10 Questions to Evaluate and Advance Your Career

Guest article by Jared Scherz, TeacherCoach

No matter your field, consider the situations below. They apply to every profession, including teaching.

Russel is a mid-level executive at an international beer company. Friends admire his so-called “dream job,” yet he sometimes fantasizes about a pile-up of suds on the factory floor. Michele is the COO of a mid-sized family business: well paid, with a flexible schedule that lets her attend her children’s sporting events. Still, she wakes up on Sunday afternoons feeling unwell, to the point of taking pregnancy tests despite a waning romantic life.

Millions of people imagine getting fired so they can pursue a dream career, while just as many remain unhappy but never explore alternatives. Whether we feel trapped by salary, worry about starting over, or lack clarity about what would make us fulfilled, many of us settle for “good enough” instead of seeking work that sustains us.

The more passive we are about our careers, the deeper we can sink into that stuck feeling. The real risk is that the very job meant to support us ends up consuming us—draining energy, harming relationships, and undermining well-being.

If your work is increasingly draining you—whether through chronic stress, diminishing purpose, or emotional exhaustion—it’s time to evaluate whether the balance of costs and benefits still makes sense. A straightforward way to assess this is to compare the extreme downsides of your role against its potential upside. When the unpleasant parts consistently outweigh the gains, your unhappiness is understandable.

Stress at work comes in many forms, and its cumulative effect can harm physical and mental health. When the frequency and intensity of job stress exceed your capacity to cope, the job becomes a threat to your well-being. You don’t want to risk relationships or ignore warning signs of decline, as Michele and Russel did.

The next question is whether you have the ability to change your situation or are subject to pressures beyond your control. If you haven’t discussed your concerns with leadership or proposed ideas to improve working conditions, that conversation is a clear first step. If you need support framing the discussion, working with a career coach or trusted professional can help; most people benefit from outside perspective and practical guidance when navigating change.

Before deciding whether to leave or stay, explore the full range of possibilities that might be contributing to dissatisfaction. Ask yourself these key questions to gain clarity:

  • When did you last feel creative at work, and what prevents that from happening now?
  • How invested are you in your organization’s mission and vision?
  • Do you engage in meaningful dialogue with colleagues and leaders?
  • How much effort do you put into developing the people who report to you?
  • Do you take pride in your work, and does that show in your attitude?
  • When was the last time you asked your supervisor or team for encouragement or feedback?
  • How seriously have you pursued your own professional development plan?
  • Which conflicts remain unresolved, and why have you avoided addressing them?
  • Are you taking care of yourself through nutrition, sleep, and exercise?
  • To what extent are your needs being met at work and outside of work?

Answering these questions honestly can reveal whether the problem lies primarily with the job or with unmet needs and patterns you bring into the workplace. If you conclude that you genuinely enjoy the work but the work environment no longer supports you, then it’s time to make a practical plan for next steps—whether that means improving conditions where you are, shifting roles internally, or exploring new opportunities.

About Jared Scherz, Ph.D., M.Ed., ACS

Dr. Jared Scherz is a clinical psychologist, author, and educational consultant who has worked with educators for over twenty years. He earned a Master’s in Education from Penn State University and initially served as an elementary school guidance counselor before completing his Ph.D. He is the owner of Integrated Therapy Center in New Jersey, the creator of PsychPro, and the founder of UFeud, a social platform aimed at reducing school violence.

In his coaching, consulting, and therapy work, Dr. Scherz emphasizes that sustainable change requires understanding what keeps a person feeling stuck. He helps educators feel more peaceful, whole, and purposeful, guiding them toward greater professional and personal fulfillment. His vision for TeacherCoach is to provide educators worldwide with integrated services for personal growth and professional development.