What I learned and how I earned in 2024

My wild and wonderful year in review.

It all happened here.

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Before I get stuck into this annual review, a quick announcement! I’m running a Portfolio Career Operating System Live Q&A on January 15 AEST / January 14 PT. It’s a chance for you to ask any burning questions and see the OS in action before the early bird pricing of $299 USD wraps up. From January 20 the price will increase to $497 USD.

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At the start of this year I had two major goals:

1. Build my personal brand and hit 5k newsletter subscribers

2. Diversify my income beyond done-for-you (fractional and consulting) into done-with-you (advisory, mentoring) and do-it-yourself (digital products)

Both goals felt like a pipe dream back in January. At the time I had 369 subscribers and 100% of my income came from fractional work with startups, but I aimed high. In this Substack post on January 5th, I wrote:

“In 2024, I’m committing to Putting Myself Out There more online. The idea of doing so scares the shit out of me…but I know that I want to have impact. I want to help people learn from my successes and wild mistakes while founding a business. I want to save people time by sharing knowledge and skills from over a decade of working for global brands and from five years of working for myself. I want to connect with those who are also on the building-or-creating-something-meaningful path. And to do that my work needs to be seen. My words need to be read. And that ain’t going to happen unless I show up and share. So this year I’m having a crack at writing more frequently, broadly and loudly. I’m having a crack at sharing online daily. Despite the fear. Despite the self doubt. Despite the stress. Despite the anxiety. Because desire trumps fear every damn day of the week.”

At the same time as publicly declaring my intention to show up online, I privately set a goal that 20% of Q4 revenue would come from advisory and mentoring, and that I’d launch a digital product and make one sale. If I did both of those things, I’d be happy.

Where I landed

Personal Brand

I published 51 newsletters (and counting), posted 820 times to social media, went on 2 podcasts, wrote 10 guest blogs and got profiled in 4 articles.

Portfolio

I worked fractionally with 2 startups, advised 6 founders, mentored lots of portfolio careerists and launched 1 digital product that, just 2 weeks in, has exceeded my wildest expectations.

What I did (and didn’t do)

Today’s post is focused on how I grew my offering and diversified my income, but if you’re interested in how I built my personal brand in 2024 check out this previous post.

January

• Started the year off with mad goals and good vibes

February

• I was deep in startup-land working with an American client and most of my mornings started at 7 or 8am with a slew of back to back meetings. It was energising work but an exhausting schedule and as a result writing felt like a slog

“My newsletter growth slowed down this month even though I was posting consistently on LinkedIn. It’s a bit sad but I’m proud that I’ve kept going, even though sometimes I don’t really want to.” - February 20

March

• Nothing of note

April

• I put my money where my heart was and kicked off with a new mentor who I’d known for years and admired from afar. She had the type of career I’ve always lusted after; a serial entrepreneur turned advisor, investor, board member and speaker (among other things)

• Through some enlightening convos I started letting go of the need to have a clear plan for my business and trust that because I was doing the work the pathway would become clear

“I realise that I actually don’t need to have the answer as to where I’m heading yet, I just need to be in the moment, put in the work, continue writing my Substack and trust the process.” - April 30

May

• On May 24 I published a piece that had been sitting in my drafts for over six months. It was titled ‘Saying goodbye to traditional work and why I’m building a portfolio career instead’, and it would go on to change my entire trajectory

• The response was massive and I knew that I’d tapped into the zeitgeist and voiced something so many people had experienced but couldn’t name - the portfolio career

• I decided to place all my bets on exploring this topic because I knew that it was inherently broad, meaning I could niche down while continuing to write about lots of things and not feel creatively restricted. I’d found the ‘non-niche niche’, otherwise known as the niche jackpot

June

• I started receiving DMs from readers asking if I offered portfolio career mentoring. It was the first clear market signal that I had this unique skillset that could be highly valuable to others

“I’ve started receiving inbound interest for mentoring, totally unsolicited. Part of me wants to run headfirst because the opportunity is there for the taking and it’s another way to have impact, the other part of me wants to start small and test the offer, structure and pricing. I think I’ll do the latter because my thesis is always ‘start small to go big’.” - 17 June

• I started quietly taking on mentoring clients and progressively increased my rates to see what the upper price limit might be. I tested new questions, formats and structures. I became clear on the best way I could help people one on one

• Like magic, referrals for startup advisory also started trickling in. I had officially entered my done-with-you era

July

• I killed an art project I’d been working on for months and even though doing creative work for creativity’s sake is a major life goal, the timing just wasn’t right

“I’ve taken on way too much and am literally drowning, and while it kills me to write this I’ve decided to drop my art project because continuing will likely kill me even more. I know I’ll do it someday, but today is not that day. Today is the day for building scalable income.” - 15 July

• Turned away a lot of fractional client work. The money was tempting but the cost to my time and energy was not

• Learned that a solid and successful portfolio career is as much about what I don’t do, as it is about what I do

August

• After much deliberation I made a decision not to monetise this Substack through paid subscriptions even though tons of people have said they’d happily pay, because:

  • The cost of commercialising my creativity is too high

  • I want to have as far reaching impact as possible, and paywalling my ideas is in direct conflict with that ambition

  • This newsletter drives leads to other areas of my business, and those leads are more valuable than the cash I’d make from subscriptions

• Got comfortable with this decision…don’t show me the money!

