What Kris Jenner's face has to do with portfolio careers, getting sold on yourself & why you need an IRL strategy
Your weekly guide to building a pro-passion, anti-hustle portfolio career
⏰ 60-SECOND TAKEAWAY
What Kris Jenner's facelift says about your 40+ portfolio career advantage
The sales breakthrough transforming our Club members' confidence
Why going IRL is your secret income weapon in an AI-obsessed world
AI Tip of the Week: How voice journaling can uncover beliefs about your business
This week's Human Design Q&A: Projector marketing without the pushy energy
“At 40+, you've stopped giving a shit what others think, so you can finally build a portfolio career that aligns with who you are instead of who you think you should be."
💭 WHAT’S ON MY MIND
I've been ranting about Kris Jenner's latest facelift on social media this week. I finally figured out why it pissed me off so much, and what it has to do with portfolio careers.
While she's spending money trying to look 25, women 40+ are convinced they need to compete on youth and hotness to build successful businesses. The message is crystal clear. If you're over 40, you'd better look 20 while building your empire.
This isn't just celebrity nonsense. It's seeping into business culture. This week we learned that Workday is facing a lawsuit for recruitment tech that allegedly discriminates against applicants over 40. Our fears about being 'too old' aren't paranoia anymore.
What annoyed me is that women are already drowning in impossible beauty standards, and now some of us won't even consider stepping into a new business or career because our confidence is shot to shit. But here's what I want you to take away: at 40+, you have established networks, proven expertise, and enough financial stability to take calculated risks. Most importantly, you've stopped giving a shit about what everyone else thinks, which means you can finally build a business that actually aligns with who you are instead of who you think you should be.
We also know that the average age of founders behind the fastest-growing US ventures is 45. Women in their 40s and 50s outperform younger founders in both revenue and longevity.
Sallie Krawcheck founded Ellevest at 49. Janine Allis launched Boost Juice from her kitchen at 39. Schiller and Robinovitz co-founded Sloomoo Institute in their 50s, creating a multi-city experiential empire.
While Kris Jenner is trying to turn back time, these women leveraged exactly what their age gave them: experience, perspective, and the wisdom to stop caring what others think.
Your wrinkles aren't your weakness. Your decades of experience are your competitive advantage.
🫣 INSIDE THE PORTFOLIO CAREER CLUB
"Getting Sold on You" Sales Breakthrough That Changes The Way You Feel About Selling
This week in the Portfolio Career Club, we dove deep into what I call integrity-based selling, because, unsurprisingly, most members were terrified of sales conversations despite having decades of corporate experience.
The irony is that most of us have been "selling" ourselves in job interviews and managing stakeholders for years, but the moment we have to sell our own services, we freeze.
The challenge.
During our Sales Lab, members revealed their biggest sales blocks:
Believing sales was "dirty" or manipulative based on past icky experiences
Feeling like they needed more credentials before they could confidently sell
Panicking about pricing conversations and stumbling over their value proposition
Absorbing clients' energy through their open centres and losing confidence mid-call
The Human Design connection.
Each energy type has distinct sales superpowers when they stop fighting their design:
Generators/MGs: Natural magnetism when they're genuinely excited about what they're offering
Projectors: Incredible ability to see what clients need when they're properly recognised and invited
Manifestors: Can confidently inform and initiate without seeking permission or validation
Reflectors: Offer unique perspective that clients crave when they honour their natural timing
The framework we implemented.
The 6-Step Integrity Sales Structure that I use for every discovery call:
Set the tone: Regulate their nervous system by outlining the call structure upfront
Get curious: Ask about priorities, challenges, and desired transformation
Create congruence: Share your program promise, unique method, evidence, and handle objections
No on-the-spot decisions: Never pressure someone to make an immediate decision, especially with emotional decision-makers
Follow up with value: Fortune is in the follow-up (takes 4-7 touches on average)
Close ethically: Clear next steps without destabilising their nervous system
Real transformation story: I shared my own sales breakthrough with the group – how my sales anxiety actually stemmed from a teenage retail job where customers called me "overconfident." That single comment had shaped 20 years of shrinking in business conversations. It wasn't until I implemented my own "get sold on yourself" exercise and started practising the 6-step structure that I felt different. Now I approach every sales call from a place of genuine excitement about the value I deliver, rather than apologising for taking up space.
