A GUIDE TO BEING A 21st CENTURY BOSS

10/16/2018
LB Culture

Advice from self-employed success stories.

Text by Claire Milbrath

“Put. That coffee. Down. Coffee's for closers only.” -Glengarry Glen Ross,1992.

Gone are the days of the suit-clad bosses who fount better business aphorisms, and with it went the culture of getting ahead,’ supposedly. The term “yuppie” was first used in 1980, to describe a minority of young urban professionals, workaholics with dollar signs for eyes. The world was hungover from free-spirited fun followed by war, recession and disillusionment. It was no longer cool to be broke, and if you didn’t have a phone in your car you weren’t getting laid. The 1980s’ burgeoning corporate culture spawned a personality type - see a young Alec Baldwin in pinstripe and rolex. Dale Carnegie’s How to Win Friends & Influence People carried countless people up the ladder of success





Nowadays, such books seem about as outdated as a literal Business Degree. Today the number of business owners under 30 has fallen by 65% since the 1980s. But it’s not to say that the era of the self-made man is over. Millennials are born entrepreneurs. According to Forbes, 60% of millennials consider themselves entrepreneurs, and 90% recognize entrepreneurism as “a mentality.” Fresh out the womb and millennials are planning their re-brand.


The 21st Century Boss doesn’t own a brick and mortar business, they own ideas. The rapid rise of freelance is making bosses out all of us. People are calling this the 4th Industrial Revolution. A groundbreaking study found that 50% of millennials are now freelancing. In America alone, freelancers contributed to $1.4 trillion annually last year. Intellectual Property (IP) has become a trillion-dollar industry.



Illustration : Cole Kush


Thanks to Steve Jobs and Normcore, it’s impossible to spot these trillionaires in the crowd. The wealth signifiers of the past, sports car and a nice suit, have been traded in for Tevas and a skateboard. Scouting for your future husband has turned into a nightmare game of Wheel of Fortune. But at least you can work from bed! You can work wherever you please. With the help of social media and e-commerce, anyone with a computer can be a 21st Century Boss. The numbers don’t lie; millennials want flexibility. More and more people are starting their own brand, or managing their own contracts.

Given the surge of boss mentality within millennials, it’s odd that the biz-psychology culture of the 80s isn’t more prevalent. Where is our generation’s “How To’s” best-sellers? I certainly never picked up any self-help-success books, or shouted “Yes I can!” at a conference for career empowerment. Although, I have seen the book Never Split the Difference: Negotiating As If Your Life Depended On It, exchange hands in hushed voices. If 21st Century Bosses are winning, they’re getting their pointers from experience and knowledge sharing.

Pick that coffee up and read our Guide to being a 21st Century Boss straight from the bosses’ mouths