Building a portfolio career


I became an unintentional entrepreneur.

I struggled to sit behind a computer at a desk all day, being super strategic about how I used my 10 vacation days a year.

Grad school taught me that I enjoyed the freedom and flexibility of being a student.

I learned that my best ideas didn't come from sitting behind a computer, but being out in the world.

Living in France gave me "creative constraints" that limited me in terms of how I could work. Instead of complaining, I figured it out. It was more rewarding because of that.

My blog became my business card and opportunities started to come my way.

More than 10 years later and I have yet to look for work—it comes my way. I'm extremely grateful for that. (But now I want to be more proactive in pitching ideas and launching my own endeavors.)

American start-ups started to think about alternative business models. (The birth of the gig economy.). Companies—and even CEOs—could reach out to me directly because I was findable online.

My social media reflected my work, worth ethic, and personality. (Hello, swimming pools and garden gnomes.)

I got in at the right time, and I had platforms to further promote my offerings. I also also had built a community online whom I could share with.

People could discover my services through another platform, or I could send people to the platform. It became easier to be found, and created a sense of trust. (But as they started to take a larger cut, I took on myself, along with the promotion.)

Passive income meant I could keep earning money after the real work was done.

My greatest fear in a typical day job was getting bored. Different kinds of work kept me stimulated.

Learning to manage my time and motivation was a learning curve of its own. There’s no one to tell you what to do.

Each different project and experience would benefit other projects. Different kinds of work also meant different income streams.

I’m a self-employed “slasher” who does many things (designer/ writer/ educator/ coach), and a creative who wears many hats. I’m not reliant on one client to pay me. I've never had all my eggs in one basket. I didn't know this path existed when I started on it. It found me, and I found how I thrive.

Without knowing it, I created a "portfolio career" comprised of different slices of the pie, with income coming from different people and places.

One day I met Samantha Clarke in London, and she gave a name to how I work: portfolio career. She uses the definition: "A portfolio career is a collection of multiple strands of work (that might include part-time employment, freelancing, or self-employment) that when combined are the equivalent to or more than a full-time strand of work."

Tiago Forte uses the term full-stack freelancer as a way to describe this style of work: “manage a portfolio of income streams, not a job based on one set of skills".

He goes on to describe this type of work as potentially including "both products and services, online and offline businesses, digital and physical products, active and passive income sources, in-person and remote interaction, individual contribution and group collaboration, and offerings that are low margin and high margin, mass-produced and customizable, high risk and low risk, monetized directly or indirectly, short-term and long-term, or any combination of the above." Yet somehow we are never taught to think like this.

At one point in my own journey I had wondered if I should throw in the towel and go for a "real job" because those were really the only examples I was seeing around me and in the media. Then I read Tiago's article and was reminded I wasn't alone and there were different ways of approaching work. (I also knew I liked how Tiago thought because he also had courses on Skillshare).

Sometimes we see a view of someone online, but when it comes to business we often only see one thread of how they earn their living. It was seeing his pie chart visualizing his different income streams that made me more excited. What we earn doesn't always correspond with how we spend our time. Some parts of the pie we do because we love it, others for money (but never just for money—we want to keep our sanity in the process ;) ), and then there are the things we do some things despite the money because it's what brings us alive.

Over the past few years I joke that I became a "faux freelancer". I had back to back contracts where I was an independent contractor. In both cases it started as something smaller and kept snowballing into more. I often worked from the office and was treated like an employee, and that work alone was enough to sustain me (but not always fulfil me). I insisted on keeping my independent contractor status because I wanted to have the freedom to say yes to other projects (also, until I became French I wasn’t allowed to be a salaried employee in France). One reality of these kinds of projects is the longer you have a large chunk of income from a single client, the harder it makes it to leave. Other times you finish the work and the contract ends. Every project is its own beast.

The major contracts are great for having steady income, but sometimes can be hindering when it comes to having time, energy, and brain power to put into your own projects that you want to be pursuing. When building your own client base you have to build trust, and it takes time. Just because you launch something doesn’t mean it will take off over night.

While most people assume that my tours are my main business, because they’re one of the things I talk a lot (they’re more concrete and visual, so it’s easier), they are actually one of the smaller segments of my “income pie”. For the past several years I’ve had large client contracts that make up for more than half of my income. I also do various coaching and consulting, as well as workshops and facilitation. On top if it, I still receive passive income from my Skillshare classes – which are all over 6 years old! (I get paid for the work I did back then.) Every year the size of these proportions of what I earn change.

Year to year can change due to intentional shifts in the type of work you want to be doing, but also things like the passage of time means 6 years later my Skillshare payouts are lower than they were back when I launched my courses. It makes sense. And is also a good reminder that when you are your own business you also are responsible for promotion and marketing your offers. Also, technology can change, platforms can decide to take a higher percentage, leaving a platform can affect the number of people who can find you. You’re ALWAYS learning to stay on top of your game.

This year I’m launching new offerings and new income streams. The fun thing is I’m exploring new combinations, like my Deep Dive Exploration Day which mixes my tours and creative coaching for a day of creative exploration while seeing the city. Not only is it fun and challenging for me, but I meet the coolest people from it. (Tip: the kind of work you put into the world influences the clients you attract.) When you have a portfolio career you get to carve your own path and write your own rules. Sometimes you don’t know if something will work until you try. Friendly reminder: there’s not one way of working.

Running a business or portfolio career is managing a living breathing organism. While it can be scary at times (see this post on momentum, riding the wave, and getting back up again), it also has it's own natural rhythms that need to be nourished. At times I can feel like I'm a juggler juggling multiple acts at once, but on most days, I'm pretty damn excited to be doing what I'm doing. Even if most people will never understand it. 😉

What’s your take on portfolio careers? Can you relate? Have you seen any other examples? Who else do you follow has a portfolio career? I’m always curious to learn more!

I often share thoughts on different ways of working in my weekly newsletter Connect the Dots. 💌
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