If you’re miserable in your job, you’re probably asking yourself: Should I stay in a job I hate? It’s a tough question—one I’ve wrestled with more than once.
One Christmas, I worked three different retail jobs at the same time. The long hours, cranky customers, and soundtrack of non-stop holiday music wore down my will to continue. By the end of the season, I was exhausted and completely demoralized.
Then there were the administrative jobs—the ones that seemed fine at first but slowly drained the joy from my life. Each month, the expectations grew, the environment became more toxic, and I started dreading Monday mornings.
I stayed in those jobs because I thought I had to. Because I needed the paycheque. Because I was scared of what would happen if I left.
When It Makes Sense to Stay
If you’re wondering, Should I stay in a job I hate? know that there are practical reasons to stay—at least for now:
✅ You need the income while you figure out your next move
✅ You’re gaining skills or experience that will help you transition to something better
✅ You’re using the job’s benefits (like paid education or healthcare)
✅ You need stability while managing personal responsibilities
These are all perfectly valid reasons to stay in a job you don’t like (and don’t let anyone pressure you to find your bliss or your passion if you’re not in a financial position to do so).
But staying out of loyalty to a company? That’s likely to hurt you in the long run.
Companies Can’t Be Loyal to You
Your boss might support you. Your coworkers might feel like family. But at the end of the day, a company exists to serve its business interests—not yours. If they need to make cuts or restructure, your years of dedication won’t necessarily protect you. A company’s loyalty is to its bottom line and its investors (if it’s a company with investors). Very rarely is a company loyal to individual workers.
And that’s not even a bad thing—it’s just how business works. Acknowledging it is neither good nor bad. But if the only reason you’re staying is because you feel guilty about leaving, ask yourself: Would the company hesitate to make a business decision that affects me?
How to Plan Your Next Steps
If you’ve realized it’s time to move on, don’t panic—you don’t have to quit tomorrow. The best way to leave a job you hate is to make a plan so you’re not jumping into the unknown without a safety net.
Start by asking yourself: What’s my next move? Do you want to find a new job in your industry? Switch careers? Start freelancing? Once you have a goal, you can take steps to make your transition smoother.
✅ Build a financial cushion – If possible, start setting aside extra money so you have savings to support you during the transition.
✅ Upgrade your skills – Take courses, attend workshops, or start freelancing on the side to prepare for your next move.
✅ Expand your network – Connect with people in your desired industry or reach out to mentors for advice.
✅ Test the waters – If freelancing is on your radar, start small with a few projects before making the full leap.
✅ Set a timeline – Choose a realistic departure date and create a plan to reach your goal before then.
When I Finally Left, Everything Changed
For a long time, I thought I had no choice but to stay in jobs that made me miserable. But when I finally made the decision to quit my job and go all-in on freelancing, a huge weight lifted off my shoulders. It was terrifying and exhilarating.
And here’s what I learned: You don’t have to wait until you’re burned out and desperate. You can start planning your exit now—on your own terms. You don’t have to wait until you have nothing left to start planning your next steps, if that’s what you want.
If freelancing is something you’ve considered but don’t know how to get started, my Freelance with Confidence guide will help. It gives you a step-by-step plan to build a strong foundation so you can leave your job when you’re ready—with a clear path forward.
💡 Right now, it’s on sale for just $14.99 CAD (regular price $25), but only for a short time!
You can also check out my Freelance Success Toolkit for templates, guides, and resources designed to help you build your freelance business.
You don’t have to stay stuck forever. Make a plan, take the first step, and start moving toward something better.