Categories All

Navigating Entrepreneurial Success with Portfolio Career

Background: A Journey of Diverse Chapters

I’ve worn many hats throughout my career, each chapter marked by unique challenges and accelerated learning. From my early days as a military engineer to donning executive roles at Coca-Cola, COO of Google Europe, and various global technology CEO positions, I’ve lived and worked in nine countries. My thirst for new challenges and a desire to give back have been the driving forces behind my career choices. The diverse experiences in military, big business, and technology roles have stretched me to the limits, shaping each decade of my professional journey.

In 2020, I embarked on a new venture, founding The Portfolio Collective. This initiative aims to help professionals navigate, launch, manage, and grow successful portfolio careers. This has evolved into a thriving global community of over 10,000 portfolio professionals. Alongside leading The Portfolio Collective, I engage in my own portfolio career, mentoring founders and CEOs, guiding investors through the intricacies of technology, and supporting Oxford University’s entrepreneurial initiatives.

Inspiration and Resilience: A Personal Anecdote

In 2007, while at Google, a pivotal moment occurred when my 5-year-old daughter was diagnosed with a brain tumor, and the prognosis was grim. Larry Page, Google’s founder, extended unwavering support, even offering to back me in curing cancer. Though I considered the proposition seriously, I chose not to pursue it. The immense faith and support during that challenging time left an indelible mark. Thankfully, my daughter recovered, underscoring the importance of resilience and the human connections that transcend professional boundaries.

Handling Criticism and The Blurring Lines of Work-Life Integration

Criticism, when valid, is an invaluable tool for growth. I approach it with seriousness, aiming to enhance my skills and leadership abilities. If the criticism is unfounded or irrelevant, I either challenge it or choose to ignore it. Perfection isn’t attainable, and some flaws are meant to coexist. It’s crucial to discern between constructive feedback and noise, focusing on the former to evolve personally and professionally.

The traditional boundaries separating work and life are fading, and I embrace this evolution. In an era of flexible working and portfolio careers, who you are and what you do are intertwined. You have the autonomy to work where you want, with whom you want, and steer your career trajectory. The responsibility for success rests squarely on your shoulders, a shift I find empowering.

Navigating the Transition : Overcoming Fears and Barriers

Transitioning from a traditional career to a portfolio career offers individuals the prospect of embracing variety, flexibility, and autonomy. This shift is a highly individualized process, and our community of over 10,000 members worldwide, many of whom have successfully transitioned or are currently in the process, reflects the diversity of approaches. Rather than hastily diving into the portfolio career realm, a thoughtful approach is essential. This involves assessing one’s unique skills, identifying ideal clients, crafting a personal brand, strategizing client acquisition, determining pricing structures, outlining service delivery methods, and exploring collaboration opportunities. Our platform addresses these pivotal questions and more, offering a wealth of insights through a combination of articles, courses, and community networking to guide individuals on their journey towards a fulfilling portfolio career.

There are three main fears/challenges that professionals have when launching a portfolio career:

  • Fear of loneliness – leaving the comfort blanket of having a work team, plus employer finance, HR, IT etc to support you. 
  • The complexity of running a business – as a portfolio professional you are the CEO of a one-person company. You need to become an entrepreneur. 
  • Ability to generate consistent income – all smart people know they can make some decent money from side hustles, but can you generate decent income 12 months per year?

These are all solvable problems, which is why we launched The Portfolio Collective – to help people overcome their fears and achieve success. We tackle loneliness through having a supportive community, complexity through our courses and articles, and earnings through helping our members define who they are, what they offer and how to win work. 

Portfolio Careers in Action: Pursuing Passion and Personal Fulfillment

The pandemic accelerated the adoption of portfolio careers, showcasing the efficiency of working with portfolio professionals. CloudNC, a Series B autonomous manufacturing company, exemplifies this shift. By engaging with The Portfolio Collective, they replaced full-time CXOs with fractional professionals, reducing costs while maintaining productivity. This strategic flexibility is becoming a hallmark of successful businesses in today’s dynamic landscape.

Lockdowns prompted reflection for many professionals, leading to a shift in priorities. A Forbes survey in 2022 revealed that 71% of highly successful professionals intended to shift to a portfolio career within three years. This transition allows individuals to escape toxic work cultures and long commutes, pursuing personal fulfillment and work-life balance.

In a portfolio career, showcasing personal passions beyond core work enhances professional profiles. Members of The Portfolio Collective engage in diverse activities such as charity work, beekeeping, drone racing, and triathlons. These activities not only bring authenticity to profiles but also contribute to a more fulfilling life.

The Globalized Workforce and Remote Collaboration

The globalized workforce has opened up unprecedented opportunities for remote work and global collaboration. With in-demand skills, language proficiency, and reliable internet connectivity, professionals can collaborate globally without the hindrance of visas. Forward-thinking companies and independent professionals are breaking down geographical barriers, recognizing that collaboration is more important than proximity.

Advice for Aspiring Portfolio Professionals

For those considering a portfolio career, my advice is to start planning now. If time permits, explore a side hustle, saving each dollar earned to build a financial buffer. Setting up a personal consulting company, expanding your network, and building a personal brand are essential foundations for success. If you find yourself at a crossroads, consider joining The Portfolio Collective, where we support individuals worldwide in understanding, launching, managing, and growing their portfolio careers.

Ben Legg’s entrepreneurial journey is a testament to the power of resilience, adaptability, and a continuous thirst for learning. As the landscape of work continues to evolve, his experiences offer valuable insights for professionals seeking fulfillment, variety, and autonomy in their careers.