Should I Stay or Should I Go?
Should I Stay or Should I Go?
Quitting for..."The Right Reasons"
Hi all!
If this is your first email from me, check out the archive here. Every week I highlight a specific career topic and share some personal musings, conversations I’ve had in my network, and links to resources.
Thanks again for reading along, subscribing, and for sharing your career situations with me. I realize I’m catering to a broad audience here and on Instagram, so if you have specific questions and want to chat 1:1, email me!
This week we scratch the surface on a big topic: quitting.
Musings
Who among us, on our worst days, has not daydreamed about this deeply satisfying scenario:
There’s a lot to cover on the topic of quitting: how to artfully do so, how to preserve relationships, should you do it without a backup plan etc. In an attempt to reflect your feedback of 'brief, amusing insights please’, I’ll focus only on one small subtopic of quitting here:
How to know you’re quitting for the right reasons.
When you have a deep knowing that quitting is in fact the right decision for you, you probably won’t enact it by rage-smashing office supplies. It’s kind of like a breakup where when you know you’re fundamentally growing apart, and breaking up is not an empty threat, or a means of testing boundaries.
I think of this kind of misalignment as the type that will probably worsen as time goes on. Two below are common ones:
Values misalignment: this can be blatantly obvious (e.g. treatment of employees), or in the form of subtle cultural norms (e.g. you value radical transparency, your organization is passive aggressive and avoidant), but it’s becoming clear to you that your ethos and your company’s ethos are increasingly divergent
Structural misalignment: these often involve factors like location, stage of the company, organizational setup of the company that prevent you from doing the work that you want to be doing
Compare these to something like compensation misalignment, where it may only be a matter of time before the gap is closed, (although to be fair, compensation misalignment can be a symptom of a type listed above). That type of quitting seems more straightforward.
If you’ve been having prolonged thoughts of quitting lately, I encourage you to do a quick gut check:
The reciprocity of feeling that you are adding value (working on things that matter), plus being valued by your team and organization is essential to job satisfaction. There are bound to be ebbs and flows in this dynamic, but if these are diverging over time, perhaps it’s time to move on.
Questions to consider:
Can you take action to close the divergence - Is there a skill gap that you can close with training or experience? Can you rescope the role to match what you value doing, or be valued for? Can you have a conversation with your manager to discuss where you feel undervalued?
If your hands are tied, or your organization can’t support these actions, consider if the misalignment will solve itself, and how long you are willing to wait for things to change
Conversations
This week I chatted with someone who had been dealing with a long period of structural misalignment in her role.
She had risen quickly up the ranks at a later stage startup, and had worn many hats: strategy, general manager, corporate development to name a few. She was extremely talented, and had been very nimble as the company grew, but as the company’s focus and leadership reshuffled over time, she often felt overqualified for some initiatives, and yet simultaneously micromanaged.
We removed emotion from it to reflect on what the company was going through. In its growth trajectory from Series B to Series D, the company vacillated between a phase that was ‘caught up’ to her level of expertise, and a phase where the company lagged behind. In those time periods, the reduced amount of strategic work could be handled by the CEO alone, leaving her stuck doing the administrative work. In the first few years of her time at a startup, these ebbs and flows were exciting, but by year four, this didn’t align with her values of doing high level/transformative work.
Then we dove deep into the emotion of the situation. Phew… so much emotion was tied up in feeling undervalued in a role. We talked through feeling slighted or inadequate when projects were taken away, or when her role was relegated to junior-level work. We talked about feeling shaken up by the mismatch of what she perceived her strengths to be vs. what she was being given to work on.
It’s almost impossible to not take things personally when these feelings arise, but we worked hard to focus on the objective nature of the situation: it wasn’t that her skillset or strengths were somehow declining, it was that the company and its needs that were changing.
The corporate take: This dynamic isn’t unique to startups. An example of structural misalignment in a corporate setting can occur as a result of a large reorganization . For example, you used to work on a wide portfolio of projects at a smaller company (or division) and are acquired into a larger, more complex system where multiple people do your job. Those same feelings of frustration over reduced responsibility, while simultaneously doing more administrative work also apply here.
So what happened with our Alice? She quit.
A few months into her new role, she feels way more at ease, more valued and generally in a better place. Despite having the exact same title in her new role, the new company was actually structurally set up to give her the types of projects she wanted on a consistent basis. It was well-funded, and planned to be acquisitive in the next year so her medium-term mandate was clear. It’s possible that the structure of her prior role could have changed again (in her favour) in the long term as the company matured. However, a longstanding dynamic of frustration and resentment had been created that was very hard to undo.
Quitting isn’t always the right answer, and there’s certainly risk in a new role, but it can sometimes be a much needed recalibration. The residual resentment and growing pains were checked at the door, and her new management team saw her unequivocally in a leadership role.
Resources/Links
Medium article on “How to Know When It’s Time to Quit”, a good mix of pragmatism and emotions
This is a framework that’s been repeated in a few different tech companies, but Zappos pioneered it in 2008: “Paying Your Employees to Quit” , to ensure that their employees were excited (almost fanatical) about joining the company. It’s a good test for values alignment early on
Cool ladies doing cool things: Shaina Harrison is the Program Director for “New Yorkers Against Gun Violence” and doing incredible work in the classrooms of the Bronx. “The over-all message of her curriculum is that fear, racism, and powerlessness are at the root of gun violence. She believes that finding your ability to speak reduces both racism and powerlessness—the former by letting people know that the stereotypes are false, and the latter by creating the sense of strength that comes from speaking out.”
Tell me about you!
How have different quitting situations felt for you? Where have you felt full closure vs. where have you left with some animosity or feel like you’ve left something on the table?
What else has prompted you to consider quitting?