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8 Ways I Outsource my Life as a Creative Small Business Owner

Reading time: 10 min.

Awwwwww, yeah outsourcing. Here in this day and time, we have the most workaholic culture in the history of the world. As a Christ-follower, my constant lesson is how Jesus’ unhurried pace stands in stark contrast to our twenty-first-century pace.

Part of that for me is learning that B+ work is good enough.

That plenty of the list (especially now as a mom) will never get checked off—and that’s okay.

Another part?

It’s learning to loosen my grip and let someone else do it … even if (especially if) that means figuring out how to move dollars around and pay for it.

8 Ways to Outsource as a Small Business Owner | Ashlyn Writes

There was a funny article in Town & Country talking about how helpful it feels to outsource something, and I used to feel like it was pretty “bougie” too. Tim Ferris really put virtual personal assistants on the map for a lot of folks when he talked about outsourcing in his book The 4-Hour Workweek.

In Walden, Henry David Thoreau asks “The cost of the thing is the amount of what I’ll call life which is required to be exchanged for it”  … that’s the place I’ve had to come to as a creative small business owner.

So yes, you need to definitely see if you can replace the task with a high-value time investment.

Yes, the dollar amount is important.

But all of that leaves out the cost in LIFE.

What about the life trade-off? With outsourcing, do you get more life back … and if so, that’s worth it to you?

Time is money as an entrepreneur.

Let’s get down to it — have 8 things I outsource to get your wheels turning. I’ll talk through:

  • Why housekeeping is #worthit in my book
  • Where to start if inboxing stresses you the heck out
  • The #1 thing to think through if um, you’re not even good at something you have to do in you business … spoiler: quit it.
  • Bonus Tip: How I built my team


If you’re looking for more outsourcing tips, make sure you join thousands and grab my free guide 5 Things to Outsource in Your Business Checklist.

No. 1: House cleaning

We’ve had a house cleaner for about a year now, which means—checks notes—she’s saved us about 52 marriage arguments.

I used to get so bent out of shape over getting things tidy on Saturdays, mostly because (in my Type A, checklist-oriented style living that probably makes me a flight risk to live with most days) I wanted the home clean by Saturday lunchtime … and Wes was more than happy to help me after his morning tee time.

We had budgeted for a housekeeper for a year before I finally trusted the budget and finances to see it through. I kept thinking we could save a little bit of money if I just did it myself. I’m NOT a speedy cleaner—it was taking me entire half-days to clean the house on the weekends, too … time I wanted to be going to a yoga class!

| Related: Where to Spend Your Money as You Build a Creative Biz: Small Business Investment Tips |

This is one outsourcing task I don’t think I’ll ever give up if at all possible. 🙂 Now that I’ve seen the stress it saves our marriage, and the time it gives me back to spend Saturday mornings at yoga or with my little baby boy, I will FIGHT to make that additional $200 a month to pay for the housekeeper.


To crunch numbers for ya, Willie Mae’s team comes every other week for a deep clean … it’s a cool $100 each time. During the off weeks, I spot clean. To note, a Roomba won best Christmas present of 2017 for me—it’s scheduled to run every other day via the app on my iPhone, because #germanshepherdfur.

This takes so much stress off my plate.

No. 2: Taking notes on calls

As a small business owner who works online, I rely on calls over the internet to service clients.

I’ll jot down notes during the call, but when I need to review in greater detail what was said, I turn to Rev.com. This website is soooo million-bajillion times better than any Fiverr person I’ve found.


It costs about a dollar a minute, so it’s a low enough price point that you can easily bake it into your service cost. I’ve used it from onboarding calls with brides for their calligraphy suites to more deep-dive calls with copywriting clients for funnel build-outs—it’s ah-mah-zing.

Related: 8 Productivity Apps So You Can Make the Most of Your Time

No. 3: Scheduling calls

On the subject of calls …

I hate all the back and forth about calls asking where’s the link/reminder we have a call tomorrow/etc., not to mention all the email ping pong just to find a time that works for both parties.

