272: Should You Stay, Go, or Redesign Your Role? How to Know When It’s Time to Exit

You’re a high achiever. You don’t quit easily.

But lately… you’re starting to question whether staying is helping you grow—or slowly holding you back.

If you’ve been feeling stuck, unchallenged, or misaligned with your current role or leadership—or perhaps deep down, something just feels off—this episode is the gut check you didn’t know you needed.

Because here’s what I hear all the time from women in tech:

“I should be grateful. I have a good job.”

“Maybe it’s just me. Maybe I’m the problem.”

“This isn’t ideal… but I’ve worked so hard to get here.”

“Maybe tech as a whole isn’t for me anymore.”

“I don’t want to quit—I just want it to feel better again.”

And perhaps the hardest one:

“I know something’s wrong—but I can’t tell if it’s fixable, or if I’m just afraid of starting over.”

If any of those thoughts sound familiar, know this:

You’re not alone.

And you’re not crazy.

You’re just ready for a clarity audit.

Because feeling stuck isn’t always burnout.

It isn’t always about needing a break.

Sometimes… it’s your leadership maturity kicking in.

It’s your internal compass telling you: you’ve outgrown this.

Or: this culture is no longer aligned with who you’ve become.

In today’s episode of Leading Women in Tech, I’m going to walk you through:

🔹 Why high performers struggle to recognize when it’s time to move on

🔹 The five subtle signs you’re out of alignment in your current role

🔹 And the career reflection prompts I use with my executive clients to decide:

Should I fix this… or is it time to go?

🎯 Stick around to the end for five questions that will help you get unstuck this week—without blowing up your life or second-guessing yourself into paralysis.

​​The Real Cost of Staying Too Long

Let’s talk about what happens when we don’t listen to that quiet gut feeling… when we stay because we think it’s loyal, or “not that bad,” or simply because we’re too exhausted to figure out what’s next.

Because here’s the truth:

Staying too long has a cost.

And that cost often shows up before we’re consciously ready to admit something is wrong.

If you’re the woman who’s overextended herself – the woman who is the go-to, the glue, the reliable one—

you’re usually the last to admit you’re burned out.

You’ve normalized exhaustion.

You’ve internalized the idea that loyalty = leadership.

You may be telling yourself that without you the team will fall apart. It’s not fair to leave your team behind. 

But here’s what I want you to consider:

Are you staying out of strategy… or out of habit?

If you’re the only woman in the room, or just feel lonely, irrespective of those around you —if you’ve broken barriers and earned the seat at the table,

it’s easy to feel like leaving a misaligned org is quitting.

But staying to prove yourself in a space that doesn’t value your leadership isn’t grit—it’s depletion.

Leadership burnout doesn’t always look like collapsing.

It can show up in surprising ways such as 

• Being numb to your wins
  
  
• Or Feeling stuck but overworking anyway
  
  
• Perhaps you’re losing sight of your why
  
  
• And all too often, nodding along in meetings but thinking, “What’s the point?”
  
  

And then there’s the slow fade of career stagnation where You’re no longer getting invited to the big strategic conversations, or perhaps your responsibilities are growing, but your influence isn’t. There’s the frustration that promotions are going to people with less experience. And you’re working harder… but being seen less.

Here’s the hardest part:

When you stay too long, your leadership brand starts to erode.

You go from being seen as a visionary… to being seen as safe.

And “safe” doesn’t get promoted.

So ask yourself:

• What am I trying to prove by staying?
  
  
• Am I aligned with the values this company operates by—or just enduring them?
  
  
• Would the next level of me choose this role again?

This isn’t about jumping ship at the first frustration.

This is about using your executive mindset tools to evaluate your reality—not just justify your loyalty.

Because long-term leadership growth isn’t just about what you can do.

It’s about where your energy, values, and vision are being amplified.

And if they’re not?

Then it’s time for a real conversation—with yourself—about what staying is actually costing you.

Here’s the thing about stagnation—it rarely shows up in a performance review.

You’re still doing your job. Still getting results.

On paper? You look like a success story.

But internally? You feel… off.

