The Most Important Career Choice You'll Ever Make

Ready to reach for the stars and tackle every obstacle that stands in your way? Advice from someone who's been down that long hard road.

learn more about Steve Tobak

By Steve Tobak

Opinions expressed by Entrepreneur contributors are their own.

When it comes to navigating your career, each of you has a choice to make: settle for what comes your way and make the best of it or reach for the stars and tackle every obstacle that stands in your way.

I know that sounds like a very "black and white" decision, but, when it comes to this particularly thorny question, I do believe you ultimately do have to choose. There simply is no "middle of the road" answer that works, in my experience.

While it's clearly a tough and very personal decision that nobody should deprive you of, knowing what to expect from each of the two paths might make your decision and maybe even your journey a little easier and perhaps more successful.

Since I decided long ago that the path of least resistance was not for me, I can't tell you much about that. But I can tell you everything you want to know about the road less travelled – the one full of possibilities and pitfalls, opportunities and obstacles, and dreams that at least have the possibility of coming true.

Why didn't you take the easy path?

For me that was never really an option. I was born with very little to parents who hated their jobs and were miserable about it. They always managed to make ends meet, but it was a constant struggle, to say the least. And it was hard to miss how those boring dead-end jobs wore them down day after day, year after year. That alone provided powerful incentive to search long and hard for a fulfilling career.

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It certainly didn't hurt that my dad wanted a better life for his kids and never let us forget it. The particular path was ours to choose, but a strong work ethic and sense of self-reliance was drummed into us from an early age. Besides, life growing up on the streets of a crowded inner city was full of challenges and adversity. There was simply no reason to expect work life to be any easier.

How did that line of thinking shape your career?

Once you accept that competition is just life's way of weeding out the weak, you eventually figure out that confronting challenges head on and with a can-do attitude will lead to positive results. And that in turn leads to the conclusion that you're at your best because of life's challenges, not in spite of them.

From there it's just a short step to the realization that you should constantly challenge yourself, so that's what I've always done. If the company I worked for wasn't cutting it or I wasn't moving up as fast as I thought I should, I networked and interviewed until I found a better opportunity somewhere else. I never settled for less than I thought I could achieve. That kept my professional growth and career trajectory moving up and to the right.

What about the popular wisdom that you should do what you love?

It should come as no surprise that doing what genuinely interests and excites you will probably lead to the best outcome. But what people generally don't realize is that's by no means a simple or static equation. I've always said that when work stopped being fun I would do something different and I think that's pretty solid advice.

Our lives are constantly in flux. Events change our perception and our perspective changes with experience. It's only natural that our personal and professional goals and interests would also evolve over time. So don't feel pressured to find that "one thing" or do it until the end of time.

Life is long and your career is a marathon, not a sprint. Don't hesitate to pivot and change direction as needed.

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What's your most counterintuitive observation?

Two things. First, I was surprised to learn that the hard road turned out to be the fun road. There's a simple reason for that. When you challenge yourself to do your best work, things generally turn out well for you. A great career is its own reward, but material success doesn't hurt either. Both give you freedom to follow your dreams and do what you enjoy for a living. There's another word for that: fun.

Second, while I spent nearly twice as many years climbing the corporate ladder as I did running my own business, at this point I have to say that the former was far easier for me than the latter. I certainly don't regret the decision and the jury is still out on the outcome, but one thing's for sure: the entrepreneurial life is by no means easy, it's not for everyone and nobody should take that path lightly.

What's the single most important piece of advice you'd give those starting out?

The most important lesson I learned in 30 years, hands down, is to take big risks and set aggressive goals. Do it when you're young and have little to lose and plenty of time to do it again and again.

I learned early on that those who stick their necks out to help their companies and solve their customer's problems are richly rewarded. That's how you make a name for yourself, develop a reputation as someone who gets things done and build a successful business career. It's the same whether you work for yourself or someone else.

Actually, there's one more thing. Try not to take yourself too seriously. A little humility and a sense of humor go a long way.

Related: Great Entrepreneurs Do What Can't Be Done

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.

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