Generalist Examples: Anna Mackenzie

Welcome to the very first edition of Generalist Examples. A series that breaks down how HTG (happy thriving generalists 🎉 ) are finding their home at work. At GW we’re building the workforce of people building thriving, non-traditional careers on their own terms! Anna is one of our faves.

Today you’ll learn:

• what a portfolio career is (and isn’t)

• how to land your first 3 clients

• how to pick a niche

• the secret to becoming a loved writing figure

Hope you enjoy! Screenshot your fave part and tag @generalistworld on LinkedIn and we’ll amplify you to our 20,000+ audience.

Also, we’re hosting an open event with Anna next month on “why generalists are built for portfolio careers”. RSVP here!

👋 Milly

ps: I’m > < this close to closing the doors for our winter cohort, reserve your space here! 🌀 

Hello! Who are you and what’s your career story?

Hey! I’m Anna, a Startup Advisor & Operator, Portfolio Career Mentor and Writer of the popular newsletter Anna Mack’s Stack. I’ve had an ultra squiggly career working across corporate, small business, high growth startups and scale-ups, as the founder of my own brand and now a solo operator with a portfolio of projects, clients and income streams.

Here’s how it all began…

In my last year of uni in 2012, while my fellow Commerce grads were applying for jobs at the Big 4..

I went on to spend ten months going through an intense recruitment process - the most insane experience of my life so far - before bombing out at the final round and being told I couldn’t reapply for seven years. It was devastating.

I then slowly and painfully picked myself up off the ground and landed a job with Japanese fashion retailer UNIQLO as part of the founding team to help launch the brand in Australia. I moved to Singapore and Tokyo to learn the ins and outs of the business before coming back to open the first three mega stores.

A few years later I landed a Project Coordinator role at beauty retailer Mecca (Australia’s version of Sephora) and after a few quick promotions found myself leading the Concept Development and Retail Innovation team. I worked directly with the Founder and Exec team, bouncing from city to city to scout the coolest retail experiences in the world (literally a dream!).

I sleuthed my way through Saks Fifth Avenue in NYC, undertook espionage at Ulta in LA and plonked myself on a plush velvet couch at Le Bon Marché in Paris meticulously observing lines of traffic throughout the space.

I took all of the inspiration and learnings back to HQ and used them to design the beauty store of the future.

A couple of years into my time at Mecca I got the entrepreneurial itch and, alongside two friends, started a dinner series called the lady-brains supper-club, which brought together entrepreneurially minded women over good food and great wine. The dinners spun into a podcast interviewing female founders at the top of their game.

We quickly built a cult following and landed a contract with the biggest media network in the country, and I then took a massive risk and quit my job at Mecca to go all in.

Over the next 5 years we grew our podcast audience to hundreds of thousands of listeners, interviewed over a hundred inspiring founders, worked with Australian Fashion Week as the official podcast partner two years in a row, won Best Commercial Campaign at the Australian Podcast Awards, invested in a start-up from our community and supported hundreds of women through our programs. It was a wild ride, my first experience navigating the extreme highs and deep lows of building something from nothing.

I had this gnawing feeling that I didn’t want to devote all my energy to one thing - a full time job or a full time business - rather I wanted variety and vested interest across many. I ultimately listened to my gut and made the decision to leave the business, and while I wasn’t totally sure what would come next, I made a commitment to follow my curiosity and not stop until I created a career that offered me freedom, creative fulfilment, meaning and money.

What are you doing now?

Almost two years later, I’ve built a multi-six-figure portfolio career of many clients, products, projects and income streams:

• I help startups from Pre-Seed to Series A start, grow and scale their businesses globally. I work with both AU and US businesses with a focus on consumer brands (specifically beauty) and B2B tech. My engagements are in a fractional, consulting or advisory capacity, depending on the scope.

• I'm a Portfolio Career Mentor, helping those who aspire to leave the 9-5 (or who already have) build a diversified and sustainable portfolio of work

• I write the popular weekly newsletter Anna Mack’s Stack, where I share weekly guidance and practical insights to help others build a portfolio career and life on their own terms

• I offer a digital product called the Portfolio Career Operating System; an all-in-one productivity tool and educational resource designed to help people run their portfolio career like a well oiled machine

In my first year portfolio-ing I earned over 2.5x my highest ever annual salary, and in just 15 months of publishing online I’ve grown my newsletter from 0 to ~7k subscribers. These results tell me that I’m on the right track, but for me the real measure of success is how I wake up feeling each day, and how many people I’m positively impacting through my words and ideas.

Hang on, what’s a portfolio career?

Great question! A portfolio career is defined as having several part-time jobs or multiple income streams rather than one full-time gig. In my mind, it has two defining characteristics:

• It involves pursuing multiple passions, interests and types of work

• It’s never static and always evolving

To me, a portfolio career can be made up of many things:

• A part time job (eg. working 3 days a week for a company)

• A part time business (eg. working 3 days a week for your own company)

• A done-for-you service (eg. contracting, consulting)

• A done-with-you offer (eg. coaching, mentoring, advising)

• A do-it-yourself offer (eg. a digital product, online course)

• Creative work (eg. writing, podcasting, Tiktok-ing, playing music)

• Giving back (eg. volunteering, pro-bono work)

• A mix of any or all of the above

This type of structure is loosely defined by design and it’s a dream for us generalists! It allows us to flex different skills in different ways, at different times and in different contexts. It also keeps things varied and interesting.

