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The author is former global head of Bank of America, and is currently the managing director of experts at Seda.
In the 1995 film The Heat, Robert De Niro’s career criminal life lives by basic rules. Leaving a financial career means you’re less likely to raise your hair than running away from a bank robbery, but the dilemma is similar. Can you pursue a new full-time position, create a “portfolio” of gigs and side hustles, or leave immediately?
Multiple portfolio passes have been selected. It’s a combination of consulting, writing, nonprofit committees, and personal projects ranging from respect to Rowdy. It promises freedom and flexibility, but the trade-offs are real.
The biggest attraction of a portfolio career is control. No boss, hierarchy, no bureaucracy. There are no attachments and there are loose connections that allow you to exit freely. You choose what you are doing and when. That freedom helps explain why a 2024 study by Platform Malt found that 62% of highly educated freelancers in Europe were satisfied with self-employed.
However, multiple lives come with slaves of their own kind. Instead of a singular master, report to multiple overlords, including clients, board chairs, collaborators, and editors. A clear corporate chain command chain is left to a series of competing asynchronous requests.
Therefore, you need to set boundaries. It’s easy to say “yes” too often when you’re starting out, but without discipline, your portfolio life can be crazy overextension and burnout. The former managing director I know has set strict limits on three core roles to keep you sane. Even that sounds like a lot.
There are also social factors. Despite Cutthroat’s reputation, finance is a team sport with a significant portion of (mostly) office friendship. In contrast, multiple tasks can be isolated. Most days, there’s little need to dress up beyond a presentable shirt for video calls.
But the most difficult sacrifice is giving up influence. As a senior banker who leads a team, you set strategies, allocate resources and manage people, even if you are subject to strict surveillance. The assistant jumped at your request, support appeared when the phone called, and juniors laughed at your jokes as you had problems with their careers. In multiple lives, that authority dissipates. Former colleagues say that as consultants or executives, their views are recognized but often ignored – until a real crisis makes people pay attention. You will appear, you will make your claims, and the world will continue.
The singular approach has its drawbacks. Takes many bankers who move into the family offices that manage the fate of Ultra Rich. Unlike a portfolio career, you can’t “go out” one difficult client without losing leverage and quitting your entire job. A former community has experienced a life as a reliable persuasiveness to the yacht clan. Another complains that he is always called by the mercury principal. And in these lean outfits, former bunkers are often seen as expensive overhead rather than a respected “talent”;
And market reality is made into shape, whether it’s singular or plural. In the 50s or 60s, it is difficult to secure a full-time role, especially in new fields. One friend considered applying to be a detective constable at Met until he learned that the typical age limit is 57.
It turns out that multiple roles are also difficult to obtain. Board sheets are short, often assigned to retired industry executives. Freelances demand merciless fuss and can be difficult to earn rewards. I lost the number of people who called “choose my brain.”
Ultimately, your choice depends on what you optimize. Using multiple carriers allows you to define success on your own terms. There are no promotions to pursue, but no one is making your judgment anonymously through a 360-degree performance rating. Conversely, full-time roles provide clarity and structure, but after roaming freely as a banker for many years, you can feel like you’re rejoining the pack.
Some ex-financies switch options and figure it out as they go. One friend spent six months as temporary Chief Financial Officer, getting frustrated, consulted a freelance, dismissed it as “Mickey Mouse,” and eventually returned to the big bank.
So, do you choose a beach corner office or laptop? Depth and commitment of one thing, or a lot of width and flexibility? Both have trade-offs. The real luxury lies in making choices entirely.
