5 Questions You Need to Ask Yourself Before You Quit Your Job

You’ve finally decided it’s time.

All of the planning, plotting, wishing and hoping is done.

You’ve decided to quit your job and pursue your passion. 

Excellent. Let me first say – congratulations. What you’re doing takes a lot of courage.

Having said that, there’s always a bad time to make a good decision. For example, if you’re in the middle of a cash crunch and one of your family members is ill and needs regular treatments, it may not be the best idea to quit your job even if you’re generally convinced it’s the right thing to do for your future.

So, now that we understand each other, let’s dig deep and look at the hard questions you need to ask yourself before you finally send that email, smirk at your superiors and moonwalk out of the office.

1. WHY are you quitting this job?

This might sound like an obvious question to start with, but it is possibly the most important one to ask. And what I’m about to say might sound like a controversial statement, but humor me for a minute here.

The entrepreneurial life is NOT for everyone.

That’s right. Some people are simply not cut out to be an entrepreneur. And while you may not be one of those people, it is still a good idea to gain an objective analysis of your situation before you make the leap.

Starting with WHY is a great practice to guide you through the tough times in life. What’s so bad about your current job? Is it the workload? Do you not like your boss? Maybe your desk mate has a funky odor about them? Are you not being paid enough?

Once you start outlining your objections or complaints, know that there is a way to fix all of them and still hold your position at the company. You can negotiate better pay, more flexible hours and even change teams or departments, if that’s what’s got you down. There are lots of people who are perfectly happy at their day job. Just make sure you’re quitting for the right reasons.

2. WHAT is the one thing that automatically makes your new job offer or project desirable?

Maybe you’re quitting your job to pursue a different career or start your own business. Sometimes, you can get so frustrated with the monotony of your current job that anything “different” starts seeming desirable. Any company but this. Any job but this. Right?

I know how you feel.

Before you accept another offer of employment, consider this – different is not better. Only better is better. Which means, while the novelty of a new company might sound desirable in the short run, once you settle in, you’re going to be faced with the same problems. Don’t just settle for another offer because it pays more. Dig deeper. Find out what the company or business you’re going after is like from people who’ve been working there for a while.

3. How is this going to affect my financial situation going forward?

If you’re quitting your job to join another company, you might have a fair idea of how your finances are going to look like in the foreseeable future. But, if you’re quitting your day job to start your own business, this is something you need to consider very carefully.

Building a business takes a long time, and it might take even longer for your project to become profitable. How are you going to manage your expenses in the interim? Do you have a plan for earning some kind of income on the side (by doing some kind of consulting, freelance or part-time work)?

Great things happen when you take a leap of faith and venture out into the great unknown. But, it’s always a good idea to have a plan of action for when things don’t go your way.

4. Am I in the wrong line of work?

When you’re young, it’s very easy to just join a company or accept the first decent job offer that comes your way. Before you know it, several years have passed and now you’ve come to a point where you are considering a switch. Here’s something you should be asking yourself – Is this what I really want to do with my life?

Put your magic hat on and try to paint a picture of the future. Are you an artist trapped in the corporate world? Are you an athlete who’s stuck behind a desk? Because if you are, then you shouldn’t just jump from one company to the next. Take some time and really consider if you’re comfortable with working in an office for the next 5-10 years. If not, it might be time to broaden your horizons.

5. If I absolutely HAD to excel at my current position, how would I do it?

Having a couple of negative people in your team or an annoying boss can give rise to resentment that gradually builds until you’re no longer comfortable working at your current organization.

But, if you had no other option but to succeed (whatever your definition of that term might be) at your current job or organization, what steps would you take? Would you look for some professional certifications that can help you gain greater leverage and promotions at your company? Maybe you could attend some networking events and come up with ideas/potential partnerships that you can present to your bosses? Maybe you could have a heart-to-heart with your boss and let him know that you’re capable of much more, and that you’re ready to be put into a leadership position?

Often, the resentment you feel towards your job isn’t a problem with the job itself, but your attitude towards it. If you’re willing to adopt the right mindset and ask yourself the hard questions, you will find a way. If you ask yourself all of the above questions and decide that it’s the best option for you to quit your day job and work on your business, you’ll be able to step into your new venture with much more clarity, knowing that you’ve explored all of your options.

If you can go through this list and you still feel compelled to leave, then you've given yourself more critical information to process. Perhaps you are just one step away from chasing after that passion. We would know: we've been in your shoes. 

We understand how critical it is to give entrepreneurs and independent professionals the time they need to ask these questions. That is why we created Dubsado – a complete business automation system that takes care of all your invoicing, bookkeeping follow-ups, client proposals, lead management, form creation and so much more, so you can listen to your inner calling and put your best foot forth into the world.