It's never easy quitting a job before you embark on a new job search unless you absolutely despise it. But there could also be awkward moments. Your boss might try to get you to stay or you want to maintain relationships without burning any bridges.

Before you take the leap, here are some significant questions to think about. If you're on the fence, the below should also help you decide if the decision is right and if the time is right. There is also a time to stick things out.

1. Am I Still Learning or Growing?

If you are an ambitious person who wants to learn from experienced professionals, this is key. Have you learned everything there is to learn from a mentor or co-workers? Is there still room to grow and to become a better version of yourself in your current role? Or could you grow into a bigger or higher role?

If the answer is no, what doesn't kill you makes you stronger. It could be time to toughen up, build some grit, and grow a thicker skin. Grin through the lessons, even if they are hard. You could learn some valuable insights along the way that will shape your being in your career. 

If the answer is yes, it might be time to jump ship. Let's move beyond the proverbial glass ceiling and ascend. 

2. What Is My Plan Afterward?

Have you thought about what you will do after quitting? Do you have a plan? If you are jumping straight into another role, great. But be prepared that there is the possibility that things may not work out the way you want them to. Maybe the role is not quite what you hoped it would be. Perhaps your responsibilities are more than outlined in the job description?

Or maybe everything works out. If you are able to continue to sustain yourself financially, that's good news.

If you plan to search for a job for a while, what is your time limit? Have you set a deadline? How much savings do you have to keep you going?

If you are deciding on a sabbatical, you will need to save more money in the leadup to quitting to last you. Plan ahead in months and even up to a year. 

Don't forget to build in some leeway in case things don't go your way.

3. How Will I Continue to Make Money?

Will you jump into freelance work on the side while searching for a new career opportunity? Will you take up part-time work, or a contract role with more work-life balance to help with your search? Or do you have backup funds to last you for a while as you find a new role or transition between industries? 

Take the time to think about how you will financially support yourself. Think about the sustainable aspect of your plan as well.

4. Do I Have Any Money Reserves?

Make sure you have a safety net for a rainy day. Sometimes companies hire aggressively and expand quickly. A lot of people could be hired in the process, only to be let go a few months later because of the fast growth. This is not to say that not all companies can withstand a fast expansion. This is just an example, but it goes to show that you should prepare for unexpected situations. You may not have to prepare for the worst. But thinking through some scenarios can help prepare yourself financially and mentally. Ideally, save between three to six months of expenses before you quit.

5. Do I Tell My Coworkers & When?

Some companies hold a written policy that does not enable you to notify your colleagues. This is sometimes until one or two weeks before your departure. In this instance, adhere to the requirements and keep them to yourself until then. Try not to let up that anything is changing until the time comes.

You also don't want anyone else to know before you have told your manager or direct report. Remember, the first point of contact should be human resources. Keep it official and get it in black and white for your employment records.

The Bottom Line

It is difficult to transition between careers, no matter what. You could be employed in the same role in a different company or changing careers entirely. Even if you're about to embark on a sabbatical, transitioning is still a gradual process. Before starting the next chapter of life, make sure you think through these questions as a guide. 

Got a job lined up and already preparing for a job interview? Read Tips to Upgrade Your Job Interview Skills.