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Watch: How to turn your skills into a portfolio career that fits - lessons from a cross industry leader

Written by Outsized | 10/1/25 8:00 AM

                                                           

The portfolio career is no longer a niche concept. Fractional executives, independent coaches, consultant-creators, multi-sector advisors: the model of one employer, one title, one income stream is giving way to something more fluid and, for the right person, significantly more fulfilling. But getting there requires more than leaving a corporate job. It requires clarity about what you are genuinely good at, what the market will pay for and what kind of work actually gives you energy.

In this session, Michelle, a strategic product and transformation leader who has worked across automotive, insurance, healthcare and chief of staff roles before building her own coaching and consulting practice, shares her personal experience of making that transition and walks through the frameworks and practical steps that helped her find her footing.

Watch the full recording here:

What you'll take away from the session:

  • A clear definition of what a portfolio career actually is, including fractional roles, consulting practices, coaching and hybrid combinations, and how to assess whether it is the right structure for where you are now

  • How to identify your superpower by paying attention to what people consistently praise you for, even when you dismiss it as just part of your job

  • Why two to three working identities is the right number to test at any one time, and what happens when you try to pursue more

  • A structured exercise to develop your one-liner value pitch: what you help people do, using what superpower, with what outcome

  • The concept of the personal board of directors, including who you need in your corner as an accountability partner, a devil's advocate and a supportive peer, and why this matters more in a portfolio career than in a corporate one

  • The importance of failing fast and discarding working identities that do not fit, and why the process of elimination is itself a form of progress

  • What the typical stages of building an independent practice look like, from initial uncertainty through niche discovery, confidence crisis, collaboration and eventual refinement  

     

This session is interactive and discussion led. Participants share their own one-liner pitches during the session, and Michelle gives real-time feedback on each one.

Hit play and take the first step toward understanding what your portfolio career could look like.