ask a boss

‘I’m Ashamed of My Work History and Want to Make a Career Change at 40’

Photo: The Cut

Dear Boss,

I was relatively successful in my 20s. I got a job right out of college and climbed the ladder, going from an assistant position to a director position, all at the same workplace. I even accomplished some pretty amazing things — many of which are still in place. My personal life exploded in my 30s as my marriage took a turn toward the abusive, and I became a worse and worse employee, eventually agreeing to resign under (appropriately) frosty terms. I got a part-time position after that, but I hadn’t pulled myself out of my tailspin. Then I had a kid and took care of my parents while they died and eventually ghosted my last employer out of shame because I felt like I was failing. I know how bad this sounds.

I am now in my early 40s. I went through tons of therapy, went back to school, got a second bachelor’s degree in a completely unrelated field — graduating magna cum laude with a major department award — and now I’m trying to find a job. I’d like to go to grad school, which tends to be rife with mentorships and placement help, but I don’t have the hands-on work experience I need.

I am deeply ashamed of the past several years (but proud of my recent academic achievements). I know I messed up. And I understand the ways that I messed up. And I’m not trying to make any of it okay. I’m applying for entry-level jobs. I don’t want to ride on my prior work experience. But my years of instability took a toll. Right now, I don’t have any references. And I’m obviously older.

How should I address this period of instability in job interviews? How do I talk about my prior life? And how do I find a job without references? Are there positions that don’t require them these days? I’m absolutely willing to volunteer, but I’m having trouble finding places to do so.

First, please hold in the forefront of your mind that your career didn’t get screwed up because you’re a screw-up. It doesn’t sound like you’re lazy or irresponsible or cavalier about commitments. It sounds like a series of really tough things happened in your life that interfered with your ability to maintain a career that, up until then, had been going great. You clearly have work ethic, a sense of responsibility, and the drive to do well professionally. Life decided to have its way with you, as it sometimes does.

I’m stressing those facts because carrying shame over what happened will just make a hard situation harder — and it sounds like it’s misplaced.

Frankly, even if you had been a screw-up — even if there was nothing external that got in your way and you just had a period of messing up for no good reason — you’d still be able to recover from this. What you do in one decade of your life can absolutely make things harder for you later, but it doesn’t consign you to working entry-level jobs forever after.
You can repair this and get a career back.

You, in particular, have a bunch of things going for you: First, you had years of professional success before things imploded, and that’s evidence of your abilities and drive. Second, you have a newly minted degree, which in many ways will act as a professional reset. That’s especially true if your degree has a clear professional path to it; for example, if you got an accounting degree, many employers are going to be more interested in what you achieved in school than what you did in unrelated jobs five or ten years ago. (That effect has a time limit on it though, so take full advantage of it now while you’re still a fairly new grad.)

Third, you have a very understandable excuse for what happened previously — which you can concisely sum up for interviewers as “I was dealing with some family issues, including having a child and ill parents, which are now under control. I’m excited to refocus on work.” You’re far from the only person whose career got sidelined by family or health issues, and that’s going to be understandable to your interviewers. It’s also pretty credible, since you have that earlier track record of achievement to point to.

In fact, it might even make sense to look at your résumé and see if you could simply leave off the jobs from that chaotic period. Your résumé is not required to be an exhaustive list of everything you’ve ever done. It’s a marketing document, and while you can’t lie on it, you’re absolutely permitted to leave off jobs that don’t strengthen it. So one solution might be to leave off the work from the worst period of time, which will mean those employers aren’t going to be contacted as references, and you won’t need to explain what went wrong there. The trade-off, of course, is that it’ll leave a chunk of time on your résumé without work experience, but if you’re asked what you were doing with that time, you can honestly say that you were raising a kid, helping your parents, and working at jobs that weren’t your professional focus at the time. (To be clear, without seeing your résumé and exactly what impact this would have on it, I don’t know if this is definitely the right solution for you. But it’s an option to consider.)

Regarding references: Did you do any internships or other jobs while you were in school? If so, those may be more relevant references now than jobs from further back would be anyway. Employers usually prefer recent references, so they might be perfectly satisfied with those. If that’s not an option, there are employers who don’t check references — but you’re not going to know who they are until you’re pretty deep into the hiring process (and you can’t really ask at the start without raising red flags). But you probably will find some employers who don’t.

For those who do check references, your best bet is honesty: “I was dealing with a number of issues in my personal life, including sick parents, who I cared for until they passed away, and a new baby. It affected my ability to focus on work, and the references from that period will reflect that. I can offer you references from before that period, which will be excellent, although they’re from longer ago. Or I can offer you people who worked with me more recently, while I was in school.” You could add, “I’m hoping that my track record of achievement in school over the last four years will demonstrate that period is behind me.”

Some employers will be wary of this. Others won’t be. You only need one who isn’t — because that employer will let you start rebuilding your work history. And once you have a strong work history there, the next job search after that will be far easier, because what you’ve done recently will always be more relevant than what happened long ago. (And that period will become “long ago” at some point.)

You’re in the hardest part right now. But it’s going to get a lot easier.

Order Alison Green’s book, Ask a Manager: Clueless Colleagues, Lunch-Stealing Bosses, and the Rest of Your Life at Work, here. Got a question for her? Email Her advice column appears here every Tuesday.

‘I Want to Make a Career Change at 40’