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Why It’s More Important to be Shrewd Than Smart: Outsmarting the System with A Simple Formula for Success

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It's been years since I worked at the global investment company where I started my career, but I never forgot S.B., the woman who taught me it was totally possible to outsmart the system.  

She was poised, always elegantly dressed, smiled and made eye contact with everyone and made them feel like they were the only person in the room. She began her career at age 18 as a clerk working on the cash desk that traded bonds for the company. While she was there, she used tuition reimbursement to earn her BA in finance at Northeastern her MBA at Boston University, and her CFA. She then retired at age 36 after having 3 kids, after working there for 18 years, as the formula to access retirement benefits used combined age and years of employment. No college debt, a big pile of cash and good healthcare. The trifecta. 

In a sense, she had replicated, for free, the combination of experience, community, and cash flow funding what would now cost several hundred thousand dollars' worth of education. That was in the 1990’s, tuition reimbursement still exists but has become more scarce and more limited, and that large insurance company eventually went public and was sold off for the benefit of its shareholders.  

Could someone replicate this process now?  I say yes.  

In my house, we have a rule for our family on how to approach both college and the future: a simple formula 

Soft Skills + Hard Skills + Internships 

I’ll give you an example of how it works: my son got into a selective university and decided to major in political science and jazz studies. Prior to his senior year, he developed his own jazz blog, which allowed him to practice writing web copy, and earn some ad revenue from the site. Already we have soft and hard skills in each column. A friend told him about a judge taking kids for a month-long internship at the end of his senior year. He learned all about how our county court system works and met lots of interesting people. He’s generally a man of a few words, but practicing small talk is an important skill too. And learning the decorum of a workspace that’s formal like court. 

My daughter had an interest in ecology and the environment, but also has an interest in art and design. She joined the earth service corps at our local YMCA, started an Instagram account all about invasive species, and got involved with her art department where she helped design and paint a mural depicting the evolution of an organism in the science wing of her school. She never took an AP class, nor even tried to take a standardized test yet was accepted to her first-choice college. She intends to do an internship this summer with the department of environmental protection in our state.  

College is a gating and credentialling phenomenon as much as it is intrinsic education. It tells the person in charge of hiring: you are one of us and we will categorize treating you a certain way. College signals you have resources, at the very least parents who didn’t need your household labor for four years to support the family. That in itself is a huge deal and a signal that this candidate has spent time building connections, both community-wise and synaptic. Once you identify your passion and your path, it becomes easier to figure out what to pay for the college experience. It’s a perfectly reasonable path to go to a local school or community college, or to take advantage of tuition reimbursement and knock down those classes over time. Especially when you pair them with other parts of the formula. 

Another easy way to identify a potential career path is to make note of someone you admire and seek out their Linked In page. You will quickly see that most people did not go to a selective college, but instead were the product of a lifetime of efforts, big and small.