Let’s break down some of the subtle signs you’ve outgrown your role or your company—especially if you’re a high performer:

1. Boredom, irritation, or even indifference where there used to be curiosity or energy.

Tasks that used to challenge you now feel rote. You’re coasting—but not in a good way.

2 .Promotions that no longer feel worth the cost.

The next rung up? It feels like more meetings, more politics, more burnout—but not more meaning.

3. Growth stagnation:

You’ve mastered the job. You’ve solved the team’s problems. But there’s no new challenge on the horizon.

You’re no longer being stretched—you’re being contained.

4. Values misalignment with leadership.

It could be subtle—like decisions that make you wince. Or bigger—like staying silent in rooms where the culture no longer reflects what you stand for.

Stagnation is not a reflection of your worth.

It’s not about being ungrateful or impatient.

It’s your inner wisdom telling you it’s time to evolve.

Let me tell you about Sandra, a VP of Engineering at a mid-sized SaaS company.

When we started coaching, she’d already spent 7 years at the same company—growing from manager to director to VP.

She loved her team. She had equity. She had a seat at the table.

But for the last year, she’d been waking up dreading Monday meetings.

And still—she kept telling herself, “This is what I wanted. I should be happy.”

She actually came to me to explore whether she should quit tech. 

Here’s what was really happening:

• Her values had shifted—but her org’s hadn’t.
  
  
• Her peers stopped challenging her thinking.
  
  
• And her leadership… no longer inspired her.

But she was loyal. She didn’t want to “abandon” the team.

So she stayed.

And in those 12 extra months?

She lost confidence. She stopped speaking up. She got passed over for the CTO role—because she was seen as “stable” but not “CTO material.”

The good news?

Once we named the misalignment, she started exploring.

Six months later, she landed a role at a mission-driven company, re-energized her career—and most importantly, started trusting her instincts again.

Remember:

You don’t need to be in a toxic environment to know it’s time to move on.

Sometimes, you’ve simply outgrown the space you once fit in.

And that’s not failure. That’s growth.

Signs You’ve Outgrown Your Role or Org

Here’s something I see all the time in my executive coaching:

Women who’ve built their identity on being the high-achiever. The go-to. The one who always figures it out.

So when the role no longer feels right?

They don’t leave — they double down.

They try harder in a system that no longer fits them.

It sounds like:

“I should be able to make this work.”

“Maybe I’m just tired.”

“It’s not that bad. I’m lucky to have this job.”

“I don’t want to look flaky or ungrateful.”

But here’s the truth:

High achievement doesn’t mean staying stuck in a job you’ve outgrown.

And loyalty is only noble when it’s mutual.

You’re not a quitter for wanting more.

You’re not disloyal for recognizing that your growth has outpaced your role.

But when your identity gets wrapped up in being the fixer, the linchpin, the one who can “handle anything”?

It becomes harder to hear your own inner voice that’s quietly saying: This is no longer it.

So if you’re feeling stuck, tired, or misaligned—pause and ask:

“Am I staying because this is still serving me… or because I don’t know who I’ll be without it?”

Letting go of a role, company, or leadership status can feel like letting go of who you are.

Leaving is not quitting. It’s evolving. And choosing something better for your future.

Is It Time to Move On? The Real Checklist

Let’s cut through the confusion.

If you’re still unsure whether you’re stuck in a slump or genuinely misaligned, here’s a leadership checklist I walk my clients through.

These are not things that show up in your performance review.

But they’re some of the most common signs it’s time to move on from a role — especially for high-achieving women in tech.

Ask yourself: Are one or more of these true right now?

✅ Do you have a Values Misalignment

If you no longer feel proud of how decisions are made—or how people are treated, there could be a values misalignment between you and your org. If you find yourself biting your tongue when you used to speak up. Or perhaps the leadership you once respected now feels disconnected or even toxic. Then this is a sign to move on. 

✅ Are you in a Toxic workplace or something that is Diminishing Your Leadership

If you feel drained after interactions with key leaders. You’re not getting coaching or stretch opportunities—just tasks and vague feedback. Your voice feels minimized, or worse, ignored. Then this is somewhere that isn’t serving you. It’s time to move on. 

