2019 in Review: Highs, lows, and lessons from my first year as a full-time business owner
It’s been 12 months since I took the leap and became a full-time freelance copywriter.
Since then, some days have been amazing and some have been tough, but overall I’m so thankful for this year and the wonderful entrepreneurs I’ve been able to work with.
So, let’s dive into the highlights, struggles, and lessons from 2019; your questions about this past year; and what I’m planning for 2020!
The Highlights
To start, here’s what went well in 2019:
I took my copywriting business full-time – and had a profitable first year!
Even though I’d done a few copywriting projects on the side over the past few years, 2019 felt like the year my business really began.
I wanted to enter in with realistic expectations so I wouldn’t get frustrated or burned out right away. So, I set a goal of getting through this first year without dipping into our family’s savings – and I was able to do that!
Between my income and my husband’s, we were able to cover our month-to-month expenses without touching our financial security nets.
Next year I have some bigger financial goals (like getting back to saving for retirement) but I was proud to earn a decent profit in my first “real” year of business.
I connected with some amazing entrepreneurs.
The best thing I did for my business growth (and my overall wellbeing) was building genuine relationships with other entrepreneurs.
This didn’t mean I approached people in hopes of pitching them or getting something out of our relationship (ew, no).
Instead, I reached out to fellow entrepreneurs from a sincere desire to connect one-on-one and support each other. And it led to some wonderful conversations, helpful insights, and true friendships – as well as leads and clients.
This also led me to attend the Domina Retreat in Austin, TX, this past April with about 15 other female entrepreneurs. It was an incredible opportunity to meet some of my freelancing heroes and to connect with entrepreneurial ladies who were in my shoes—or had been just a year or two ago—and I came home feeling encouraged and inspired.
After Domina, I decided to be more intentional about reaching out to other entrepreneurs (i.e. total strangers) for coffee dates. At first, I was afraid they’d think I was weird or that I wanted to sell them something, but over time I realized that, like me, a lot of people appreciate being able to have an honest conversation with someone who understands what it’s really like to be self-employed.
I finished the year having had coffee dates with about 20 entrepreneurs (both in-person and over video calls) which feels like a huge accomplishment for this introvert. And I’m excited to continue getting to know these business owners (and more new friends) in 2020.
I started using Instagram for my business (and learned so much from it).
For the first six months of the year, I occasionally posted business content to my personal Instagram feed – but I always felt like I was spamming my friends.
When I finally started a separate account for my business, I thought Instagram would be a necessary evil, something I had to do to be a business owner. But I was totally wrong.
Connecting with people on Instagram has allowed me to understand what my audience wants to hear from me and has led to some wonderful real-life friendships (and clients, too).
It’s also pushed me out of my comfort zone; a few weeks ago, I finally faced my fears and hopped on an Instagram Stories video for the first time to share some copy tips. I felt totally awkward, but I received so many kind messages that what I’d shared was helpful, so I’m hoping to get on video more in 2020.
Even though I’ve found it time-consuming to create the posts and content, investing some time into Instagram been well worth it because of the real connections I’ve been able to make there.
I found a joyful new exercise routine.
Since January, my friend Emily and I have been meeting twice a week for yoga classes at our local no-frills gym, and I’ve completely fallen in love with yoga.
I’m not “good” at yoga by any means—I’m not flexible, strong, or balanced by nature—but after spending close to 100 hours on the mat this year, I’ve been blown away the changes I’ve seen in my body and mind.
I have real arm and back muscles now. I enjoy the feeling of stretching. And I can challenge myself in poses that I couldn’t even do this time last year.
Taking a few hours out of the middle of my workday for these classes—two days a week—has been a significant time commitment. But I can’t think of a better way to balance out the stresses (and posture issues) that come with running an online business.
Other highlights from 2019:
I traveled to Portugal in February to help my husband with a video shoot – and we got to explore the beautiful cities of Lisbon and Porto while we were there.
