10 things I learnt about you*

*portfolio careers

ICYMI, over the last four weeks I’ve been head down conducting discovery research into the portfolio career space. I've surveyed 210 people and interviewed 30 across a broad range of life stages, industries, circumstances and backgrounds. When I started this fun project my intention was to:

1. Connect with others on the same path

2. Use insights from conversations to make this newsletter the best it can possibly be

3. Identify opportunities to further support people entering portfolio careers (a community, platform, book, products, services etc.)

4. Share learnings to continue driving the ‘future of work’ conversation forward into the…well, future

I met with:

• A creator with 300k followers on Tiktok who is looking to diversify her income streams beyond brand sponsorships

• A former founder who shut down her very high profile fashion label to consult and advise climate science groups

• A McKinsey consultant who spent his entire career working towards partner, before realising it's not what he wants anymore

I spoke with men and women, singles and parents, those in their 20s - 60s, and people from Australia, New Zealand, America, Germany, Finland, England, Scotland, Canada, Singapore, Thailand, Israel and Dubai. I met with founders, C suite execs, leaders, managers, ICs and people who were already out on their own building successful one person businesses.

Many of my assumptions were validated and others were totally smashed, but one clear message came through:

We’re collectively searching for a new way to work that offers freedom, flexibility, creativity, impact and cash.

5 Common Existential Struggles

1. Dealing with the perceived loss of status when leaving a fancy job to build something that others don’t understand.

When you decide to walk away from [insert sexy job title here], you’re probably going to face an existential identity crisis. Who am I, if not a CEO? What am I good for, without the backing of [insert high status company name here]? Where do I stand, without the status of my job? This is a hard one to overcome because there’s tension: we want to follow our heart and pursue our dreams, yet constantly compare ourselves to those we’ve left behind.

"I look at my friends who are high up at [brand] with good salaries and jobs and sometimes I wish I was there, even though deep down I know I don’t want to be. How do you escape the story that a portfolio career is a step back rather than a step forward?"

2. Believing a financially lucrative portfolio career is possible.

Multiple income streams sounds great in principle, but is it actually feasible? Is it really viable? According to my research, some (but not all) people are sceptical about whether they can replace their annual salary, let alone out earn it. My thoughts: it’s not easy but is it possible? Absolutely.

“Financial stability is my main concern. Giving up a reasonably secure and well paid corporate career that I’ve built for 16 years is a scary proposition.”

3. Packaging up your skills and experience into a clearly defined offer.

This one is such a struggle because it flips everything on its head:

• Current system: the employer scopes a role, creates a position description and may or may not put up an ad. You review the position description, make a judgement about whether you’re a good fit, and apply or put yourself forward.

• New system: you’re the product. You have to scope out your capabilities and package them up with a price. You must communicate them in a way that makes sense. Prospects make an assessment about fit based on what you project, and decide whether or not to engage you.

Don’t get me wrong, the whole ‘think of yourself as a product’ thing is tough, but a lot of people get stuck believing they need the perfect offer, perfect pricing, perfect tagline and perfect pitch before they start approaching others. But in my experience, conversations with prospects should inform your offer, not the other way around.

“I'm doing all these different things with different people who remember me for various reasons, but I don’t know how to articulate that as ‘this is what I do’. I think it’s the control freak in me that needs everything to be perfectly defined, and it’s keeping me stuck.”

4. Generating work beyond people that you know.

Your first few clients will inevitably be people you know. Your next few will likely be people who know people you know. But what comes after your network (hot leads) and your network’s network (warm leads) are exhausted? How do you win work from cold, hard sales? This question came up a lot.

“I haven’t had to do any formal sales yet because all my current clients have come through my network. But I need to have a plan for when I have to eventually go out and generate work beyond the people that I know. And I have no clue what that plan is meant to be.”

5. Loneliness.

The inevitable trade off of freedom, flexibility and autonomy is the loneliness that comes from operating as a silo. We all crave community, good conversation, feedback on our work and encouragement that we’re on the right path. The need for connection is universal.

“I don’t know anyone else who has a portfolio career, there isn’t anyone in my inner circle doing something similar. I sometimes find it lonely and struggle with the uncertainty of it all.”

5 Surprising Findings

1. The portfolio paradox.

Everyone feels like they’re the only one experiencing their particular problem, yet ironically I can count on one hand the major challenges people face. We feel alone in our struggles, but we’re not. Everyone around us is dealing with similar things.

“I often feel like I’m speaking into the void. I’m like, hello? Is there anyone out there who understands?”

2. People’s risk appetite for self employment differs across countries.

Aussies and Europeans were willing to take on more risk, largely because of our strong social welfare and public health systems. Our American counterparts expressed the most hesitation about doing their own thing because it’s crazy expensive to buy health insurance over there.

“One of the things that makes me nervous about self-employment is the healthcare piece in America. I've had good, reliable healthcare through my employer for nine years, so that makes me stressed.”

3. People have a love/hate relationship with building their personal brand alongside their portfolio.

Having a profile attracts opportunities rather than you having to go out and hustle for them, so there’s real value to having a strong personal brand. But people either love or hate the idea of making a name for themselves online. Those that love it, love it. They know it generates leads, clients, customers and revenue:

“Investing time and effort into building my personal brand on LinkedIn has been the biggest unlock in terms of scaling my income. It’s insane how many inbounds I get through that platform.”

But the majority hate the idea of putting themselves out there because they don’t see themselves as strong writers or speakers, they’re scared of being judged by peers, or they’re worried they’re not qualified:

“One of the things I find difficult about a portfolio career is granting myself permission to put myself out there as an authority on something. I know that showing up via content is the way to build a profile, but I doubt my abilities. So I hide, and therefore no one knows what I do or how I can help.”

4. The portfolio career is ripe for a rebrand.

Many people reported feeling embarrassed that they wanted to pursue (or were working across) multiple things. Founders expressed feeling shame that they’d chosen to sell or exit even though it no longer served them, and many corporate execs said they were struggling to embrace the portfolio career as a valid life choice. The portfolio career clearly needs a rebrand, and I’m putting my hand up for the job!

“I'm embarrassed because I don't have the one thing, I have multiple things. It should be a celebration, but I still feel like I’m doing something wrong?”

5. People want to see others successfully traipsing down the portfolio path.

There are lots of people building financially lucrative, creatively fulfilling, fun, flexible, impactful one person businesses, but not many of them are proudly speaking about their achievements (likely due to finding #4). This sucks. I wish there were more people out there showing what’s possible, because as someone who’s arrived at the intersection of the money, creativity, freedom and purpose Venn diagram, I know how amazing this life can be.

“I didn’t realise a portfolio career was an option for me. I didn’t even know it was a thing. I want to work towards one but I don’t see anyone around me to act as a role model.”

Connecting the dots

It’s early days for the portfolio career and we’re all out here navigating a space that much of society doesn’t realise exists. No wonder there isn’t yet a clear path to follow. No wonder it’s hard. No wonder, at times, we feel alone.

But things are changing and I want to be part of the shift. I want to share my wins, losses, learnings and stories, to help people make sense of the nonsensical and connect all the dots. I want to lead a conversation about the future of work that’s long overdue. I want to have started building something to support all of us to live out our best portfolio life.

I’m all in.

Are you?

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🎙️ My raw, unfiltered thoughts on some of the most interesting findings:

• Believing a financially lucrative portfolio career is possible [1:16]

• Generating work beyond people that you know [7:05]

• People have a love/hate relationship with building their personal brand alongside their portfolio [9:52]

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