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How a Lifelong Secretary Amassed Millions by Paying Attention

As gatekeepers and confidants to powerful executives, PAs, EAs and Office Admins have unique, unfiltered access to the brightest minds in business. Acting as the right-hand, ideas chamber and authoritative executor to massive business deals and investment strategies, administrators are given the insight of which MBA students, entrepreneurs and competitors can only dream. 

The question is, are you paying attention? 

As NDA and ethics dictate, the information you garner as an assistant isn’t eligible for tea time banter, but it is up for contemplation and personal action. Take the life of Sylvia Bloom. As a legal secretary for a well established US law firm, Sylvia astutely observed the investments and financial decisions made by the lawyers she served and quietly amassed a fortune of $9 million, $8.2 of which she donated to charity upon her recent passing.

“She was a secretary in an era when they ran their boss’s lives, including their personal investments,” recalled her niece Jane Lockshin. “So when the boss would buy a stock, she would make the purchase for him, and then buy the same stock for herself, but in a smaller amount because she was on a secretary’s salary.”

While shadow investing your boss is a questionable practice, there’s merit in paying attention to the habits and practices of successful people around you.

Pay Attention to These 3 Things

1) How they empower others

Your boss may be boss, but watch closely how they get buy-in from others and empower their team in the process of decision making. When people feel emotionally invested in a project, initiative or vision, they are more likely to see it through to a successful end. What can you learn from their subtle and overt communication techniques?

2) How they define & follow dogma

It’s that statement they have framed on their wall, or that line they’re notorious for saying. Dig in to the mantra behind the mind and figure out how that mantra or dogma impacts their approach to business. Here are a few great examples from world business leaders.

“True success should be measured by how happy you are.”

Richard Branson, Founder, Virgin Group: Notorious for living the good life, Richard’s dogma is about seeking success on your own terms and being the gatekeeper of your happiness.

“The best way to change it is to do it. Right? And then after a while you become it, and it’s easy.”

Ursula Burns, former CEO at Xerox, current Board of Directors at Uber: Ursula started her career at Xerox as an intern and moved her way up to CEO. She’s a visionary leader whose mantra says don’t dream it, be it.

“Dress appropriately”

Mary Barra, CEO, General Motors: This simple statement became a symbol for Mary’s approach to communication and management at GM. It serves as an antidote to the restrictive, costly and time-draining policies many large corporations live by. She changed the 10-page HR dress policy into these two words. It’s a great lesson in getting to the core of matters and cutting through red tape. Read more here.

“Leave the crown in the garage.”

Indra Nooyi, CEO, PepsiCo: No matter how big and important you are in the office, ditch that seniority in your personal life. Build relationships with family and friends without using your professional status.

“Never do anything in life if you would be ashamed of seeing it printed on the front page of your hometown newspaper for you family and friends to see.”


Warren Buffet, Investor & Philanthropist: Keep ethics and a moral compass at the core of all your actions. While Buffet believes hard work and smart decisions making got him to where he is, he also believes he “won the fallopian tube lottery.” Circumstance, however, does not exempt one from ignore this important mantra.

3) How and with whom they network

Your boss’s network is a goldmine and you are the gatekeeper of this network. Diary management is most likely part of your day to day job; pay attention to the meetings you arrange. Who is attending and for what purpose? Understand how your boss networks and the decisions making process for giving up time. Insert yourself when appropriate and establish your authority and personal connection. You never know when this extended network may become valuable. 

Will you be a secret millionaire by shadow investing your boss? Maybe not. But you can most certainly take advantage of your insider position to learn valuable business and decision-making skills that lay beneath every successful executive. Harness your environment and carry learnings with you to the next.

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