5 Questions to Ask Yourself Before Pursuing Your Dream Job

Years ago, an associate of mine was working in a job that had already made him more money than most Americans earn in a lifetime. Right out of college, he landed a position with a major tech company and helped design several iterations of the world’s leading networking equipment.

Some might call my associate’s career a study in success—a perfect example of how a smart, hard-working, enterprising individual could still do great things in America. Only, the man wasn’t happy. In fact, he was miserable. He was tired of networks and technology and wished his life had taken a different direction. In other words, he felt trapped.

He was also paralyzed by fear. He attributed most of his success to luck, circumstances, and youthful enthusiasm. More than halfway through his life, how could he dramatically change its trajectory, yet still meet all of his financial obligations? More importantly, did he have what it took to do something new?

The man eventually hired me as a career coach, and several months later he made the transition into a C-level position at a leading nonprofit organization. When he and I reflected on his success, he said, “I think it’s the questions we discussed, the ones right at the beginning, that made it all possible. Once I realized I could answer them all in the affirmative, I knew I had what it took to make a change.”

Those questions are reproduced here:

1. Can you invest hours of your free time in learning something new?

   Most people’s dream job—whether it’s a director of marketing, a boarding school history teacher, or a chief information officer—requires a high degree of expertise in a diverse set of specialized skills. Those skills take time, effort, and intentional practice to master.

2. Are you willing to accept rejection?

   It’s the extremely rare individual who lands his or her dream job on the first interview. Just as J. K. Rowling received dozens of rejection letters before having her first Harry Potter manuscript accepted, most dream job seekers will have to deal with being turned away by HR.

3. Do you know how to talk with people?

   Whether it’s fair or not, few people will recognize your expertise and value if you don’t introduce yourself to them. Old-fashioned networking is essential to finding most dream jobs. The more people know or hear about you, the more likely they will be to hire you—or point you in the direction of the perfect opportunity.

4. Can you discipline your thinking and achieve emotional detachment?

   For most people, one of the biggest barriers to landing their dream job is self doubt. The human subconscious has a negativity bias by default, which leads us to constantly question our plans. Thankfully, practice and mindfulness can transform our thinking and dramatically decrease self doubt.

5. Are you willing to put happiness above money?

   According to psychological researchers, earning more than $75,000 per year (adjusted for local COL) doesn’t contribute to the average American’s overall level of emotional well-being. While not every dream job comes with a pay cut, some do; others may require substantial education or relocation costs.

“What is my dream job?” you wonder. “And do I have what it takes to achieve it?” Only you can answer the first question, but the answer to the second is a resounding yes. If you’re motivated to pursue the job of your dreams, you absolutely can achieve it.

If you’re interested in reading more about how to find your dream job, my friend Whitney Johnson has a new book out titled Dare, Dream, Do: Remarkable Things Happen When You Dare to Dream, which is available at bookstores nationwide, as well as on all major online retailers, including Amazon, B&N, and Indiebound.