A friend married a world-class chef and was a little surprised when the mac & cheese rolled out at dinner time. After spending all day creating extraordinary food for other people, the last thing she wanted to do at home was cook another five-star meal.
That’s the “cobbler’s children have no shoes” phenomenon: we can spend our professional lives doing something exceptionally well for others and neglect doing it for ourselves, for a host of reasons.
In some ways, I’ve lived this paradox my entire life. I’ve been immersed in finance since 3rd grade. Growing up, the dinner-table conversation was deals, companies, markets, real estate, Alaskan oil pipelines, buy this fence company, sell that belt company. By the time I got to college, Mac & Cheese syndrome had already kicked in. After thousands of dinners dominated by finance, the last thing I wanted to study was a subject I’d been over-saturated in for as long as I could remember.
Yet, in my early 20s, finance called me home. Over the last 33 years, my career has spanned asset management, wealth management, investing on behalf of some of the largest and most sophisticated pools of capital in the world, designing and developing the technology and analytics that drive financial decision-making, including platforms and tools used by millions of investors and advisors overseeing hundreds of billions in assets.
Despite all that, I experienced my own version of the cobbler’s kids shoes in my own personal life, which made me curious about what sits underneath the cobbler’s kids and mac’n cheese behavioral patterns.
Solomon’s Paradox
Solomon’s Paradox is a psychological concept that helps explain it. Named after the Biblical King Solomon, famous for offering wise counsel to others while making some remarkably poor decisions in his own life, it describes the human tendency to reason more wisely and objectively about other people’s problems than our own.
Psychological distance partially explains Solomon’s Paradox. When we advise someone else, we can see the whole chessboard. When we advise ourselves, especially when it relates to our own family, money, career, health, company, or well-being, we’re standing on the chessboard. We’re a piece on the board not the player seeing the whole game.
I see this phenomenon among some of the smartest people I know in finance: portfolio managers, PE professionals, tech founders, and executives. They understand markets. They understand businesses. They know what they’re supposed to do. But knowing and doing are two different things. Expertise and objectivity are not the same thing. Emotion enters. Ego enters. Unhealed wounds enter. Loss aversion, confirmation bias, overconfidence, and personal history enter. Intelligence hasn’t disappeared; objectivity has. Over 33+ years in the investment business, I learned early and often that removing as much emotion and bias as possible from financial decision-making is a key to long-term success.
A great advisor doesn’t need to prove they’re smarter than a sophisticated client. Their value is helping a smart person see the whole chessboard, bringing the psychological distance, objectivity, perspective, discipline, and coordination that can be remarkably difficult to provide for ourselves.
Part of the human experience is having emotional and psychological blind spots. Honestly examining our own blind spots is grueling, exhausting work. Many of us avoid it. And that’s human. After all, denial isn’t just a river in Egypt. It’s a sophisticated psychological defense mechanism; while designed to protect us, denial ultimately prevents us from seeing the whole game.
And all of it is okay. Sometimes the world-class chef just can’t make another five-star meal. Sometimes the cobbler needs someone else to make his own family’s shoes; and sometimes, even the most financially experienced and sophisticated are well-served by engaging an advisor who sees the whole game.

