It’s Lonely at the Top as a Portfolio Professional!

It’s Lonely at the Top as a Portfolio Professional!

If you think it’s lonely at the top, try being a portfolio career professional. While traditional

career paths often provide a clear structure, team environments, and a sense of belonging,

portfolio careers can feel like navigating a maze—complex, hard, and yes, lonely.

In the world of portfolio careers, you’re not just wearing one hat; you’re juggling multiple

hats, sometimes all at once. Whether you’re consulting, sitting on boards, mentoring, or

exploring entrepreneurial ventures, the demands on your time, energy, and attention are

relentless. Each role comes with its own set of expectations, and you’re expected to

masterfully switch between them, all while maintaining a sense of purpose and cohesion.

It’s no wonder that many portfolio professionals feel stretched thin and isolated.

The Complexity of the Portfolio Career

Portfolio careers are not linear. There is no steady ladder to climb, no singular metric for

success, and no consistent team to lean on. Instead, you’re navigating a network of

interconnected roles, relationships, and responsibilities. This complexity can lead to a

constant feeling of being stretched beyond your agile capabilities. As I wrote in my blog

Stretched Beyond Your Agile Capabilities, the pace of change today demands a level of

adaptability and resilience that few are prepared for—and for portfolio professionals, this is

magnified tenfold.

Each opportunity in your portfolio often requires a different skill set, a different mindset,

and a different level of emotional investment. You might be coaching a startup founder in

the morning, advising a corporate board at lunch, and brainstorming a new venture idea in

the evening. The transitions can be exhilarating but also exhausting. And through it all,

you’re often navigating these challenges alone, without the camaraderie or collective

problem-solving that comes with a traditional team.

The Weight of Imposter Syndrome

Loneliness at the top is compounded by a phenomenon many portfolio professionals know

all too well: imposter syndrome. In my blog 71% of US CEOs Experience Imposter

Syndrome, I explored how even the most accomplished leaders can feel like they’re not

enough. For portfolio professionals, this feeling can be even more pronounced. You’re

constantly stepping into new arenas, adapting to different contexts, and proving your worth

in a variety of roles. It’s easy to question whether you’re truly equipped for the demands of

such a diverse career.

Finding Your Peer Power

The antidote to this loneliness and complexity is finding a forum of peers who truly

understand the unique challenges of a portfolio career. In my blog Confidential Portfolio

Peer Forums: Finding Your Next Path, I highlighted the power of connecting with others

who are navigating similar journeys. Peer forums provide a safe, confidential space to share

experiences, seek advice, and gain perspective. They remind you that you’re not alone in

your struggles or successes.

Portfolio careers may be lonely, but they don’t have to be isolating. By intentionally building

a forum of like-minded professionals, you can create a sense of belonging and support that

counteracts the challenges of this path. You’ll find that the complexity, while daunting, also

brings opportunities for growth, creativity, and fulfillment.

So, yes, it may be lonely at the top—but with the right mindset and the right peer forum,

you can turn that loneliness into a platform for connection, purpose, and impact. After all, as

portfolio professionals, we’re not just navigating our careers; we’re designing them, one

opportunity at a time.