How have you built your portfolio career so far?

When I decided to go out on my own I had no clue what I was going to build or how I was going to build it. I didn’t know what my ‘niche’ would be. Being a generalist, I wasn’t sure what I’d plate up at the services buffet. I didn’t have a strategy for selling myself in nor did I know who I was supposed to be selling myself in to. Not having a clue made zero difference to my ability to meet people and create work for myself. I just got moving.

• My first task was to network my little baby heart out. Experience told me that my first projects would come from someone I knew, or at the very least from someone who knew the people I knew, so I gave myself two months and reached out to everyone I could possibly think of. Most of these conversations led nowhere…but some of them did. One led to my first client. Then to my second. Then to my third.

• At the beginning of 2023 I made the commitment to write for thirty minutes a day. I had no intention of publishing anything, I just wanted to do what I loved and cultivate it as a habit. But as I grew in confidence I started pitching to publishers, and soon landed regular freelance writing work. Nine months later, fuelled by positive feedback from the professionals, I started my newsletter. Then I started posting on LinkedIn and Notes every weekday. I experimented with Tiktok. Slowly but surely, work opportunities began arriving in the inbox rather than being generated through my blood, sweat and hustle. I put my ideas out into the world and the world began talking back.

• 32 weeks into writing on Substack I stumbled upon what would become my niche - portfolio careers. I had experimented for almost 8 months (!) writing about random business and life stuff before finding a topic that sat at the intersection of what I enjoy writing about and what others enjoy reading. My takeaway? You don’t choose a niche and then start. You uncover a niche through the very act of starting. And continuing. For ages. As long as it takes.

• As I started getting traction with portfolio careers my startup brain kicked into gear and I spun up some discovery research, interviewing 30+ and surveying 200+ people. I uncovered about a gazillion pain points that I was uniquely positioned to help solve.

• I started receiving DMs from readers asking if I could mentor them to build a portfolio career too. I listened to this market signal and, after 3 months of beta testing behind closed doors, officially launched my Portfolio Career Mentoring offer.

• The more people I mentored the more I realised there was a real problem I could solve at scale: the overwhelm and stress that portfolio careerists experience when running every facet of their one-person-business - Sales, Marketing, Product Development, Client Work, Operations, Admin...the list goes on. I knew that my deep experience as a Startup Operator could help others, and so the Portfolio Career Operating System was born: an all-in-one OS designed to streamline workflows, save time and minimise burnout while focusing on the things that drive more revenue, happiness and fulfilment.

How has being a generalist helped you grow your portfolio of work?

I see my generalist skillset as my core competitive advantage. I’m equal parts left brain and right brain, meaning I’m just as comfortable coming up with sales targets and managing cash flow as I am writing a compelling story or creatively directing a photoshoot.

Practically speaking, being a generalist has helped me win consulting, fractional and advisory work with startups at the Pre-Seed to Series A stage quite easily.

These founders are dealing with a slew of problems and are consistently putting out fires, and need people with broad skillsets that can a) see the big picture and diagnose a problem quickly, b) develop a strategic plan to solve said problem and c) execute to a high standard across multiple functions, domains and teams.

In discovery calls I ask questions to uncover the biggest challenges they’re facing, and then adjust how I present my skillset to position myself as the perfect solution to their problem.

Being a generalist has also helped me build my portfolio of work because I’ve been able to easily pivot on the fly, flex skills or strengths up and down depending on the context, and switch my focus (Product, Marketing, Brand, Sales, Research, Customer Experience etc.) according to what my business needs. This ability to make decisions and move quickly is enabled by my broad generalist skillset and the confidence that I know enough about enough to figure the rest out.

Where to next?

This year my intention to expand my work and impact across three areas:

1. My interests: voraciously pursuing my curiosity and expanding my knowledge of ideas, frameworks, philosophies, industries and cultures.

2. My income: increasing my earnings by doubling down on revenue streams that have proven product-market fit.

3. My impact: writing more, sharing more, speaking more, teaching more and reaching more people worldwide through my words and ideas.

My 2025 goal is to empower 1000 people around the world (many of them generalists!) to start or grow their portfolio careers and build a life that sits at the intersection of freedom, creative fulfilment, meaning and money. My longer term goal is to write a book about building a life outside traditional systems, structures and norms.

Where can we find you?

I write a weekly newsletter for those who have exited (or want to exit) the traditional 9-5 and build a financially lucrative and creatively fulfilling portfolio career made up of multiple clients, projects, passions and income streams over on Substack

→ Subscribe to Anna Mack’s Stack here.

You can also find me on all corners of the internet:

• My website: www.annamackenzie.com.au

• LinkedIn at Anna Mackenzie → here.

• Instagram at @annaclmack → here.

• Tiktok at @annaclmack → here.

If you’re interested, here are two ways I can help you leverage your generalist skillset to build a portfolio career of your own:

1. The Portfolio Career Operating System: learn and implement the exact system I use to run my multi-six-figure portfolio of work across startup consulting and advisory, mentoring, writing, speaking gigs and digital products.

2. Portfolio Career Mentoring: 1-1 sessions to help you build a career that sits at the intersection of freedom, creative fulfilment, meaning and money.

ps: I’m >< this close to closing the doors for our winter cohort, reserve your space here! 🌀 Just hit reply if you need flexible / parity payments!