Celebrating 4 Years of Serve Me the Sky Digital

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Celebrating 4 Years of Serve Me the Sky Digital

This May marks four years of running my own business full-time. A four year anniversary may not be a big deal to some, but it feels important to me. Four years of successfully running my business, even through an unprecedented global pandemic and economic turmoil? It is a big deal!

As I said in my newsletter this week, running Serve Me the Sky Digital is the most satisfied I’ve ever felt in my work life. I spent four years in higher education and earned a master’s degree in educational administration, then pivoted to nonprofits and worked in marketing at a startup incubator. I learned a lot at those jobs, but both were not a great fit for me.

Since diving into self-employment full-time, I’ve had opportunities I never would’ve guessed would come my way and have been happier all around. Glowing testimonials from clients I love working with make me proud of how far I’ve come and thankful to be where I am in my career right now. 

Let’s get into some of my favorite projects, lessons I’ve learned, and a glimpse ahead!

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Celebrating 3 Years of Serve Me the Sky Digital

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Celebrating 3 Years of Serve Me the Sky Digital

It’s hard to believe that this month marks three years of running my own business. Strangely enough, this is the third business anniversary I’ve celebrated during the COVID pandemic. My first business anniversary was a few months after the pandemic started, in May 2020, and the second was in May 2021, just as we were all starting to get vaccinated. It’s certainly been a challenging time to start and sustain a business! I’m grateful to all the amazing clients I’ve worked with along the way who have made it possible for me to continue on this fulfilling journey of self-employment.

Without further ado, I’ll share with you some of my favorite projects from the past year, lessons learned along the way, and what I’m looking forward to in the future.

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Celebrating 2 Years of Serve Me the Sky Digital

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Celebrating 2 Years of Serve Me the Sky Digital

Picking a business anniversary is a funny thing. There are many dates I could have chosen: June 2017, when I signed my first freelance client. July 2018, when I got my DBA. But the day I chose to celebrate is May 6th, because that’s when it felt most real. That was the first day I sat down to work for myself full-time after walking away from my stable day job.

When I celebrated this milestone last May, we were two months into a global pandemic that no one would have guessed we’d still be living through a year later. Running a business during a global pandemic is hard! It seemed that with many organizations, when times got tough, marketing was an easy thing to slash from the budget. To get me through a slow time, I picked up some part-time work as a contact tracer, which was fascinating and engaging. Business has been ramping back up, and I’m so excited about that!

In addition to running a business during a global pandemic, I also had to navigate doing so while helping care for my mother as she declined due to stage 4 cancer, then grieving and taking bereavement time while self-employed. This year was a lot to handle. I’m proud that my business is still standing here strong today, after a super difficult year.

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On Taking Bereavement Time as a Freelancer

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On Taking Bereavement Time as a Freelancer

This topic is unusual for a business blog where I typically talk about marketing and social media strategy, but I thought it would be interesting to explore and helpful for other freelancers going through similar situations. In late February, my grandma passed away at 93 years old, and in early April, my mom died of cancer at 59 years old. Hell of a way to start the year! Not working at a traditional company where I could check in with HR and get standard bereavement time, I was uncertain about how I would navigate taking time off to grieve. Here are a few things that worked for me over the past few months:

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Celebrating One Year of Serve Me the Sky Digital

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Celebrating One Year of Serve Me the Sky Digital

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.

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.

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2019 in Review

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2019 in Review

It’s hard to believe that 2019 is coming to a close already. A lot has changed this year. Back in January, I was working full-time at a startup incubator. As I close out the year, I’m sitting at a Wayfair desk in my home office with my dogs snoozing nearby. 

I wanted to take some time to pause and reflect on everything I’ve achieved this year (at the risk of sounding braggy), because it’s important to remember how far we’ve come and to celebrate it. And besides, as a self-employed person, no one else is going to celebrate for me! Let’s do this:

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

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

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.

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6 Lessons from My First Month of Self-Employment

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6 Lessons from My First Month of Self-Employment

Today I’m celebrating. Why? It marks the one month anniversary of me leaving my full-time job to pursue the great adventure of self-employment. No regrets so far! I’m trying not to let myself wear rose-colored glasses all the time; working for yourself can be lovely, but I know it won’t always be easy.

I’ve learned a lot in the first month (and I know there’s more to learn ahead!). To celebrate the one month milestone, I’m sharing a few of the lessons I’ve learned so far.

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