These Boots are Made for Walkin’ . . .

Six Questions to Ask Before You Quit.

If you’ve been around the Forge community for any amount of time, you know we’re pretty intent on not giving up. It's part of our core values, and how we intentionally show up every day at home and at work.

But it is not without irony that we also talk to people . . . every day . . . about quitting their jobs.

Knowing when to quit something is not an easy task. My suspicion is that, in general, we quit far sooner than we should. When I have the opportunity to sit down with people and help with career coaching, most often they are genuinely trying to discern: when do I stop trying and move to something else?

Here are a few things I’ve learned along the way, and the questions that seem to help the most when you're deciding whether to stay or go:

1. Are you running from something—or to something?
There’s a big difference. Leaving because you're frustrated, tired, or bored is very different from moving toward something with intention. If you’re simply trying to escape a bad situation, there’s a good chance you’ll end up in a similar one. But if you have a clear sense of what you want next—and why—it may be time.

This is one of the reasons we always ask a lot of questions around job movement: we want to know what did not work where, so it doesn’t happen again in the next job. Creating a vision for what is important to you and where you want to go will help you run “towards” something.

2. Have you stayed through the hard middle?
There’s always a messy middle. After all, it is work, and not vacation. The whole quote about “if you find a job you love, you don’t work a day in your life…” I’m sorry, but I’ve never known that to be true in anyone!

But not just difficult… there is a stretch of time where the learning curve flattens, the novelty wears off, and the job feels... well, boring. But growth often happens after that point. I tell my team—and especially my kids—that being bored isn’t a bad thing. Sometimes it's a sign you're about to break through. Don't confuse boredom with a red flag.

3. And what about values?
This one really matters. If your values and the company’s values fundamentally don’t match, it will be a tough road to hoe. No matter how much effort you put in, it may never quite feel right. Misalignment here can wear you down over time, even if the job checks all the right boxes on paper. If you’re constantly having to shrink or shift to fit in, it’s worth paying attention.

4. Do you know yourself?

Not in the Socratic sense, but we are all more likely to lean one way or another. I’m far more likely to get irritated and bored, whereas my husband (former Marine!!) will work on a home repair project for months before calling an expert. :) Are you more likely to quit too early or stay too long? We all have a tendency one way or the other. The right thing may very well be the opposite of what your natural tendency is.

5. What story will you be proud to tell five years from now?
I love this question. It’s one I’ve asked myself many time, in some iteration or another. Imagine you're sitting across from someone five years from now, explaining why you stayed—or why you left. Will you be proud you gave it one more shot? Or will you wish you’d made a change sooner? Which version feels like growth? Which decision aligns with who you’re becoming, and who you want to be?

6. Have you had the necessary conversations?
Before you make a move, be honest: have you advocated for what you need? Have you asked for feedback, support, clarity, or change? Sometimes, we quietly simmer in dissatisfaction without ever giving the situation a chance to improve. Both sides of the aisle—employer and employee should be having the direct conversations around frustrations and challenges before you get to the quitting point.

Not every situation can change, but many never get the chance.

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It is worth noting that we are all in incredibly privileged positions to have the career autonomy that we do here in the free world. I believe with my whole heart that you can create a life you actually want to live, with a lot of grace, grit, and resilience. But with these privileges comes responsibility.

At Forge, we are passionate about helping you make an intentional move, not a reactive one. That means sometimes we’ll cheer you on as you take a leap toward something better. And other times, we’ll gently encourage you to stay, do the hard work, and see what happens when you don’t quit.

Here’s to doing the next right thing, one day at a time.