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Risk It All When You Have Nothing to Lose

Take A Chance When You Are Young

My brother and I frequently get together to discuss our entrepreneurial ambitions – it’s our pastime. He’s 37 and I’m 35. Currently, he’s freelancing in photography and media while I’m trying my hand at writing. We both have full-time jobs, a family, and kids, which doesn’t leave much time to launch a billion-dollar empire. 

We’ve been having this same conversation of “starting our own business” for 15+ years. Over time, we’ve masterminded some of the grandest of ideas. Indeed, I still lay claim as founder of Uber Eats – I was calling it OnlineEats back in the day – and Netflix. Of course, these were simply ideas for which we never took action. 

And herein lays the moral of this story – I wish I would’ve risked it all when I had nothing to lose

Pursue Your Entrepreneurial Ambitions

Teenagers and young adults are raised to believe it is their duty in life to go to college, study hard, graduate, and get a job. And that’s an acceptable path for most. But, if you have an entrepreneurial spirit or a desire to build something of your own, I encourage you to pursue it.

You see, by going to college, getting a job, and progressing in that job, you’re creating the greatest dream killer of all – comfort. The deeper you get into your career and life, the harder it is to take a different path later. 

Comfort is a dream killer

Age Brings Greater Responsibility

Suppose you’ve been promoted a couple times since starting work and you’re pulling in $100k with a 10% bonus. You have great health insurance, and your company matches your 401k dollar for dollar up to 10%. You get 4 weeks of vacation and they’ve recently implemented a hybrid work environment, so you’re working from the home office 3 days per week. Sounds pretty good, huh?

During this same time, you decide to get married and start a family. You’re fortunate – the Mrs. is pregnant within a month, and you have a due date 9 months later. You can’t very well start a family in a one-bedroom apartment, so a new house and mortgage is in the cards. And that 2-door Honda Civic won’t very well fit a car seat, so time to go mini-van shopping.

Now tell me, at this point in life, are you going to walk away from your job to go live a dream that pays nothing? A dream that may crash and burn? Of course not! Doing so would be irresponsible. Don’t get me wrong – jobs and families are blessings and I’m a strong advocate for both. But as you progress deeper in your career and into adulthood, you inherit responsibilities you didn’t have at 19 or 20 years old. 

Risk It When You Have Little To Lose

My advice is this – take a chance right out of high school or college when you’re too young, poor, and naive to know any better. At a time in life when, even if you fail, it won’t cost you your livelihood. When you have fewer responsibilities in life. Before you get too comfortable. 

It’s easy to take the career path after failing on the entrepreneurial one. But not so easy the other way around.

Caleb McCoy
Caleb McCoyhttps://thehindsightinvestor.com
Caleb is a certified Project Management Professional (PMP) and founder of The Hindsight Investor. He's employed by a Fortune 150 company and one of the largest electric utilities in the world. Caleb manages a team of Project Controls professionals with responsibility to control scope, schedule, and cost for projects preparing the electric distribution grid for green-enablement. Caleb founded The Hindsight Investor after discovering a passion for investing and personal finance and aims to create content that provides value to like-minded readers.
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