Anna Vos is an old friend whose adult life I have followed with great interest. We grew up in the same neighborhood and took a lot of the same classes through high school, then moved in opposite directions out of our hometown for college. Even now, we share an affinity for big glasses and short haircuts, which makes me think we’d still have things to talk about if we ever found ourselves in the old neighborhood at the same time.
Anna trained as an opera singer at Roberts Wesleyan College and since then has been living a delightfully creative life in Rochester, NY with her husband and two kids. I’ve seen her spin cooking, singing, and most recently, calligraphy into small business ventures. Because I’ve been so apprehensive about what skills I could actually use to start a business, I asked Anna to share her experience as an entrepreneur with wakeupshakeup. Read on for her thoughtful, candid, and gracious advice!
Do you identify as an entrepreneur or do you prefer another descriptor?
I suppose entrepreneur will work as an adjective. My husband recently called me a “serial entrepreneur,” which I initially took as an insult, assuming he meant I start things but don’t finish them, but he assured me he just thinks I have a lot of good ideas. 😉
You’re a woman of many talents. Tell me about your business(es).
My full-time job is taking care of my kids. I have a three-year-old girl named Ruby, and a six-month-old boy named Rory. They are pretty cute and fantastic and utterly frustrating, but being their mom and full-time caretaker is the best job I’ve had so far. I also own Owl Post Lettering, my Etsy shop and by far my most fun side hustle. I teach bi-monthly pierogi-making classes (and soon brush calligraphy!!) at the Rochester Brainery, which is this super cool community classroom and art space in Rochester. I started taking classes there a few years ago (gnocchi! embroidery! cake decorating!), and applied to teach pierogi, which has been very popular. I also maintain a very small Mary Kay business.
Maybe the last time we saw each other in person, I remember talking about how you wanted to open a bakery, so you’ve long had some entrepreneurial ambitions. What appeals to you about running your own business?
Ah, the bakery…that was a big dream. I do love to bake. I love to feed people. You know what I don’t love? The incredible amount of money and risk involved in opening one’s own bakery. And 4am. I hate 4am. And if you’re a baker, you have to get up really early. So…no. Or you can do it out of your home, but you have to clear tons of hurdles and there’s all kinds of regulations and it’s just. so. hard. Plus, if you’re charging for your time in addition to materials, which you absolutely should be doing, the prices really have to be high, since you’re not making things in bulk as a single baker. So now I just bake for friends’ birthdays and I can leave my kitchen a mess and not get up at 4.
I think, in a lot of ways, running your own business is both appealing and terrifying. Opening a proper brick-and-mortar-type place would probably not be a good fit for me, especially right now as a stay-at-home mom, but with something like an Etsy store, I can do it from home. Plus my Etsy shop is a great excuse for me to buy art supplies and make pretty things for people. I just sent a piece to Australia last week! It’s all very exciting.
How did you end up in that space after studying opera in college?
After college, I ended up in a space of really not knowing what I wanted to do, but knowing I didn’t want to pursue opera professionally any further. I realized it wasn’t particularly healthy for me to be in an industry where you have to be almost ruthlessly self-promoting, and that I wanted something that had more normal hours and a more normal lifestyle than what you can really expect from a career in opera. Also I really hated to practice. (red flag! haha) I did as much as I needed to get by for my studies in school, but not much more, so that career just wasn’t the right fit.
At this point in my life, I’ve been trying to focus on things I really love. My kids. I love being home with them, most minutes. It’s challenging, but changes all the time, and I love watching them grow up and being there every day. I did really love baking for a long time, and I still love it as an extra-curricular, but it’s a relief not having to try to make money off it, honestly. I love lettering. I think I’m decent at it, and I am constantly trying to make more time to practice it. I’m pretty sure I practice this way more than I ever practiced singing in college (sorry, professor!). I’m even going to teach a class on beginner brush calligraphy in October at the Brainery! The first class sold out, so we have more dates scheduled in November and December. Lettering is so big right now, but it can be really overwhelming to try to entirely self-teach. I took one online class, and I’m looking forward to providing people a more streamlined way to learn the basics in person.
Are you working for anyone else right now? If so, what do you do there? If not, what was your last full-time occupation?
In addition to the gigs I’ve already mentioned, I also work one night a week playing music at group homes for disabled adults. The residents are really fun, and it’s nice to have something that takes me out of the house. It’s also been nice for my husband to get some one-on-one time with our kids. My last full-time job was working as an administrative assistant at my alma mater, which I loved. Before that I did customer service and waited tables.
