Embracing a Portfolio Career as a Multi-Hyphenate

Exploring a way of work that incorporates many projects and passions.

For the first time since our son was born nearly a year ago, we will have dedicated childcare. This means it’s time for me to officially (well…part-time) get back to work! While I’ve continued to create in a variety of ways since he was born, I haven’t had the capacity, or structure, to jump into something new (especially as we’ve been navigating an international move with our two littles ones.)

However, if I’m being entirely honest, my limited capacity hasn’t been the sole reason I’ve yet to resume work. After becoming pregnant with our son, and deciding to step back from my co-founder position at our tech startup, I’ve found myself in this limbo of sorts in regard to my career, majority of which stemming from a place of self-doubt. While I feel I could write a book on the lessons learned and identity shifts from this past season of life, for today’s post I want to focus on something that has been a main source of stagnation: my resistance to my multi-hyphenate nature.

As I’ve reflected on why I’ve felt such shame and frustration around this, I’m reminded of the many external voices I’ve come to internalize from years of building businesses, listening to coaches and podcasts, following social media “experts,” reading countless books and articles, and hearing advice from well-meaning friends and family. All of which seem to share a common message: until you can focus, you won’t be successful.

Over the years I’ve found comfort in my role as “co-founder.” It was a singular title I could confidently stand behind while simultaneously wearing many hats. However, when startup life was no longer compatible with my personal life as a mother of two, I questioned where that left me. While my limited capacity was reason enough to leave my co-founder position, another is that I simply have many passions, interests and ideas, and when I have something new I desire to pursue, I fully lean into that, which over the past 8 years has looked like burning down one business in pursuit of another (which is obviously not sustainable nor satisfactory, however has taught me many lessons and skills in the process.)

After coming to the conclusion that building a start-up was no longer in alignment, I began exploring the possibility of a new career path. Surely there had to be a path that allowed me to honor my multi-hyphenate self in my career, while simultaneously continuing to prioritize my family and life outside of work, right? When I came across the concept of a “portfolio life” from Harvard professor, Christina Wallace on the 10% Happier podcast, it felt like a permission slip (although unnecessary) to build a career and life in the way I deeply desired.

According to Christina Wallace, there are three tenets of a Portfolio Life:

1. You are more than any one role or opportunity.

2. Diversification will help you navigate change and mitigate uncertainty.

3. When (not if) your needs change, you can and should rebalance.

More recently, I stumbled across

Anna Mackenzie

on Substack who shares her insights on building a portfolio career composed of many projects and income streams. From my point of view, Wallace’s approach to a portfolio life is about building a flexible, “future proofed” career that provides you with more freedom, balance and opportunity. On the other hand, I feel like Anna’s perspective is more focused on the portfolio career itself, which I find particularly interesting as a multi-hyphenate.

Reading through Anna’s six-part series on Portfolio Careers, I found myself nodding along to each sentiment. And again, while I didn’t need a permission slip or something to validate my inner knowing, feeling seen in someone else’s experience is a vital part of our personal growth and a beautiful part of humanity as a whole. Her posts have granted me a renewed sense of motivation to embrace my diverse interests and experiences, and to stop trying to force myself to do just one thing.

I thought this brief overview by Anna on portfolio careers was very well-stated:

A portfolio career is defined as having several part-time jobs or multiple income streams rather than one full-time gig. In my mind, it has two defining characteristics:

• It involves pursuing multiple passions, interests and types of work

• It’s never static and always evolving

To me, a portfolio career can be made up of many things:

• A part time job (eg. working 3 days a week for a company)

• A part time business (eg. working 3 days a week for your own company)

• A done-for-you service (eg. contracting, consulting)

• A done-with-you offer (eg. coaching, mentoring, advising)

• A do-it-yourself offer (eg. a digital product, online course)

• Creative work (eg. writing, podcasting, Tiktok-ing, playing music)

• Giving back (eg. volunteering, pro-bono work)

• A mix of any or all of the above

The idea that our careers can be composed of not only one, but many projects, passions and interests is exactly the type of career I’m hoping to create, and if you’re reading this, I’m sure you are too.

As I prepare to re-enter the world of work and business, I plan to do so by beginning to build my own version of a portfolio career. Here’s my initial idea of what it might look like: *emphasis on the word initial as I know this will inevitably change (I mean…isn’t that the entire point of a portfolio career?)

1. Freelance Consulting

This is where I’m really going to experiment with a “multi-hyphenate” approach, as I’ve noticed that trying to create super specific offerings has stifled my creativity and prevented my forward progress. While I’ve continuously heard “the more specific the better” I simply can’t bring myself to “niche down,” at least right now. I’m ok with my business (at least initially) not being as profitable or “successful” as I experiment with what feels most aligned and inspiring.

2. Personal Projects

While I love working with other founders to help them realize their visions, I also know that I need full creative freedom to turn my own ideas into realities. I plan for personal projects (like this newsletter), both small and large in scale, to always be a part of my work and practice. Last year I self-published a multi-sensory zine project which was so much fun to create, and I already have some ideas in the works for the future!

3. Part-Time Job?

I’m also leaving the door open for a potential part-time job opportunity. I am someone who really loves to do my own thing, however, I’m also in a season of life where some stability would be greatly appreciated. After years of a variety of business ventures, I know that building and scaling a business, whether it’s a tech start-up or growing your client base as a freelancer, requires a tremendous amount of time and energy. Therefore, if I can find a position that’s in alignment with my current phase of life, as well as with my passions and skills, I’d definitely be open to it.

Most importantly, I plan to keep flexibility at the core of my portfolio career, allowing room for pivots, growth and opportunities.

In summary, I’m releasing the need to weave all that I do into one cohesive offer suite or story, and instead will lead with my unique perspective and follow the ideas and projects that light me up. Luckily, I’m not the only one who craves this way of work. Lately I’ve come across many others here on Substack whose words have inspired and deeply resonated, and I’d love to share them with you too:

1. Cate Scott Campbell
   /The Ecstatic Review: I am so happy to have discovered Cate’s work, as I find her perspective on multi-hyphenates so insightful and articulate. Not only does she write on the topic in a brilliant, cohesive way, but she also works alongside people and brands to help them connect all the dots. Be sure to read her recent series “What to say you do when you do it all.”

2. Hannah Ashe
   /Chez Hanny: I really enjoyed Hannah’s recent post “Could you thrive on less?” where she explores the benefits of part-time work. As a mom to two little ones, I plan to work part-time until our youngest is off to school, however, as Hannah outlines in her thoughtful article, part-time work isn’t solely for those with kids. Part-time work provides a way to explore different professions, projects and passions, and can be an essential part of a portfolio career.

• Rishad Tobaccowala/The Future Does Not Fit In Containers From The Past: Another fantastic series to follow is this one by Rishad Tobaccowala where he explains why a “company of one mindset” will be critical for career success. I especially resonated with this sentence “Better get used to thinking of ourselves as modules unbundled from any one particular company or construct but ready to plug and play and manage a portfolio of gigs.”

I’d love to hear your thoughts and/or experiences with building a portfolio career! Please leave me a comment or send a DM so we can continue the conversation.

As always, thank you for being here.

Until next week!

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