“Should I Quit My Job?” How to Properly Ditch Your 9 to 5

By AAwosika07 | Careers

Mar 30

If you’re asking yourself, “Should I quit my job?” the answer is yes.

Most people who have jobs should quit their jobs. But they can’t. And you probably can’t either. At least not this very second.

How do you quit a job you hate, tolerate, or feel lukewarm about and replace it with a dream job or a business that helps you make a full-time living?

I can only speak from experience. Sometimes, it doesn’t even feel like I did all the work to pull it off, but I did. Some words of hope for you — I used to be so extremely lazy you wouldn’t even believe it. I love that because it gives me hope for everyone.

I know enough people who have successfully quit their jobs to know it’s possible. The intricacies of our paths were different, but the core philosophies and actions were the same.

It’s weird. On the one hand, quitting your job just takes a series of gradual steps that are easy enough to achieve in and of themselves. It’s not…hard. But also, it’s super hard.

Hard because the steps combined are daunting. And also hard because you can’t do the steps in a vacuum. You have to do them on top of having the job. I’m not like other self-improvement writers who, well intentioned or not, want to sell you a dream.

I’m one of the biggest dreamers out there, but I’m also a hardcore pragmatist. Do I believe you can successfully quit your job? I sincerely, genuinely, and passionately believe this. But I can’t live your life for you. I can only show you the way.

I’ve been you before — optimistic yet skeptical. I remember thinking to myself, “Am I crazy? Can I really pull off this crazy pipe dream?” Your feelings are normal, but you have to overcome them.

Here’s what I learned in the process of building my writing career on the side, while working a full-time job, and eventually quitting.

Without This, You Won’t be Motivated Enough to Quit Your Job

“There are only two ways to influence human behavior: you can manipulate it or you can inspire it.” – Simon Sinek

If you want to start a side-hustle or look into building a skill that can lands you the job of your dreams, make sure the new path is compelling to you.

I didn’t take myself to seriously right away and make this huge proclamation that I was going to quit my job, but when I stumbled into writing, I started to realize pretty early on that I wanted to do it for a living. And I never felt like I had to force myself to work on my writing. I felt compelled to do it.

Most people fail at quitting their job and making the switch to something better because their reasons are superficial.

Sure, everyone wants to quit their job and starting some cool online business like you see on Facebook Ads looks cool and sounds good, but is that really what you want to do? Everyone wants financial freedom, but that’s too vague to sustain you. You get the outcomes, freedom and income, as byproducts of doing something you enjoy. Not even love, per se, but a truly above-average level of enjoyment.

You want to find something you can get good at. I don’t know if I love writing itself. I know I love increasing my competence at it, though. Mastering something makes you passionate. And alignment with your strengths gives you the best chance at pulling it off.

This leaves you in a tough spot.

On the one hand, finding something as closely aligned to your strengths and tastes as possible will give you more compelling reasons to follow through and learn the skills, but you don’t want to fall into the trap of thinking this magical and singular passion is going to fall into your lap through contemplation.

I constantly preach the idea of creating a 90-day experiment. I created a checklist you can use to identify potential strengths and paths for your life (found at the bottom).

Use it to find an experiment to run for 90 days and judge your results only after you’re done with your trial period. If you’re trying to start a side hustle or just build a profitable skill, spend your 90 days doing that. If you want to switch careers, spend time learning the skills that field requires, e.g., take a coding course.

90 days into my writing career I had no money, an email list size of zero, and knew nothing about the deeper levels of marketing it would take to turn my writing into a career, but I knew I really, really, really liked to write. And that was enough.

Next, Comes the Stick

“How in the hell could a man enjoy being awakened at 8:30 a.m. by an alarm clock, leap out of bed, dress, force-feed, shit, piss, brush teeth and hair, and fight traffic to get to a place where essentially you made lots of money for somebody else and were asked to be grateful for the opportunity to do so? ” – Charles Bukowski

Once you find an experiment that sticks, the compelling reasons will pull you closer to the end goal. Use your current job to push you, especially if you hate it.

The first three years of my writing career, I made little to no money, but I knew I was going to see it through. Why? Because there was no way in hell I was going to spend my life working at a job.

I liked the job I had well enough, project manager then marketing director at an agency, but there will little things about it that irked me and pushed me to keep hustling.

I hated dealing with annoying and troublesome clients. Now? There’s no amount of money worth working with someone like that and I can control who I work with. I hated the fact that I had to listen to whatever my bosses told me to do, even if they were wrong. I hated being paid way less than what my services were worth, which is the nature of being an employee.

