We recently connected with Katie Rose Hester and have shared our conversation below.

Alright, Katie Rose thanks for taking the time to share your stories and insights with us today. Before we get into specifics, let’s talk about success more generally. What do you think it takes to be successful?

I think one of the biggest success-hacks is to surround yourself with curious, informed, engaged people. It’s good to remember that success is almost always a group effort, and it tends to happen slowly over time, as you learn. Once you start leaning into the idea that success is cumulative, I think that’s when good stuff starts to happen.

As always, we appreciate you sharing your insights and we’ve got a few more questions for you, but before we get to all of that can you take a minute to introduce yourself and give our readers some of your back background and context?

This is a big question! I’ll start with the easy bit.

My business, Offscript Content, provides comprehensive content strategy and production services to B2B product-led businesses, most often in their start-up or scale-up phase of growth. Having worked in product-led businesses as an internal Head of Brand & Content, I’ve seen firsthand how saturated the marketplace is for these companies, and how difficult it can be to truly cut through and differentiate your content from everything else out there. So, my goal is to simplify this area of marketing for businesses, and help them create a really incredible library of content that serves their commercial purposes while also engaging their audience.

Now, for the trickier stuff:

Before I became a marketer and started Offscript, I was a lawyer. I absolutely loved the work, but I hated the environment, and I (unintentionally) left the practice in 2016 after getting fired for taking one day off (which I always like to stress was a Friday – when I say I hated the environment, this is the kind of thing I’m talking about).

The period after I left legal practice was tough. I’d spent my entire life and education preparing to be a lawyer, so I had no idea where I was headed, and I had a really difficult time breaking into a new industry. To put the whole journey in a couple of lines: I spent the next five years working temp jobs and teaching myself how to be a marketer, and in February of 2021, following a few quarter-life crises, one Trans-Atlantic move, a pandemic, and thousands of job applications, I finally landed a job on a marketing team. From there, I worked my way up pretty quickly, landing a role as the Head of Brand & Content for a tech company, which is where I worked until I decided to make Offscript (which I’d been growing very, very slowly in the background) my full-time thing.

And now, in addition to the work I do for clients, I share my career journey online and I’m pretty passionate about having conversations with women about anything related to career-building or professional pivoting. That’s what The Offscript Podcast is all about, which I started when I launched the business. I not-so-jokingly refer to the podcast as my “life’s best work,” and it’s my current passion project.

I’ve also pledged that at least 50% of Offscript’s clients will always be founded, funded, or led by women. Basically anywhere that I can support other women in business – by sharing their story or collaborating with them to create great content – I want to do it.

And that’s Offscript (and me) in a nutshell. My business is content strategy and production, and I love it! But my passion is exploring career journeys and professional pivots and really digging into the stories of the women around me.

What’s a lesson you had to unlearn and what’s the backstory?

As a former attorney (and current elder millennial), there’s plenty of lessons I’ve had to unlearn!

Law school and legal practice have a funny way of tricking your brain into thinking that everything matters the same – and that everything matters A LOT. Meaning, for a long time I thought that all mistakes were equal. Earlier in my career, I would panic and really beat myself up for even the tiniest errors, oversights, or misunderstandings. There were many years where I don’t think I ever once felt professionally relaxed, much less confident or fulfilled. Thankfully, I’ve gained some experience and perspective and now I’m able to more clearly identify what’s worthy of a little emotional energy, and what’s not.

Interestingly, I think the biggest shift in this area came from becoming a people manager myself. When a member of my team would come to me and tell me that they made a mistake, I would automatically enter into “figure it out” mode. Most of the time, there was a solution to whatever problem we had. And on the few occasions that there wasn’t anything we could do to walk back an error, we owned it, moved forward, and tried to learn from it. And the world kept spinning. I guess being the person who sets the tone for how mistakes are handled was the best way for me to really get better at handling them!

We’d love to hear the story of how you turned a side-hustle into a something much bigger.

Offscript was my side hustle for three years before I went all-in on the business.

When I moved to the UK from the US in March 2020 (on the first day of the first national lockdown, no less), I had no job and no network. The pandemic made it very hard to go out and meet people, so for a long time I was just applying to jobs online and hoping for some traction, which never materialised.

I was finally able to follow up with a marketing agency owner that I’d met some years before and stayed in very loose contact with, and he connected me to another agency who had a need for content consultants. I’d never done anything like that before, but they took a chance on me, and a few months and a few connections later, I landed my first client. Around the same time, I finally found a full-time job on an in-house marketing team at a tech agency, but I kept up with my client on nights and weekends.

One year after I landed that first in-house job, I was offered a role as the Head of Brand & Content for a bigger company, which I took. The role was incredibly demanding, so I didn’t have the time or energy to expand my side hustle for most of the two (or so) years that I worked there. But when that business was acquired, I figured I should try to create more security for myself, and that’s when I found a few more clients, all through word of mouth. My plan was to leave my full-time role after the acquisition was complete (I wanted to make sure my team had a smooth transition), but I ended up getting laid off with a bunch of other people, and so the plan was accelerated by a few months.

Fortunately, I’d managed to get a handful of clients under contract, so the only things left ahead of launch were tick-box items like getting my website built, and setting up my podcast.

Less than a month after I launched, I landed another client, which really reinforced for me that I made the right moves, at the right times.

Contact Info:

• Website: https://offscriptcontent.com/
• Linkedin: https://www.linkedin.com/in/kathryn-rose-hester/
• Other: The Offscript Podcast on Spotify: https://open.spotify.com/show/1Gq9zTYGxsTK3j0mQkl1Pf?si=61fe44d6eccf4231 The Offscript Podcast on Apple: https://podcasts.apple.com/gb/podcast/the-offscript-podcast/id1726344330

Image Credits
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