When faced with a tough or scary career decision (or other life decision)—like moving to another country, or switching industries—picture yourself old and gray, telling your grandchildren about your life.

The actual project you work on has considerably less effect on your job satisfaction than those two factors, yet candidates tend to spend not enough time interviewing their future manager, and often miss taking a more detailed look at their future team.

In that reflection, if you take the path you’re considering, and even if you fail, will you be proud of the boundaries pushed and what you learned from tackling your endeavor? Looking back on your life, will you be more likely to regret taking that path or regret not having taken it?

When people consider a new job opportunity, their focus is usually entirely on the actual job or project (and the compensation, if relevant). Unfortunately, they neglect two critical aspects of job satisfaction.

It is essential to realize that the forces of nature in recruiting will often work against you. Recruiters and hiring managers look for candidates who have already demonstrated success in the skill or role they need. Therefore, they are likely to offer you a job where you continu...