your next move

‘I’m Disappointed in Myself for Staying at My Job So Long’

A woman who has short, cropped black hair and is wearing cat-eye glasses and a black-and-white polka dot top looks off to her left. She is sitting behind a laptop and there is a coffee cup on her desk.
Photo-Illustration: by The Cut; Photos: Getty Images

Hi, Kimberly,

I have been with my employer for 21 years and have been terribly unhappy for the last five years. I work at an international nonprofit as a program manager. I’ve evolved as a person over the last 20 years, and I am no longer comfortable working at an organization that lacks diversity within senior management. My supervisor does not care for me and does a great job at making me feel undervalued and unappreciated. As a result, my confidence has taken a hit and I doubt my professional abilities. I am disappointed in myself for staying with this employer for so long and feel that potential employers will view my longevity as a negative. I stayed at this job for comfort (e.g., flexible schedule, minimal supervision), but I sacrificed professional development, growth, and compensation.

Recently, my spouse and I decided to purchase a home in Texas. My current position is not remote, so the realization that I will need a job is looming over me. Over the last six months, I have applied for several positions. I’ve interviewed for several of these positions but I struggle with landing the job. I recently purchased your book, Next Move, Best Move, and have been diligently trying to assess my skill set, identify my deficiencies, and identify my passion. My goal is to move into a more senior position where there is room for development and growth and to be fairly compensated. What are some steps I can take to gain my confidence back and revive my stalled career?

It sounds like it’s definitely time for you to make a career change, and not just because you’re physically moving to a new state! However, there’s no need to be disappointed in yourself for staying at your current company for such a long time. While you may not have the compensation that you desire right now, having flexibility in your schedule and autonomy can be priceless. Longevity isn’t necessarily a bad thing, either. Employers may be excited to see that you’re willing to remain at a company for a significant amount of time. One of the biggest complaints employers have about mid-career professionals is that they move on too quickly.

While you’re looking for tactical advice on the exact moves to revive your stalled career, we need to first address your mindset. I am not discrediting that you’ve been working in what sounds like a toxic work environment. Not getting promoted, being underpaid, and feeling undervalued is a recipe for disappointment. However, it’s crucial that you don’t bring that baggage and bad energy into your hiring process with new companies and hiring managers who are meeting you for the first time. It’s like going on a first date and complaining about your terrible ex-partner; it doesn’t go over well. You can avoid this by curating stories about your work experience that focus on your strengths rather than the interpersonal challenges of your current workplace.

Reviewing your track record of success at this job will help you regain your confidence. Yes, you’ve been miserable for the past five years, but you’ve also likely navigated challenging work situations that you can now leverage to show hiring managers you’re ready for a higher-level role. Ask yourself the following questions:

  • What are the top five skills that you’ve gained from your current job as a program manager?
  • What are your peers going to miss most about you when you resign?
  • What was the biggest professional challenge that you overcame?
  • What opportunities have you had that you never expected to be able to experience in your current role?
  • Outside of the flexibility, what has kept you in your current role?

The answers will help you objectively evaluate your experience and pull out the opportunities you should highlight when moving into your next role. I coach all my clients to prepare three success stories and three “do-better” stories to use in their interviews. The success stories showcase you as the “hero” in a work situation, while the “do-better” stories showcase a scenario where you achieved less-than-desirable results and learned key lessons. The more you practice these stories, the more comfortable and confident you will be in your interviews.

Don’t forget to leverage the STAR method to answer each and every behavioral question in an interview. Explain the situation or the role and company you were in; the task or the objective you were working toward; the actions or the steps you took in order to achieve the objective; and conclude the story with the results you achieved. The more complete the story you tell about your work, the more confidence you can instill in the hiring manager.

Last but not least, since you’re no longer comfortable working at an organization that lacks diversity within senior management, use your interview processes to gather information. While you’re interacting with stakeholders, make sure that you’re taking note of who you have the opportunity to meet and don’t hesitate to ask for information on the organization’s demographics. You may be able to find a lot of information about the executive leadership team on LinkedIn or the company’s website, but you’ll want to understand the makeup of your potential team, too.

Career and leadership-development expert Kimberly Brown helps readers make sure their next move is the best move. Listen to the Your Next Move podcast here and keep up with Kimberly on her website.

‘I Stayed at My Job for Too Long and Now I’m Miserable’