How I'm building my portfolio of clients, projects and income streams.
The Portfolio Career Explained, Part 3
A couple of weeks ago I wrote about saying goodbye to being anything full time and hello to being many things part time. It turns out many people were curious about how I made the move from “traditional” work to a portfolio career, so this week I’m sharing the steps I took to get started. But first, some useful context about me:
My career through line is that I’ve always worked in business - for corporates, funded startups, small businesses and in my own.
I’m a generalist who feels as comfortable coming up with a creative concept as navigating my way through a spreadsheet. I’ve worked across strategy, operations, sales, marketing, brand, innovation, product and everything in between. A blessing or curse depending on how one looks at it (I choose the former).
I launched Uniqlo in Australia, led Retail Innovation at beauty brand Mecca, and then co-created an award winning entrepreneurship podcast called lady-brains.
I’ve been self employed for five years but over the last eighteen months have broadened my horizon: I now consult and contract for startups, advise and mentor founders, write, host panels and events, partner with brands and am also working on something new (more on that another time).
After many ups and downs I genuinely feel like I’ve arrived where I’m meant to be. I earn good money, have relative freedom and do meaningful work with people I admire. I’m not special though, this type of life is achievable for anyone. I believe it. I know it. I’ve seen it.
How I began:
I started without a clue.
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.
I networked 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. I had breakfast with former podcast guests, sent DMs on LinkedIn to solo operators I looked up to, met up with old colleagues and sent cold emails to founders of startups that were interesting. I asked everyone I met who they thought I should reach out to next. 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.
I wrote daily.
At the beginning of 2023 I committed to writing for thirty minutes a day with no outcome in mind. 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 this newsletter. Then I started posting on LinkedIn and Notes every weekday. 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.
I said yes more than I said no.
The beginning was all about volume: meeting lots of people, sending lots of emails and talking about how I could help to anyone who’d listen. I took on all kinds of work to build a series of case studies. Was every opportunity a good one? No. Were all projects a perfect fit? No. Did I charge what I should have? Also no. But it meant I was able to get runs on the board. And in the beginning, runs on the board are all that matter.
I set myself a goal to secure retainers.
Once I realised this portfolio career thing was going to be viable I set my sights on securing a retainer/s that would cover all my living expenses. I targeted founders who’d just received funding because I knew if a startup was cash rich they’d be looking for good people to help them execute. I’m a get-shit-done kinda gal, and within a couple of months I had three regular clients.
I prioritised my emergency fund.
Once I had financial security I funnelled every spare dollar into an emergency fund to cover three months of personal expenses. I wanted at least ninety days of runway to find new work if everything went to shit, and I knew a full emergency fund would bring me peace and give me options.
I created structure around my tasks.
Managing multiple clients, personalities, types of tasks and personal projects can make even the best plate-spinners among us have a mini meltdown, and so I knew that I needed to build out some robust structures to help me stay sane. Say hello to Notion, my personal operating system where I store ideas and notes, write essays, manage social media, map out consulting work, manage my money and tasks. Anna Mack’s OS has dashboards for:
My purpose, vision, goals and habits
My daily and weekly to-dos
Capturing and storing ideas
This newsletter
Social media
Networking and sales
Client work
Templates and SOPs
General life and business admin
I get off on well designed systems and structures, there truly is no greater pleasure in life. Minimal friction, maximum output, minimal busy work, maximum creativity.
I designed my optimal schedule.
As I discovered how and when I like to work, I developed simple rules for my time that allow me to be the most productive, happy, non-stressed version of myself. For example:
I never take meetings on Mondays. This allows me to ease into the week and focus on deep work and creativity straight up.
All client meetings and virtual coffees are scheduled on Tuesdays and Thursdays.
Thursday nights are when I polish (or sometimes scramble to finish) my newsletter before its Friday deadline.
I don’t take meetings after midday on Fridays and use this time to wrap up loose ends, clear the inbox and tick off admin before closing out the week.
Sundays are sacred and solely for writing.
Ideally I’d add another rule here - no meetings before 11am - but I work with lots of people based in the US so 7-10am is prime meeting time. As a non-morning person this used to suck but I’ve learned to work within this constraint. New life mantra: early to bed, early to rise.
I hired a personal assistant.
When I was in a financial position to do so, I hired a wonderful PA to manage my personal inbox and calendar, field inbound enquiries, manage guest blogs and interviews, and do other admin. This expense might seem like an indulgence but I see it as an investment. She frees up my headspace for client work and creative projects rather than having it clogged up with the mundane.
I built a website (eventually).
For the first year of portfolio-ing I didn’t have a website because I simply didn’t need one. Opportunities self generated as a result of my writing and connecting with people, so I chose to invest my time elsewhere. Ruthless prioritisation, people.
Writing remains my number one priority no matter how hectic things get.
This newsletter is my most valuable asset even though it earns me exactly zero dollars and zero cents. It connects me with likeminded people, generates new work and most importantly brings me an immense amount of joy. It’s a channel for me to be seen and be heard. It’s a channel for me to have impact. I love it here and prioritise it above all else.
The first step is the hardest.
It’s no exaggeration to say that my life has changed dramatically over the last eighteen months, and while it might seem like I had a Big Strategy the reality is that I had no fucking clue where I was going or what I was doing. The future has only become clear as I’ve put in the reps, it’s only now that I can feel the destination and start to see the pathway there.
Some people will tell you that you need it all figured out before you decide to create a new life for yourself.
They’re lying.
You don’t need everything figured out before you start. You’ll figure it out through the very act of doing. The doing is what matters. The most and only important thing is to begin.
Begin, even though it may be confusing or uncertain or unclear.
Begin, even if you have no clue.
Begin, even if no one in your life understands it.
Begin, even if you don’t understand it yet.
Begin without fear or knowledge of what comes next.
Just begin.
This post is part three of a seven part deep dive into Portfolio Careers:
Saying cya to “traditional” work, and why I’m building a portfolio career instead. Read here.
WTF is a portfolio career? Read here.
How I built my portfolio of clients, projects and income streams. This post.
Skills you need to run a successful one (wo)man show. Read here.
One thing they don’t tell you about working for yourself. Read here.
To portfolio or not to portfolio, that is the career question. Read here.
🏃🏻♀️ What’s been standing in your way of getting things in motion?
🙏🏽 Do me (and them) a solid, share this with a mate who needs to read it?
Anna, the below words are so true and should be freeing and inspiring for many because one thinks you have to have everything figured out, when really you just need to figure out that you want to start.
"Begin, even though it may be confusing or uncertain or unclear.
Begin, even if you have no clue.
Begin, even if no one in your life understands it.
Begin, even if you don’t understand it yet.
Begin without fear or knowledge of what comes next.
Just begin."
Anna, I'm just starting out a new career path. And it feels scary some times. Stories like yours are what that inspires me and keeps me rolling. Your ideas on structure are very useful and I'm going to try them for myself too. Thank you for this letter.
And I'm sorry that you are sick. Get well soon.