Ep 122 Career: How to decide if you should quit your job (or get a promotion)

Show notes

What’s going on, everybody? Welcome to the 122nd episode of The Crazy One podcast. As always, I’m your host, Stephen Gates, and this is the show where we talk about creativity, leadership, design, career advice, and all sorts of other things to help empower creative people.

You can listen to all the episodes, get show notes, and find a whole lot more over at thecrazyone.com—that’s “thecrazy” and the number “one.” And while you’re there, do me a favor: next time you’re on your favorite podcast platform, leave a review for the show. It could be as simple as hitting the stars or writing a few words.

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The Setup: Why We’re Talking About This

Today’s episode comes from a place that’s really close to home. Every week, I do three free 30-minute mentoring sessions through ADPList.org—a fantastic global platform where you can get free mentorship and career advice.

Through those conversations, two questions consistently come up:

1. Should I quit my job and do something new?

   Post-pandemic, a lot of people feel stuck or misunderstood. Their bosses don’t get them, their values have changed, or they’ve simply outgrown the work. They’re trying to figure out: Should I stick it out or go find something new?

2. How do I get promoted when I feel ready but nothing’s happening?

   They’ve been doing the work, having the conversations—but leadership isn’t making a move. And now they’re wondering if they’re being overlooked or overstaying their welcome.

 

At first glance, these might seem like totally different issues—but they’re actually connected. Both situations hinge on clarity, communication, and action.

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The Real Questions Behind the Questions

Whether you’re trying to figure out if it’s time to leave—or pushing for a promotion—both situations often stem from the same underlying questions:

• Where do I truly stand?

• Is my company or leader really investing in me?

• What needs to change—and what will I do if it doesn’t?

 

And, this part can be hard to hear: you might be part of the problem. Sometimes it’s a leadership issue. Sometimes it’s a lack of awareness, communication, or personal growth on your side.

That’s why we need a structured, honest approach to get real answers and direction.

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Important Disclaimer

Before we go further, I need to say this clearly:

If you’re in a toxic, abusive, racist, sexist, or harmful work environment—leave.

Now. This episode isn’t for you. You don’t need clarity—you need distance and safety. There’s no value in investing in a broken system that’s hurting you.

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What You’re Really Missing: Perspective

The #1 thing people are searching for—often without knowing it—is perspective.

When you first join a company, everything is fresh. Your perspective is wide open. Over time, that narrows. The positives become normal. The negatives start to dominate your attention. I call this frustration blindness—where all you see is what’s wrong, and all the good things fade into the background.

It’s easy to think a new job will fix it. And sometimes, that’s true. But in many cases, people leave behind something amazing simply because they lacked clarity. I’ve nearly done it myself. At one point, I was so close to leaving Starwood after three years of stagnation. But I stuck around—and a call from Apple changed everything.

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The Approach: Structured Clarity

To move forward, you need a real conversation with your boss or leadership. Not a list of demands. Not a venting session. A conversation.

Here’s how to structure it:

1. Define the Issues (3–4 max)

Write down the key blockers. Be specific. They should be realistic, actionable, and not just about you—ideally, they affect others too.

If you come up with 15 problems, that’s a sign it’s time to go. If you’ve got a few real issues, this process can help you fix them.

2. Set a Timeframe

What’s a reasonable window to see change? This creates accountability. Your boss may not be able to solve everything overnight, but you should agree on a timeframe—and check in on it.

Mismatch in timelines? That’s data. If they need two years and you’re only willing to wait six months, this probably isn’t going to work.

3. Establish Your Bottom Line

What will you do if nothing changes?

• Will you quit?

• Start interviewing?

• Transfer teams?

 

Whatever it is, don’t bluff. If you say you’ll leave and don’t, you lose all leverage. Follow-through gives this conversation power.

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How to Have the Conversation

Set up a dedicated 45-minute to 1-hour meeting. Don’t try to squeeze it into a 15-minute window or slot it between high-stakes meetings. You want both of you to be present and focused.

Start with empathy and investment:

“I want to stay. I love the team and the work. But I’m struggling with a few things, and I want to be honest and transparent about what I need to be successful here.”

Then, outline the issues. Make it clear that your preference is to stay, but inaction will lead to a different outcome.

Tailor your approach to your boss:

• Solution-oriented leaders: Come in with clear problems and proposed fixes.

• Collaborative leaders: Ask open questions and co-create solutions together.

 

This creates two-way accountability. You’re not just making a request—you’re inviting partnership.

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Documentation & Follow-Through

After the conversation, send a written recap. Document:

• The issues discussed

• Agreed actions and timelines

• Dates for check-ins

 

This reinforces the seriousness of the discussion. If they’re slow to respond or brush it off, that’s your signal.

And if nothing changes? Follow through on your bottom line. Because otherwise, you’ll never be taken seriously again.

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Why This Matters

This isn’t just about getting a raise or changing jobs. It’s about understanding your worth and owning your career path.

Too many people just quit. They avoid the tough conversations. But if you’ve invested in your team and your work, you owe it to yourself—and them—to at least try.

And yes, quitting can feel selfish. Especially if you’re a leader. But sometimes you have to choose yourself. Just make sure you’ve done everything you can before you do.

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Final Thoughts

No one’s going to fight for you harder than you fight for yourself.

This process isn’t easy. But it’s how you move from frustration to clarity—and from being stuck to empowered.

Whether you stay or go, you’ll know that you made the choice from a place of strength, honesty, and self-respect.

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As always, show notes are over at thecrazyone.com. That’s “thecrazy” and the number “one.” Subscribe so you don’t miss new episodes. And yeah, I’m showing up more consistently now—so hey, a little self-five for that.

Leave a review. Let me know what you think.

And finally, legal wants me to remind you these are just my opinions. They don’t reflect any past or future employers.

But most importantly:

Thank you. Time is the only real luxury we have. I’m humbled that you chose to spend some of it with me.

So go out there. Have the conversation. Fight for clarity. Fight for yourself.

And, as always, stay crazy.

Tagged as:
career clarity career crossroads career development career growth career strategy decision-making process ho job change navigating career challenges overcoming blind spots promotion strategy self-reflection Stephen Gates The Crazy One podcast