Five Things to Know Before Becoming an Entrepreneur



Published On

May 24, 2022

Over 38 million people quit their jobs in 2021 for something different, and the pace continues in 2022. It’s being called “The Great Resignation,” as workers are considering better opportunities in business and quality of life. Scott Dust, professor with Miami University and Chief Research Officer at Cloverleaf, perhaps more aptly calls it, “The Great Reprioritization.” 

Fundamentally, due to the distress and disconnectedness caused by the pandemic, better compensation and benefits elsewhere, and the rise in expectation of more flexibility and fulfillment, people have been reevaluating their life, work, and happiness trajectory. A new job with a new company or a new career can be just the change one is looking for to make that big improvement and a life upgrade.

But there’s another category of quitters. They are even bolder than those making job and career changes. They are even bolder than those making the leap to self-employment. This category of quitters, or “re-prioritizers,” are those who make the leap to become entrepreneurs and create a new product or services company.

These aspiring entrepreneurs are the biggest risk takers and if fortune favors them, the next job creators, and next wealth creators. These are the daring individuals who quit paychecks to pursue a big dream or a big opportunity. Steve Jobs referred to them as “the crazy ones, the misfits, the rebels.”

They aren’t showing up in the statistics yet – but they will. We haven’t seen them yet, but we will. Rest assured, bold new entrepreneurs are making their leaps right now. Amazon, Apple, Zoom, Nike, Salesforce, Minecraft, Starbucks, Red Bull, Spanx, Instagram, and 23&Me were all started by people who left paychecks to chase a dream.

And no one knows this better than TIGER 21 Members. A vast number of TIGER 21 Members worked tirelessly on becoming entrepreneurs and, in turn, first-generation wealth creators. They understand and remember the incredible risk they took when they left their jobs and careers to pursue their startup. Sometimes they made the leap when times were good, even more often when times were not so good.

Let’s be clear that becoming an entrepreneur is not for everyone, and timing can be everything. It takes a deeply committed person or persons, a viable path to success, and a dash of good luck. It is also an outsized threat to oneself, career, finances, mental health, and relationships – even if you’re successful.

But for those who must answer the call to do big things and know they must make the leap, here are five critical things to know before you go, things that are likely to increase your chances for entrepreneurial success:

#1: Becoming an Entrepreneur is a Lot Harder Than You Imagine

Most everyone dreams of being rich and successful. But those who have achieved this rare air will tell you it was a long, hard road behind the scenes. There was always a tremendous sacrifice in time, relationships, fun, and a large amount of risk taking and financial insecurity all along the way. This is more than most people are willing or equipped to do. Accepting and preparing yourself for multiple years of struggle (but never giving up) before you turn the corner on success, is the winning strategy for those determined to become an entrepreneur.

#2: Success Bias is Real

People like to see and read about success, it’s inspirational and aspirational. Failure is uncomfortable to see and read about – unless it’s a mammoth and spectacular failure, we love to read about those! It’s human nature to personally hide failures and promote success. So, we tend to see success stories in the traditional media and (what appears to be success) in social media. This is not reality, as most startups struggle or fail. We need to seek out and learn from the struggles and failures before making the leap to becoming an entrepreneur.

#3: Beware of Confirmation Bias

Confirmation bias is the tendency to see critical information as confirming one’s views or beliefs, when in fact, some or much of the information is pointing in a different direction. Entrepreneurs are great at “willing” their way to success, which often requires an undying, relentless, uncompromising belief in a vision, but this very strength can be a weakness that produces lethal blind spots and fatal decisions for their businesses. Those who are determined to become an entrepreneur need a love for the truth and smart, trusted advisors and team members around them to help elude confirmation bias.

#4: “Follow Your Passion” Isn’t Always the Best Business Advice

Not all business types are inherently profitable and not all business “concepts” can be a real business, i.e., not enough people will pay money (or the necessary amount of money) for the product or service offered. And, you can find that pursuing the thing you love (i.e., photography, yoga, graphic design, cooking, event planning, gaming, etc.) as a business can run the risk of burning you out and making you loathe the very thing you (used to) love. Having a plan to elevate yourself above the hands-on “doing” of the work, prioritizing your time toward business development, and building a team that you manage, is a winning strategy to become a successful entrepreneur in a field of your passion.

#5: Something Better is Usually Better Than Something New

Many aspiring entrepreneurs dream of creating or inventing something new. They often think that is the way to make it big as an entrepreneur – invent something amazing, get rich! For sure this happens and is a path for some, but the vast majority of those that experienced entrepreneurial success  created or provided something “better” for the market, not necessarily “new”. Better is typically lower risk, generates income faster, and produces more millionaires per square mile than creating “something new”.

So, here’s to the dreamers and the leapers. We need you. The world needs you. You take on great risk, but you unlock great reward – not just for yourself, but for everyone you employ and all who purchase your product or service. The pursuit of happiness is one of our most precious unalienable rights – seize the day, but look and learn before you leap!

About Allen Clary

Allen Clary, Tampa Bay TIGER 21 Chair, is also an Adjunct Professor of Entrepreneurship at the University of South Florida. He is also a co-founder of the non-profit Tampa Bay Wave startup accelerator where he has served as founding board member, Entrepreneur in Residence, and Director of Investor Relations. Allen frequently speaks on the topics of entrepreneurship and is an advisor to several early-stage companies. Allen serves on the Board of Advisors to the USF Center for Entrepreneurship where he also received his MBA and was awarded Entrepreneurship Outstanding Alumni of the Year in 2013. Allen recently published his first book, “Quit to Start – How to Discover Your Best Idea, Gain the Confidence, and Plan Your Escape.”

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