Portfolio Career Podcast

Melissa Wong returns five years after her first appearance to talk about her new book, The Fluid Career. She and David dig into why multi-hyphenates and portfolio careerists are best positioned to weather AI-driven job anxiety. They also reflect on David's own career transition over the past year. Enjoy!

An audit can be much more than an assessment, it can be the beginning of a great conversation. This episode explores how providing business owners with an audit creates something tangible to discuss, encourages collaboration, and helps uncover opportunities together. I did this last summer when I was transitioning, wanted momentum, and it went better than expected. Learn all about it here.

Taking chances can change the direction of our lives. In this episode, multiple voices share their perspectives on taking risks, embracing uncertainty, and saying yes to opportunities, even when you don’t know exactly where they’ll lead.

When I use social media, I am often projecting something. A story. A message. An event. Something. And at the same time, there is a lot more going on in my life that I often do not post about, or know where or how to do so. Insert: a Now page. It is a page on my website that I can communicate what is holistically top of mind to me. It is very handy when communicating with people digitally too. Learn more about this webpage and why you need a Now page.

Olivia Leavengood shares her journey from full-time Chief of Staff to bootstrapped Founder to fractional chief of staff, and she's now niched down into helping B2B founders master founder-led sales. She breaks down why niching down is key to building a fractional or consulting practice, why warm referrals drive most early-stage B2B sales, and how AI is shifting where founders should spend their scarce time. Olivia also introduces her "When to Think of Me" doc, a simple, low-fi alternative to a personal website that keeps her top of mind with her network. Enjoy!