Celebrating One Year of Serve Me the Sky Digital
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A celebratory cookie cake baked by my husband, Tim 🥰
It’s been just over one year since I went full-time with my business. On May 6, 2019, I sat down at my grandma’s old desk in the guest room, booted up my new MacBook Air, opened up the Gmail business account I’d just created, and wondered, “What the heck do I do now?”
The good news is, I figured it out, slowly but surely. Day by day. One of the many tricky things about working for yourself is that there’s no go-to person you can ask for all the answers. I’m lucky to have awesome self-employed friends who were always down to brainstorm, a super supportive husband, and a great community of people cheering me on.
When I quit my day job, I had just 2 clients on retainer. That was it, and I was terrified. The stats look a little different now: I worked with 44 clients in my first year of business. There was a lot of variety to my work: 12 writing projects, 10 nonprofits, 9 one-on-one consultations, 6 paid speaking engagements, 2 higher education institutions, 2 small businesses, 1 startup, 1 political candidate, and 1 multinational corporation that I can’t talk about (yet) because of an NDA.
A sampling of the clients i worked with in my first year of business
I’m really proud of everything I’ve accomplished with my business in this first year. So today, I’m taking an opportunity to look back and reflect.
What I Love Most
I did a trivia game on my Instagram Stories to quiz people on fun facts about my business. One of the questions was about things I loved most- and it was hard to narrow down the list, because there’s so much I love about being self-employed!
Flexibility
The flexibility of working for yourself is pretty fantastic. In the past, I’d stressed about taking a long lunch or meeting someone during the workday to do an I Heart Roc interview over coffee. I constantly felt guilty. Now, as my own boss, I don’t have to worry about that! I can come in later, read a book for an hour over lunch, or call it quits at 4pm if I feel like it. Sometimes I enjoy my work so much that I fail to take advantage of the flexibility, but that’s another issue entirely!
Choice
Hands-down, the best part of running my own business is having the opportunity to choose who I work with and what kinds of projects I work on. I’m almost never bored, because I pick work that I find engaging and meaningful. I feel so grateful that I get to this every day! There are some projects that get tedious after awhile, or aren’t 100% up my alley, but for the most part I’m thrilled to get to do work I genuinely enjoy.
My Biggest Challenges
As I mentioned before, it can be tough not having someone else to look to for answers. That’s something I still deal with, even one year in. A fellow business owner once told me that by the 18-month mark, that starts to wear off. We’ll have to see if that holds true come November!
Figuring out Fit
I never would have guessed it would be so hard to figure out which opportunities are right for me. A lot of opportunities have come my way, and some are truly a terrible fit. And in some cases, I’ve had to learn that the hard way, by trying it and having a crappy experience. Sometimes it’s a bad fit interpersonally, sometimes it’s the work itself, or the organization. Either way, I think I’m getting better at vetting opportunities. I’ve always had a hard time saying no, but I’m working on it!
Pricing
Folks who are new to freelancing often ask me: how do you figure out how much to charge? That’s still a challenge for me! There are so many variables that go into making the decision. It depends on the scope of the project, the type of organization, how much research is required, how much time, how much expertise. That’s why I don’t publish rates on my website--I customize proposals for each prospective client based on a conversation. I’m getting better at this with practice!
Estimated Quarterly Taxes
Last but not least, figuring out estimated quarterly taxes has been a pain. I don’t think many non-self-employed folks know about this! When I filed taxes for 2018, before I had gone full-time with my business, I realized that estimated quarterly taxes were a thing. I learned my lesson and had to pay a penalty. I did better for 2019 and paid my federal estimated quarterly taxes each quarter, but not the state ones. And my Quickbooks estimates always seemed a bit off, so I still underpaid a bit on the federal level. I’m going to keep working at this one, but I may soon need to hire an accountant!
Surprises Along the Way
Strategy versus Management
One surprise I’ve run into is that I prefer working on social media strategy projects to social media management. I love all things social media and always enjoy following the latest trends, staying up-to-date, and thinking critically about what makes great content. But the day-to-day management of a brand’s account isn’t my favorite task. It requires you to be tethered to your phone, constantly checking and responding to comments and messages, which can be draining. I started working on more strategy projects this year with a variety of different nonprofits and that’s something I hope to do more of as I move into my second year of business!
