We recently connected with Jenn Prochaska and have shared our conversation below.

Jenn, looking forward to hearing all of your stories today. We’ve love to hear an interesting investment story – what was one of the best or worst investments you’ve made? (Note, these responses are only intended as entertainment and shouldn’t be construed as investment advice)

It was a cold and rainy morning. I stood there shivering with my daughter as we waited for the school bus to arrive. When it did, I watched her climb aboard and stood there waiting for her to wave once she sat down. She didn’t. She didn’t even look at me. She was still mad, and she’d been mad for weeks.

I couldn’t blame her.

My 3-year-old copywriting business was booming, but I had more work than I could handle on my own. I’d brought in other writers to help but I was still working day and night. Before I knew it, I project managing more than writing. I hate project managing.

And I was crabby. Every day, all day, all I thought about was work. Rather than play with my two daughters, I worked. I was burning out.

I kept thinking I need to do better. Work harder. I’ll work just this evening turned into every evening, which is why my oldest was mad at me.

At least I’ll make a lot of money, I thought. Only not so much — while my business earned more revenue than ever before, I actually took home less than ever before.

That was it. Something had to change, but I didn’t know what.

That’s when I made the best investment of my entrepreneurial journey and joined The Copywriter Club mastermind.

The “Think Tank,” as it’s called, is led by two wildly successful copywriters who bring together copywriters from all over the world at various stages in business. We were all balancing working ON our businesses with IN our businesses. With my 12-month membership, I received private coaching, and on the very first call, two things happened. One, I cried, releasing all my built-up tension and two, I got some serious clarity.

Through that mastermind experience, I was empowered to niche into foundational brand messages for small businesses. It’s the work that brings me the most joy. I also gained a community of supportive writers, all rooting for each other. My operations (or lack thereof) became a central focus, enabling me to streamline how my business runs. We were coached on mindset, which shined the light on thought patterns that were no longer serving me.

“I need to do better and work harder” became “I need to do differently.”

I learned how to set and keep boundaries.

I got my life back. It was by far the best investment in my business and myself I’ve made thus far.

I still remember the day my daughter waved goodbye on the bus. Not only did she wave as the bus pulled away, but she kept waving until we physically couldn’t see each other. We reconnected — I reconnected to what’s important, and I’m never letting go again.

Jenn, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?

As a Message Strategist + Copywriter, I help businesses define their foundational brand messages and voice. It’s too hard to do it for yourself. I should know! I’ve hired writers to help me define my own.

Effective marketing starts with messaging that’s differentiating, authentic and consistent. All content creation comes from these foundational elements. It’s like having your passport to the world, which is why I call my signature service The Message Passport.

Through my Message Passport process, my clients gain insights and clarity. Included are voice of customer interviews, message mining and analysis, and a brand voice finder session. I create their Guiding Force, Brand Promise, Unique Value Proposition, Brand Positioning Statement and One Key Message. They also receive a robust Brand Voice Guide, detailing everything from word choice and punctuation to cadence and readability.

Anyone writing or creating on behalf of the business should follow this Message Passport, so every single message is aligned in tone and content.

From there, I write their website (optimized for search), and for a few select clients, we write blog posts and emails.

I’m most proud of creating something like the Message Passport because it helps small businesses market like the big brands.

We often hear about learning lessons – but just as important is unlearning lessons. Have you ever had to unlearn a lesson?

As the daughter of entrepreneurs, I grew up knowing what it’s like running your own business.

I specifically remember my parents loading my younger sister and I into the minivan in the middle of the night. A delivery had to be made. Whoever was supposed to make it couldn’t do it on time, so my dad was going to make it. Whatever the customer needed, he did.

He followed two axioms:
The customer is always right.
Always stay flexible.

Fast forward a couple of decades, and as a business owner, I found myself drowning. I was trying to ensure the customer was always happy (because they’re always right) by flexing with whatever they needed. That’s fancy talk for I had zero boundaries. My work / life wasn’t balanced, and I felt pulled in multiple directions. At the end of the day, my work suffered, so no one was winning.

It was a mindset coach who pointed this out to me. I had to learn that clients (when they’re the right ones) will happily respect my boundaries as long as I’m clear in setting those expectations. I also learned that being flexible doesn’t mean being hyperfocused on only what someone else needs. For example, as soon as an email would come in, I felt compelled to answer it. This meant my inbox determined my day, often to the detriment of true priorities. As a writer, I need space to create, which means long blocks of time when I don’t answer emails. It also turns out my clients don’t expect an answer right away. Who knew?

Challenging previous ideas is absolutely necessary when what I’m doing isn’t working. What may have been true back in my father’s day doesn’t have to be true today.

Alright – let’s talk about marketing or sales – do you have any fun stories about a risk you’ve taken or something else exciting on the sales and marketing side?

I call this story “The Time an Ad Wrote Itself.”

To build my email list, I learned to write and post Facebook ads. I had to do this after my kids went to sleep because my days were filled with client work.

One night, I was working on setting my ads up. Sitting on my couch, in my jammies, I tried to stay warm while the snow fell outside.

Writing Facebook ads is a specialty unto itself, and while I don’t mind writing them, I absolutely hate setting them up in the backend. It was around midnight, and I was barely staying awake. I had one more ad to set up before I could crawl into my warm bed.

The ad wouldn’t work.

Every time I hit Enter to upload it, nothing happened.

Worse, the screen would go back to the beginning, and I’d have to start over again: enter the copy, upload the image, define the audience, define the location, determine the price and campaign.

Three times I had to start over.

I was too tired for this, so I cried uncle, angrily shutting my computer and heading off to bed. Annoyed.

The next morning, I woke up to more notifications than I’d ever received before. Apparently, one of my ads did go live. Well, part of an ad. The image was posted with a fragment of the caption.

Lucky for me, the caption was “Business owners” with an image of a mug that said “live a life you love.”

It worked perfectly. I couldn’t have written it better myself. Because, of course, I hadn’t written it! Not intentionally anyway. It had posted part of what I’d originally written. What it had cut off was a list of all the things business owners do. Looking back, it was too stiff, too preachy, too much.

It was too complex to connect.

It’s hard to write for yourself. In this case, the universe/fate/God, whatever you call it, did it for me.

I also never wrote Facebook ads again, opting to instead hire experts.

Contact Info:

• Website: thewritedifference.com
• Instagram: https://www.instagram.com/thewritedifference/
• Facebook: https://www.facebook.com/thewritedifference
• Linkedin: https://www.linkedin.com/in/jennprochaska

Image Credits
Sarah Beirne Photography