Kelsey O'Halloran

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My 2020 year in review (and 4 lessons you can use to grow your business)

I don’t know about you, but I think 2020 was the year that refined us.

It pulled us out of our comfort zones and pushed us face-to-face with our fears.

It stripped us of everyday luxuries we used to take for granted – things like coffee dates, gym workouts, hugs from family, and celebrations with friends.

It took away so much.

And yet, it offered so much in return. Clarity on what truly matters. Permission to slow down. Confidence that we can do hard things.

Probably a lot like you, I’ve grieved this year many times over. But at the same time, I’m so deeply grateful for everything it’s taught me.

So, today I’m diving into a review of this past year – to reflect on the big takeaways and hopefully give you some inspiration to build and grow your business in the year to come. Let’s dive in!

4 business lessons I learned in 2020

Every client is a gift.

I’ve always said I’m grateful for my clients, because it’s true. But this year I’m feeling it on a whole new level.

In 2020, I had the opportunity to help 20 entrepreneurs craft clear, strategic, and heartfelt copy to grow their businesses – which, let’s be real, was an amazing opportunity in and of itself.

But in a year when so much was unknown, the economy was crashing, and my husband was largely out of work in the wedding industry, these clients allowed us to continue putting food on the table and paying our bills (not to mention growing my business to new levels).

Thanks to them, my husband and I were able to keep our savings intact, take occasional time off to rest and recharge, and continue planning for our future dreams.

It really is true that every time you support a small business, you’re supporting a family.

So this year, I’m over-the-top grateful to the business owners who entrusted me with their voices – and it’s been an absolute honor to be a part of their growth, too!


Ebbs and flows come with the territory.

I used to be terrified of slow seasons in business.

If I sensed one coming on, I would kick things into overdrive and do whatever I could to fill the gaps in my calendar. Deep down, I think I was afraid that if the work slowed down, it wouldn’t be long before my whole business fizzled out along with it.

So, when COVID-19 hit the U.S. this spring and my inquiries suddenly froze, I found myself coming face-to-face with some of my biggest business fears.

And here’s what I found out: I could slow way, way down – and I would still be okay.

That slow season only lasted for a month or two, but it gave me time to streamline my systems behind the scenes, to innovate new ways to serve my audience, and to simply take a breath and remember what it felt like to be a human, not a machine.

And when the work picked back up, I knew I didn’t have to go back to my frenzied pace.

I’ve realized this year that instead of fighting to keep work from slowing down, we can lean into all the different seasons of our businesses.

Because those ebbs and flows aren’t just natural, but necessary. And slowing down might just be your biggest catalyst for growth.


Being an entrepreneur means having the freedom to change your mind.

It seemed like such a good idea at the time … 

Earlier this year, I launched a new service: a one-day “copy refresh” for entrepreneurs who didn’t have the timeline or budget for a full website copy overhaul.

I was excited to offer a faster alternative to my typical four-to-six-week process. And my clients seemed to love it.

But after a few months of incorporating this package into my offerings, I started to realize something was off.

Because here’s the thing – I’m a “deep-dive” person. I don’t want to hang out in the shallows; I want to pour hours into getting to know you and your brand so we can craft a true-to-you message that turns readers into your dream clients.

And I realized that when it came down to it, I wanted so much more for my clients than a simple copy refresh. I wanted them to walk away empowered, with a clear, strategic message they could use to grow their business for years to come.

It’s not that the one-day refresh was “bad” or that it didn’t serve my clients. I’ve heard nothing but great feedback from those who went through the process, and I’m proud of the results we’ve created together.

It’s just that the way I was offering it at the time didn’t fully align with my deeper purpose of wanting my clients to feel seen, heard, and known through our work together, and to walk away feeling empowered to use their voice.

But here’s one of my favorite things about running a business: if we don’t like something, we have the freedom to change it.

So, even though I ended up retiring my copy refresh service, it led to two new services my clients and I truly love:

  • The Clarity Intensive – a copy consulting intensive where we deep-dive into your messaging strategy and develop your unique brand message, so you can write your own content with ease, not overwhelm.

  • A day rate service for my returning clients, so we can continue using the strategic foundation we’ve established to grow their businesses and tackle any copy projects on their to-do lists.

All that to say, sometimes a “failed” experiment is the best way to find what feels right for you and your business. So don’t be afraid to try something new – you never know where it might lead you.


We’re better together.

You know what really made all the difference in my business this year? This community of entrepreneurs.

From those who brought encouragement in the toughest moments of 2020 to those who shared their gifts and helped my business grow, I can’t imagine this year without the conversations and collaborations I’ve been able to have with these amazing people.

A few of the highlights included:

  • Being interviewed on a podcast for the first (and second!) time – thanks for having me, Hannah Murphy and Alora Rachelle!

  • Streamlining my client experience (and saving myself so much time and headspace) through Charlotte Isaac’s incredible Dubsado DIY program.

  • Hiring Becca Koebrick Design Studio to seriously upgrade my brand identity. I can’t recommend her work or her incredible process enough!

  • Starting work with my amazing coach, Amanda Joyce Weber – she’s been an absolute game-changer in shifting my marketing mindset and becoming more confident and effective as a business owner.

  • Hiring my first virtual assistant, Caitlin Powell! I’m so excited to have a wonderful team member on board to help me be more consistent in my marketing, show up fully for my clients, and maintain a healthy work-life balance.

  • Connecting with so many other fellow copywriters, creatives, and business owners through DMs and coffee dates.

Business is so much better with friends! From the bottom of my heart, thank you for being part of my community this year – and for welcoming me into yours.


Looking ahead to 2021

I know most of us just want to be done with this year already – but I hope we’ll take some of it with us into 2021, too.

I hope we’ll continue to see every single client as the gift they are, to welcome seasons of slowness, to embrace our freedom as entrepreneurs, and to lift one another up every chance we get.

In 2021, I’m looking forward to serving a smaller number of clients, but on a deeper level.

I’m excited to launch my first digital products to help entrepreneurs write their own website copy with ease (more on that coming soon, I promise!).

And I truly can’t wait to see what another year of this small business adventure will hold.

Curious about how we could collaborate on website copy and grow your business in 2021? I’d love to chat with you! Book a free Copy Chat call with me to get started.


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