3 Important Questions Ambitious Women Ask BEFORE Leaving Their Job

What do The Clash and ambitious mid-career womxn have in common?

In the words of the punk group’s 1981 hit, they both wonder: Should I Stay or Should I Go

If you don’t know the tune, it goes like this:

Should I stay or should I go?

At work, you’ve probably asked: ‘is this still right for me?’

If I go there will be trouble. 

When considering leaving, you might think: ‘Oof. Finding a new job is gonna be a whole thing…’

If I stay it will be double.

But then you veer back to: ‘yeah, but staying here is not going to work either.’

Stay in a role or go.

Neither solves all your problems.

Both take massive amounts of energy. 

That leads us to today’s topic:

“Is it time to leave my job?”

 

In this blog, you will learn: 

  • The 2 main reasons that drive my clients to consider another role

  • What leaving your job will solve and what it won’t

  • What 3 questions to ask yourself before leaving

 

What drives the need to leave

If you’re here, it’s probably because you’re unhappy or dissatisfied at work. And when that feeling is bad, it can do a total life takeover, which makes it hard to see what’s really going on.

Because it’s such a pervasive experience, it can be helpful to isolate the thing keeping you from enjoying your work right now. 

When working with high-potential women leaders in my Career Strategy GS program, I see 2 key reasons people think of leaving.

 

1. Lack of clarity

“Is this role right for me?”

“Is working for this org leading to opportunities I want?”

“Am I in the right industry anymore?”

“Do I like where I’m headed?”

“What do I want my work to be about?”

These questions might plague you in meetings each morning or even keep you up in the middle of the night. 

These questions focus on 2 key areas:

  • Uncertainty about your future - the anxiety of not knowing where you’re heading or if this job will get you there. 

  • Uncertainty about your meaning - if what you’re currently doing aligns with a mission you care about. 

2. Lack of mobility & growth

You work hard, and you’re crazy productive. But you’re not being rewarded with the promotion, raises, and growth opportunities your work deserves. 

Maybe you aren’t connecting to leadership, and it’s costing you. Not getting ahead as quickly as you’d like might even mess with your sense of accomplishment or progress.

You may think there’s no path to the next level for you. Your next thought is wondering if changing organizations will fast track your success. 

Both reasons can lead to feeling disconnected and demotivated at work and at home, losing self-confidence, and more.

Why leaving may not solve the problem

Many of us have had the experience of changing relationships or moving, or even getting a new haircut, thinking it’s going to change our lives entirely.  Then you make that change and quickly realize you’re right back where you were.  

Similarly, if you identify with either of the underlying conditions I just mentioned, then jumping to a different organization, industry, or role will not fix your problem. Without addressing those questions head-on, it may take years before what you want aligns with what you do. 

The instinct to jump is very normal. When we’re in discomfort, it can feel overwhelming. And terrible. And humans are programmed to get away from discomfort as fast as they can. 

Making a move as big as changing roles or industries is something to work through when you are in a resourceful place. A place of clarity and calm vs panic or frustration. 

Because my clients are doers and achievers, it can feel like leaving is taking massive action in the right direction. This feels particularly true when that direction is AWAY from the pain they’re currently experiencing. 

Here’s the kicker:

Getting away from pain is not the same 

as getting what you want. 

Absolutely, leaving will distract you from the pain for a while. For a time, it might even make you happy. Without gaining clarity to a few key questions, you will likely find yourself in the same situation at the next place you go: unclear about your future or unable to connect with leadership. 

The result: spending years, not months, to get clarity on your strategic path.  

Though stagnation or jumping into something new can feel like the only two ways out, I invite you to consider a third.

I’ve had clients show up, sure they need to leave their organization. They’re not moving up or they’ve been there too long and don’t know if it’s still right for them. After only a month of getting clear on what they ultimately want and what their mission is, they realize that not only are they in the right org, there is a path to promotion AND meaning by designing a new role. 