Acuity has been my go-to online scheduler slash internet robot secretary for a while, and I still love it! (Side note: Calendly is great too, but I had a few issues with it. They’re based here in ATL and I always hate to break up with an Atlanta start-up, but Acuity’s just been better).

Related : 3 Productivity Mindset Shifts That Grew My Business Quickly

Acuity lets me block out 6 meeting slots on Thursdays—a few always reserved for current clients, and a few for new business calls—1 virtual coffee meeting a week, and 2 Friday in-person lunch dates a month.

Remember, it’s ok to say no or push people to a tool like this to chat with you. You’re running a business!


$10-15/mo.—click here to get started with Acuity fo’ free.

8 ways to outsource my life as a creative small business owner- ashlynwrites

No. 4: Grocery shopping

The other day, I was sick, the baby was sick, and I needed to run to the grocery store to stock up on medicines, chicken noodle soup, Gatorade, etc., meaning I’d have to get him out of his car seat and the whole nine yards when we both were germy.

In that moment, paying $8 for someone to bring it to me?

Uh, yes pls.

My tools of choice here are Instacart or Amazon Prime Now—since Whole Foods is a ~*WHOLE*~ lot cheaper now that they’re in the Amazon fam! On Sundays, I sit and do our fam meal planning, add items to the app, and get things delivered. These apps have also helped keep me from putting random things in my cart as I waltz the aisles.

Typically, we have a family rule that we don’t do Instacart or Amazon Prime Now for groceries unless it’s over about $70 worth of groceries. In my opinion, this only works as a time/money saver if you’re using it for your big weekly grocery haul … otherwise, it’s just cheaper to run to the grocery store for an item or two.


Varies depending on the delivery service—we really like using Instacart and Amazon Prime Now.

No. 5: Administrative tasks & project management

I have Rachel and I think every small business owner needs a Rachel. 🙂

My inbox was a huge source of stress for me rounding the corner into my second full year in business. Despite all my work to email ninja, I was drowning in emails … mostly because of a personal problem. 😉 Customer service drains me emotionally, and my strong suit is overarching business strategy and client work.

Hiring Rachel was one of my best business decisions because operations and virtual assistant work light her up—she manages the inbox, schedules appointments, reads my emails, flags them for follow-up, and responds to the ones she can take care of.

This frees me up to get solitude to think, to write, and to create.

I’ve blogged before about what you need to know about hiring/outsourcing before you make the move, and I can’t say enough about making those decisions sooner than you’re ready to.


Dependent on the VA—sweet Emily Yost saw a need in the creative industry for a match-making of sorts with entrepreneurs and virtual assistants, filling the void with her Outsourcing with Love service. BRILLIANT!


No. 6: Bookkeeping & Payroll

Oh heck yes.

My students inside The Art of Efficiency™ know that I say I think you need to know enough about something to be dangerous before you hand it off. Bookkeeping is like that—before I paid to have it done in the business, I did it every week, meticulously spending a few hours every Friday. It got my non-finance minded brains in gear to run a business, but after time, I saw that those 3 hours were better spent elsewhere.

I think this is a great goal to get off your plate if you haven’t.

Having a bookkeeper means I can look at a high-level at my PnLs, digest the numbers I want to track, and monitor the budget so I can make financial decisions for my business. BUT when it comes to categorizing the Amazon order for the flash drive I needed or hawk-eyeing my accounts for any weird expenditure, those things are off my plate.


I pay about $450 as an S-corp with multiple team members on payroll for this service, but started at $300/mo. as an LLC.

No. 7: Reading

This one’s new to me!

I’m a voracious reader, but I didn’t get really into audio books until this past month. My sister in law and a buddy told me about Libby, an app that just uses your library card to log you in. Hellllooo, free audiobooks (and digital books, but I’m a nerd for book smell so those aren’t my style)!

Related:Energy & Time Management Tips Every Creative Entrepreneur Needs to Know

When I’m folding laundry, soaking in the tub, or washing bottles, I just put on my headphones and listen to a chapter.



No. 8: Editing

A friend texted yesterday to ask if I edit my YouTube videos—I don’t. (In fact, I breakdown exactly how I built my team here.)

