wielded risk.” username=”via AshlynSCarter”]

We just wrapped up the most financially successful promotional period I’ve had in my business, but with every “Ashlyn, I want this so badly, but I can’t invest right now” email that pinged in my inbox last week, my head tilted: I totally get it. I was there, too.

But still, I have a question.60% of all small businesses that open in a given year need under $5,000 to get going according to the Census Bureau. Starbucks, Apple, Mattel … there are plenty of Fortune 500 businesses that ramp up on a bootstrap budget.

But—if you don’t mind my asking—what are you investing in? Are we sold a lie that you can be a creative entrepreneur without having to play good ol’ fashioned capitalist game of risk?

Out of all the flashy tools out there, it can be overwhelming to know where to spend your hard-earned money as a creative small business owner, all while keeping your business lean and practicing wise stewardship.

No, spending money to make money isn’t 100% of the time the right answer. Yet, at the same time, sometimes I watch other business owners fizzle out, and I have to wonder is it because you didn’t ever invest in the resources that put you in the game.

Here are the tested, tried-and-true investments that helped us grow a sustainable, profitable business.

One: In-person Events

How I did it: $4,000 on Illume retreat, credit card debt.
Time in business: Two months before going full-time
I brushed past my COO’s office, walked outside and called my husband.
“Wes, she just put tickets up for sale. There aren’t many. This conference is going to be so good. The speakers are like, girls I idolize. I think I can make this investment back, I have enough calligraphy jobs on the books for the next few months and Lara Casey just asked me to help copy edit her book and another magazine said I could write for them—the money isn’t there yet, but it will come in by June. Over time, I THINK I should be able to pay this off.”
small business investment tips from Ashlyn Carter creative copywriter at Ashlyn Writes Illume Retreat

Faithful, yes.Wise with money, yes.Natural leader, yes.

Man that just survived his new bride being hospitalized for anxiety, depression, and anorexia, regularly telling him she wasn’t sure she wanted to be alive anymore and was finally excited about something? Also, yes.

“Sure. We’ll try it.”

I put a $4,000ish charge on the American Express that day, and monitored the accounts like a watchdog.

One speaker I met has bought around $11K from me in copywriting services. One bought $900 in coaching from me and asked me to speak at her own conference, another speaker who booked around $900 with me, and I met my business coach I ended up trading services with.

So yes, we made it back. It was terrifying, but I learned this: make conferences count, even if you’re shaking in your boots, you have to put yourself out there to make the investment back. I was absolutely terrified to stand in that room with names like Cottage Hill magazine’s editor Katie Selvidge, Kat Schmoyer, Bonnie Bahktiari, and Jenna Kutcher.

TBH, I didn’t even know what I wanted to DO as a business owner, really.

How to make sure you’re getting the ROI:

  • Set goals before every live event you go to. Who do you want to meet? Hint: Aim for deeper, not wider relationships. You’re never going to walk away from a conference being BFF with everyone, we just don’t have that kind of capacity.
  • Implement what you learn, even if it’s hard.
  • Don’t be afraid to raise your hand and get feedback on your business during allotted time for that.

Two: Group Coaching

How I did it: $3,000 for Heather Crabtree’s 6-month Savvy Business Circle program, broken up over 6 months, paid with cash

Time in business: 7 months after going full-time

Another huge risk, mostly because I felt like I was too early in business to be worthy of something as fancy sounding as a business coach—but I was wrong. I needed someone to get under the hood and tell me the hard things.

I met Heather Crabtree at Inspired Retreat. We were both speakers, but she was a big deal so I basically stared at her for 3 days … finally Heather came up to me and said she was kicking off her coaching program again, would I be interested.

Um, yes.

And then I mentioned the price tag with Wes and we had a lovely family discussion.

$3K on coaching. That sounded crazy to me having just passed the 6-month business mark!

