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July 29, 2022

Becoming a Portfolio Professional, with Ben Legg | The Ironhack Podcast

Career coach and Portfolio Collective founder Ben Legg visits the Ironhack Podcast to tell us all about portfolio-based careers and how to transfer skills to your new career path.

Frida Chacin Kulak - Tech Writer


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You’re reading an interview with Ben Legg, straight from The Ironhack Podcast. Every week our hosts, Tim and Dan, catch up with Ironhack alumni, teachers, and other tech professionals for industry deep dives and personal success stories.

To listen to this episode (or to binge-listen to every single one, we wouldn’t judge you!) check us out on Spotify, or wherever you find your favorite podcasts.

Ben Legg is a portfolio professional and the CEO of The Portfolio Collective, which you can read more about below. Ben, in his own words, helps people reinvent themselves and society for the better; to achieve this, he creates learning materials and gives career guidance and coaching to entrepreneurs and independent professionals, teaching them how to stand out from the crowd and build their own unique portfolio careers. He believes that community support is vital for single-person businesses, and is here to tell you all about it.

The Portfolio Collective, a Community for Independent Professionals

A: My name's Ben Legg, and I’m the CEO and co-founder of The Portfolio Collective, based in London. The Portfolio Collective was founded in early lockdown last year, and it's designed to help professionals anywhere in the world launch and sustain successful portfolio careers. A “portfolio career” basically means you make money in multiple ways, as opposed to having just one day job, and it's forecast that about half of all professionals in the world by 2030 will effectively have multiple income sources rather than just one day job, and, like so many forecasts, that’s being accelerated because of the lockdown. We realized that being a portfolio professional is quite hard and quite lonely, so we said, let's build a community that helps make it less hard and less lonely.

Q: Nice. you said that you started it in lockdown, was it a lockdown idea or was it something that you were kind of cooking away on for a while?

A: It kind of happened to me, as opposed to the other way around. I gave up my last full-time job nearly a year before lockdown and launched what I now call my portfolio career, which was primarily helping founders build great companies. I love building companies, products, communities... And so it was a mixture of angel investing, mentoring, board jobs consulting, and I also filled in the gaps in synergistic ways.

And then, lockdown happened. And friends and family started contacting me, saying they were done with corporate life and asking about my career, so I just gave them a zoom link and said, let's chat, doing four or five of these chats a week saying: here's what I do and here's why I think it's kind of cool.

But I like structure and having clear thoughts in my head, so I started doing research and writing articles and, when my calendar got crowded with people asking for help and telling their friends, I knew I needed to do this more efficiently. I started running a workshop every week talking about portfolio careers and thought leadership, but they asked questions I didn’t have the answer to about things like website platforms, taxes, branding, LinkedIn and networking, and so on. I realized I didn’t just need the answers; we needed community. It's really lonely being a portfolio professional. 

I was just seeing all these intertwined needs, so in June of 2020, I set aside some money, posted a job ad for a co-founder on, and launched The Portfolio Collective.

Portfolio Careers as the New Work Paradigm

Q: And you said that you didn't coin the phrase “portfolio career” yourself, it existed before The Portfolio Collective.

A: Yeah. A management author, Charles Handy, wrote about it in the eighties. He was primarily talking about ex CEOs who sit on boards and give speeches, but there's so many other kinds of careers that he wasn't referring to.

Q: So, to break that down, a portfolio career means someone uses lots of different skills that they've maybe learned in their past career, transferable skills, to form income from multiple sources in a freelancing portfolio.

A: And the range of skills can be massive. If you're a portfolio professional, you're a one person company and you want to have a unique personal brand that stands for something.

Q: That sounds absolutely fantastic. As you know, at Ironhack, we teach four disciplines: Web Development, UX/UI, Cybersecurity, and Data Analytics. More than ever, they’re skills that can be full-time jobs, but they lend themselves so well to freelancing different projects for different clients.

A: Our lovely community is already getting employers who come looking for talent, the vast majority of them coming from the startup ecosystem. As you're probably aware, startups and venture capital and investment have been mostly booming throughout lockdown, and startups are much more pragmatic than big old-fashioned corporations in terms of how they hire. They have limited resources and unpredictable growth; they can't afford a complete full-time management team, and their needs for talent might change, so they get maybe a part-time CFO and maybe an interim COO to teach them how to run the business. And for marketing, an expert to build the brand in three months. And they’ll manage it with more junior people after that. There's lots of temporary talent needs coming and going, which lends itself very well to portfolio professionals because that's the kind of work they want: they might have one client at a time on short projects or work with five clients at a time for a bit.

Q: The statistics on the industry acceleration is crazy. Industries have been pushed forward by about seven years. Portfolio careers must be booming more than ever before.

A: A McKinsey report that looked at digital adoption had this forecast that most industries, or most habits, were going to be brought forward between five and fifteen years. And the forecast that half of the workforce would become portfolio careers was moved from 2030 to 2027.

Q: Do you find that the people you work with and the professionals in The Portfolio Collective have a digital focus or is it spread across a wider range of different industries?

A: Most of our members are digitally savvy and confident about it, but they don't necessarily sell digital skills. Portfolio pressure comes in all shapes and sizes. Our community tends to be mid-career, mostly 30 to 55, and they come from all backgrounds and professions. They feel confident they can add value to the startup ecosystem. 

