Building a Portfolio Career: Diversifying to Design the Career You Want

We were joined by Sarah Ing - career and leadership coach for engineers, consultant, and former VC-backed founder and engineering leader - and Seth Blank - startup exec, founder, board member, and multi-time advisor (and Enrich member!) - for this wonderful discussion of how to Build a Portfolio Career.

Here are our notes from the conversation:

• Getting Started with a Portfolio Career

  • Start where you are: leverage your current skills, contacts, and curiosities

  • You don’t need a master plan, just take the first imperfect opportunity

  • Don’t get hung up on job titles! solve problems, not roles (be curious)

  • Treat early advisory or side projects as experiments, not commitments

  • Seth: “Take the first step, even if it’s not perfect. That first board or advisor role gets your foot in the door.”

  Networking & Building Opportunity

  • Use your existing network and ask directly for intros

  • Try unique approaches like voice messages instead of cold DMs (Sarah’s tip)

  • “Who in your network might need advice?” is a powerful question to ask mutuals

  • Most success comes from warm intros and specific positioning

  Time Management for Busy or Introverted People

  • Protect your time like a business asset: set calendar boundaries

  • Carve out blocks for deep work, reflection, or side projects (even one hour counts!)

  • Be transparent with your employer about your capacity (when needed)

  • Start small, then expand as energy and confidence grow

  Positioning Yourself as a Generalist

  • Focus your narrative around the problems you’re great at solving

  • Generalist does not mean aimless: your range is a strategic advantage

  • Highlight your ability to work cross-functionally and translate between teams

  • Framing is everything: you’re not “doing a lot”, you’re building adaptable solutions

  • Sarah: “Challenge the perception that being a generalist is a weakness. Highlight your ability to work across boundaries.”

  Moving from Free to Paid Advisory Roles

  • Start with nonprofit or pro-bono advising to build credibility

  • Connect with investors, board members, and founders who value your expertise

  • Be clear about the value you offer (don’t undersell yourself!)

  • Think in frameworks: time expectations, equity vs cash, vesting schedule, max hours

  • Sarah: “Ask: Does this rate feel fair for the value I’m offering, not just the hours I’m putting in?”

  Recommended Next Steps

  1. Map your skills, interests, and current contacts and see what overlaps?

  2. Reach out to your network and ask who could use your brain!

  3. Start with a low-stakes project (mentoring, advising, content)

  4. Protect your time and block hours for creative or advisory work

  5. Practice telling your story around solving problems, not holding titles

  Shared Wisdom from the Session

  • Overcome imposter syndrome by taking action

  • You don’t need to be “ready,” just start somewhere

  • Network authentically and strategically

  • Boundaries are what make side work possible

  • A portfolio career is a journey, not a destination

Thank you to our two panelists for their advice, stories, and encouragement!