What does life look like after a demanding career in law, banking, or professional services? For many, the answer is a portfolio: a mix of board seats, advisory roles, and selective consulting. Freedom at last.

Craig Coben isn’t so sure it’s that simple.

Writing in the Financial Times in September (behind their paywall) the former global head of equity capital markets at Bank of America notes that portfolio life brings “its own kind of servitude.” The single employer disappears—but is replaced by multiple clients, chairs, and collaborators, each with their own expectations.

“If you’re not disciplined,” Coben writes, “then portfolio life can degenerate into frazzled overextension and burnout.”

His rule of thumb comes from a former managing director who caps himself at three core roles. Even that, Coben suggests, may be ambitious.

It’s a useful provocation. For senior professionals preparing to step away from their main career, the instinct is often to say yes—to stay relevant, to keep busy, to explore. But the shift from imposed structure to self-imposed discipline is harder than it looks.

The question isn’t just what opportunities to pursue. It’s which ones to decline.

How many roles is right for you? If you’d like to explore that, please give either Jane Harris (07973 488 539) or George Wilkinson (07875 570 365)] a call or drop us a line at contact@careermilestones.com