YOUR SALES CONFIDENCE QUESTION: What past experience created a limiting belief about sales that you're still carrying into your portfolio career conversations?
🤬 UNPOPULAR OPINION
Most portfolio careerists are obsessed with building "location-independent" businesses, but this digital-first mindset is actually limiting your income potential.
Here's what I've noticed:
The portfolio career community has become so focused on online everything that we've forgotten the premium value of human connection. We have all fallen into this path of online courses, providing support virtually, and networking through DMs.
Meanwhile, I've just had my most profitable quarter yet, and it's directly tied to going back to IRL.
The data that changed my mind:
My in-person strategy sessions command 3x higher rates than virtual ones
80% of my highest-value client relationships started with face-to-face meetings
As AI tools flood every industry, clients are actively seeking "human-first" experiences and paying a premium for them
Why we're getting this wrong:
We've confused corporate-mandated office returns with intentional human connection. Just because forced proximity is soul-crushing doesn't mean all IRL interaction should be avoided.
More importantly, as AI becomes the default for content creation, customer service, and even coaching, our humanness becomes our scarcest asset. Clients can get strategy frameworks from ChatGPT, but they can't get the nuanced insight that comes from reading body language, feeling energy in a room, or experiencing genuine human intuition.
Your Human Design Type actually determines how crucial this is for you. Projectors and Manifestors especially thrive with strategic in-person presence, while Generators and Manifesting Generators can leverage group energy for better decision-making.
The strategic IRL approach for portfolio careerists:
Premium intensives instead of monthly retainers
Intimate industry gatherings you host, not attend
Local partnerships with complementary businesses
Quarterly client appreciation events that strengthen relationships
Real results: Since adding Melbourne VIP strategy sessions to my offering, I've signed three new private clients who specifically mentioned wanting to work with someone "real" in an increasingly automated world.
The unpopular truth: While everyone else is building faceless online empires competing with AI, your willingness to show up IRL becomes your biggest competitive advantage.
If you are interested in hearing more how to build your presence and personal brand using human design, on July 1st I am launching something specifically designed for portfolio career professionals, reply to this email and I will add you to the list
🤖 AI TOOL SPOTLIGHT
Ensuring Women Portfolio Careerists Lead in AI Adoption
Each week, I'll share an AI tool, tip, or strategy specifically designed for portfolio careerists. This isn't just about tech, it's about ensuring women claim their rightful place in the AI revolution.
“61% of men report that generative AI substantially boosts their productivity in professional settings, only 41% of women feel the same benefit. This 20-point gap isn't just a statistic, it's an opportunity for us to change the narrative.”
This Week’s Insight:
Voice Journaling for Portfolio Careerists
Everyone's obsessed with prompting AI for content creation and automation, but I've been experimenting with something completely different. Using AI to analyse what I'm actually saying out loud about my business.
Why voice journaling works
In Human Design, the Throat Centre is where we express our truth and manifest our ideas into reality. When we speak our thoughts aloud, we often access insights that never surface in written form. Your voice carries emotional nuance, hesitation patterns, and authentic breakthrough moments that typing can't capture.
How I'm using this with clients
One of my Portfolio Career Club members started sending me daily CEO voice notes about her day. Wins, frustrations, decisions she was wrestling with. After a month, I fed all the transcripts into Claude and asked it to identify her recurring empowerment themes.
We then created a personalised set of mantras drawn directly from her own words during her strongest moments. Instead of generic affirmations, she now has phrases like "I trust my pivot instincts" and "My weird combination of skills is exactly what they need." Language that came straight from her mouth during actual breakthroughs.
Simple implementation
Record spontaneous voice memos after client sessions, networking events, or those 3am breakthrough moments
Transcribe with Otter.ai or Letterly app (both have generous free plans)
Upload to Claude or ChatGPT with this prompt: "Analyse this transcript for recurring confidence patterns and limiting belief language. What's one insight I'm missing about my own growth?"
Why this works for portfolio careerists
Speaking is more natural than writing when you're processing multiple income streams, client feedback, or career pivots. AI can spot patterns in your spoken language that uncover subconscious narratives, both empowering and limiting.
Bottom line: Your voice contains data about your mindset that even you don't consciously notice. Let AI help you mine that gold.
🙋🏻♀️ ANSWERING YOUR PORTFOLIO CAREER DESIGN QUESTIONS
Each week, I'll answer a Human Design question from a reader. Submit yours by replying to this email with "HD Question" in the subject line.
