"Am I the problem or is my job?" + 2 other career questions smart people are asking me right now

A deep dive on 3 of the questions high performers asked me when they wanted more in their careers.

Sep 15, 2025

Welcome to Reframed! Work is complex, career advice shouldn’t be.

I'm Ashley Rudolph and I write this newsletter for people ready for the next level in their careers. Reframed readers describe the experience best: “It was really the perfect complement to coaching, because in those moments where I was like, I should message her, I was like, you know what? I swear, she wrote a newsletter about this.”

What story is your career telling right now…and is it the one you want?

“Hi, I’m Ashley - I've heard really great things about you from Chris*! How’s your night going?”

“That’s so nice of Chris! It’s going well, my day was hectic though — things are pretty crazy at work right now.”

“Oh?”

“Yeah. I’m in the middle of a re-org and that’s actually going well. I just had my performance review and I got an “exceeds expectations” rating. But…”

“…..what?'“

“I haven’t told anyone at work this yet, but I got a job offer from a competitor and I’m seriously considering it. It’s solid, but I love my team and I’m not sure what to do. Sh*t, don’t tell Chris.”

“It’s okay, I won’t.”

I hear the tension between leaving something good and still feeling like you’re doing the right thing.

CONTEXT

Whenever I meet someone new, the topic of work inevitably comes up. Not in the boring “so what do you do?” kind of way, they feel compelled to share something deeply personal about how they feel at work.

So I listen and, if they ask, I offer my advice.

Maybe this happens because they know I’m a coach, maybe it’s because I make strangers feel heard, or maybe it’s my aura (lol). These convos unfold similarly for me almost every time.

It takes guts to ask big, honest questions about work. And what I’ve noticed is that once people do, there’s power in realizing they’re not the only one asking those questions.

So today, I’m opening up some of those conversations to you — the real questions people asked me and what I offered in return. If you see yourself in any of them, I hope it gives you a little clarity or, at the very least, helps you feel a little less alone in your thoughts.

Let’s get into it.

STRATEGIES AND INSIGHTS

3 Smart Questions People Asked Me About Work Last Month

1. “Am I the problem or is it the situation?”

This problem stems from things not feeling quite right at work. That unease creates a desire to explore what else is out there. When we break it down a bit further, some of the underlying questions are:

“I used to be really good at this — now I feel like I’m getting everything wrong.”
“I’m clashing with my manager and I don’t know why.”
“I got feedback that doesn’t feel true, but I can’t stop thinking about it.”
“I’m not motivated anymore, and that’s not like me.”

What these moments have in common is a shift in how work feels. It stops feeling intuitive. The stuff that used to flow starts feeling clunky. And when people are used to being high performers, their first assumption is: maybe it’s me.

This is the part of the coaching conversation where I insert my questions (we love questions over here!):

When did this start to feel off?
What’s changed — the role, your relationships, you?
What would need to be true for this to actually work again?

In some cases, we dig into misaligned feedback. I walk them through 4 feedback filters that I use:

Is it true and useful?
True but irrelevant?
Untrue but politically important? (this one is KEY and often overlooked)
Or untrue and discardable?

That alone tends to scratch the part of their brain that's stuck.

In other cases, it’s not feedback at all. It's misalignment with a manager, like one client who was clashing with her boss over a difference in communication styles. I see this a lot with high achievers. Some of us want a more collaborative and dynamic partnership with managers, riffing off each other, like a brainstorm. This goes awry when you report into a manager who expects and prefers the more common executive leadership approach: bring me solutions, base your recommendations on data, and reduce info pollution.

What helped this client was realizing her manager processed information differently than she did. He needed the bottom line first, then space for collaboration. Once she started leading with what she knew and then asking for input, the entire dynamic shifted.

Sometimes the problem is the way you’re working, but if it’s really you or your job, keep reading.

2. “Should I stay or should I go? Tell me the truth.”

This usually comes up when things aren’t bad, but they’re definitely not great. The role is fine. The team is fine. But over time, fine turns into stuck. And at some point, they start to wonder: Is this just a rough patch or am I done here?

