When Your Job Is Just Comfortable Enough to Stay Stuck

I ran into a former colleague the other day who was stuck in the most dangerous place: just comfortable enough to stay miserable.

I’ll show you how to steer clear of this familiar but draining situation.

And, if you’re in this situation, sending hugs. This technique might show you a way out.

And the best thing: it can be applied to many arrangements that are no longer serving you but you can’t quite find the clarity to stay or go.

The Dangers of Sticking with a Job That is Just “Meh

We’ve all met someone like my ex-colleague. Maybe you’re even seeing shades of yourself in this story.

He wasn’t happy.

He admitted his job was annoying, frustrating, and drained the life out of him most days.

But here’s the kicker—he wasn’t miserable enough to leave. The comfort of the salary, routine, and familiarity held him back. Sound familiar?

That’s the trap many of us fall into.

Why We Get Stuck

Comfort has an insidious way of making us numb to dissatisfaction.

It’s not bad enough to take the leap.

But it’s never quite good enough to feel fulfilled.

We end up just surviving, hoping that things might magically improve one day.

Spoiler: they rarely do without deliberate action.

The Power of Kill Criteria

Here’s where the concept of “kill criteria” comes in. A kill criterion is a pre-determined point where we can decide that if certain conditions aren’t met, we quit. It’s powerful because it removes the ambiguity. We’re no longer stuck in “maybe next quarter will be better” mode.

The best part?

It’s never too late to set kill criteria

Whether we’re 6 weeks into a job

Or 6 years.

We don’t have to feel like the time spent was a sunk cost. We can always make a decision that honors our futures.

Sidenote: After I published From Dilemmas To Decisions, I was surprised at how popular this tool was. It was initially introduced as an optional part of the decision-making process. However, many readers told me how much it changed the game for them.

OK, let’s go through it step-by-step.

How to Set Your Own Kill Criteria

Think of this as a mental contract with yourself. Here’s how I do it:

  1. Draw the line in the sand: I determine the threshold at which I say “Not good enough.” What do I need from this job to feel like it’s worth staying? Is it more growth, better pay, more flexibility, or just feeling less drained?
  2. Set a Time Limit: I decide how long I’m willing to wait for those conditions to improve. Six months? A year? If things haven’t improved by then, I start executing my exit plan.
  3. Pull the Trigger: Just like my ex-colleague, it’s easy to rationalize staying stuck because the pain isn’t unbearable yet. I put certain guardrails in place to make sure I follow through if things haven’t improved. This can look like an accountability buddy or cohort or some kind of precommitment that incentivises me to follow through.

Why Kill Criteria Work

Having clear criteria for leaving a job doesn’t just give us permission to quit—it empowers us to make more intentional decisions about our careers or any other long-term investment. Kill criteria put us in the driver’s seat rather than feeling like we’re at the mercy of our circumstances.

Important in this process is to set regular review dates. My rule of thumb is quarterly / every 3 months. This folds nicely into my quarterly review. However, if you don’t review quarterly, it can be as simple as setting a reminder at your desired frequency and answering: “has my kill criteria / criterion been fulfilled?”

And whether you decide to stay or go, you can take the next steps powerfully and decisively.

Setting kill criteria ensures you don’t wake up one day and wonder where the last five years went. Instead, you’ll know you stayed for the right reasons—or walked away when it was time to move on.

Takeaways:

🔨 Set your non-negotiables: Define what conditions must be met for you to stay in your job.

🔨 Establish a timeline: Give your employer (and yourself) a clear deadline to see improvements.

🔨 Honor the kill criteria: Don’t let the comfort of routine stop you from making changes when they’re needed.

Need Help Figuring It Out?

If you’re in that grey zone of not being sure whether to quit or stick it out, I’d love to help you work through it. I’m exploring the idea of offering small career decision-making cohorts, where you can discuss your kill criteria with fellow professionals facing similar dilemmas. If that’s something you’d be interested in, hit me up on any of my channels with the message “KILL CRITERIA” and let’s start the conversation.

Here’s to making braver choices!

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