✅ Do you have a Lack of Visibility or Growth Opportunities

If despite delivering results, you’re overlooked for high-impact projects or promotions. Or you’re doing more, but gaining less. If your ideas aren’t landing, even though you’ve done the work I’ve talked about in previous episodes around making sure you’re voice is heard, then you’re being used, but not being seen. And it’s time to move on. 

✅ Perhaps you have Chronic Burnout

If this isn’t just a busy season but it’s always a busy season and you feel like you’re running on fumes—and it’s been that way for months. If you’re work feels like a grind, not a mission. If you’re irritable, exhausted, or emotionally numb more often than not. Then this is a sign that you need a change. 

✅ If you’re No Longer Learning or feeling Challenged

If you’ve mastered the role. If you’re not growing new skills. If you dread meetings, coast through your workday, and feel under-stimulated. There’s no upward path that excites you. Then this is absolutely a reason to move on. 

🎯 These are not just frustrations.

They are signs of career misalignment.

And for many women leaders, especially those who’ve been told to “be grateful” or “wait your turn,” these signs get dismissed until burnout sets in.

Misalignment, unfulfillment, not being heard, not growing all cause burnout. 

If you stay too long you’ll be like Sandra thinking ‘tech isn’t for me’ when perhaps the answer is simpler and it is that your current company and leadership team isn’t for you. 

You deserve better than just coping.

If you ticked two or more of these boxes—it might be time to ask:

“Is this job still aligned with the leader I want to become?”

“But What If You Can’t Leave… Yet?”

Maybe your gut says it’s time to go…

…but your life, finances, or circumstances say not yet.

If that’s you—take a breath. You’re not alone.

If you feel trapped in golden handcuffs, family obligations, visa requirements, or a deep sense of loyalty, let’s unpack the difference between real blockers… and fear disguised as logic.

Some of the reasons I hear all the time for not leaving include:

• “I’ve invested too much time here. If I stay just another year I’ll get that promotion.” This one is often coupled with a promotion plan where the goalposts keep moving. But the reality is that those goalposts will keep moving.
  
  
• “I won’t find this salary anywhere else.” This one is quite honestly the most common and I get it. You’ve got a mortgage. You’ve got a family. Perhaps you’ve got kids about to go to college. Money matters. That’s OK. But do your homework – and remember that a starting point on a job listing is just that, a starting point. I’ve had a client recently double the basic comp when she was offered the job. The recruiter thought there was no wiggle room, but the CEO wanted my client, so they eventually doubled her base and more than doubled her bonus as a result. So be curious about what is out there instead of assuming!
  
  
• “It’ll look bad to leave right now.” This one really hurts when we feel like this. It might be that you’ve just taken on a big project, or you’ve only been in the role a few months. There are many reasons why we say ‘it will look bad’. Make sure you identify precisely why you think this.
  
  
• “It’s probably just me—I should be grateful.” This one always hits a raw nerve when I hear it. I can’t help but think we’ve had some gaslighting going on to feel this way at all
  
  
• And then the classic: “If I just work harder, they’ll notice.” Seriously, we need to stop believing this. You need to either change how you talk about what you do and make sure you’re visible or accept they aren’t going to notice and get out.
  
  

Let’s be clear: All of those are often myths, not facts.

They sound strategic—but they’re usually fear, self-doubt, or outdated career advice in disguise. There’s often something going on. But the reality isn’t that simple, and if you dive deeper there is likely another path forward if you’re willing to look for it. 

Let’s Talk Golden Handcuffs

This one comes up a lot with my executive clients.

You’ve got equity, RSUs, a retention bonus, or a compensation package that looks great on paper.

But here’s the hard truth: if the cost is your energy, health, visibility, or growth—you’re not winning.

One of my clients came to me saying:

“Toni, I can’t leave—I’ve got a $400K retention bonus in 12 months. No one will ever match that.”

Fast forward a few months…

She landed a role at a Series B startup that not only matched her compensation over 12 months, but offered more autonomy, strategic input, and energy alignment than she’d felt in years and a title bump that her resume definitely needed. 