In these moments with clients, it would be irresponsible of me to blindly preach the gospel of follow your dreams! Quit and figure it out! You’ll be okay!

Especially not when the data and headlines look like this and this.

So I don’t.

But I also know that it’s a mistake to assume that someone else’s job search will look like yours. Some people apply to two roles and get callbacks in a week. Others apply to 100+ and hear crickets.

The difference isn’t always talent.

My advice? Explore the market while you still have a job.

Talk to people. Ask for intros. Reconnect with your network. Apply to jobs that genuinely look exciting. If nothing clicks, you still have a job. You can try again.

Now, back to the question. When clients ask, Should I stay? Should I go? what do I tell them? I ask:

What would need to be true for you to want to stay?
If you’re staying for 6 more months, what needs to shift in how you’re working or thinking?
Can you stay without leaking resentment into your work or reputation?

Because you can stay. There’s no shame in choosing stability. But if you’re going to stay, you have to be able to commit to doing a good job. Staying and becoming disgruntled may damage your professional reputation and honestly, you don’t have time for that. And if you’re unsure about what you want next, I like to ask:

What are you hoping a new job gives you that this one doesn’t?
Is that something you could get here…if you asked?

PS - if you still have that little pit in your stomach, I wrote about how to know when it’s time to quit.

WORK WITH ME

If you read this and thought, “This is exactly what I need help with”, I’m taking new clients (Director level and above). Let’s connect, click the button below.

Explore working with me

3. “How do I maximize my current position to set myself up for my next move?”

I usually get this question from the highest of high achievers — the type of people who are thinking 10 steps ahead of everyone else around them. Complacency? They don’t know her.

These aren’t people looking for the next step. They’re looking at how every step fits into the bigger picture. They move through their careers like chess players. It often plays out like this:

If they’re orchestrating a re-org or part of one, they’re asking, what's my strategic advantage here?
They’re not just accepting a new team, they’re thinking, how do I leverage this moment to expand my leadership platform at the company?
Switched managers three times in two years? Great. Another chance to build an advocate inside the system.

The way they move is a reminder: your current role isn’t just a job, nor is it just about doing well. It’s a launching pad. The question is — are you treating it like one? There’s a lot we can learn from how they operate:

1. They treat every season as a chance to build their professional narrative

They know that doing good work is not the same thing as building a strong reputation. So they ask:

What’s this chapter about?
What do I want to be known for when I leave this role?

When one client landed a trial exec role, the first thing we talked about wasn’t “how to prove herself”. The conversation we had was about: what priorities or accomplishments over the next 30 days will make you undeniable? Only then did the conversation shift from “what do I do?” to narrative building — because how you do the work matters.

Every week, she reflected on this question we crafted together:

“What did I deliver and what did it unlock for my team, my manager, or the business?”

2. They build while they wait for their next opportunity to crystallize

One of my clients was working on managing up in order to succeed at doing the delicate dance of aligning multiple executives. So we strategized and decided that coalition building was the right path forward:

We identified allies.
She pre-socialized decisions.
She became known for leading through complexity without drama and that built trust faster than any meeting or single slide deck ever could.

3. They don’t measure their value by volume

Here’s what I mean. They know that the value of their work is not just about the number of projects or wins they’re managing, it’s about their overall impact. Yes, there are times when you’re tasked with more because you can handle it. But other times, the better you are, the fewer but bigger things you’re trusted with.

So when I coach someone in this spot, I ask:

“What are you building right now that no one else could?”
“What would make your executive team think, ‘I’d fight to keep them on this team’?”
“What are the one or two huge wins you want to walk away with from this role?”

It’s about turning your current opportunity into a launching pad.

CLOSING THOUGHTS

So, there you have it. A rare peek inside my coaching business, the conversations that I’m having with clients, and how I’m advising them to get to the next level. If any of these questions hit home, you’re on the right track.

Keep asking better questions. That’s how you build a better career.

See you next week.

Ashley

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