This week's question:
"I’m a Projector building a portfolio career as a business strategist. I know I’m supposed to ‘wait for invitations,’ but I feel like I need to actively market myself to get clients. How do I balance my design with the reality of running a business?"
My response:
This is the number one challenge I hear from Projector entrepreneurs. And you’re right, you’re not meant to sit back waiting for work to magically land in your inbox.
Here’s the nuance:
You’re not waiting for business. You’re creating the conditions for recognition.
As a Projector, your energy is precious and powerful when used strategically. Rather than chase clients, focus on making yourself easy to recognise as the go-to expert in your space.
Try this:
Be seen, not salesy. Share insights publicly, comment thoughtfully on others’ content, or speak in spaces where your ideal clients are already active.
Ask great questions instead of offering advice uninvited. This invites people into your world without pushing.
Position yourself where recognition naturally happens. Prioritise targeted visibility over wide promotion
When someone says, “I’ve been following your work,” or “Can I pick your brain?” that’s your cue. That’s your invitation to offer something more concrete.
A quick note on balance:
You might hear things like “spend 70% of your energy on being visible and 30% on outreach.” While that’s a useful guideline, it’s not a rule. As a Projector, less really is more. You don’t need to be everywhere - you need to be clearly visible in the right places.
Your gift isn’t about waiting. It’s about being so deeply insightful and well-placed that the right people can’t help but come your way.
Presence and Positioning are a core part of what I teach in the Portfolio Career Club and key to a sustainable and successful portfolio career. If you’d like to hear more, here is the link for the September waitlist
🤳🏼 THIS WEEK’S MEME
I felt like this was a perfect illustration of the changing nature of work. We all need to be continuous learners, adding skills to our toolkit as we execute our work.
Do you have a meme or image about work/careers that you love? Respond to this email, and I will share it in the next newsletter.
⚡️ WHAT'S LIGHTING ME UP THIS WEEK
📚 Reading: "The E-Myth" by Michael E. Gerber– This book is helping me uplevel my thinking as I scale and sort between working on the business vs. in the business.
🎙️ Listening: Pivot with Kara Swisher and Scott Galloway is a favourite of mine. Each week, they cover business, tech, and politics. I love their unfiltered analysis, bold predictions, and witty banter.
🌀 Practice: Open Head Center curation – I've been experimenting with "inspiration audits," where I track which ideas feel genuinely exciting versus which feel like mental pressure from others' urgency. My completely open head centre in human design picks up everyone's "you should do this" energy, so I'm learning to pause and ask: "Is this MY curiosity or someone else's agenda?"
🧵Threads worth reading: check out this LinkedIn post by Leila McGlew where she talks about how people are quitting social media in exchange for IRL spaces with real connection. The comments section blew up!
💭 Question I'm sitting with: "What would change about how we build businesses if we prioritised sustainable energy over scalable systems?" (This has been reshaping how I think about growth – I'd love to hear your take. Reply with your thoughts!)
🌀 LAST WEEK'S READER WISDOM
My question: "How might we redefine success metrics for portfolio careers beyond just financial outcomes?"
Franklin nailed it with this framework:
Portfolio career success metrics should include:
Network building: Are you connecting with people for current and future opportunities?
Expert positioning: Is your content establishing you as the go-to person in your field?
Life integration: Does your portfolio career give you freedom to prioritise health and relationships?
Future growth: Can you scale this into the business you ultimately want to build?
💌 LOVE NOTES FROM THE CLUB
And if you are looking for support to kickstart your portfolio career in 2025, here are some ways to work together:
Register Your Interest for the September Portfolio Career Club Intake
Get your Hyper-Personalised Human Design Career Insights Report: Personalised analysis revealing your innate work style and leadership potential, blending Human Design with strategic frameworks
Check out my Portfolio Career Mentorship: Corporately-honed, consciously-led 1:1 portfolio career mentorship for visionary women (taking interest for June, 2 spots available)
FREE Download: Guide on how to Kickstart Your Portfolio Career using Human Design, download here
FREE Quiz: Find out your Portfolio Career Archetype here
Jules, these insights are brilliant, real and honest. Reading this article clarified a few areas of my business that I was needing to hear. Thank you!
Great insights and helpful tips! I'm really fond of the questions you propose regarding metrics for success in a portfolio career. I made a note of them!