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The Highs and Lows of My 11 Year Legal Career

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As my time being a lawyer and a director of a law firm comes to a close, I’ve been reflecting on the highs and lows of my legal career.

I graduated from Uni in 2006 and was admitted to the bar in 2007. I sold my law practice a few weeks ago, and Dennis King Law’s last day of trading as a law firm is 21 July 2017. I have decided it’s time to go all in with Automio.

Now that my days as a lawyer are numbered I’m feeling a real mix of emotions – exhilaration, freedom, relief, strength, inspiration and shitting my pants. But I’m also feeling hugely sentimental about my legal career which has been such an important and vital part of the journey.

Here are seven highs and lows from the past 11 years. Let’s start with the lows so that we end on a high note.


  1. Dad dying
    My business partner and father died last year. In my recent blog post How I Survived the Death of My Business Partner I talked about some of the bad stuff that happened and how unprepared we were in terms of succession planning. It was such a hard time but I learned a lot about resilience.
  2. The stress
    A year after I became a director of Dennis King Law our practice manager retired and I became the managing director. This meant that I carried out the role of practice manager as well as my role of lawyer/director. At the time I had no experience managing a law firm and was thrown in the deep end. I still had a full fees budget to achieve and the pressure I put on myself was massive. This stress continued for years and it changed me – it altered my personality and not in a good way.
  3. Seeing a client lose nearly everything
    One of my clients who I admire and care about greatly lost nearly everything he owned. It was awful to watch and I felt so helpless that there wasn’t more we could do. He showed great strength and courage throughout his ordeal which has been such an inspiration.
  4. Initial website #fail
    It cracks me up to think about this now, but at the time it wasn’t so funny. When I first launched Legal Beagle in 2012 I expected people to flock to our fancy new website and become clients. But instead….crickets! At first I was very discouraged by this and let the website sit there basically not being used for nearly 2 years while I sent it negative vibes. Then I got my shit together and upskilled in digital marketing and after that we had no trouble getting clients through Legal Beagle, and it became an important part of our firm.
  5. Working with family
    Working with family certainly has its ups and downs. I’ve also put “working with family” under my list of highs below. There is that cliche that you should never work with friends or family. While I’ve had a mostly positive experience working with family, there have been a couple of issues over the years that have been really stressful.
  6. Staff issues
    Over the years we’ve had a couple of staff issues and I find it so hard not to take them personally. I have what some consider to be very high expectations. I’m clear about our firm’s expectations and do as much as I can to make people successful, so when someone consistently doesn’t perform I take it hard as it feels like such a massive failure on my part.
  7. No longer enjoying being a lawyer
    It has been quite a long time since I enjoyed being a lawyer, but I only realised this recently. I only came to realise this when I listened to a radio interview I did last year and heard the passion in my voice when I talked about Automio, and the doom and gloom in my voice as I spoke about being a lawyer.

And now for the highs!


  1. Becoming a director at 26 years old
    I became a director of DKL on 1 April 2010 when I was 26 years old and I’m proud to have achieved this at such a young age. I remember the Law Society initially not being so keen on the idea!
  2. Law Awards 2009
    Such an awesome and memorable night! We were a team of about 9 or 10 people at the time and we did a roadtrip from New Plymouth up to Auckland to attend the awards night. We were nominated for an award but didn’t win it. But the whole thing was so much fun and a wonderful team bonding experience. Plus we got this special snap:

  3. Clients & colleagues
    I have been privileged to work with many fabulous clients and colleagues who have inspired me in so many ways and taught me a lot, particularly about leadership and resilience. A number of these clients and colleagues have become close friends and I’m glad these people will continue to be part of my life now that I’ve sold DKL.
  4. Launching Legal Beagle
    Launching Legal Beagle was such a fab moment for us. We didn’t know it at the time, but launching Legal Beagle was such an important step in the Automio journey. It was through Legal Beagle that I realised we needed document automation software in order to sell online DIY legal documents, and none of the automation software in the market was what I wanted. So we decided to build our own automation software and Automio was born.
  5. Meeting the dream team
    I have been so fortunate to have met a super-talented bunch of peeps who I’ve worked with over the last four years or so – Matt Sagen, Mike Mitchell and Kelsey McEwan. Matt, Mike and Kelsey initially worked with me in Dennis King Law and Legal Beagle – Matt and Mike as developers who built our Legal Beagle platform, and Kelsey as one of our lawyers. They’ve since worked tirelessly to bring Automio to life, and are hanging around as we transition from law firm to software company. Along with Ian Frame and Zac Bingham who have started working with us in the last 12 months, I’m proud of the excellent team we’ve put together.
  6. Working with family
    I mentioned above about some of the challenges of working with family. But there is a lot of excitement to be gained from working and succeeding at something with people you care about. It provides a huge amount of joy. For example, when Legal Beagle won an award at the NZ Plain English Awards a couple of years ago, Mum (our practice manager), Dad and I went to the Awards night in Wellington to celebrate. It was special to be able to celebrate a business success like that with my parents.
  7. Working with a wonderful business coach
    When I took over as managing director of the firm we used Karen de Beer from Results Group as a business coach. Karen was a fabulous mentor to me and taught me all about strategic planning, goal and vision setting, and accountability. I’ve used a lot of the stuff Karen taught me to get Automio off the ground. My experience with Karen taught me me that using coaches and external consultants in my business can be hugely valuable, and asking for help is OK.

So what’s next?

I have no idea what the next 11 years will bring, but I’ve never been so excited about life. I feel free and so fortunate that I get to do the work that I am meant to do and have such a clear vision for.

Will I return to being a lawyer again one day? Hard to say. I don’t think so though. I do know that I want to fiercely help the legal profession stay ahead of the wave of change and use technology to improve their careers, businesses and lives. I do know that I don’t want to get so stressed and busy again that I lose this feeling of freedom – I want to be free to spend time with my family, free to do the work that really matters, free to think deeply about my vision for Automio, free to try to solve the world’s problems over cocktails with my BFFs, free to take care of myself, and free to travel to places I wanted to visit in my 20s but didn’t have time to.

What about you?

What will your career or business look like in 11 years? What are you doing now to stay ahead of the wave of change hitting the legal industry? What are you doing to defend your career, business and income in the age of automation? Life is not a dress rehearsal folks, so take action now.

Stay classy,


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