Leadership

An executive career: a portfolio, not a linear path

For leaders the linear path more recently took the form of a corporate ladder. But this only gave the impression of opportunity and self-determination. Happily modern execs are granted genuine autonomy and choice – but capitalising on these opportunities requires a mental reset: seeing your career not as a path to be followed, but as a portfolio to be developed. It’s a mindset shift that I’ve undertaken myself. And the experience has led me to help other leaders do the same.
Published on 
August 30, 2024
By 
Angela Catalan

The idea of a career path is firmly lodged in our collective brains, for good reason. For most of human history people spent their lives plying a specific trade. It’s why Smiths are named Smith.

For leaders the linear path more recently took the form of a corporate ladder. But this only gave the impression of opportunity and self-determination. Take a step to one side and you could fall right off.

Happily modern execs are granted genuine autonomy and choice – but capitalising on these opportunities requires a mental reset: seeing your career not as a path to be followed, but as a portfolio to be developed.

It’s a mindset shift that I’ve undertaken myself. And the experience has led me to help other leaders do the same.

Is your career really on the right path?

Traditional executive career paths are inherently restrictive. Most will see you develop an ever narrower and more specialised set of skills, particularly if you stay within the same organisation.

The ‘job security’ provided by a full-time employer is a bit of a façade. Working within one company makes you totally reliant on it. Your ability to face new challenges and gain new skills is decided by the business and often restricted. If the organisation fails, you fail with it.

Career paths also tend to be singular – you’re either an engineer or you aren’t – and inflexible. You rarely choose when or where you work, and as an exec, you’ll usually organise your life around your work. It should be the other way around.

Your career as a portfolio

I’ve always been a doer; someone who likes to have a few plates spinning, who finds comfort in discomfort. I never fit into the traditional career path mould. I’ve worked at bars and nightclubs, sold EFTPOS machines door-to-door, gone corporate, founded startups, and been a professional photographer, yoga teacher and jewellery designer.

Some might see this as a directionless, scattergun approach to a career. I don’t, because every single experience taught me something valuable.

Hospitality showed me the importance of the customer experience. Door-to-door sales taught me about rejections and resilience. In corporate tech I learned how to bring an idea to market. The startups revealed my strengths, and showed that I should stick to them. I’ve become a better public speaker through yoga.

So I had a thought: what if we did away with the career path concept? What if you treated your career like the group of developmental experiences that it is? And what if you could work on your own terms, rather than someone else’s?

A career portfolio is a representation of your collective knowledge, skills and experience. It sits in direct contrast with the career ladder concept seen on resumes and LinkedIn profiles. Rather than following your career path, it views your professional history as a rich and interconnected tapestry.

And it is the perfect complement to the idea of fractional leadership.

The rise of the fractional leader

Armed with my personal career experiences, and with professional corporate and startup experience, I saw an opportunity to help others take a less traditional approach to their career. So I started Shepherd, which aims to take fractional leadership mainstream.

Fractional leaders see their careers as a portfolio to be developed. They are highly knowledgeable, skilled and experienced executives who work in multiple companies on a part-time basis.

The concept melds the flexibility of the gig economy with the rewards of high-level leadership, most often in the exciting startup space.

Fractional leadership embodies the portfolio career mindset. It sees you work within a number of startups simultaneously, exposing you to new challenges and turbocharging your professional development.

You enjoy total professional flexibility. Able to decide when and where you work, you can prioritise your personal life whenever you need to. And you enjoy unmatched professional resilience: if the market changes, you can change with it, because you don’t have all your eggs in one basket.

Since switching to a portfolio approach to my career and income streams, my professional growth has exploded, improving by an order of magnitude in the last three years. Shepherd is my effort to help fractional leaders enjoy that same transformation.

What’s more, the benefits of fractional leaders are every bit as enticing for businesses, particularly startups. Fractional execs comfortably outperform consultants and are more cost-effective – and potentially more impactful – than full-time leaders

How to build a portfolio career as a fractional leader

How do you build a career portfolio? Here are some top tips for someone who’s done it before:

  • Undertake a mindset shift: Think of your career as a portfolio to diversify, not a path to progress down. The beauty of your portfolio? It’s one-of-a-kind. You’re unique, you’re valuable, and your portfolio proves it.
  • Complete a career stocktake: List the knowledge, skills and experience you’ve developed over the years. Go beyond paid roles and formal education to factor in hobbies, interests, passion projects, side-hustles and voluntary positions, as these can drive personal and professional growth that is every bit as valuable.
  • Never stop learning: Unlike a career ladder, there’s no natural endpoint to a career portfolio. Invest in education, and diversify your portfolio in the process. Make the time to acquire skills and knowledge – everyone gets 24 hours in a day, it’s all about how you spend them.
  • Be a ‘yes’ person: At least in the beginning. Certain opportunities will only come your way once. By diversifying your portfolio as much as possible as early as possible, you give yourself more opportunity to find your true talents and passions.
  • Build your brand and portfolio: Do it in public. Talk about it. Let people see the diverse experiences you've gained and are exposing yourself to. Accept opportunities to speak about your field of expertise. Network actively.

Build your career portfolio with Shepherd

At Shepherd we’re helping to power the shift towards fractional leadership.

That’s good news for both leaders who are looking for a more fulfilling and better way to work, and for startups looking for transformative leaders on flexible and adaptable terms.

If you’re ready to build your career portfolio as a fractional leader, we’re ready to help.

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