But what I learned was the ROI in having someone at Heather’s level on speed dial: she could help tell me how to price my packages, to tell me things I didn’t want to hear (“Honestly? I get confused when I land on your website. It’s not clear.” “Nope. That’s a weird package name—don’t do that. Too confusing.”), and how to handle booking my first $5k package client, when all I’d done up to that point was a $2,800 package.

How to make sure you’re getting the ROI: 

  • Attend the trainings. It’s so easy to skip video calls and virtual “meetings,” but this is how your coach gets to know you.
  • Make the most of office hours and contact avenues. Some coaches are okay with texting, and some even comfortable with your calling them in the middle of the day with a question. Work it, girl! Use that resource.

Three: The RIGHT courses.

 How I did it: First was Modern Calligraphy Summit for $299—I was now full-time with calligraphy, and needed to know how to price myself, copyright my work, and digitize my pointed pen work for invitation suites. Paid once in full with cash … so, it knocked out a good chunk of a big order I had.
Time in business: One week after going full-time. I’m now 17 months in and have X% budgeted towards education every month.
I feel like online courses get a bad rap, but here’s the thing.
Maybe it’s us.
Maybe it’s you.
Sure, sometimes the content isn’t presented well, or the teacher clear in explaining (and that’s why you need to be picky about who you learn from!), but maybe you and I need to be smarter consumers when it comes to online education and business ownership.
Any of my students will tell you I’m not one of those course creators who disappears after my students purchase, and I really think it’s because I’m a bit batty about trying to train you to get THROUGH a course. What good are all of these if we don’t finish them? If we don’t learn how to apply knowledge?

The best courses I’ve taken have ranged in price, from Todd Herman’s 90 Day Year that I paid $997 for to Amy Porterfield courses (all of them, so around $2,400) to the $29 Trello for Business course I purchased from Think Creative Collective (now a sweet client!).

There are good tools out there that can help you short-cut your journey to a creative, radically fulfilling life.

If there’s a course that will teach you in a chunk of hours what it will otherwise take you DOUBLE that to figure out, then it’s probably something to weigh and try to plan to afford.

How to make sure you’re getting the ROI:

  • Pick courses that teach you things you can’t figure out on your own, or that give you skills that will help you make more money. Hobbyist courses are a blast too—I’ve totally paid for courses that teach me a skill that I want to learn for the heck of it, but those aren’t the kinds of courses I’m talking about here.
  • Start looking at your time and energy as your most precious investment. More on that below.
  • Gamify getting the investment back.


Four: Outsourcing

How I did it: First was paying a graphic designer $200 to create 3 InDesign workbook templates for me to use. Paid cash. Next was hiring on a studio manager to review and pack calligraphy orders at an hourly rate. Paid cash.

Time in business: Graphic designer, 10 months. Studio manager, 11 months.

This is more or less where I am right now, and the point I’m having to learn to steward well.

Growing a team—or even just hiring contractors—is super scary, and being able to have a listening ear to my client Nancy Ray’s Foundations in Teambuilding program has been so helpful.

But outsourcing can look simple at first, tools like MeetEdgar and ConvertKit, digital butlers and robot secretaries that can streamline your system. Those are worth investing in, too.

Some of my favorites have been:

MeetEdgar – for social media scheduling
BoxFox – for client gifts
HoneyBook – for canned responses and client systems
ConvertKit – for email drips
Acuity – for calendaring

After I started doing that for a while, I hired on a studio manager to spell check and pack all of our calligraphy orders, and then was ready to inch up to paying associate copywriters and a bookkeeper.

Your time and energy is your most precious resource—more precious and finite than money.

[bctt tweet=”Your time and energy is your most precious resource—more precious and finite than money. ” username=”via AshlynSCarter”]

If you can stay in your lane, do the things you’re good at, and learn to see your time as money, it works.

Think about it this way: what’s your hourly rate? And then, would you pay a terrible [insert job you’re not good at, whether it’s website coding, graphic design, etc.] that amount to turn in bad work?

