DEAR ELLA

Dear Ella - I'm 55 and a VP. I used to want the bigger job. Now I spend Sunday evenings wondering how much longer I can do mine. Should I stay or should I go?

Dear Ella, I know I need rest. The problem is that knowing it and actually doing it appear to be two entirely different skill sets. I can take an afternoon off. Technically. I can sit on the couch while thinking about Monday, answer a couple of texts, make a list, solve a problem no one has asked me to solve yet, and feel vaguely guilty that I am not doing something useful. Apparently, I have learned how to stop moving without actually resting. And when I am really tired, I s

Dear Ella, I have been doing this for a long time. I have experience. I have made hard decisions. I have led teams, handled crises, navigated politics, recovered from mistakes, and figured out things I once had no idea how to do. Other people seem to trust me. So why do I still feel like I need permission before I completely trust myself? Before I make a recommendation, I want more evidence. Before I disagree, I check whether someone else sees it too. Before I make a big deci

Dear Ella, My boss has started pulling me into more senior meetings, asking for my opinion on things outside my role, and giving me harder assignments. I’m flattered. I’m also suspicious. I’ve been around long enough to know that being good at your job can earn you the exciting opportunity to do even more of it. How do I know if I’m actually being developed for something bigger? Signed, Cautiously Flattered Dear Flattered, Ah, the corporate courtship phase. More access. More

Dear Ella, I think they may be easing me out.

Dear Ella, Last week, I led a tough meeting with senior executives about our marketing strategy. I made the case. I answered the hard questions. I held the room. Afterward, people told me, “You owned that room.” Then I walked down four flights of stairs to the farthest ladies’ room I could find and threw up. Apparently, I can look completely in command while my body is filing a very different report. Why does leadership still feel like danger when, by every external measure,

Dear Ella, By most external measures, things are going well. I have the title. Meaningful scope. A strong team. Senior leaders trust me and include me in important conversations. So why am I so tired?

Dear Ella, I was in a meeting last week where everyone seemed ready to approve a plan that I thought had a significant flaw. How do I challenge a decision without becoming the person everyone wishes had taken the afternoon off?

Dear Ella, We made a decision in Tuesday’s meeting. Everyone agreed. We even finished early. By Thursday, several people were raising concerns they had never mentioned in the room. I had concerns too. I just was not sure they were important enough to interrupt the momentum. How do you know when to speak up?

Dear Ellal, I have a bad habit. I make a recommendation, then immediately dress it up as a possibility. How do I stay open without making my expertise sound optional?

Dear Ella, Why is asking for help so hard? I am perfectly comfortable helping everyone else. I review the proposal, fix the budget, rewrite the email, calm the client, and remember the deadline no one else wrote down. But when I need help, I suddenly become a pioneer woman.

Dear Ella, I know I overfunction. I catch problems early, fill gaps, clarify expectations, and make sure the work gets done. When someone brings me a problem, I usually know the answer. So I give it to them. It’s faster for everyone.

Dear Ella, I keep getting described as “so collaborative.” Lovely, right? Except lately, “collaborative” seems to mean “available for any half-formed project, ownerless problem, or last-minute cleanup no one else wants to touch.” Meanwhile, the people who protect their time are called strategic. I do not want to become colder. But I am starting to wonder whether I have trained people to treat my helpfulness like an office utility drawer. Handy. Reliable. Full of things no one

Dear Ella, I am constantly praised for being reliable. People trust me with hard things. But I am starting to wonder whether being reliable is keeping me in the support position instead of moving me into greater influence. What do I do? Signed, Useful but Underpowered Dear Useful, Ah yes. The gold star of corporate womanhood: “so reliable.” It’s lovely. It’s flattering. It’s also how you quietly become the organizational pack mule. Reliability is a beautiful thing right up un

Dear Ella, I received feedback that I need to work on my “executive presence.” When I asked what that meant, I got a cloud of words: confidence, polish, gravitas, command, warmth, clarity, less detail, more authority, stronger voice, better energy. So, apparently, I need to become a weather system. I am not opposed to feedback. I want to grow. But this kind of feedback makes me suspicious because it seems to mean different things depending on who is saying it. I do not want t

Dear Ella, I have become the person everyone comes to when something is unclear, urgent, politically sensitive, or quietly falling apart. At first, I was proud of this. I was trusted. I knew the history. I understood the people. I could see around corners. I still can. But now I am exhausted and, if I am honest, resentful. People say things like, “You are the only one who knows how this works,” or “Can you just take a quick look?” or “We need your eyes on this before it goes

Dear Ella, I made a recommendation in a meeting last week. It was clear, relevant, and directly tied to the decision we were supposed to make. The room moved on. Ten minutes later, a male colleague said almost the exact same thing. Suddenly people were nodding. Someone called it “a smart way to think about the problem.” Another person said, “That may be the direction we need.” I wish I could say this was the first time. I do not want to become the woman who keeps saying, “As

Dear Ella, I have always been known as collaborative. I listen. I ask good questions. I try to understand the full picture before I push back. But I have noticed something. As long as my collaboration means helping, smoothing, improving, or making someone else’s idea work, everyone loves it. The minute I disagree, name a risk, slow something down, or say, “I don’t think we should do that,” the temperature changes. Suddenly I am being “negative.” Or “resistant.” Or “not a team