Most people distract themselves from the ills of their job. They numb themselves with Netflix, weekend activities, booze, whatever. Instead, redirect that energy to better use instead of distracting yourself from it.

Don’t like your job? Good. Use it as fuel.

Negative emotions have power. I often used negative visualization to stay on my path. I pictured what it would be like to have to do this for the rest of my life and it terrified me more than working on my projects did.

Do you want to spend a third of your entire life at a job you don’t want? A third of your life. Think about that when you’re tired, distracted, or don’t have motivation. Think about that when you don’t want to get up early before your 9 to 5 and work on your side project.

I used all sorts of negativity to push me. I told the story in my book about how I could barely afford to buy my daughter some pet fish. How, politically correct or not, I felt emasculated by my inability to provide and used it to persist. I absorbed those little shots to my ego all the time —  having to look at prices at the grocery store, getting reamed out by a client, looking at my measly paycheck.

I took them all personally.

Was this the healthiest route? I don’t know. But I don’t have a job anymore, so, yeah.

Don’t Burn Bridges, Build Them

“A desk is a dangerous place from which to view the world.” —JOHN LE CARRÉ

You want to make the switch from your current job to your full-time business or dream job as seamless as possible.

The career switch scenario is straightforward. Once you land a new job, you can quit your old one. For making the side hustle a full-time gig, though, it depends on your psychological makeup and risk tolerance.

For me, I wanted to have about six months of cash set aside and I wanted my side hustle income to exceed my current job income for six months straight. Even when I had things lined up, I hesitated to pull the trigger. My business coach actually convinced me to make the full-time leap.

I’ve told the story before, but a series of strange and unfortunate events led to me quitting my job.

First, my marriage was in shambles and I was in the process of moving out of the house. Due to said stress, I seriously screwed up a marketing campaign and pissed off a major client, leading to a week suspension.

Then, as I was at the airport on my way to visit a friend to take my mind off things, I get a notification for my scheduled meeting with my coach, which I didn’t want to take at all. She told me to take everything happening in my life as a sign.

This was the moment to act. She told me to request a month sabbatical to test the full-time gig. Once I got a taste of that life, I never went back.

Even though life pushed me in that direction, the bridge was still there.

You can focus on building your bridge for as long as you see fit. You can keep your side hustle for years if that makes you feel comfortable. Maybe you need a year’s worth of cash. Only you know your temperament.

But just know, you might need to give yourself that push. Even when the stars are aligned, making that leap is hard because you’ve been trained your whole life to be dependent on that steady income or that routine you’ve become accustomed to.

Once you come out on the other end, you’ll realize the truth about living your life on your terms with a career or business you truly enjoy.

Understand The Situation At Hand

“Every time you say yes to something you don’t want to do, this will happen: you will resent people, you will do a bad job, you will have less energy for the things you were doing a good job on, you will make less money, and yet another small percentage of your life will be used up, burned up, a smoke signal to the future saying, “I did it again.” – James Altucher

Getting your career and financial problems solved doesn’t fix your life, but it does knock over some major obstacles that help you focus more on fixing your life.

When you’re not worried living paycheck to paycheck or stressed out about the conditions of your job, you have more bandwidth to focus on your self-actualization.

See, having a job you hate or tolerate doesn’t just rob you of the time spent while you’re at the job, but it also robs you of the present moment and detracts from your mental clarity when you’re not at work.

It’s hard to focus on ‘personal development’ when you’re broke. Why do you think divorces happen? It’s not just the money, but the state the two people are in having to come home from those environments and unloading all that stress on top of each other.

Quitting your job frees you from the cascading negative effects of having it.

Quitting a job you hate is, without question, the number one domino many people need to knock over in life. Don’t ask yourself “Should I quit my job?” Tell yourself you want your sanity and life back because this is a life or death situation.

Bad jobs lead to early graves. Stress can literally kill you. And on the way to that demise, you get the reward of having to hate a third of your life.

The tone of this post isn’t super positive because you need your ass kicked right now. The level of effort it will take to overcome your job is monumental, which is why so few people do it.

Self-improvement is the process of becoming the exception to the rule.

Someone who reads this post will pull it off.

I hope it’s you.


About the Author

Ayodeji is the Author of Real Help: An Honest Guide to Self-Improvement and two other Amazon best-selling titles. When he's not writing, he enjoys reading, exercising, eating chicken wings, and occasionally drinking old-fashioned's.