I started working with a proofreader to edit the final drafts of my copy for clients. Knowing that she’ll catch any pesky mistakes that slip through the cracks has given me so much more confidence in the final product I’m delivering.
I continued running (I’ve been at it for about 15 years now) and finished a half marathon on the Portland waterfront with one of my best friends.
I had the opportunity to work with business coach Adam Brantley for the first few months of the year, and I also did a copywriting mentor session with Kayla Hollatz this past summer. Both of them were so encouraging, and their insights and advice helped me move my business forward in more ways than I can count.
The Struggles
This year was wonderful in so many ways, but it wasn’t perfect, and it definitely wasn’t easy. So, let’s get real about what didn’t go so well.
The first six months were slooow.
I worked with just three clients for the first six months of the year. Thankfully, one of those was a long-term retainer-type client, so I was still able to bring in a decent income during those months.
But by July, I was starting to doubt whether my business was going anywhere.
Then, slowly, new leads started coming in – mostly through referrals and relationships (are you sensing a theme here?). And by this fall, I’d finally built up a decent portfolio so I didn’t have to cringe whenever a prospective client asked to see samples of my work.
In the second half of the year, I worked with 9 clients – and I’m all the more grateful for each of them because of the way the year started.
Looking back, I can see that my slow start gave me time to develop my process and work on my business – but man, it was tough feeling stuck in the middle of it.
I made sacrifices financially.
Even though I was proud to get through my first year of business without touching my savings, I didn’t earn as much this year as I did my last job, and that was an adjustment.
Leaving my corporate job meant giving up my family’s only regular source of income, since my husband is a small business owner too. As two freelancers, our health insurance premiums cost more than our mortgage payments in 2019. Ouch.
This past year, I didn’t put any money toward financial goals like saving for retirement, time off, or our next car. (If you saw my current car, you’d know how important and unglamorous that last goal is.) And while I still contributed to our checking account, my husband and I mostly relied on his income to support our lifestyle, which put more pressure on him and his business.
Thankfully, we’re used to living pretty frugally and my income is becoming steadier. And I’ve already budgeted to start saving for retirement again at the start of the new year.
But I wanted to acknowledge that when you make a big financial decision like quitting your job to start a business, it’s bound to have an impact on your family, your long-term goals, and your day-to-day comforts.
I overemphasized productivity.
If you asked me how my day was going anytime this year, I probably responded with something like, “It’s great! I’m checking everything off my list!” or, “Not great… I haven’t really gotten much done.”
I’ve always had this problem of equating my day’s worth with how many hours I worked or how many things I accomplished, but it became even more obvious when I started working for myself.
During work hours, this mindset led me to put client work ahead of everything else; I neglected marketing my business, working on passion projects, resting, etc. And on evenings and weekends, I often found myself thinking or talking about work, even when I thought I was being totally chill.
I know this is a longtime struggle for me, but I want to be more disciplined in this area of my life in 2020 by limiting how many hours I work in a day, setting aside time for my own projects, and keeping the email app off my phone (I deleted it a month ago and it’s already helped SO much).
5 Lessons I Learned This Year
1. Relationships are vital to growing your business. I’ve said it a few times already, but it’s true. Genuine relationships—not awkward “networking connections”—have helped me grow personally and professionally this year.
2. Just showing up can be enough. On the yoga mat and in my business, I learned this time and time again this year. Getting to class, sitting down at the keyboard, taking one small step and then another. Consistent action in one direction can add up to something amazing over time.
3. It’s okay to have a broad niche. I’d heard how important it is to niche down, so I started the year with a very narrow niche: website copy for wellness entrepreneurs. But as a new freelancer struggling to get clients, that niche turned out to be too narrow for me. Halfway through the year, I broadened to serve service-based entrepreneurs, and I’ve loved working with creatives, tech companies, and some wellness entrepreneurs, too.