Sending the SkyMail Club
Back in September, I launched my own monthly newsletter. I was nervous! I’d written newsletters before and often found it to be painful, tedious, and predictable. But I knew that email is one of the only things you truly own, compared to a social media platform that could be shut down at any time, so I decided to give it a try.
Turns out, writing the SkyMail Club newsletter each month has been one of the most fun parts of running my own business! The newsletter is a really unusual and fun mix of stuff; I always include book recommendations, songs and podcasts to check out, social media tips, interesting articles, and funny TikToks. It’s basically just a curated selection of things I like that are thought-provoking or entertaining, and it’s a great way for me to stay connected with my audience. I’ll definitely be keeping that up, and may even bump it up to twice a month!
Public Speaking
When I worked in financial aid at my alma mater, I had to do a fair bit of public speaking. I’m pretty comfortable with it, and once I started doing it for my business, I leaned in and started loving it!
I had six paid public speaking gigs during my first year running my business, and they were so fun. I even did custom workshops for some local organizations! As a college student, I thought I’d be a teacher someday, but when I student taught, I was frustrated by how some kids didn’t seem to want to be there. When I started teaching workshops, I loved that everyone genuinely wanted to be there! It’s refreshing to have an engaged audience that participates and asks great questions.
One of the downsides to public speaking is that you’re putting yourself out there, which can be nerve-wracking! Every time I’ve taught somewhere like the Rochester Brainery or 540WestMain, I obsessively check to see how many tickets I’ve sold and hope it’s not a poor reflection on me if it’s not “a lot.” I also struggle with reading comments submitted on feedback forms--I internalize the negative ones and ignore the positive ones! I can’t believe some of the things people write on those forms. I’m trying to get better at taking those comments with a grain of salt!
Kicking off a custom workshop for the rochester regional library council
Treat Yourself as Legit
When I started my own business, I never realized that one of the key components of being taken seriously as a business owner is to simply… treat yourself as legit! We all have feelings of impostor syndrome sometimes, but we can’t let them rule every moment of our professional lives. A lot of how I market my business is tied to myself and my personal brand, but I try to keep it real. I’m honest about my challenges, and I celebrate my wins, big and small. I never discount my business or try to make it seem less-than. I don’t downplay my successes. I treat myself and my business as legit, but at the same time, I try not to take myself or my business *too* seriously. Because what’s the point if you can’t have fun?
Book Club
While it’s not directly related to my work, I did start a book club this year, and I love it! It’s been a great way to meet people and discuss awesome books. It’s not a marketing play necessarily, but it’s a nice way to stay connected, especially during COVID-19 when we’re all stuck at home.
What I’m Looking Forward To
It’s hard to look ahead in the midst of a global pandemic! So many events have been canceled and the world is a totally different place now than when I quit my job a year ago. Plus, goal setting doesn’t come naturally to me. I love to get things done, but sometimes it’s hard for me to step back and figure out precisely what I’m hoping to achieve. When I do mull it over, four things come to mind:
Strategy work. As I mentioned, I really enjoy working on strategy projects. I especially love working on social media strategies for nonprofits. I help them review what’s working, what’s not, and what peer organizations are doing, then I provide recommendations on best practices and creative tactics they can utilize to achieve their goals.
Writing projects. This past year, I did some really neat writing projects, particularly with higher ed clients. I have a master’s in Higher Education Administration and spent four years working in higher ed, so I’d love to do more writing for higher ed clients!
Fun writing. I was super proud to get bylines in McSweeney’s, Bustle, and Spine Magazine! I’d love to do more fun writing like that in the future. It doesn’t pay the bills, but it’s always a blast to do more creative pieces, particularly humor writing.
Online courses. Since I’ve enjoyed teaching workshops so much, I’d love to launch online workshops or even my own course someday. It’s a long-term goal for sure, but definitely one I’m interested in pursuing!
Thanks so much for reading, following along with my journey, and supporting me every step of the way! I can’t wait to see what my next year of business will bring. You can stay up to date on my self-employment adventures by signing up for my unboring email newsletter.
