Everyone Expects to Reach This Career Milestone After Years on the Job. Apparently, I Don’t Have What It Takes.

Good Job is Slate’s advice column on work. Have a workplace problem big or small? Send it to Laura Helmuth and Doree Shafrir here. (It’s anonymous!)

Dear Good Job,

I’m a 39-year-old woman, and I have been volunteering for various organizations since I was old enough to do so. I’ve been working paid jobs since I was 16. I have a lot of skills in various areas: customer service, technical, mechanical, and creative, among others. I’m enthusiastic and hard-working. If I don’t have a skill, I’m more than willing to learn, whether that’s on my own or on the job. I can think on my feet, and I’m calm during emergencies or heightened situations. I don’t shy away from a challenge. I’m not afraid to say I’m wrong or ask for help. I can also take the initiative and work pretty independently. I try to get along with all of my co-workers and supervisors (and I think I’m well-liked), and I’d say I strike a good balance between work and socialization on the clock. I’m well spoken and articulate, and can easily be a public-facing figure. I’m good at taking direction, as well as knowing what the big picture is and how we as an organization could make changes and improvements to the experience for both the staff and customers. I notice details that others miss. In short, I think I’m an asset to any organization.

But, in the 20-plus years that I’ve been working, I’ve never gotten a promotion of any kind. I’ve worked in three jobs where I’ve had to train my manager, and multiple others where most of my co-workers would ask me for guidance. I try not to overstep my bounds and stay in my lane, but I know that sometimes, because of my experience and eagerness to help and get the job done, some managers may feel threatened. However, I’m also very open to criticism, and if anyone expresses any displeasure or wants me to do something differently, it’s not a big deal to me.

What’s wrong with me? What is it about me that doesn’t scream pay bump or management material? I realize that how I see myself may not be how I come across to others, but I have also never gotten any negative feedback. My reviews (when given) are always positive. But I feel like I’ve been stuck at entry-level positions forever. Whenever I apply for something higher than that, I never get an interview. I’ve tried rewriting my resume to pass the screeners, but it never does. And at my age, without a managerial title, I’m at an extreme disadvantage. Especially since I don’t have a bachelor’s degree (I am working on it, though). I really don’t know what to do. I was taught my whole life that companies wanted workers like me, but the reality is quite different. If it matters, I am also biracial, and I look what used to be referred to as ethnically ambiguous. I don’t think race has been a factor in not getting these promotions, but looking back, it’s also kind of hard to know for sure. Other than working hard and being good at my job, how can I show my managers that I’m a good candidate for promotions?

—Level Up

Dear Level Up,

Nothing is wrong with you—you sound like a great catch for any workplace—but your employers are not as aware as they should be of all that is right with you. Let’s start with what you can do in your current (or next) workplace. If you haven’t asked explicitly for a raise or promotion before, start doing so. It will feel awkward and weird, especially if you don’t come from money or aren’t used to tooting your own horn. But your boss, unless they’re entirely new to management, has experience with these conversations, and it’s literally their job to hire and retain good employees. Come prepared with a list of your achievements, especially those that improve the employer’s profits, reputation, customer loyalty, staff morale, or any other metrics your boss is likely to care about. You’ve already gotten started by writing out your letter.

This is just the beginning of the process. Your boss will have to figure out a budget to give you a raise or promotion, or these changes might happen at a certain time of year, so they probably won’t give you an answer right away. If your boss says you don’t have the right skills for whatever the next step is, ask if you could shadow someone to learn some of those skills, or if there are certain trainings you could take to up-skill. Thank your boss for their time, and say you’ll look forward to a follow-up conversation.

When you’re looking for jobs elsewhere, unfortunately, the lack of a bachelor’s degree might be a limitation. How close are you to finishing? Ask to speak with a career counselor at the educational institution where you’ve been taking classes. Ask for a review of your resume, about jobs boards, and for advice about the quickest way to complete your degree. If you’re close, focus on that for now because it might open up new jobs. (It’s ridiculous and exclusionary that so many job descriptions call for a BA even when it’s irrelevant for the work, and hiring managers with any sense or courage should strike that requirement when they can. Read Level Up’s question again to see the kind of great employee you’re missing out on!)

You probably are facing implicit bias and even explicit bias in the workplace. Too many managers overlook women and people of color when they offer promotions, connections, or mentoring. Asking for a raise or promotion—emphasizing your accomplishments and potential—might clear out some of the sexist, racist, ageist expectations they’ve been pickled in. Another type of bias might have hindered you as well: Bosses often take for granted employees who are competent, who don’t need as much attention or guidance as other people. Make yourself stand out by telling them explicitly that you want to keep improving your skills and advancing in your career.