The myth that “no one will pay me this much again” is just that—a myth.

In today’s market, companies will move mountains for the right candidate who can solve their problems.

But recruiters don’t know that. In fact I hear all the time from clients that a recruiter says ‘there’s no wiggle room’ only to find there is further down the line when the offer is actually on the table. That story of my client who doubled her based – my client had decided if they wouldn’t move on base that she’d walk. The recruiter seemed to be the blocker so after a weekend of thinking she sent a very nice email to the CEO saying ‘thanks but it seems like we can’t move forward, so let’s stay in touch’, and that just set off an avalanche of events that resulted in a very very nice offer. The clincher once my client actually started in the role – the Recruiter never even took the money conversation to the CEO! The CEO has since fired that recruiter, but this happens all the time. So don’t assume you can’t get the comp you want. Wait until you are negotiating.  

The key is positioning yourself as that candidate, the one that they want above everyone else. Then you can negotiate and negotiate. 

But… What If You’re Really Stuck (For Now)?

Perhaps there’s a visa situation, a kids in school situation which makes it hard to move and you are struggling to find a remote job. 

Not every transition is immediate.

But that doesn’t mean you stay passive.

Here’s what I coach my clients to do when leaving isn’t an option today—but staying exactly as you are isn’t either:

1. Renegotiate Scope
   
   → What can you take off your plate?
   
   → Can you shift toward more strategic projects, delegate differently, or reset performance expectations?
   
   
2. Set Internal Boundaries
   
   → Stop defaulting to “yes.”
   
   → Create clear start/stop times, say no without guilt, and block time for your own career planning.
   
   
3. Build Visibility + Prepare to Leap
   
   → Use this time to update your LinkedIn, clarify your next role target, expand your network, and position yourself.
   
   Don’t wait until you’re burned out to start looking.

Just because it feels like you can’t leave doesn’t mean you shouldn’t be looking. It’s surprising what’s out there if you take the time and network. So get your resume and LinkedIn profile in order and start building your network of executive recruiters. 

If you know you can’t leave this month, ask yourself: 

“What’s one thing you can shift this week to make your current role more aligned—even if you’re not ready to leave yet?”

Even a 5% shift in how you show up can start to change everything—your energy, your confidence, and your options.

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Alright—back to the episode.

But What If It’s Just a Rough Patch? 

Before you rewrite your entire career path… let’s take a pause.

Not every season of dissatisfaction means it’s time to leave. And I think this moment of pause is why we all stay stuck. We don’t make deliberate choices in our careers, even if we do make deliberate, strategic choices in our actual job. 

Sometimes, what you’re experiencing is burnout, a rough quarter, or a leadership challenge that’s solvable with reflection—not resignation. So rather than assuming one way or another. Let’s dig into this too so you aren’t sat in the ‘I absolutely have to go’ or ‘I should never leave because it might be a rough patch that will pass’. Let’s get clarity.

Here’s the key: You need to learn to tell the difference.

Burnout can mimic misalignment.

When you’re depleted, overfunctioning, or carrying too much invisible labor, everything can feel wrong—even the parts you used to love.

And bad cycles can cloud your clarity.

Maybe it’s a restructuring, a difficult team member, or a new boss that’s thrown off your rhythm.

Just this last week I was working with a client who’s organization is going through a huge reorg and she’s been incredibly disillusioned by it all. But when we scratched beneath the surface of her frustration there was a lot to be positive about and be excited for as they move beyond the reorg. 

So it isn’t always about leaving —but it always means something needs attention.

True misalignment runs deeper.

When things mean you need to leave it feels like a consistent, low-grade ache. You’re not just tired—you’re disconnected from the purpose, the leadership, or the direction of the work.

So how do you tell the difference?

Here are 3 self-coaching prompts to help you reflect:

1. “If I had a month off to fully rest, would I want to come back?”
   
   If the answer is no, that’s important data.
   
   
2. “What’s the real reason I’m staying—and is it aligned with who I want to become?”
   
   Fear, familiarity, or loyalty aren’t bad reasons—but they might not be good ones either.
   
