Opening
Careers no longer follow a single ladder, and the freedom of a portfolio life comes with a hidden bill. Without a team around you, every dip in work becomes a dip in confidence. Claire Skillen came to this conversation with a remedy that is social before it is professional.
The remedy is closer than most of us assume.
The idea
Claire Skillen is a business strategist whose career dances between holistic therapies and business consulting, a living example of the portfolio career she described. Our conversation explored why connection, mentorship, and a core support group matter so much when your working life is self directed.
A portfolio career intertwines several paths, and each path benefits from people who know your whole picture rather than one job title.
Claire’s grounding tip for anyone living in a condo or apartment became one of the episode’s most shared moments, a way of steadying yourself in the body when your home is also your workplace and the walls feel closer than they should.
Her career itself is the argument for the portfolio life, moving between holistic therapies and business consulting without losing the thread of either.
She spoke about mentorship as a relationship that works in both directions when each person understands the whole picture rather than a single job title, and about the women in science and technology network on Vancouver Island that she pointed listeners towards as an example of community built on purpose.
We explored how career paths intertwine, and how the ability to make a meaningful impact grows when the people around you understand several of your strands at once.
The idea she returned to is that a support group is not found, it is built, deliberately and maintained with intention, and mentorship flows best between people who understand the whole of each other’s working lives.
What I took from it
Claire described the working life I have assembled for myself since moving to Canada in 2021, and the support group she describes is exactly what I set out to build that year. When your career is a portfolio, your people are the portfolio’s backbone.
I have learned to treat those relationships as infrastructure, not luxury. The lesson I carry is that support is something you design, not something you wait to inherit. The support group I built that year is still carrying me, strand by strand.
Three things to try this week
- Sketch your portfolio on one page, every professional strand you currently hold, and note who supports each one. Gaps will show quickly. Include the strands that earn little money but hold much meaning. Keep the sketch where you plan your week, so the gaps stay visible.
- Name your core support group out loud, member by member. If it has no members yet, invite one person into it this week with a specific ask. One honest conversation is enough to begin. The group grows from there. Name the support you need as precisely as you would name a project.
- Try Claire’s grounding tip. Take three slow breaths with bare feet on the floor before your next working block, even in a small apartment. Three breaths take less than a minute and change the hour that follows. Grounding before work sounds small, and it changes how the day begins.
Watch and go deeper
The conversation with Claire is embedded below. Watch it for the portfolio career stories and the grounding tip. Connect with Claire through LinkedIn.
Explore Claire Skillen on LinkedIn.
New conversations land on the Rediscovering Connection channel most weeks, and you can subscribe at the Rediscovering Connection channel.
Close
A portfolio career needs a portfolio of support behind it, built strand by strand with the same intention we give our work. The people who know your whole picture are worth finding on purpose, and the portfolio is only as steady as the support beneath it.
Explore the certification, then sit with the question this article closes on.