Making the Toughest Decision of Your Life

The career choice between a corporate job and entrepreneurship is life changing, for good or ill. Don't let anybody talk you into either.

learn more about Steve Tobak

By Steve Tobak


Opinions expressed by Entrepreneur contributors are their own.

If you've ever woken up one day and realized that you've been on the wrong path and there's no way to turn back the hands of time, then you've experienced one of life's worst feelings: regret mixed with hopelessness, since there's simply no way to go back and make things right.

Considering the number of critical decisions we make throughout our lives, I'm sure it happens to everyone at one time or another. But that doesn't make it any easier when it happens to you, especially when the choices you've made did irrevocable harm to your health, finances, career, or, God forbid, someone else.

In the end, outcomes always come down to choices. If you make mostly good decisions when it counts, all things being equal, you'll lead a good life. If you generally make poor decisions, you're going to have a rough time of it.

The same is true of career decisions -- figuring out what path to choose. Granted, you can change your mind, but every time you do, you've lost time and opportunity. You certainly don't get an unlimited number of chances, so it's a good idea to make them count.

The problem is the overwhelming amount of content that glorifies the massively over-hyped entrepreneurial path. Unfortunately, much of it is click bait written by amateurs out to make a buck. They pick up on popular fads and sound bites that play with the hungry content consuming masses.

You know what I'm talking about. Their titles always include keywords like rich, millionaire, billionaire, leader, brand, millennials, culture, engagement, productivity, habits, beliefs, emotional intelligence, positive thinking and the occasional mention of Tony Robbins, Tim Ferriss, Richard Branson or Shark Tank.

Not to be cynical, but let's face it, deciding whether to pursue an entrepreneurial path is among the most critical decisions you'll ever make. It's a good idea to make an informed decision based on common sense and reason, not what passes for common wisdom in a hype-crazed online world. If we're agreed on that, then consider three key factors:


Proponents of the entrepreneur route will often cite euphemisms like "no risk, no reward" or "no pain, no gain," but you never hear them mention the flipside – the cost of failure. Which is odd, since most startups and small businesses do fail. The inspirational quotes are true, but so are "no risk, no loss" and "no risk, no pain."

Entrepreneurial failure obviously costs money, but just as important are the time penalty and the emotional toll from seeing something you believed in and worked hard on go down the tubes. And nobody ever thinks about the opportunity cost -- all the opportunities you passed up while otherwise occupied on your own gig.

Another popular meme is that it's never been easier to do your own thing. That's true, but it's true for everyone. The barriers to entry are virtually nonexistent and the competition is enormous. With millions entering overhyped fields like content marketing and coaching, it's nearly impossible to differentiate and make a decent living.

The beautiful thing about a career in the corporate world is that, aside from college, you really don't have to risk any of your own capital. You get to learn and gain experience on the job, and get paid in the process. Granted, you might end up in a dead-end job, so you have to aggressively manage your career and continue to make wise choices.

Related: 5 Things Every Entrepreneur Should Know About Risk-Taking


Maximizing your earning potential essentially boils down to six activities: 1) figuring out what you love to do, 2) gaining exposure to new opportunities and people, 3) setting goals and being disciplined about achieving them, 4) working really hard, 5) striving to be the best, and 6) positioning yourself for long term success.

Interestingly enough, those same six factors apply equally to entrepreneurs as well as those in the corporate world. I call it a wash.

Related: What Determines the Winners and Losers in Entrepreneurship?


If you have schooling or training in an in-demand field, my bias is toward gaining experience and exposure to opportunities and like-minded people in the corporate world rather than going it alone right out of the gate. Even if you do plan to start your own business, better to learn the ropes on someone else's nickel while getting paid doing it.

On the other hand, it's hard for those without an education or marketable skills to get a foot in the door in the corporate world, and even harder to fight your way to the top of the corporate ladder. It can be done, but I'd give entrepreneurship the advantage in that situation.

What you do with your life is your business and no one else's. After all, you're the one who's going to have to live with the consequences. If I were you, I'd make well-informed decisions based on objective advice from trusted sources and your own instincts, not because you read that it's what you're supposed to do.

Steve Tobak

Author of Real Leaders Don't Follow

Steve Tobak is a management consultant, columnist, former senior executive, and author of Real Leaders Don’t Follow: Being Extraordinary in the Age of the Entrepreneur (Entrepreneur Press, October 2015). Tobak runs Silicon Valley-based Invisor Consulting and blogs at, where you can contact him and learn more.

Related Topics

Editor's Pick

Everyone Wants to Get Close to Their Favorite Artist. Here's the Technology Making It a Reality — But Better.
The Highest-Paid, Highest-Profile People in Every Field Know This Communication Strategy
After Early Rejection From Publishers, This Author Self-Published Her Book and Sold More Than 500,000 Copies. Here's How She Did It.
Having Trouble Speaking Up in Meetings? Try This Strategy.
He Names Brands for Amazon, Meta and Forever 21, and Says This Is the Big Blank Space in the Naming Game
Business News

American Airlines Sued After Teen Dies of Heart Attack Onboard Flight to Miami

Kevin Greenridge was traveling from Honduras to Miami on June 4, 2022, on AA Flight 614 when he went into cardiac arrest and became unconscious mid-flight.


How to Detect a Liar in Seconds Using Nonverbal Communication

There are many ways to understand if someone is not honest with you. The following signs do not even require words and are all nonverbal queues.

Business News

Influencer's Team Speaks Out After Being Slammed For Selling Instagram DMs for $10,000: 'False and Inaccurate'

Emma Chamberlain's merchandise website went viral after one fan noticed a particularly pricey offering.

Science & Technology

How This Innovative Technology is Making Healthcare More Affordable and Accessible

As part of telehealth, mHealth can improve the healthcare system by increasing access to care, improving communication and saving money for patients and providers.