Jack of All Trades
One of the oldest English expressions is “Jack of all trades” which dates back to Old English in 1390 when, during Medieval Times, it was considered a strength for a man to be knowledgeable and capable in several different skills. One might even suggest that since that was really the end of the Dark Ages and the beginning of the Renaissance, that the Jack of all trades may well have morphed into the Renaissance Man of broad talents and expertise. But then someone added “Master of None” in the 18th Century to put a proverbial wet blanket over the characteristic. As the world modernized with the advent of the first Industrial Revolution, specialization became more and more prized and a Jack of all trades was thought of less as a multi-talented individual and more as a dilettante or amateur. Someone then thought to dampen the insult of the added line by again adding “but oftentimes better than master of one”, which returns the expression to a slightly positive and certainly less negative connotation.
There is an age-old battle that rages between being a specialist and being a generalist. I certainly saw the contrast often in the banking world. Generally, the power of the solo practitioner or professional is in the high degree of specialization attained in some niche but highly relevant space. The problem with specialization is always that the focus on that niche is most often fleeting. The demand for that expertise burns bright, but does so only momentarily as the world moves on to some other arcane interest. Specialization is both comforting and angst-ridden. The comfort comes with the normal sense of security that accompanies deep expertise. It reduces uncertainty and builds confidence. The downside is that should there be a mistake made or a detail missed, there is nowhere to hide because you have held yourself out as a definitive expert whose entire raison d’etre is to know everything there is to know about some specificity. Meanwhile, the generalist has the advantage of broad expertise that crosses many boundaries and enables integration of ideas without acknowledging that there may be more specificity that exists or is needed. Generalists can bring diversity to the party and are good at innovation through cross-fertilization. Specialists command the greatest respect and often the greatest immediate compensation, but generalists have more sustainable skills and are thought to be better managers of a broader enterprise.
It is hard to say what drives some people to be specialists and others to be generalists. I like to think that specialists are less willing to be wrong and therefore less humble people. Generalists must always be less absolute in their positions and through an ability to accept their own fallibility are often more confident and more able to address adversity of surprises. Specialists tend to be thorny, Generalists need to be conciliatory. You can tell from my way of defining these roles that I prefer to think of myself as a generalist or a Jack of all trades. And yet, I do expert witness work because I do have expertise which is notable in several arenas. But I believe that my strength as an expert may actually be in the breadth of my expertise rather than in its depth.
I spent the bulk of my career moving from one position to another crossing about every line that exists in banking. I have done sell-side banking and buy-side banking. The early part of my career was in the sell-side or what people generally call investment banking. I covered financial institutions as well as corporations and have done domestic, international and multinational banking. I have worked the structuring and lending markets as well as the trading markets in both cash and futures arenas. I’ve structured and sold highly complex derivative products into the most sophisticated clients in the world and I have built and run the emerging markets business. That means I did the east/west travel between London, New York and Tokyo/Hong Kong/ Singapore, where the big hitters operate. And I also did the north/south traveling into Latin America, Africa, SE Asia and the undefined markets like the Middle East and Eastern Europe. The Emerging Markets gig was especially interesting because it was about taking sovereign debt that had become like molasses in terms of marketability and repayment and turning it into something better that would give a faster path to cash. It was simultaneously highly specialized and yet equally highly creativity-focused. What it all gave me was a very broad perspective and as I shifted from the sell-side to the buy-side I was able to bring a wealth of ideas over to the more staid side of the business. On that side I have run businesses that catered to high net worth individuals as well as large institutional clients. Within money management I have run defined benefit plans and defined contribution plans. I managed traditional debt and equity products, but also hedge funds and private equity, not to mention all the varieties of mutual fund and registered products.
That background causes me to characterize myself as a generalist, but as it turns out lots of the diverse arenas I was required to learn about and play in were also highly specialized. I think its fair to say that I can most often think of specialists who know more than me in any given market or about any given instrument, but I know very few who have the combined depth and breadth of markets and products that I can credibly command. That tends to make me a versatile expert for the assignments that come my way. Its funny because I don’t think I could have designed a better background to be an expert witness in finance even though I had no clue that would be where I ended up. It has also occurred to me that I have a natural predisposition to be more of a jack of all trades, master of none sort of person because if you just look at my non-work activities you can see the tendency. In sports I have played many sports but would not suggest that I am world class in any of them. I enjoy being credibly good in the sports I do pursue and that is especially so in sports where people do not expect someone of my size to be any good at all. Squash was such a sport for me. I have played many racquet sports and most people do not take me for a good squash player, but the truth is that squash is a game that requires at most a step or two in any direction and while quick reflexes are important, the scale I bring to what is called the T at the center of the court is such that I am both hard to see around and even harder to run around. It all works to my advantage, but I am sure there are many good squash players that would make mincemeat out of me.
I am finding that the real benefit of being a Jack of all trades and a generalist are blossoming for me in retirement. Someone who focused on tennis, for instance, would be lost if they could no longer play tennis. I have such a large array of options both of things I can claim competence for and then those that interest me and I enjoy doing, that I feel never at a loss for things to entertain myself. This is how things like writing and gardening have come to the fore in retirement for me. I am always dropping some activities and taking up others and I think my generalist attitude makes it easy for me to both attain a level of proficiency without needing to be world class in any of them. It’s an aptitude that is serving me well in retirement and I am always proud to say with equal emphasis that I am a jack of all trades and just as happy to be a master of none.