September

• I walked away from a major client, a tech startup I’d been working with for over 18 months. The stakes were rising as they embarked on a Series A fundraise, and I knew I couldn’t continue operating at the speed of light for them if I wanted to build out my own offering. This was a scary call since they represented 70% of my income, but I took a deep breath and decided to back myself

• Ran a massive piece of discovery research into portfolio careers, interviewing 30+ and surveying 200+ people. I uncovered about a gazillion pain points that I was uniquely positioned to help solve

• The plan started crystallising. Things starting taking shape. Everything started popping off

“It’s the last month with [main client] and I generated over 1000 new subscribers in 30 days. This is insane to me given that at the beginning of the year I’d be lucky to scrape together 1 every few days. What is happening?! I’m taking this as a sign I made the right decision.” - 30 September

October

• Did a major revamp of my website

• Officially launched my mentoring and was shooketh by the quality and calibre of the people signing up. People from the biggest tech companies in the world. CEOs of almost-billion dollar businesses. Former exited founders

• Wrote a lot of affirmations like ‘I know stuff’ and ‘I can help people’ and ‘I’m qualified to mentor these superstars’, and so on

November

• After writing this piece on portfolio career positioning and talking about one of my superpowers (being a strong operator) I started conceptualising a digital product; my personal Operating System that I’ve used to run and grow my portfolio career for years

• I dangled the carrot and ran a couple of polls to gauge peoples’ interest. There were bites

• I began templating my entire OS, and adding examples and training videos etc. and gave it to a bunch of my mentoring clients for feedback

• Iterated, got more feedback, iterated, got more feedback

• Sat on it for a week or two deliberating whether to launch in the lead up to Christmas or wait until the new year. Twiddled my thumbs

• People started DM’ing asking where the OS was and so I made the call to launch. I created a waitlist page and within 24 hours had over 200 people sign up

• Felt butterflies

December

• Launched the OS on December 9 with one goal: to make one sale

• Made one sale within 3 minutes

• Made more sales

• Made my first sale while sleeping

• Got clear market validation, brain broke, mind expanded

• Reached out to every customer letting them know I was here if they had questions, and asked if they could trickle through feedback as they got into it

• Received epic feedback and some eye wateringly good testimonials (I’m still crying)

• Received some constructive feedback about the setup process and quickly created onboarding guidelines and a checklist so people immediately made the OS their own and saw the value within the first hour

• Continuously tinkered with the website and tracked changes to conversion

• Woke up one morning and realised I’d achieved every goal I set for myself in 2024

What I learned

• Build products off the back of insights about pain points your customers have. Conduct a short piece of research if you have to. Speak to lots of people

• Validate everything before you build it. Signs of validation include: inbound requests or enquiries, lots of people asking you for the same thing, sign ups to a waitlist, pre-sales

• Perfection and excellence are not the same thing. You can let go of a need for perfection but still strive for excellence in your work

• Your personal brand is a force multiplier and if you commit to 12 months of consistently showing up online it can change your life

• When you start getting traction you’ll get copycats, impersonators and people that rip off your work. This is heart wrenching but you can choose to use this as fuel. Take bigger risks, come up with more original ideas, stay ten steps ahead

• Trust the process and keep going, even when it feels like you’re going nowhere (or backwards)

If you’ve made it this far, thank you. I truly hope my little ‘stack has helped you in some way this year - whether it’s taught you something, inspired you to take action, challenged you to think differently, offered a different perspective or perhaps even sparked an idea that’s changed how you live your life. If I’ve done just one of these for you, then I consider this year a success.

And with that, dear friends, the 2024 season has to come to a close.

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The last little chit-chat of the year 🫶🏼

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When you’re ready, here are two ways I can help:

1. Portfolio Career Mentoring: 1-1, personalised mentoring (with yours truly) to help you build a career that sits at the intersection of freedom, creative fulfilment, meaning and money.

2. The Portfolio Career Operating System: an all-in-one operating system designed to help you streamline workflows, save time and minimise burnout while focusing on the things that drive more revenue, happiness and fulfilment. The exact system I’ve used to grow my portfolio to multiple six figures across fractional, advisory, mentoring, writing and digital products. Learn more here.

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