Dear Good Job,

I made a couple of serious mistakes in a detail-oriented position, which led my manager to write an email about my errors and make a change in a new duty. I also cannot seem to write a presentation that satisfies. My manager has lost trust in me, and I don’t know what to do. Should I quietly job hunt or try to work out something here? Any advice?

—Why Can’t I Stop Messing Up?

Dear Why Can’t I Stop Messing Up,

Everybody makes mistakes at work. The best we can do is learn from them … and then make fresh new mistakes. It sounds like you’ve been agonizing over these mistakes, so the first thing to do is forgive yourself. Writing a presentation is hard enough without this torment.

Do update your resume and look for other jobs, because it’s possible your boss is planning to fire you. But let’s talk about how you can try to regain trust with your boss. I suggest you schedule a meeting with them to discuss the mistakes, share what you’re doing to improve your accuracy, and ask for additional guidance. Try to meet before your annual review, for two reasons: so the annual review isn’t an agonizing recap of these errors, and to show your boss you’re making progress before they rate your performance and potentially reduce any annual raise.

You don’t specify how you reacted after making the mistakes, so for future reference, when someone points out a mistake you made, you should apologize, accept responsibility, and thank them for alerting you to the problem. That’s a good way to start this discussion. Thank your boss also for the follow-up email. If it contained any suggestions about how you should prevent future mistakes, like additional training or reviews, tell them you’re following their advice. Show that you take these mistakes seriously (which you do!) and are addressing your boss’s concerns. Propose some additional ways you can improve, and ask for your boss’s ideas. Would it be useful for you to review past presentations to learn more about how to make them successful? Look into workshops that are relevant to your job duties and ask if you should take them. Offer to share your work earlier in the process to make sure you are aligned with your boss’s vision.

If your boss has already decided you’re a screw-up, they’re a lousy boss with a narrow understanding of people’s career development. A decent one would be encouraged to see that you’re trying to improve and will want to help you do so.

Finally, if you get overwhelmed easily in stressful situations—and dealing with a possibly contemptuous boss is one of the worst work situations—come with a list of points you want to make so you don’t forget anything, and a tissue in case you start to cry.

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Dear Good Job,

After over two decades as a first responder, I’ve concluded that the 24/7 schedule and chronic stress are more than I want to handle anymore. The problem is, emergency dispatching is the only job I’ve ever had, and I’m clueless as to what I should do next.

I’d love to get into a new field (I think project management would be a great fit for my skill set), but I’m at a loss as to how to start. I’m working on a few certifications, but I have no professional network outside public safety. With so many entry-level jobs being taken over by artificial intelligence, I’m worried about ever convincing someone to hire me. Not to mention, I’m 45 years old! Are midlife career transitions really a thing?

—The World’s Oldest Noob

Dear The World’s Oldest Noob,

Welcome back to the job market! It’s a mess out there, but you have valuable skills that will help you figure out the job search as well as a new job. For anyone who isn’t familiar with the job description, an emergency dispatcher is typically the first responder: the person who takes 911 calls, sends police or fire or ambulance services, monitors multiple communication channels, and generally gets people through the worst times of their lives. Noob, thank you for doing this work, and congratulations on sticking it out for two decades.

If we break it down, your challenges seem to be: discovering what sorts of jobs would appeal to you, training for them, building your network, and translating your existing skills into the lingo of whatever career you’re pursuing. You’re probably already scouring LinkedIn and other job sites for openings near you. Keep an open mind and research lots of job titles; let yourself dream a bit. You mention that you’re working on certifications. If any of these have a trainer or any human involved, ask that person for advice, both to find out about job openings and to start building your network. What have people with this certification gone on to do? Where are jobs typically posted? Is there a professional society you could join to meet other people in this career?

You probably know people who left emergency response (thinking broadly to include dispatchers, firefighters, health care workers, or anyone you interacted with) for other careers. Get in touch with them. Your message will be partly transactional, because you do want their advice and connections. But it doesn’t have to be just transactional. Ask how they’re doing; tell them you have fond memories of working together; compliment them on some quality or ability you admired. (If the person was a jerk, you can, of course, skip any of these steps.) Update them on any gossip from your formerly shared workplace. Tell them you’re thinking about changing careers. They’ll be happy to hear from you and want to help.

Start spreading the word to people who aren’t in related professions as well. Friends, family, and acquaintances can all be part of your greater network. There’s no shame in telling people you’re looking for another type of career, and you never know who knows somebody who knows somebody.

When you start applying for jobs, craft a resume that matches the job description as closely as possible. For your specific skillset, that might mean describing your experience as something like: problem-solving under pressure, aligning time-sensitive work across divisions, clear and immediate communications, working with the public, etc. If you have ever trained new hires, congratulations, you have experience in education, training, and onboarding. Your team must have updated its technology several times, which means you have experience evaluating and adopting new technology. Don’t worry about your age; focus instead on your experience, knowledge, competence, and courage.

—Laura

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