 Ashlyn Writes Shop Ordering Your Productivity
How to make sure you’re getting the ROI:


Three Free “Investments” that Work

  1. Taking bootstrapping seriously. Listen, if you’re gonna bootstrap? Do it like a champ. Here’s how I filed things in Google Drive, and I also printed out freebies and made myself a complete filing cabinet for reference. I used them. I applied them.
  2. Deep diving into someone’s brain via their podcast. I feel like we splinter-listen to podcasts, hopping from new episode to new episode. But I got my best experience when I picked one entrepreneur and went back to the beginning with their content.
  3. Tracking my time. Learning that if I plan to spend a morning re-designing our 2018 client magazine and suddenly it’s 3 p.m. and I’m still Googling InDesign hacks, welp. Maybe this isn’t the wisest use of my time. Click here to read my blog post on tracking your time.


In sum, I don’t blame a single one of the potential students who shot me an unbelievably kind email about how they so badly wanted to invest in my program, but couldn’t at the time. I really get it. I’ve been there. And I appreciate every email.

But it does make me wonder.

If not this … then what? Where ARE you spending money for your business … or, are you getting ramped up on a spending plan that WILL help you be freed up to invest in your business in a few months?

It takes money to make money, I think.

In all of this, I feel confident because of three things:

First, I know my hourly rate, and I hawk-eye it. I say no—a lot. I don’t do weekly coffee dates so people can “pick my brain.” I do two a month, and when they’re gone, they’re gone. And if they get filled up with friends first, they do. Just because you can doesn’t mean you should. I believe in saying no—a lot. Here’s a list of things I say no to.

Secondly, we have a plan, and we work it. I worked with Shanna Skidmore this past year to define a job for every dollar in my business, and that’s freed me up a lot. We know what I actually need to make, so when I hit it, I’m done … I don’t have to book clients out of fear that we won’t make ends meet in the business like I did the first few months. Shanna’s Blueprint Model opens doors again in January, and you can sign up here to be first to know—I’m leading a small group through it and would love for you to join me!


Finally, I am a big fan of praying and sleeping on all financial business decisions. Here’s one of my favorite prayer resources for small business owners from my friend Val!

Okay, what about you? How have you learned to steward money—AND time—in your business?Want more? Head to the AW Shop to check out productivity and goal-setting resources!

Reading Time: 10 Minutes Reading time: 10 min. I’m going there—today, I want to talk about small business investment tips that have worked for me. My friend Stacey (a side-hustling stationer buddy with a sweet day-job as a campaign manager at a major non-profit fundraising agency) and I crunched over leaves after work yesterday in sneaks on a walk […]


💻 4. Own/run a small business & looking for a best-in-class copywriting agency? Add an insanely smart group of word whizzes to your contractor rolodex: tell us in this form what you need! →

✏️3. Need to master your message, write your site, & launch it to sell--without the 4-figure price tag for a pro copywriter? Copywriting for Creatives has served more than 2,227+. Get on the waitlist here!

📧 2. CopyBank.Club: Want 3 email copy templates per month? Snag that monthly copy drop, AI copy prompts, hooks, & more starting at $20/mo. It's like a subscription box, but make it copy. →

🍾 1. The Copy Bar: Needed stud copy like, yesterday? Get ASAP copy frameworks + templates to-go-style, starting at $29, when you saddle up to The Copy Bar template shop

here are 4 ways I can help ya—

whenever you're ready, 

comments +

  1. Loved reading this post Ashlyn! 🙂

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

about page

I need help writing my


just $9 (yes, f'real) → 

You're in your boss era—Let's make the bots work for YOU. 💅🏼

Snag instant access to my Notion template of 200+ AI Prompts to rev up your junior copywriting bot team, see what AI tools I use to create powerhouse conversion content, and more.

get the little black book
of ai copy

all-new: snag yours—

shop our trainings

book a discovery call

view our services

Totally ~*done-zo*~ with rage deleting
drafts & staring at the blinking cursor?

Step inside our copy cave.

(we have snacks & dogs.)