6 Things I'm Thankful for as a Small Business Owner

I’m very grateful for my canine coworkers.

I’m very grateful for my canine coworkers.

For a long time, Thanksgiving has been my favorite holiday. As an angsty teenager, I grew disillusioned with Christmas and the way we lie to kids about the whole Santa thing. I also worked at Target from age 16 to age 23, and felt increasingly frustrated at America’s consumerism. I’d work on Black Friday and watch people fight over discounted Wiis, yelling at Target team members because we ran out of their favorite season of Breaking Bad on DVD. (Ok yes, these references are making me realize it’s been awhile since I worked at Target! Wiis and DVDs? Wow). 

Thanksgiving became my favorite holiday primarily because of the food. As an added bonus, my birthday usually falls right after it, and gets lumped into the family Thanksgiving celebration. Stuffing, pumpkin pie, and presents? Sign me up.

In recent years, though, I’ve come to appreciate Thanksgiving as a reminder to pause and take stock of everything I have to be thankful for. This year feels particularly special, because it’ll be my first Thanksgiving as a self-employed person. I wanted to reflect on the things I’m thankful for as a small business owner.

1) Helpful Tools & Resources

There are a lot of fantastic tools and resources out there to help people grow their businesses. I took the Creative Class last year, which taught me a lot about processes and efficiency, but I am especially grateful for the Creative Class Slack channel, where I’ve met a lot of other freelancers and formed some friendships. It’s great to have a place where you can brainstorm with other like-minded creatives!

I’m also thankful for Hubspot Academy and the many certifications they offer. I renewed my certifications this year, including Social Media Strategy, Content Marketing, Email Marketing, and Inbound Marketing. Their educational content is fantastic and always up-to-date with the evolving industry.

2) Amazing Clients & Opportunities 

This year, I’ve had the chance to work with some fascinating clients across different industries. I’ll share a year in review post in December, but I’m truly grateful to have had the opportunity to work with such interesting people on meaningful projects. I helped Cameron Community Ministries with a pro bono social media strategy, I got to interview authors I love for Spine Magazine, and I’m even writing email campaigns for a graduate program at Case Western. I love the variety of my work!

I also had some really fun speaking opportunities this year. From co-presenting at Upstate Social this year with my good friend Elise Miklich to leading a workshop on digital storytelling for area librarians, I’m thankful for the chance to share my knowledge with others.

3) Health insurance

One of the main impediments to going self-employed for many is health insurance. Without my husband’s health insurance (and love and support, of course!), I wouldn’t have been able to leave my job to work for myself. As part of our health insurance plan, Tim contributes to an HSA that covers therapy, which has also been invaluable. 

4) Dogs as Coworkers

I’ve had awesome coworkers in the past, and I’ve had aggravating ones. Who hasn’t? But now, my dogs are my coworkers, and that is undeniably wonderful. We go for a walk together each morning, hang out together at lunchtime (on the back deck in summer, or cuddling on the couch in the winter), and sometimes one of them will give me a commiserating look if I’m on a tedious conference call. Can confirm: dogs make great coworkers.

5) Flexibility

A highlight of self-employment has been the increased flexibility. Because I’m not stuck at a desk from 9am-5pm every day, I can run to Wegmans or the post office in the middle of the day, head to a morning workout class, or take a long lunch. I can also work in leggings or sweatpants, migrate from my desk to the couch if I feel like it, or call it quits early and read a book. My workload is variable, and right now I’m in a heavier workload season, so my flexibility has decreased a bit, but it’s something I make sure to appreciate and luxuriate in when I have it.

6) Supportive Family, Friends, & Community

I couldn’t have launched Serve Me the Sky Digital without the support of my family, friends, and community. Rochester is an amazing, tight-knit little city, and my internet friends have been so kind and supportive as I embarked on this journey of self-employment.

Friends like Suzanne, Katya, Devin, Elise, Ana, and so many others have been there to listen to me vent and offer words of encouragement.

And of course, my parents, my brother, and my husband have all been so supportive. Especially Tim- without him to talk through tricky situations, brainstorm pricing, and listen to my excited hopes and anxious concerns, Serve Me the Sky Digital probably wouldn’t exist. Thanks, Tim.

I’m grateful to all these wonderful, supportive humans. At Thanksgiving and always.


What are you thankful for this holiday season? I’d love to hear! Share your thoughts with me on Twitter- just tweet me at @servemethesky. More more insights, anecdotes, and recommendations, check out my unboring email newsletter!