Jen — The Thoughtful Rebel

CASE STUDY TESTIMONIAL

Jennifer Kirkwood, Golf Design Consultant

Helping golf brands think beyond product and into long-term commercial strategy, Jennifer focused her experience into one niche she loved; repositioning herself as a high-level creative partner rather than a project-based designer.

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What was going on in your business and your life when we started working together? I had been in this cycle of working long-term contracts, mostly through word of mouth. But you get to a certain age and people start retiring, and that word of mouth starts to disappear a little bit.

I realised I was kind of operating in a vacuum. I just kept spinning.

I also had that freelancer mindset of, “Whatever you need me to do, I’ll do it.” And I knew that just wasn’t right anymore.

I wanted to focus on something I really loved, but I didn’t know how to shift into that. And honestly, the hardest part was setting my own message in my own head.

What concerns did you have about working with Rosie? What were you hesitant about? Money…and that’s funny because I’m not afraid to spend money on tangible things. But this felt different because you can’t see it.

I take courses all the time. I invest in information. But I hadn’t invested in how I think about my career. This was different. It felt like therapy at times - in a good way. It was digging into why I think the way I do.

But once I made the decision, I never second-guessed it. Not once.

I now lead with my expertise and attract partnerships that are meaningful, financially viable, and creatively fulfilling.

How did you feel after one of our early sessions? e.g The Portfolio Review. Mostly I felt relief. Like, okay, I’m back on track. I can do this.

Sometimes it was frustrating too, because digging into your own process is hard. As creatives, so much of what we do is muscle memory. Breaking that down and explaining it felt difficult.

But I usually got off the call thinking, “I can do this.”

What tangible results did you gain from our work together? I hadn’t really used LinkedIn strategically before, now it’s a weekly rhythm. I talk about business decisions, cost structures, who you should be paying attention to in the market.

I also bring my life into it - living in the mountains, having horses, the discipline of that lifestyle. I tie it into golf and business.

People tell me they enjoy my posts or that they’ve learned something. And often, the people who comment aren’t the ones who reach out - but they’re watching.

The biggest shift for me was realising I’m smart too. I don’t have an MBA, but I’ve been in enough big meetings to know how things really work. I stopped shying away from that.

What other results did you gain from our work together? One of the biggest things was slowing down. I’m naturally fast. I want to move and fix and execute. Now when I’m on clarity calls, I feel more centred. I’m listening differently.

It’s not just about them hiring me. It’s about whether I can really help them and whether we’re aligned. I’m not just pricing out a project anymore. I’m walking them through a process. That leadership shift was big for me.

How has the type of client you attract changed? I’ve always worked with bigger companies, but I didn’t fully realise how much value I bring from that experience.

Now I attract higher-level founders and executives - people who understand business and investment.

I talk a lot about cost, margins, and mistakes in my marketing now. One bad production decision can cost you $20,000 or more. People started to see that I’m not just designing - I’m thinking ahead for them.

I’ve recently learned the term “fractional creative director,” and that feels right. I can come in, listen, guide, and lead - without them having to hire someone full-time.

That shift has changed the conversations completely.

What do you think would have happened if you hadn't hired Rosie? I think I would have been grasping for projects. Pricing one-off jobs. Trying to fill gaps. Now I’m building longer-term brand relationships. I’m thinking further ahead. I’m positioning myself differently.

How would you describe Rosie to a friend? What’s it like working with Rosie? Someone told me before we started that Rosie can seem direct and blunt, but it’s because she really cares. That’s accurate.

Rosie is very business-like, but also warm. She doesn’t feed into emotional spirals, but she won’t dismiss them either. She interrupts them.

Rosie pulls something back from earlier in the process and says, “Remember this.” And it would click.

I made the right decision. I’m a second-guesser by nature. I have never second-guessed this.

Want these results in your business & mindset?