About

Thank you for coming to my blog!

Send me an email at deanrobertwatson@gmail.com if you have any questions. I’d love to hear from you.

Portrait headshot of Dean Watson

About me:

I’m Australian

I was born in Mitcham, Victoria. I lived in Heathmont until the age of 7, before we moved to Warranwood. My family live there to this day. I would describe my relationship with Australia as a complicated one. I love the nature, the sporting culture, the humour and the freedom of growing up in a country like that. I struggle with the individualism, entitlement, tall poppy syndrome and racism.

Australia has so much healing to do and it starts with the indigenous people. You can’t have a great country and neglect the foundations.

Auckland, New Zealand is home

In 2015 I moved to Wellington with an ex-girlfriend. We lived there for 10 months. The way the country made me feel never left me, even when she did. After a few more years back in Melbourne, an opportunity to move to Auckland for work came up in mid-2019. I jumped at the chance and never looked back.

Opportunities New Zealand has given me:

  • A feeling that I belonged somewhere
  • First paid TV comedy writing gig
  • First full time job
  • Great friends
  • A feeling that I’m okay just the way I am

This country has been very good to me and every time I update this About page I am reminded of that!

I don’t know almost everything

I thought I used to know things, but lately I have realised that I don’t really know anything.

Some of the different lives I’ve lived include amateur golfer, comedy writer, TV producer, EdTech start-up founding employee and creator of the world’s most popular online writing competition for high school students.

At one time or another, I thought each place was my final destination. I lead my life with a big heart. I have gotten better at looking at the data and pairing that with my intuition to make good decisions. I move through life like a strangely intense tortoise. It’s hard to watch the hares race on by, but intense tortoises like me are happiest making a few small, meaningful steps every day. We all end up in the same place eventually.

I’m a pretty happy person

I read a lot on how to improve myself and then I put into action what I’ve learned. When something works, I tell as many people as I can. I make mistakes. All. The. Time. At home, at work, when nobody’s looking. I call them out as kindly as I can, see what I can learn and do better next time. I think that this is the engine room of a great life.

People and EdTech light my way

I’ve worked in EdTech startups for 10+ years, but I don’t consider myself that much of a tech person. I’m more of a people person. For the last few years, I’ve worked in sales and business development and it might be the first time I’m really doing something that welcomes what I’m truly good at: like connecting people, connecting with people, asking questions, community building and documenting systems and processes.

Why I choose to continue working in EdTech:

  1. The people that work in it for any reasonable length of time are very mission driven. People who are only in it for the money don’t go into EdTech, so it filters out the sort of people I struggle to connect with at a values level.
  2. I don’t have kids and don’t plan to, so working in EdTech is a great way to give back to the next generation. I love this part of what I get to do so much.

More about me:

  • I like to watch cricket, golf, AFL and football highlights. I rarely watch an entire game. Highlights, I always have time for. Sport makes me happy and makes me feel safe.
  • I love being good with money. 9 years ago my grandpa gave me a copy of The Barefoot Investor and it changed me life. I invest in low-cost index funds so I can invest my time in the people I love and the things I want to do. I don’t believe in real estate as an investment.
  • I’m a messy minimalist. I own very few things. But my partner and my colleagues will be the first to tell you that I tend to spread them out.
  • I love chocolate. But it is possible to love something too much. A couple of years ago, I had set a rule for myself to only have one piece per day (with the exception special occasions). Every couple of visits to the dentist I have another go at implementing the rule.
  • I love nice restaurants. During cashflow positive times, every Saturday, Sierra and I will pick a restaurant and have the best time.
  • I am an eldest child. My brother is a graphic designer, working for my dad’s graphic design business of 30 years. My sister works at a university in a halls of residence. Mum works in the cafeteria of my old school. I love living in a different country, but I miss everyone a lot.