Should You Pivot... or Pile On?

Hey there —

It’s been a minute (okay, a few minutes 😅) since I last popped into your inbox.

Since then, this list has grown with tons of new subscribers (hi!) and I’ve been deep in pitching mode for my forthcoming book, Going Places, all about redefining ambition, identity, and success when your career plans don’t go as planned.

So it feels like the right time to reinstate our weekly inbox dates — with something I’ve been hearing everywhere lately:

“Should I pivot into something new, or should I build something on the side?”

In other words:
Do I need a switch — or should I stack?

Let’s break it down:

🔀 When to “Switch”

You’re craving change. You’ve outgrown your current role or industry, and you’re ready to rebrand. A switch is a bold move — usually into a new job, company, or field altogether. 

This could be right for you if:

• You’ve mentally quit your job but still show up on Zoom
  

• You’re craving new skills, new projects, new people
  

• Your values or interests have changed in a big way (like, say, after a few “once-in-a-lifetime” global events) 

🧱 When to “Stack”

You’re not necessarily unhappy — but you want more. More autonomy. More creativity. More variety.
Stacking your career means adding something new without leaving your job (yet). 

Freelancing, consulting, launching a personal brand, or starting a creative side hustle all contribute to your “portfolio career.”

This could be right for you if:

• You’re curious about building multiple income streams
  

• You want to test a new direction before making a leap
  

• You’re looking for more fulfillment without burning it all down

There’s obviously no “right” answer — only what’s right for you in this season.

But here's what I know: Stacking can build your confidence to switch. 

And sometimes, stacking becomes your main thing.

No move is wasted. 

If this resonates with where you are right now — I’ve got more coming. I’m working on new tools, stories, and resources to help you navigate your next chapter (and your next income stream 👀)!

This week’s question comes from Camille:

Yup, yup, yup- you’re preaching to the choir, here! This is your sign to stop searching for your next move by job title, and start searching by work style. Look for roles that let you move around, work with your hands, be out in the field, and lead projects, not sit in back-to-back meetings.

Ideas to get you started: Events management; community management; traveling sales; real estate; creative production; even digital media production (capturing content IRL)!

Love the newsletter but want more? Did you know I’ve put together an entire course called Pivot with Purpose? It’s a clear, proven method to break out of your “Millennial Career Crisis” and find meaning and fulfillment in a new 9-5!