THE GREAT MILLENNIAL CAREER PIVOT
I spent 15 years in luxury fashion product development, managing operations, supply chains, production timelines, and the systems that keep creative businesses functioning. Then I spent 3 years running my own illustration and product business.
Now I’m at a crossroads many of us hit in our 40s: the traditional career path no longer fits and the alternative isn’t obvious yet.
So I'm giving myself 2026 to figure it out. Strategically, not desperately.
Why This Is Happening
A creator recently called this “the great millennial career crisis” and it clicked immediately.
We were sold a version of success that no longer exists study hard → pick a career → climb the ladder → stability follows.
Instead, we entered the workforce during recessions, watched costs rise faster than wages, saw technology erase job categories, and realised that many “successful” careers aren’t aligned with the lives we actually want.
I decided I wanted to work in fashion at 14 years old. I remembered reading an article in a teen magazine (yes! A magazine) where a fashion university student was interviewed about a product she designed. I read that and it clicked with me. I set a goal, got into the right university, landed the right jobs, and kept moving up.
Looking back now I realise my goals were very short term…get a job at a fashion brand, then get the next role at a better brand. And that worked… until it didn’t.
Doing this whilst having a family never entered my mind. Needing flexibility for kids, and schedule didn't either. I never considered that my values might shift along the way.
And I believe I'm not unique in questioning everything right now. Here's how it showed up for me.
What This Looks Like for Me
After 15 years in luxury fashion product and operations, I know where creative businesses break:
Pricing strategies based on guesswork instead of data
Production workflows that collapse under pressure
Stock orders planned around hypothetical future sales
Launch processes that work once, then fail
Operational systems held together with hope and spreadsheets
I spent years fixing these problems for brands. Then I tried to build my own business — and made every mistake I used to help others avoid.
For the past 3 years, I've been running an illustration and product business while raising two young children. After I had my first baby, I realised I had an opportunity to do something a bit more creative, and running my own business was going to give me the flexibility I needed as a new mom. I was really excited. I did course after course with a baby in tow to prepare myself. I made every mistake I used to help other companies avoid. I built beautiful products without a clear audience. I bought stock based on optimism. I launched to no one.
After my second child, returning to that business felt heavy. I loved the creative work, but I couldn’t ignore the numbers anymore. At the same time, AI was becoming impossible to ignore — and I didn’t know what that meant for my career.
So I stopped. I researched. I learned how AI actually works. And I finally looked honestly at my data.
That brought me here.
The Question I’m Answering
I’m not asking “What should I do next?”
I’m asking “Where does my experience create the most leverage now?”
Right now, I’m testing several paths:
Returning to employment in operations or strategy
Building a consulting practice
Creating tools or frameworks that scale beyond 1:1 work
Or some hybrid of the above
I have the expertise. I’m exploring how to apply it properly.
The 2026 Plan (Not Just Winging It)
I'm not sitting around hoping clarity strikes. This year is about collecting evidence and making informed decisions.
Here's the plan for 2026:
1. Real Conversations (Not Networking, Research)
I'm reaching out to 30-50 people across different industries to understand:
Where businesses are genuinely stuck
Where AI helps vs where it’s just noise
What consulting actually looks like in practice
What energises me — and what doesn’t
I am getting out of my comfort zone and having real, exploratory conversations to build my information bank.
2. Workflow Testing & Documentation
Every week, I test AI-supported workflows and tools for operations, planning, and product development:
How does AI actually help with pricing decisions?
Can it speed up supply chain analysis?
Where does human expertise still matter most?
How can AI support and improve a creative product business?
What can be automated vs what shouldn't be?
I publish what I learn every Saturday. Some experiments work. Some flop. All get documented.
3. Positioning Tests
I’m testing how different framings land and what gets me excited about:
"Operations Strategist for Product Businesses"
"AI Implementation for Creative Business"
"Product Development Consultant"
"Strategic Operations Advisor for Creative Companies"
By mid-year, I'll have data on which positioning gets traction with the right people.
4. Decision Points Built In
This isn't open-ended exploration. I have clear checkpoints:
March 31: 15 conversations completed, positioning tests analysed, clarity emerging?
June 30: 30 conversations done, clear direction identified, test offers validated?
September 30: Decision made—consulting, employment, tools, or hybrid?
By September 2027, my youngest will start school. That's the hard deadline.
2026 is about making informed decisions, not avoiding them.
What's Emerging So Far
I'm only 13 weeks into documenting this publicly, but patterns are already appearing:
What energizes me:
Strategic analysis and problem-solving
Building frameworks and systems
Research and pattern recognition
Discovering opportunities, and testing new approaches
What drains me:
Work I don’t believe in
Selling products to audiences that don't exist yet (learned this the hard way)
Constant performance marketing
What's working:
Consistency (13 weeks published = longest streak ever)
Honest documentation
Testing ideas on my own business first
Building audience before building products (opposite of my 2023-2024 mistake)
What I'm still figuring out:
Do I want to work with businesses or build tools for them?
Is employment more appealing than I thought?
Where does AI genuinely help vs where it's a distraction?
By the end of 2026, I'll have answers. For now, I have questions and a process to answer them.
Why I’m Documenting This Publicly
Because:
Accountability beats good intentions
I’ll need an audience for whatever comes next
This becomes a living portfolio of strategic thinking
The conversations this creates are more valuable than silence
The risk of looking uncertain is smaller than the risk of building nothing.
What Happens From Here
Every week for the rest of 2026, I'll publish what I'm learning:
The conversations I have and what they reveal
The workflows I test and whether they work
The positioning experiments and what resonates
The uncomfortable realizations and strategic adjustments
Some weeks will be tactical. Some reflective. All honest.
If you’re mid-career, questioning old scripts, or trying to adapt without burning everything down — follow along, hit reply or DM me - I want to talk to you..
This might work. It might not.
Either way, I’ll document what happens.