   
3. “If nothing changed in the next 6 months, how would I feel?”
   
   Sometimes we delay decisions hoping things will magically improve. Be honest with yourself.
   
   

And for my burned-out high achievers that are listening:

You don’t need to blow up your career to feel better. But if your job is the reason you can’t recover… that’s not sustainable either.

This isn’t about being impulsive. It’s about practicing sustainable leadership strategies and giving yourself the emotional permission to evolve—when it’s time.

Five Reflection Prompts to Find Career Clarity

Let’s wrap this episode up with a mini coaching session in your earbuds.

You don’t need a dramatic wake-up call to decide it’s time for a change.

Sometimes, all it takes is pausing long enough to ask better questions—and listening to the answers that bubble up when you stop performing and start reflecting.

So grab a journal, a voice note app, or just a quiet walk. These five prompts are here to help you move from stuck → evaluative → empowered.

Prompt 1. Am I staying because I’m growing—or because I’m afraid?

Are you expanding your leadership, visibility, and voice?

Or just clinging to certainty because you don’t know what’s next?

Here’s an executive mindset tip for you: Fear often masquerades as loyalty. Be honest: is this still your growth path?

Coaching Self Reflection Prompt 2. If I left, what would I hope to gain in the new role?

What’s missing right now?

More impact? A better culture? Less emotional labor? A leader who advocates for you?

Getting clear on what you want helps you stop tolerating what isn’t working.

Coaching Self Reflection Prompt 3. What part of me feels most out of alignment here?

Is it your values? The leadership culture? The pace or priorities of the business?

If you feel like you’re constantly self-editing or dimming your light—that’s the definition of misalignment.

This might help you then go back to the previous question in terms of what do you hope to gain in a new role. Sometimes the things that are most out of alignment are what you’re craving but sometimes not. Sometimes they’re just misaligned. So take a moment go back and forth between these last two prompts. 

And onto prompt 4. Where do I feel invisible or under-leveraged?

Are your ideas landing? Are you in the right rooms? Are your superpowers being used—or are you just the fixer who keeps everything running?

Career clarity often comes when we notice where our value goes unseen.

And hey, as your executive coach – I want you to be seen, heard, noticed and valued. So let’s make sure that is happening. That starts with identifying where you aren’t seen, heard, noticed and valued, and doing something about it. 

And now finally, prompt 5. Who do I want to become next—and does this role support that?

This is the big one. Take everything you’ve already written down from the previous questions and then look at this in detail. 

This isn’t just “What’s the next title?”—but “What kind of leader, innovator, or human do I want to be?”

If your current environment isn’t helping you become that version of yourself, it might be time to realign.

If you want to go deeper in this work, here are a few more I keep up my sleeves when coaching: 

• Am I aligned with the mission and values of this company?
  
  
• Do I still see a path for growth here?
  
  
• Is this environment supporting my leadership—not just my performance?
  
  

My goal for you with these prompts is to truly understand and make a conscious decision for yourself, not for your company, your organization, or even your loved ones. But for you. This isn’t about jumping ship at the first sign of discomfort. And it isn’t about staying put longer than you need to. It’s about becoming a purpose-driven leader who chooses with clarity, rather than staying from fear or habit, or ditching because it’s frustrating. 

So give yourself permission this week to slow down… ask these questions… and really listen to what comes up.

Before we wrap up let’s briefly talk about How to Leave Strategically

If you’re feeling the pull to leave, don’t just quit.

Pivot like a leader.

The truth is: great leaders don’t just react. They plan. And the same is true if you aren’t quite ready to exit. Let’s have a plan. 

Leaving well—on your own terms—is part of that of having a great plan. 

Here’s how to start building a strategic exit plan:

Start with identifying a Timeline That Buys You Leverage

Don’t wait until you’re burnt out and bitter.

Decide how long you’re willing to stay: 3 months? 6 months?

This isn’t about rushing—it’s about putting you back in control.

Sometimes the situation is untenable and the strategic timeline is your two weeks notice. But if you come to this before that point, it can absolutely work in your favour to think through the timeline. 

