One Year of Olivia Smith Design

Lessons learned in my first year of full-time entrepreneurship

So much has happened in the last year, it’s wild to take a moment to reflect on how my life has changed. My husband Uriah and I moved from Franklin, Tennessee to central Virginia, re-established ourselves with our family and friends here, and had our very first baby, Abel Uriah. The launch to full-time business came out of necessity for us; I had two major job transitions, one of which was a bit unplanned, and Uriah was looking for work in Virginia. I began cold emailing clients asking if they had any work, and let me tell you, the Lord provided for our family in the most beautiful and unexpected ways. Below you’ll see the day I bought my MacBook for the business, the day we left TN to move to VA, my first baby bump photo, and my original desk set up 🤎

The day I bought my Macbook for this business.

I was able to find a groove with both retainer clients who paid monthly fees to use my services for whatever they needed, but also work on a handful of other projects, from visual identity design to website design to publishing projects. I LOVED every single project that came across my plate. I get the joy of consistently working with women’s ministry, female entrepreneurs, and small businesses, all of which I love dearly. But truly the best part is that I get to stay home with Abel. We’ve structured our days so I can design, take meetings, do admin work, etc. during his nap and occasionally I drop him off at my mom and dad’s house and work from a coffee shop. Uriah has been helping a ton too, as he’s home more frequently in this season of life.

Anyways, let’s get to the reason you came: here are some lessons I’ve learned throughout this past year:

DON'T BE AFRAID TO send COLD EMAILs.

This is how I landed one of my biggest retainer clients. I had done work with them in the past and decided to go out on a limb to see if they needed any design help, and I believe God had that relationship perfectly aligned. They did need work and the best part, they needed women’s ministry work (which is my favorite). Because our work relationship was healthy, I felt confident reaching out. In fact, I still work with them today!

Have savings in place before taking the leap.

This is a big one. Uriah and I tucked money into savings to cover a few months of expenses while I built the business and he looked for work. Thankfully we never needed to touch that money and later used it for maternity and baby expenses when Uriah had a job, but knowing there was a cushion of money gave us peace of mind. I’d recommend a minimum of three months of expenses before taking the leap.

Try a few different things so you can figure out what you like to do!

I used to offer design retainers, illustration packages, layout packages, branding, etc. etc. After spending a solid year doing this, I’ve learned that I prefer more big projects (a visual identity) with 1-2 retainer clients, versus more retainer clients and the occasional big project. I like the reliability of retainers because you can plan your income and expenses a bit easier, but I love that big visual identity projects last a few weeks and require a lot of detail. Now I only have 3 offerings: visual identities, Squarespace design, and print design. No one booked illustration packages so I nixed that. In fact, to be candid, the one illustration inquiry I had chose to not book because of my contract!

Have a client management system (I use HoneyBook).

I. Love. HONEYBOOK. It is my central system for invoicing, contracts, project proposals, and so on. I love that I can send everything in one go to clients and even set up payment plans for them. Say goodbye to the days of invoice PDFs and Venmo payments (in fact, I’d never recommend to use Venmo for your business-but that’s just me). Each client has their own portal and all communication can be kept in HoneyBook for a very organized flow. You can even see when clients open your invoices, contracts, messages, etc. I don’t have an affiliate link, but I do have a code here if you’d like to try for yourself!

Having a devoted workspace, preferably next to an espresso machine, can help with work-from-home boundaries.

Working from home can be a beautiful gift, but also insanely hard with the boundaries of work and home life. I’ve set up a very specific place in our home where I get work done. We bought a cheap standing desk of Amazon and my brother built me some great storage for my birthday. I like the separation so I don’t get distracted by laying on the couch or in bed with my laptop. It’s just me, my laptop and monitor, a keyboard, Adobe, and my beloved espresso machine to the left of my desk for quick caffeination. It’s important to me to remember that I run a business and need to show up like I would to an in-office job, so I try to do my make-up, get dressed, and be at my desk by 9:30 AM every day (right after I put Abel down for morning nap).

Keep your weekend sacred.

If you’re boss told you to come in every weekend, you would be upset, right? Therefore, I strive to keep that same rule in my business. Weekends, with the exception of very specific scenarios, are sacred in my home. I do not touch client work from Friday at 6 PM to Monday at 9:30 AM. Weekends are for my family, for recharging, for going to the farmer’s market, for shopping, for reading, etc. etc. It can be so easy to just respond to that email, to do that quick design change, to…the list goes on. But for the sake of my sanity and my family’s health, we don’t do weekend work. Now, did I respond to some emails this past Saturday? Yes, I did. Because Abel and I took Friday off to go shopping with my mom, so that was part of my weekend for me. But overall we strive not to be in work mode on weekends.

Ask God for help, for provision, and for wisdom.

Time and time again, I have felt fear and anxiety over the unknown with running a business and irregular income. But I’m not kidding, every time I have prayed for God to provide and sustain our family, He has shown up! Now I don’t believe in the “prosperity gospel” but God has not failed to provide for us financially in the exact amount we need every time. He has always brought the right client and the right project at the right time. I want to be more intentional about praying for this business and for my clients because at the end of the day, this business belongs to God for His Kingdom work. Every time I’ve asked Him to shut the door if this business is not His will for me and our family, He opens the door wider. This is God’s business and I’m eternally grateful to steward it.