If you’re reading this and thinking this might be something to look at, there’s an exercise I use with each of my clients to get the clarity they need on whether staying or going is right for them. It’s my Career Destination Excavation tool and I use it with every client in my Career Strategy GPS program to figure out their North Star. It breaks down the big question of WHAT DO I WANT into super digestible chunks that take you from “What do I do next?” to “Here’s my 5 year plan.” And it’s available by clicking here.

Before leaving, answer these 3 questions

To set yourself on a clear strategic path, it helps to know:

1. What do I want long-term?

Vision setting is a skill many high-potential women know leaders need. Yet when it comes to their own careers, that vision of where their work is taking them and their organization is exactly what’s missing. 

I call this vision your Long Term Career Destination (LTCD). Now, this is not your next role. Concentrating just on that is not strategic. Your LTCD is the role, organization, and title you end up with within 5, 10, 20 years. 

When you know your Long Term Career Destination, figuring out if your current role or org gets you there is much easier. 

 

Your LTCD is a lovely place. At the same time, it can be hard to see the big picture, so knowing what you want in key areas of your work future can help:

confirm that the place you currently work is actually right for you and you just have to tweak certain aspects of your role 

OR 

reveal that the environment or role you’re in is not at all aligned with that future.

Example: I had a client who had worked at a Big Tech company for almost ten years. When she arrived, she was unclear if she should go or stay.  When she did the Career Destination Excavation exercise, she understood:

  • What environments she aspires to

  • What skills she needs to master

  • What experiences she wants to have

  • What impact her work has on the world

That made her recognize that her organization aligned with her LTCD. She became super clear that staying was right for her. We pivoted our work to get her promoted into the right department with a role she designed. 

2. Will this role/org get me there?

Recognizing where you want to end up in 5-10 years gives you a destination. A Long Term Career Destination, even 😉

If where you currently work, what you currently do, and what it all means to you do not line up with that destination, it makes sense to draw a new roadmap. 

Example: After doing your Career Destination Excavation, you realize you want to become the CMO of a Fortune 100 company. However, you’re currently in marketing at a small boutique firm with no big org experience. That might clarify that you need to work at a larger scale, in which case moving to a bigger company is a must. 

On the other hand, you may realize you actually love the feel of your small or medium-sized firm and want to lead one in the future. It’s just that your daily activities need to shift, so you may choose to stay and attempt to get those skills at your current firm. 

Or, in that same scenario where you want to lead marketing at a small firm, you may recognize your current org’s size is a good fit. You may even see that you are in the right function, but the firm’s mission doesn’t match yours. In that case, it could be time to leave and possibly change industries. 

Part of the security we feel in a role is knowing it’s putting us on a path. Having the organization, the work you do there, and its meaning to you align with the vision of your future can restore that security in your path. 

3. What is in the way of getting or creating your vision in this org?

If the nature of the organization or its mission isn’t aligned with yours, it can be hard to control or change that. They are fundamentally baked in. Often that’s your cue to go. 

However, if those cornerstones are there, the next question is seeing what needs to change to get on your path to success. 

Often, if you are an asset to a team, your manager will work with you on creating that path – you just have to help them see where it leads. 

That can take a few forms:

  • Connecting with leadership in a new org 

  • Sharing your vision for your org and role with your manager or other relevant leaders

  • Working on a plan to shift your responsibilities so you can pursue those things

All these tactics can change what you do and where you are right now and put you on a path to your LTCD.

Conclusion

In my experience with high-potential female leaders, the reason to leave centers around not being clear on destination or meaning or not being able to connect with leadership to get to where they want to go. 

Leaving can feel like a bold choice, but it may not get you where you want to go. This makes sense if you don’t know where you want to go, what you want to do, or what the work means to you and the people you do it for. 

This is strategic legwork that you’ll need to do to set yourself up for the career success you deserve. 

Getting that clarity can be really overwhelming. After years of working with leaders at all-sized companies throughout industries, I’ve honed a tried and tested exercise that addresses the root of whether staying or going is right for them. 

If you’re reading and thinking it’s time to figure out where your career is going, there’s a link here. It’s my Career Destination Excavation tool, which breaks down this huge question: “What do I want?” into a digestible piece, so you know your North Star and your next move. To access it, click here.

Alex Cooley