I have a contractor on my team who does the post-production, editing, and posting the finished files online. Again, this gets me out of the weeds—it’s truly the part I hated—and lets me focus on the part I really like. I wasn’t even good at editing.

SOOO … to wrap up, that brings me to this question: what’s a part of your client process or workflow you can outsource? What’s a part of it you’re slow with, or just not that great at? The first team member I ever hired was my momma to check every single envelope I calligraphed for accuracy because again, I wasn’t that good at it—I was constantly misspelling things in the stack of 300 envelopes, and she vetted that so we turned in a good client product.


Bonus Tip: How I Built My Team

f you’re bringing on someone, the FIRST place to use their hours is something that is in that 80% of not-your-zone-of-genius. You can start to see this when you find the value of your time.

I’m SUPER passionate about running as lean as possible (I like 55% or less of revenue to go to overhead!), but I can’t do this all on my own—I’d run this into the ground & burn out in a heartbeat! If you’re like me, then, you’re probably ready before you THINK you are—I talk through how I grew and scaled my business to our current team size in this post here. I think this will be REALLY helpful as you start to think through what you can outsource in your business.

Here’s a quick rundown on who’s on my team and what they do— I’ll go in order of hiring:

➕My first hire on my team was my mom 🙂 she’s incredible at etiquette and I hired her to go over and look at all the calligraphy orders that I was churning out (at this point, I did calligraphy and copywriting in my business) She would proof every envelope, flag them for mistakes or notice any etiquette errors, then hand them back to me. She would also pack up the orders and help get them to the brides.

Since I don’t do that anymore, mom is not on my team but she’s always there to lend a listening ear, so I guess she still is.;) Love ya mom 🙂

➕Two copywriters. Next up I hired two copywriters to come on and support the client side of my business. Since then one of them now,( hey, Say;)) manages all of our client services for the agency side of my business. Sarah oversees the intake process of any clients that are coming on that want to work with us in a one on one capacity, whether it is a strategy hour call, a day rate all the way up to our full-service packages. She also manages the workflow of the writers that are helping out on it. ~Nothing~ in my business is written by *one* writer, everything has a team on it and she manages all that.

➕Bookkeeper. I went just over a year before I realized half my Fridays were spent looking at my little Excel spreadsheet, looking at receipts, and then typing up and adding everything. Sooo I contracted a bookkeeping team— still use them to this day.

➕Customer Service/Admin Support. Enter Rachel (fun fact, she was my college roommate). Rach is in the inbox every day. She’s essentially the gatekeeper to any messages that come into the business, any partnership requests, interview requests, customer service things, those all hit her first, and she’s managing and farming those out.

➕Content & Social Media Manager. Anna knows our brand voice and our vision for any of the writing in the business. I talk about this in a recent video, but she comes in as a second writer, but instead of working on client stuff, is focused on in house communication and content.

Now, I also still pay contractors for jobs—YouTube strategy (Trena!) and reporting to Pinterest strategy and reporting (Vanessa), and from Facebook ads (Kerry) to tech support during a launch (Danielle and Shannon).

Steering the whole ship is my integrator Rachel, who I just brought on this year, about my fourth year in business. I loved project management back when I worked in corporate but I realized very quickly that you can’t do project management of your business and run the business. Enter hirisng a integrator.

I know that seems big, but my philosophy is to hire experts. These people have other clients—similar to when I contract out my copywriting services. I only have 4 employees, everyone else is contracted.

If you’re looking more assistance with how to know if you’re ready to build your own team— click here to read through 5 things I would recommend (I learned the hard way) you should do before you outsource and how to build your own team.

If you’re looking for more outsourcing tips, make sure you join thousands and grab my free guide 5 Things to Outsource in Your Business Checklist.



How to outsource tasks and hire in your small business | Ashlyn Writes

Reading Time: 10 Minutes Reading time: 10 min. Awwwwww, yeah outsourcing. Here in this day and time, we have the most workaholic culture in the history of the world. As a Christ-follower, my constant lesson is how Jesus’ unhurried pace stands in stark contrast to our twenty-first-century pace. Part of that for me is learning that B+ work is good […]


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  1. Thanks for this blog and I am impressed with the information that informs readers like me.

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