Consider things such as the hiring market – things aren’t as bad as it often sounds – I’ve got clients landing jobs left right and centre right now. But if you’re thinking about hanging around until November, the timing isn’t so good – hiring traditionally slows down for the holidays, so you either need to start looking now in the early fall or wait until the  new year. Plan your exit around that. 

Secondly make sure you Strengthen Your Network Before You Need It

You do not need to be job-searching to start reactivating your relationships.

Start small: a coffee chat a week, a few messages on LinkedIn, or engaging with key contacts’ content.

Visibility leads to opportunity. Especially when you’re not broadcasting that you’re planning an exit.

And this is also a great time to engage with executive recruiters. You don’t need to be out there having a ton of conversations but consider whether it’s a good idea to change your LinkedIn profile to ‘open to work’ just to recruiters (not publicly) to see if there’s any inbound interest in your skill set. 

The third step is to Begin Subtle Visibility Shifts

This is the season to advocate for your wins internally, build cross-functional relationships, and maybe even share some thought leadership externally.

It’s not about broadcasting “I’m leaving”—it’s about shaping how people talk about your leadership before you go.

Then you also want to start collecting data. Make sure you’ve got the data, where you can get it, to back up the impact you’ve had in your organization. Maybe you worked on a product launch — well now it’s time to get the data about how that launch went, even if you weren’t involved in sales. Perhaps your new piece of software is helping customers — let’s quantify that. 

And finally, now is the best time to Get Coaching Support if this is something you’ve been considering. 

A lot of women come to me burnt out or after they’ve been job hunting for months with no traction. The best time to get support is before things are desperate. That way we can put in place a plan when you’re in a great situation and not running out of money. You’ll get results faster if you get the right support early on. 

If you want clarity, confidence, and a plan that doesn’t lead to another misaligned move this is the time to get support. 

If you want to exit with intention—not exhaustion , now is the time. 

But more than anything I want you to remember leadership exit is not a failure. It’s a strategy.

And even if you aren’t sure you’re ready to exit, now is still a good time to prepare. 

This isn’t “quitting early.”

This is proactive leadership.

Here’s what I coach clients to do during this “bridge season”:

1. Start Documenting Your Wins

Capture impact metrics, leadership moments, and transformation stories.

This is about more than a resume—it’s about rebuilding belief in your own value.

2. Refresh Your Resume & LinkedIn

Even if you’re not applying yet, having these assets ready gives you power.

That “hey we’ve got a role coming up—can you send your CV?” moment? You’ll be ready.

3. Reignite Your Network

Reconnect with former peers, mentors, and advocates.

Let them know you’re curious, open to conversations, or exploring what’s next.

This is not desperate—it’s savvy.

4. Reflect on Ideal Role Characteristics

Ask yourself:

• What kind of leadership do I thrive under?
  
  
• What pace of work fuels me?
  
  
• What mission or problem space energizes me?

Knowing this before you exit helps you filter out shiny but wrong opportunities.

This prep isn’t about being disloyal to your current team.

It’s about leading yourself like you lead others—with strategy, clarity, and care.

Remember:

You don’t need to decide today.

But you do need to lead yourself like the executive you are becoming.

Because stuck is not a leadership strategy.

But clarity? That always is.

And if you’re ready to find that clarity—to figure out whether you’re misaligned, overdue for a pivot, or simply under-leveraged in your current role—I’ve got something for you.

It’s a tool I created just for women in tech who are in this exact moment of their career.

It’s called “What’s Holding You Back? A Diagnostic for Women in Tech”—a quick, insightful quiz to help you identify the real friction points behind your career dissatisfaction.

Whether it’s burnout, invisibility, values misalignment, or just a role you’ve outgrown—it’ll help you map what’s really going on, and give you the next step to take.

You can grab it at tonicollis.com/whats-holding-you-back—or just tap the link in the show notes.

Because your career deserves more than guessing games.

You deserve to be in a role where your values align, your voice is heard, and your impact is fully recognized.

So take the time to reflect. To evaluate. To lead yourself with intention.

And if you need help on that journey? You know where to find me.

Until next time, my friend—don’t wait to be invited. Lead on purpose. 💜