Q: It's interesting that the age range is concentrated around the thirties bracket. When I did my Ironhack bootcamp course, I thought I’d be the dinosaur, but the average age for my course was actually 32, my age exactly. It must be a reflective period where you look back and decide you want to do something different.

A: I would definitely agree. When you’ve had a decade of work and time to reflect, tried some stuff, you've worked out a bit of what you like and don't like, and you maybe have a big name employer on your CV as well, which helps with your employability, you take time and say: I've still got many decades to work, I better future-proof myself, and I'm not sure a corporate career does that. Or maybe it just doesn't satisfy me. I want to do more for people in their twenties because about 60-70% of them will end up with portfolio careers, and things like graduate trainee schemes are shrinking so fast.

I think traditional education doesn't prepare you well for a portfolio career. People want to get at least one big name employer under their belt because that will help define them, give them a seal of approval, let's say. We need to show people in their twenties other forms of validation they can use: awards, referrals from happy customers, TED talks or articles they wrote… There are other ways to get a seal of approval.

Transferable Skills Are Crucial in the New Educational Paradigm

Q: I think there’s a certain lack of understanding around transferable skills. So very poignant of what we've been talking about. A very good friend of mine who’s had quite a successful salesman career in the automotive industry wants to move into tech now, and he'd be perfect for customer success or even recruitment, because he has really good people skills that he's been building for years, but it's a whole different industry. So how do you express this transfer to an industry where you don’t have direct experience? It’s a hard barrier.

A: It is. When people come to us and say they want a portfolio career starting from scratch, the first thing we do and where we spend the most time is asking: who are you? It's a lot of reflection. What are your monetizable skills? And a lot of them say they’re generalists, a Swiss army knife; but after they go through a structured process, most people end up with a list of 30-50 skills they could monetize. But another important question to ask is what skills you want to develop that you could monetize, because these days, for most skills, you can learn them way faster and more efficiently than you could in the past when you had to spend a fortune on an MBA.

We are running a sales pipeline as a sales pipeline. You work out what you’re selling exactly, you work out your prospects, you get efficient at communicating them and sorting and filtering, and you work out how to land the clients. A lot of the skills involved are very transferable.

Q: Are there training courses of these skills taught in The Portfolio Collective?

A: Yes, we have some training courses and one big training course called Catapult, for those who want to launch a portfolio career. Pretty much a bootcamp. You learn to work out your monetizable skills, value proposition and personal brand; to polish your LinkedIn and online presence; and to get out and start marketing, selling, listening, landing a client… You get the core skill set from us (we refer to ourselves as a lifetime accelerator!) and keep updating yourself, with support and guidance from the community.

Q: The fact that you can learn this quickly certainly resonates with the Ironhack mentality, too. Do this in eight weeks, get the basics, and go from there and keep learning on your own.

A: Life's the journey and you gotta keep learning forever, on every project and job, do short courses every year and such. Going to university once or twice and doing all your learning there just doesn’t cut it anymore.

We don't aim for perfection. We aim for momentum. And afterwards, as long as you're good at listening, you'll definitely find other ways to add value. There was a famous German field Al who said something like “No plans survive contact with the enemy”. You can make the best plans, but you’ll have to adapt and change.

Q: It's really about how you present yourself to the world. How do you think one can stand out from the crowd?

A: A little bit of a twist, like a top-up skill: a certain focus, industry or function where you have credibility and passion and that stands out and is unexpected. Find a niche. And there are other ways to stand out too, for example with the way you respond.

Q: How do portfolio professionals get work? How do you flavor yourself out there, what's the best strategy here?

A: If you’re in the early stages, you work through your network and let people know what you do. It’s often not well paid, but get people to refer you and get samples of your work to show. Focus on the network before you leverage the network. If you wanna get paid fast, you can also use a freelancer platform like Upwork or more role-specific platforms; in these, a couple well thought through and tailored applications for freelancer jobs will get you further than sending a hundred generic cover letters.

Q: The hardcore grinding can be really mentally damaging, whereas having a healthy routine and constantly, slowly building your portfolio and your name and skills will definitely get you further.

A: And there are other ways to win work. One bit of work I won literally came from an article I wrote on the future of careers. A contact in Poland read it and asked me to give a paid speech to his company board about it, because their value proposition to young employees wasn’t very attractive. The right people need to know what you are knowledgeable and passionate about at the right time.

Q: Initiatives that share this insider information, like The Portfolio Collective, are great because they come about very organically and they’re basically people getting together and helping each other. The symbiosis between a collective like this and the work we do at Ironhack goes without saying. 

We have a book recommendation related to business survival and adaptation in the face of change: Tarzan Economics, by Will Page. People have to be patient when they build their careers, and use the momentum when they leap into the unknown, and this book touches on that.

If you want to know more about Ben’s career mentoring and thought leadership, you can listen to the full Ironhack Podcast episode here.

Whether you’re aiming for a fabulous developer position in a word-class company, or you dream of starting your own Tech business, Ironhack bootcamps teach you the transferable skills that you need: grab our syllabus and start your career in Tech!

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