There is no doubt in my mind there are more benefits to taking a leap than not. But if you asked me what’s one of the biggest downsides it would be not seeing people like Neil everyday.

Meeting Neil Kenna was an absolute turning point in my life. For many reasons. Firstly he hired me to work in my dream job – for a brand I loved, doing what I knew best. I reported to Neil for two years and always felt respected, supported and aligned. Which I think is remarkable considering he is 15 years my junior. It reaffirmed to me that generational differences are an illusion – that a shared attitude toward fellow humans is what matters, no matter what your age.

Secondly, not only is he one of the most stylish men I know, Neil’s calm composure under pressure is the epitome of grace. He never lost his cool, he never spoke ill of anyone, he worked as hard as everyone else in the team and he made things happen. While still whipping up a tasty guacamole for lunch.

When Neil and I worked together he had not worked anywhere else since finishing his journalism degree at university. He started working in the retail designer stationery store kikki.K when the business was in it’s infancy. Over the next ten years he would move to head office, create the marketing department, lead the team and be instrumental in helping the founders grow the business. Then he decided to leap. Out on his own, launching his own consultancy Neil Hugh. And then I knew, the only thing really holding me back doing it for myself, was my belief that I could. The old adage of surrounding yourself with those who lift you higher rang true.

Sometimes there are people you meet in your working life who make you want to leave your job for all the wrong reasons. Meeting Neil helped me leap for all the right ones.


Neil Hugh Kenna photographed by Brooke Holm.

Neil Hugh Kenna photographed by Brooke Holm.

What did/do you study?

From my early teens I had my sights set on a career in journalism. I’m not sure where that came from, but throughout senior high school I was firmly focused on gaining entry into my desired course. It was highly competitive at the time, but I was so determined to get in that I didn’t even bother applying for other courses. I knew I needed to do well to have any chance of getting in, so I wrote my goal on the first page of my diary and glanced at it every day. Everything went to plan and I loved every minute of my degree, even though I quickly realised I no longer wanted to be a journalist.

What has been your most scary/courageous leap you’ve ever made (preferably in your business/career/life direction)?

The scariest leap I’ve made was to resign from a stable and rewarding job in order to start my own business. However I’m not sure I’d call it a particularly courageous move. I am very logical and measured by nature, so I don’t really take unmitigated risks.


What were you doing before you made your leap?

I was the Marketing Manager at kikki.K Swedish design, and having been with the company in various roles for almost ten years, it really felt like home. But everyone has to leave the nest at some point.

Who have been the biggest 3 – 5 influences in your life, in terms of your career and doing work?

I don’t really separate career from life, so my greatest influences are those who’ve helped shaped me as a person, not just a professional.

My parents have been hugely influential. They always instilled in me the belief that I could do anything I set my mind to. My mum in particular always said, “nothing ventured, nothing gained”, which is a phrase I refer to regularly. It’s a great reminder when faced with a challenge or when edging out of my comfort zone. With risk comes reward. It also echoes my broader life philosophy – that life is short.

At kikki.K I reported to CEO and co-founder Paul Lacy. He had a profound influence on me. It was a very small business when I joined the team, so to be part of such an incredible growth story was a really powerful, formative experience.

Working with entrepreneurs and owner-operators is a unique experience – incredibly demanding, but so rewarding when their drive and ingenuity become contagious. Entrepreneurs really see the world differently. I’m not sure where we’d be without them.


What did you have in place before you made the leap?

I didn’t have anything in place before I made the leap, but let’s get real; we all need to pay our bills. I’m far too considered to risk the roof over my head. My partner had been running his own business for a few years, so I knew we had at least one relatively stable income to fall back on. Fortunately it never came to that, but I am not sure I could’ve made the leap without his support.

Early on my vision only extended as far as a desire to work with differentiated brands and passionate people. I never sat down and wrote a business plan. I didn’t really have a clear idea of what I was trying to achieve. And I certainly didn’t have any “specific and measurable” goals. So in short, I didn’t do anything you’re “supposed” to do. But I’ve come to realise that that is just fine. I needed time to understand my customers and their needs; to realise the unique value I have to offer; and to let things unfold naturally. I’m always surprised when people remark that I appear to have a really clear vision. The truth is it’s not something I wrote on a whiteboard one day. For me it took time for my vision to crystalise.


What was your defining ‘I can’t do this anymore’ moment that lead you to the leap?

After years of working at a rapid pace, it took a health scare to stop me in my tracks. A week or two of bed rest provided time for forced contemplation. It was only then that I started to think about what my dream life looked like. At the top of my list was complete flexibility: the ability to travel as frequently as I wanted; to work on Sundays or tackle my inbox at 11pm; to choose who I wanted to work with – and who I didn’t. No one else was going to make that happen, so in my mind there was no choice really. To build the life I desired, I had to make it happen for myself.


Neil Hugh Kenna’s beautiful website photography featuring one of his clients, Fred International, styled by Marsha Golemac and photographed by Brooke Holm.

How did/do you overcome/work with the fear that comes with leaping? How do you decide to choose courage?

Those who know me well would describe me as logical and measured, so the concept of ‘leaping’ doesn’t really fit with my persona. In fact, while resigning from stable employment was definitely scary, I had carefully weighed up the pros and cons, and felt very comfortable with my decision. By breaking it down into the ‘worst case scenario’ I concluded that it wasn’t really that scary at all. As long as I could pay my bills, what was the worst that could happen? I really believe the greatest rewards are born from risk – or at least from facing challenge. The world’s most successful people have all taken a risk at some point, so I couldn’t sit on my hands forever. And in my experience “luck” is derived directly from action.


How would you rate your level of happiness about making your leap?
1 being sad, 10 being rad.


What’s the biggest upside to making the leap?

The biggest upside of my leap is the ability to manage my own time. Sometimes I work on the weekend. Sometimes I sleep in. Whether it’s working more or less, it’s my choice – and that to me is invaluable.

What’s the biggest downside to making the leap? And how do you get through it?

The biggest downside of my leap is probably that I spend too much time in my own head. I love the process of collaboration and the dynamics of working in a team. While I still enjoy this when working with clients, there is far more autonomous time. Still, if that’s the greatest downside then sign me up all over again!


What might be your next leap?

I have absolutely no idea.

What are your favourite words to live by?

Nothing ventured, nothing gained.
Life is short.
What is life without travel?
There’s no such thing as luck.


Who do you admire who also made the leap?

I admire anyone who is doing what they love…and for some people that doesn’t involve a leap at all. Taking the leap is not for everyone, and that is perfectly fine. As long as you love what you do, you have my admiration. Life is really too short for anything less.

A piece of advice for someone with an itch to leap?

If you can pay your bills and feed your family, then get on with it. If you can’t, then investigate part time work as a bridge to full independence. If the timing is not quite right, then start networking now anyway.


Right now: I should be packing for my 6am flight to Sydney
Hearing: Monocle 24 (Radio)
Eating: Almonds
Drinking: Green Tea
Reading: ‘A Frame for Living’ by Ilse Crawford
Loving: Planning my Summer in Europe


Every so often I’ll meet up with Neil for breakfast to connect with someone I truly admire, and he graciously says yes. I hope you have a breakfast buddy like that in your life. Because bircher and business is alway better when it’s shared.

Kylie x