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We covered changing careers last week. What about if you don’t want just ONE career? What if context switching is what makes gets you going and feels exciting? Introducing portfolio careers. Another one of those where we were already doing it before the term existed.

Quickly addressing the politics around the concept of portfolio careers, because OF COURSE we know this concept - the working class literally live off the concept of having more than one job out of necessity for staying alive. Perhaps that is also your reason for wanting a portfolio career - because you need an extra job or two to stay afloat. Very valid. Just wanted to address that some people have the option of choice, and some people don’t.

Here are some people who can help you on that journey…

The accidental glue person: How community work kept finding her (30 mins)

Nicola Earle on the villager mindset, portfolio career seasons, and skills that feel effortless.

Some advice: Start with just one extra stream and work on it slowly for a year, you don't need four or five right away.

How to go fractional (the realistic version) (34 mins)

Karina Mikhli on the 3-9 month hunt, self-employment realities, and sustainable community building.

Some advice: Realistic timeline: expect 3-9 months to land your first fractional role, and she ran her community unpaid for 2 years first.

She spills the tea on fractional marketing (29 mins)

Terra Milo on the challenges of cold outreach, introversion in public speaking and the need for authenticity and connection in a tech-driven world.

Some advice: Cold outreach via website reviews landed her fractional marketing clients - proactive business development is essential!

She's built a fire portfolio career & shares what's working right now (35 mins)

Taylor Elyse Morrison on the challenges and joys of having multiple roles, the power of asking questions, and the joy of experimentation in professional growth.

Some advice: Think like a "career scientist" running light experiments, and pay attention to shame as a signal.

See you next week!

✍️Mildred Cheng
Content Lead @ GW

📍Either Singapore/Hong Kong/Sri Lanka

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