4. Listening to your clients is key. I tell my audience to listen to their clients all the time, but for most of the year, I wasn’t taking my own advice. I knew my clients were excited about my customer interview process, but I wasn’t putting that front-and-center in my marketing and messaging. When I did, I started attracting clients who were totally sold on my process.
5. Growth takes time. Even though I tried to set realistic expectations for this past year, I secretly hoped my business would skyrocket to success. I’ve been shocked and humbled by the way my business has grown over the past six months, but I know it’s because I put in that slow and steady work for those first six months of the year. Sustainable businesses aren’t built overnight.
Your questions answered
I put out a call on Instagram to find out what you wanted to know about my first year running this business full-time. Here’s what you asked:
“Did you get bored working from home?”
Surprisingly, no!
This was one of my biggest fears when I left my day job; I worried I would become even more of an awkward hermit than I already was. But I found that without the interruptions, small talk, and social pressures of a regular office (#introvertproblems), I had more energy to enjoy time with friends outside of work.
I love working from home with my dog all day, and I know I can always meet a friend for lunch or go work from a coffee shop when I need a break from the quiet.
“How’d you avoid falling into a scarcity mindset when you were just getting started?”
On the days when I felt secure in myself, my worth, and my purpose, this was easy. On the other days… not so much. I could probably write a whole post about this, but in short(ish), here’s what worked for me:
Believing the work would come. As tempting as it was, I didn’t take on projects that weren’t the right fit. Instead, I left my schedule open for the right projects. And eventually, they came.
Accepting that I’m not right for everyone. I realized I won’t fit everyone’s timeline, budget, or idea of what they want from a copywriter. But I’d rather be a perfect fit for my ideal clients.
Connecting with “the competition.” When I stopped seeing other writers as competitors and started seeing them as peers, friends, mentors, and referral partners, I realized there’s plenty of work for all of us. And I’ve enjoyed passing leads to fellow writers whenever I can.
Feeling grateful for every client. I stopped looking left and right and focused on wowing every client I worked with, which led to happy (and returning) clients, successful projects, and more referrals.
Being reminded. Often. I’ve been overcome by insecurity, impatience, fear, competitiveness, and other feelings of scarcity many times this year, but conversations with my husband always help bring me back. For anyone experiencing those feelings, I’d recommend reaching out to a friend, fellow entrepreneur, or mental health professional who can remind you that you’re worth so much more than your next project.
“What was the most unexpected part?”
To be completely honest, the most unexpected part of this year was that it worked.
That the little steps I took in those first 6 months actually led to something. That work I do today is something I truly enjoy (and I’m pretty good at it, too). And that the amazing people I work with choose to trust me with something as deeply personal as their voice.
I still doubt myself a lot, especially when I’m in the middle of a client project and the imposter syndrome monster rears its head. But it gets a little easier with every project, and I’m so incredibly thankful for all the growth, friendship, and confidence this first year has brought.
Goals for the year ahead:
Keep writing strategic, heartfelt website copy for passionate, service-based entrepreneurs
Serve more business owners through additional products and services; I’d love to create copy templates to help DIYers nail their message
Share my knowledge abundantly, without doubting myself so much (looking at you, Instagram Story videos)
Prioritize time for my own content creation; I’m planning to set Mondays aside for writing Instagram posts, blog posts, and newsletters
Send my email newsletter every two weeks… for real (you can sign up here to hold me to it!)
Save $$$ for retirement, time off, and maybe even that new car (when I say “new,” I really mean a used minivan from Craigslist)
Automate more day-to-day activities in Dubsado so I can show up more fully for my clients in the ways that matter
Create a more thoughtful client experience; I love creating a simple, stress-free, and intentional experience for my clients, and in 2020 I’d like to explore ways to take that experience up a notch or two
Continue connecting with other entrepreneurs in-person and online. Always.
Here’s to 2020!
Thanks for being here and helping me celebrate this year! Do you have a lesson or an accomplishment from 2019 you’d like to share? Tell me on Instagram! @kelseyohalloran.