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When to Quit Your Job

Quitting Your Job

want to quit job

There were a million and one questions I asked myself before quitting my job, but only a select few that gave me the reassurance I needed to take the leap. There are so many people out there teetering on the decision to abandon the safety net of their current job to wade in the waters of the unknown.

If you are one of them, know you are not alone. In fact, 53% of Americans are unhappy at work (as per a recent study led by The Conference Board).  That is more than HALF of the population.


Furthermore,  58% of people say they trust STRANGERS more than their own boss, and 79% of people who quit their jobs cited “lack of appreciation” as their reason for leaving. (source: Forbes)

It’s no wonder that one of Google’s top search terms is some variety of “how to quit my job.” With the rise in remote work and online businesses, many are abandoning traditional full time employment all together to start a career of their dreams as solo entrepreneurs.

So, quick question. How many of you feel like you have a passion that you haven’t been able to ignore, and each time you sit in your lonely cubicle you feel like a piece of your soul dies? (Okay, maybe I’m being dramatic, but some days that is seriously how it can feel!). I know that feeling all to well.

When I was working my 9-5, I had this big, lofty dream that would set up shop on my desk. Every time I’d get a longwinded email from my boss about new policies, each time a customer ripped me a new one for something so minuscule, my dream would just look at me with an eyebrow raise as if to say “you still taking this shit?!”

So, how do you know when it’s time to quit your job for good? Follow along with these questions and try to answer them as honestly as possible. Grab a pen and paper and do this with me. If you want to download a one-page PDF with all the questions to do later, including 8 bonus questions I WISH I’d asked myself, do so here:


10 Questions to Ask Yourself Before Quitting Your Job PDF, plus the 8 Questions I WISH I’d asked myself

“What am I still doing here?”

This was an important question for me because I knew there had to be a few reasons I was still getting up everyday and clocking into this 9-5pm I didn’t enjoy. Ask yourself this question about your current position.

For me, it was for the stability. A stable paycheck every two weeks, a routine I could follow without much thought. It was an easy enough job that paid decent money. I wasn’t working on anything groundbreaking, but it was safe. I had also worked my way up in the company, so seniority was a big reason for staying put. Oh, and the debilitating fear of leaving kept me around.

Write a list of all the reasons you are still at your current job. Some may surprise you. This will also come in handy when you go to look for other jobs, because you’ll know what you did value and appreciate.

What are the pros and cons associated with staying versus leaving?

Ah, the tried and true pro and con list. I spent hours weighing the positives and negatives to both career paths. With an angel and a devil on my shoulder, I got really honest about the negative things that would come from quitting.

Sometimes, we glorify what it would feel like to quit. Envisioning throwing our to-do lists and meeting notes in the air yelling PEACE B*TCHES! can make you feel all warm and fuzzy inside. I get it.

To put it bluntly, there are going to be some really hard times when you quit. Trust me, I’ve walked through it. Picture getting up everyday with no boss to tell you what to do, no structure, no one writing your to-do list for you. This idea may sound GREAT to you, but it can be very difficult to manage productivity and motivation in this environment. Also, ain’t nobody signing your paychecks for the hours you’ve put in.

Write down the things that scare you about quitting, and what it would look like for the safety net to be rolled away. If you aren’t planning to work for yourself, and just transitioning to a new company, write down all the pros and cons of your current job versus starting fresh at a new one.

How can I set myself up financially to take the pressure off the transition phase? And how long can I last without making an income?

I’m going to bet that 99.9% of people that stay in jobs they don’t enjoy do so for financial reasons. When I started getting serious about quitting my job, I made sure to take a really close look at my finances.

The thought that gave me the most peace of mind was equating the transition to going back to school. I told myself that a lot of people decide to go back to school, for 2, 4, 8 years! Not only will they be forfeiting their income, but school isn’t exactly easy on the bank account. 

I started budgeting the same way I did in college. Taking a look at all the expenses I could give up (manicures, pedicures, hair appointments, new clothing every season, take-out meals, gas money etc.) softened the blow. I then talked to my financial advisor about setting up my portfolio to make more passive income through dividends and other income streams.

The last thing you want is for money to get in the way of your vision, because you will be easily swerved off course if money trumps your why. There will be a ton of shiny objects that distract you from why you started, make sure money isn’t one of them.

Quitting Job

Quitting your job

What is the worst case scenario?

This is my favourite question of the bunch. Seriously think about this. What is the WORST case scenario? For most of us, it’s simple. The worst case scenario would be we fail and have to get another job. Gasp.

That really doesn’t seem so bad, considering you already dislike your current job. To me, THAT is the worst case scenario. Staying in a job you hate. Let that sink in. You already have the skills to obtain a job similar to the one you carry now, so what is stopping you from giving it a TRY, and if it doesn’t work out, going back to work?

What isn’t fulfilling about my current job?

This will help you determine all the things you don’t want in your future career. Maybe it’s answering to bosses, the companies leadership style or strict policies, maybe it’s coworkers, the nature of the work, or the fact that you’ve been doing it for way too long. Make a bullet point list of everything.

What do I hope to gain out of this new career?

Piggybacking on the previous question, what do you hope will be different about this new career or company? How will all the things you listed in what isn’t fulfilling in your current career differ from this new path?

How to know when to quit your job

What will I be able to do when I quit that I wasn’t able to do before?

This is a great question to motivate you to take the next steps toward quitting. It is empowering to visualize all the things you stand to gain from being brave enough to move on.

If you’re leaping into self-employment, maybe it’s the freedom to take vacations, to improve your skills as a creative, to express yourself more, to have a voice, to learn and grow.

If you’re moving companies, maybe it’s more money to buy a home, more flexibility to travel, better benefits to get healthier, more opportunity to move up and develop new skills. A boss you don’t want to murder in cold blood… Spend some time visualizing this new life for yourself.

Is this particular job/company the problem, or am I not enjoying the nature of the work in general?

Think about the industry you are in and what is true across every job in that field. Is it just this company, or do your interests and values no longer align with the nature of this work? Are there any other roles in the company you wish you had? This will help you when you go to apply for other jobs.

Think about your superiors and the trajectory of your career. Do you aspire to move up in this company?

Can you see yourself becoming your boss one day? Or your bosses boss? If not, it’s probably time to move on. A great exercise is to picture someones career you’d kill to have. Start making decisions to lead you closer to that goal.

If you don’t know exactly what you want to do yet, but you know you want to work for yourself, ask yourself these questions:

What am I good at and what am I passionate about and how can I connect the two?

This is where you will be able to connect what you love, with what you are naturally good at. There is the sweet spot to a successful and fulfilling career.

What could I spend all day doing?

What am I an expert in? This can be anything. Home decorating, sewing, financial advice for young adults, budget travel, vegan recipes, crochet, painting, party planning, writing, organizing people, b2b marketing, you name it. Write it all down.

The biggest question of all: What do I truly want out of life?

Picture your dream life, from the moment you wake up to the time your head hits the pillow. What lights you up? What means the most to you? Is it fortune and fame or family and friends? Free time? Passive income? Freedom to travel? Freedom to pick your kids up from school everyday? Fulfillment in your work? Recognition and appreciation? What is the most important thing to you, and how can you structure your life to achieve that?

Download the fillable workbook of all 10 questions, plus the 8 questions I wish I’d asked myself prior to quitting!


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