Making Tough Career Choices: 5 Questions to Ask Yourself

Two roads diverged in a yellow wood,

And sorry I could not travel both…

Robert Frost

Last year, during one of our large leadership programs, a participant asked me about a major career choice she faced. In this case, the choice involved leaving her organization and taking a different career path. Many of life’s dilemmas, including tough career choices, become dilemmas precisely because evidence and reason fail to provide clear direction. In situations where there is no clear direction, it is important to see the matter from various perspectives.

But how does one see in a new and different light? While not a protocol for tough career choices, or more broadly, life’s dilemmas, I have found the following questions and corresponding actions, taken as a whole, to be helpful.

What do my mentors and friends think? Most people have a handful of people who know them well, have varied life experiences, and who possess recognizable wisdom about life. Whether these individuals are mentors, a spouse or significant other, other close friends, or all of the above, they are a ready resource to help one reframe career choices. Whenever I’m stuck, I talk with mentors and friends. The advice usually helps—sometimes I take it, other times not, but talking about the dilemma helps me think and feel through it.

What are my motivations? Or, phrased somewhat differently, what’s important to me? Tough career choices present opportunities to examine and re-examine what brings satisfaction and happiness; they touch virtually every other aspect of our lives. Consequently, they should be examined in the light of a person’s total life commitments.

Dilemmas often come in the form of having two or more good choices. While not always the case, I have found that looking at career choices in the broader context of what’s important in life elucidates the situation. Why would I want to do this? How does this direction fit with my family, my social life, my mental, spiritual, and physical well-being?

How does the matter look on paper? I’m not referring to the numbers. Rather, this question reflects a simple technique that I personally find helpful. I do my best thinking with a pencil and paper. Whether it’s a pro/con list or just trying to map out a direction and options, putting my thoughts on paper seems to help.

How does the matter look to the uncluttered mind? This question is about meditation. While meditation can mean many things, in this case I’m referring to clearing the mind of the usual clutter. If one pauses for 10 seconds, he or she will hear and observe a myriad of ideas, conversations, hopes, and fears firing across the brain. Trying to hush the noise to give one’s mind a respite is difficult but vital to seeing things differently and more clearly. I sometimes sit quietly; sometimes exercise.  Sometimes there is music; other times, not. Sometimes the meditation takes the form of emptying the mind and sometimes it’s meditation on personal mission or values. However one seeks to unclutter the mind, carving out protected time to clean house is essential.

Can I live with the choice? In some ways, choice is more fundamental than reason. As noted above, choices become dilemmas when the evidence and reason fail to identify clearly the path we ought to take. I’ve made a few really bad choices, and paid the price, but in most cases it works out. In the end, I act. It may be a reasonable decision, but the big choices are almost always a step of faith believing that it’s going to work out.

Ultimately, living with one’s choices requires self-confidence.  Even if a person unwittingly makes a bad choice, they must enter the situation convinced that they can either make it work or work their way out of it.  Having self-confidence to figure out things along the way is a mark of personal leadership.

Author:

N. Karl Haden, Ph.D.
President of AAL & co-author of The 9 Virtues of Exceptional Leaders and 31 Days with the Virtues