The [Tuesday] Media Diet with Anna Mackenzie

On portfolio careers, Egypt, and Kevin Kelly

Anna Mackenzie (AM) has been writing smart things about helping people re-think their careers. Her work is particularly well-timed as many people move toward a more portfolio-based approach to time and money. She’s based in Melbourne. -Colin (CJN)

Tell us about yourself.

I’m a Startup Advisor and Operator, Portfolio Career Mentor and writer of the newsletter Anna Mack’s Stack. I’m obsessed with building a portfolio career made up of many businesses, projects, income streams and passions, and teaching others to do the same.

I’ve had a pretty random career trajectory thus far. I worked with Japanese fashion retailer UNIQLO as part of the founding team to help launch the brand in Australia, before landing a dream job at Aussie beauty retailer Mecca. I then left that gig in 2017 to co-found lady-brains, a community and award-winning podcast for entrepreneurial women.

In 2022, when I realised that I hadn’t necessarily found what I was looking for as a founder, I moved on from that business. I desperately wanted to design my work around my time, my time around my life, and my life around my values and passions and dreams. Instead of being a slave to career commitments, I wanted the freedom to choose who I work with and what I work on. Instead of having just money or creative fulfilment, I aspired to have both. And instead of devoting all my energy to one thing - a full time job or a full time business - I wanted variety and vested interest across many.

Over the last two years (through a lot of soul searching and hard work) I’ve built a portfolio career I’m proud of. I work fractionally with startups, advise founders, write, mentor aspiring portfolio careerists, and offer a digital product called the Portfolio Career Operating System.

I’ve never been happier!

Describe your media diet.

I have a weirdly broad range of interests and I’m fascinated in everything from entrepreneurship and startups to the future of work, space, quantum physics, UFOs, ancient history, true crime, self development…the list goes on. I like to indulge all of these at different times and in different mediums. I love devouring a true crime documentary series on Netflix. I’m a big fan of Reese Witherspoon’s monthly fiction book picks. I spend a lot of time on Youtube learning from founders, thought leaders, authors and experts in their field. I love reading long form essays on Substack, and I also occasionally find myself on the wrong side of Tiktok.

What’s the last great book you read?

I could rattle off about a hundred but if I had to pick just one it’d be ‘Excellent Advice for Living’ by Kevin Kelly. It’s a collection of hundreds of adages to help you build a better life. Some of my favourites are ‘don’t be the best, be the only’ and ‘to move through a place you may not be permitted, act like you belong there’.

What are you reading now?

‘We Are the Stars’ by Gina Chick. It’s a memoir from the winner of the Australian version of reality TV show ‘Alone’. A fascinating read from someone who grew up in the wilderness.

What’s your reading strategy when you pick up a print copy of your favorite publication?

I used to force myself to read the entirety of any book I started even if part way through I realised I wasn’t enjoying it, which is a gross waste of time and energy (there’s nothing worse than persevering through something that I really don’t like). These days I’ll happily ditch a book after a few chapters if it’s not resonating, because there are too many epic ones out there to waste time on something that’s not my vibe.

Who should everyone be reading that they’re not?

There’s a writer on Medium (of all places) who writes personal essays under the pseudonym Adeline Dimond. She’s funny, smart, witty and a little zany, and reminds me of a modern day Nora Ephron. Highly recommend!

What is the best non-famous app you love on your phone?

Evidently I’m as basic as they come because every app on my phone is famous and used by millions of people (Spotify, Notion, Uber etc.).

Plane or train?

It depends. Plane if I care about speed and convenience. Train if I want to take the scenic route.

What is one place everyone should visit?

Egypt. Nothing compares to standing in front of the pyramids in Giza and taking in their sheer scale. Mind blowing.

Tell us the story of a rabbit hole you fell deep into.

I’m obsessively thinking about how AI is changing the nature of work, specifically how we define and measure value. Traditionally value has been tied to productivity and how much output a person can generate (a relic from the Industrial revolution perhaps?), but in a world where AI handles basic functions and even operates entire businesses, what value will us humans contribute? How will value be defined? If productivity is no longer our primary currency, what will be? This excites and terrifies me in equal measure, but I can see a world where execution becomes less important than creativity and original ideas. It’ll be interesting to see how society reorients itself. (AM)