What was your first business venture?
My first business venture was my little illegal home bakery. I named it Brown Paper Bakery and made cookies and cakes for friends and family. That was while I was working customer service at a payroll company, which was soul-sucking. Baking helped keep me sane. And now lettering gives me that same courtesy without all the dishes to wash.
What didn’t you know about starting a small business when you began, and how did you learn it?
What didn’t I know…I had no idea how to do small business taxes, but thankfully, my husband LOVES doing numbers and taxes and thinks it’s fun and is a weird guy. 😉 I’m the idea girl, not always very practical. He’s been super helpful, especially in our Mary Kay business, doing much of the administrative work and working to figure out what inventory we should keep, when to run sales, etc. For my Etsy shop, it’s very low-key still. I really only work on one thing at a time, and then it gets shipped out and I get to post it on my Instagram and feel very cool, but there’s not a lot of administrative work to be done on the back-end just yet. I have been hoping to have time to make more things to list in my shop, but only have a few available now and mostly work on commission. I actually just planned a “make-cation” in November with some friends, so hopefully I can make some big progress that weekend. My husband and I are also currently figuring out the best way to get some calendars and other gifts printed for Christmas.
Who helped you along the way?
My biggest helper is my husband, Elliot. With anything I’ve ever wanted to do, he is so helpful with figuring out what the reality of that looks like, and how best to do it, or if it’s feasible and responsible. He is encourager, numbers guy, and ready to be with our kids. If we’re also talking resources, Instagram has actually been a huge resource in learning how to hand-letter. There is a massive community of surprisingly encouraging letterers all learning from each other, and that’s been really fun to be a part of. It was actually our mutual grade school friend Melissa who inspired me to start lettering. I have always loved the aesthetics of words and writing, but I assumed it would be really hard to learn. She encouraged me to give it a shot, and I’m so glad I did.
(Ed note: I did some Facebook creeping and Melissa has a photography business. Get it, girl!)
What was the biggest surprise for you in building your business?
The biggest surprise to me in regard to what is now my lettering business is that people actually wanted to pay me to make things for them. I have never thought of myself as a visual artist, so the fact that my lettering was interesting to anyone and valuable to anyone was both surprising and flattering. I only opened my Etsy shop because friends kept asking me to make things, so I thought maybe it would be fun to use that as a tool for organization and to widen my net, so to speak. Also, now that I’ve actually thought about it, I have to say I’m a little surprised as to the number of balls in the air. I don’t really think of myself as some kind of worker bee, but apparently I like to work a little bit at a time.
What do you like and what do you dislike about working for yourself?
Oddly, I tend not to think of working for myself, perhaps because my day job doesn’t pay. 😉 I think the hardest part about these side hustles, though, right now, is making time for them. I try to get some lettering practice in every day, but most days it takes both real determination and ignoring some other tasks to do it. I have scaled way back on my Mary Kay business because I just don’t have it in me to be on the phone all the time and booking appointments at night, when I want to be with my family. Lettering is nice because I can do it for a few minutes at a time, during nap-time, watching Netflix, etc., and I can think about a piece in my head all day and then get it on paper in the evenings. So even though I’m not making a lot of money doing that, it’s the most fun, and the easiest to fit in. I would love to see it grow in the next few years.
Do you have any advice for other people thinking about starting up their own business?
My biggest piece of advice is to just go for it! Especially if you’re making things and on the fence about starting up an Etsy shop — there is hardly any risk involved at all. There’s a really small listing fee, and they get a very small portion of your sale, so there’s not a lot of downside to opening an Etsy shop, even if you end up never selling even one piece. Other businesses probably deserve a bit more consideration. Are you willing to work really hard to see any return? Are you willing to go out of your comfort zone? What are you willing to lose if it fails? Those are good questions to ask yourself. My husband helps with the numbers questions. With Owl Post Lettering, it’s a no-brainer. I use my “fun money” to buy supplies, and then I get repaid from my sales. There’s not a lot of risk. With our Mary Kay business, we keep a bit of an inventory, and so we have to be careful about how much we’re selling, ordering, etc. If we had started a bakery, that would have meant a huge lifestyle change, not to mention a large loan, and the risk of losing a lot if it failed. It’s all checks and balances, and, corny as it sounds, following your heart.
One million thanks to Anna for her time and thoughtful responses! All photos via Facebook.
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