How to pivot your career without blowing up your life

Twist, turn, reposition, repeat.

Anna Mackenzie

May 29, 2025

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In a couple of weeks I’m flying to Sydney to do a keynote speech - my first ever! - about portfolio careers.

If you’d told me 12 years ago (when I was trying to become a spy) that this is where I’d end up, I would have straight up asked what you were smoking. My international studies major and fantasies of being a silent assassin did not see this coming: who goes from romanticising a life of espionage to giving a speech about how highly leveraged, multi-channel portfolio businesses might just be the future of work?

Apparently me!

I guess it’s not totally unexpected. After all, my career has been a decade of pivoting from point A to point B and beyond.

I used to feel ashamed of this wayward wandering but these days I’m rather proud of it, because I know that it’s far easier sticking to a path that feels safe than to wade through the messy process of figuring out what makes you feels whole.

That being said, major career changes are no joke. I mentor lots of pivoting-portfolio-people (try saying that 3 times fast) and I’ve noticed that there are two main ways to go about it:

Reinvent yourself: re-skill and/or move into a new industry and start again from the bottom
Remix yourself: start with the skills you have and strategically leverage and/or position them to help you move somewhere new

Reinvention involves making the radical decision to say goodbye to your current trajectory and do something wildly different. It’s a sharp turn that’s often cut and dry.

Remixing is taking what you already have - your skills, experience, relationships, domain knowledge etc. - and repositioning them to open new doors. It’s about moving sideways and forward at the same time, in a way that slowly changes the shape of your life.

There’s no right way to pivot but each of my career moves has been done via the remixing method. Case in point:

I used my experience in beauty to land a fractional gig with a B2B tech startup whose ideal customer was a beauty brand, even though I had zero tech experience
I took the learnings from being a founder and remixed those business skills to position myself as a portfolio career mentor
I took the learnings from launching someone else’s tech product to create one of my own - the Portfolio Career OS
I’ve leveraged this newsletter to land a speaking gig even though I’ve never delivered a keynote in my life

Here’s how.

How to pivot with purpose

Step 1: Locate your pivot point

The first step in any pivot is having a good sense of where you are and where you want to go. Ask yourself:

Where am I now? What’s point A?
Where do I want to go? What’s point B?

For example, I had deep experience in beauty (point A) but wanted to land a fractional gig in tech (point B). I didn’t know where, I didn’t know how, but I made it my mission to find a way.

Step 2: Find your bridge

Once you’ve located A and B you can retrofit a way for them to connect. All you need is a single point of relevance. One skill, capability or experience that, when transferred, can get your foot in a new door. Ask yourself:

What do I know that could be valuable to the space that I’m entering?
What skills are adjacent to this future direction, even if it feels like a stretch?

In my case, I knew that applying for gigs or networking with people in big tech would probably not be my easiest entry point because I had no track record or cred. But I knew beauty. I knew startups. And I hypothesised that if I could find a tech company who served beauty brands, I’d be in with a shot.

Step 3: Cross the bridge

Having a bridge in mind is a good start but it won’t take you anywhere unless you actually cross it. Your goal is to creep into this new domain in any way you can:

Connect with context. Network and reach out to people but lead with your bridge. Show them how your background connects with their world

Get curious, have conversations and pitch your value rather than a title

If you’re struggling to get traction, ask yourself:

What could I publish, create or share that builds a bridge into this new world?
Could I start a newsletter, share on LinkedIn, organise a dinner, or host a workshop that will help move me in the right direction?

When I was on a mission to expand into tech, the stars aligned. My brother-in-law received a big chunk of venture change for his tech startup and, among other things, needed help getting brands - beauty brands no less - on board. Was it luck? Possibly. But I’d also been declaring my intention, hustling like a crazy woman and putting myself out there for months, so when that opportunity arrived, I was ready.

Step 4: Take people on the journey

“Won’t this make me look all over the shop?” I hear you say. “Won’t remixing make people think that I’m a weirdo?”.

Well, possibly. But if you craft a narrative around your decisions and journey, then probably not. You can do all kinds of seemingly random things in your career as long as you narrate the change. Storytelling is the strategy to making it all make sense.

One example of bringing people on my remix-filled career journey.

Remix, don’t reinvent

Changing up your career without blowing up your life - also known as remixing - is a skill that can be learned.

It starts by acknowledging that you need a shake up. Then comes a commitment to making that change. Then you identify the overlap between what you’ve done and where you want to go. You reframe your expertise, reposition your skills, build bridges, put yourself out there, write a bit, do a speech (!) and watch the results of your efforts compound.

You leverage one skill to get a foot in the door. You learn new skills that help you kick open another. You collect, you stack, you step, you stretch, until you’ve remixed so many times that you’re playing an entirely new song.

🎙️ A detailed look at my beauty → tech pivot:

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🫶🏼 When you’re ready, here are three ways I can help:

Free Training - Stabilise, Systemise and Scale Your Portfolio Career in 2025: learn the inbound and outbound acquisition strategies to generate a consistent flow of leads and grow your income, and the workflows to that will help you increase capacity beyond your time.
The Portfolio Career Operating System: a fully fledged system for people who do multiple things and want to do them well.
Portfolio Career Mentoring: 1-1 sessions to help you get started and build a career that sits at the intersection of freedom, creative fulfilment, meaning and money.