Is it time to break up with your job?

Why Letting Go Can Be the Most Strategic Move of Your Career

Jan 27, 2025

Photo by Nick Fewings

“Try not to resist the changes that come your way. Instead, let life live through you. And do not worry that your life is turning upside down. How do you know that the side you are used to is better than the one to come?”

— Jalal ad-Din Muhammad Rumi

The Right Time to Move On: Knowing When to Let Go

Staying too long at a job can hold you back in ways you might not even realize. Whether it’s loyalty, fear, or sheer inertia, staying in a role that no longer serves you can stall your growth and drain your energy. The key to success isn’t just perseverance; it’s knowing when to quit.

Why We’re Fascinated by Work Breakups

Why someone joins a company is usually straightforward, but why they leave is often shrouded in mystery. Whether it’s a layoff, a bad manager, a loss of passion, a promotion, or simply the decision to quit, the reasons for leaving are far more intriguing. It’s the workplace version of a juicy breakup story.

People are fascinated by work breakups because, deep down, many want to leave their own jobs but haven’t yet found the courage to take the leap. Hearing about how others made the decision to walk away—and what happened next—offers a sense of validation and inspiration. It’s as if by listening to those stories, they can build the confidence to cross the chasm themselves.

A Personal Perspective:

I have only ever worked at three companies. I spent ten years at Starbucks Coffee, twelve years at IKEA, and three years at Walmart. Over two decades at just two organizations is a long time—especially in today’s ever-shifting work landscape. When you spend a decade or more somewhere, the lines between your work and your identity blur. The workplace becomes second nature. You know the people, the history, the politics, and they know you. You’ve built personal brand equity—an internal identity that defines how others see you.

For me, this personal equity was everything. It got me promoted, put me in front of senior leaders, opened opportunities to travel the world, work on amazing projects, sit on panels, coach, lead, and manage tens of thousands. Even though I changed roles regularly, the architecture—the scaffolding of the organization—stayed the same, and that was intoxicatingly comforting. Knowing when to move on from that level of familiarity was extremely hard.

Then there were the relationships: my managers, my team, the people I worked with every day, and the real sense of duty I felt toward them. Add to that the practical aspects: tenure-based benefits, perks, salary, and title. Together, it’s like building a house and then convincing yourself to just leave the keys on the counter and walk out the front door. Leaving behind everything you have been part of building.

So, how do you know when it’s time to let go?

My reasons were always anchored in two key factors: the desire to gain new learning experiences and the need for alignment with my personal values.

Why We Stay Too Long

Letting go of a job isn’t easy, especially when you’ve poured time and effort into it. Here’s why people often stay longer than they should:

Fear of the Unknown: The uncertainty of leaving can feel scarier than staying, even in a toxic or stagnant situation.
Sunk Cost Fallacy: The more time and effort you’ve invested, the harder it is to walk away, even if it’s no longer working.
Identity Tied to Work: Many of us define ourselves by our roles, making it difficult to let go without feeling a loss of self.
Hope for Change: Believing that things will improve—a new boss, a better project, or a culture shift—can keep you hanging on.

Signs It’s Time to Move On

If you’re wondering whether you’ve stayed too long, look for these signs:

You’re No Longer Growing: If you’re not learning new skills or facing new challenges, it’s a red flag that you’ve outgrown the role.
You’re Chronically Unhappy: Persistent stress, frustration, or dread about work can indicate it’s time to go.
The Culture Is Toxic: If the environment is marked by dysfunction, favoritism, or poor leadership, it’s unlikely to improve.
Your Values Don’t Align: When your company’s goals and values clash with your own, staying can feel draining and demotivating.
You’re Stuck in Survival Mode: If you’re just getting through each day without any sense of fulfillment, it’s a sign to reassess.

The Courage to Move On

Knowing when to move on is one of the hardest—and most important—skills you can develop. Staying too long can cost you more than just professional growth; it can drain your confidence, happiness, and potential. Letting go isn’t about failure; it’s about recognizing when something no longer serves you and having the courage to seek better opportunities.

If you’re feeling stuck, ask yourself: Is this job still helping me grow? Does it align with my values and goals? If the answer is no, it might be time to let go and move on. Your future self will thank you.

Until next time, take care of yourself and those around you.

In Partnership,

Nabeela

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If you would like to learn more about the world's unhealthy relationship with work, success, and achievement and discover ways to escape the burnout loop, check out some of my other posts below.