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5 signs that you might be ready to quit your job

Making the leap from a comfortable salaried position or steady paycheck into the world of entrepreneurship and freelance can be an intimidating proposition.

When I walked away from my full-time job almost four years ago, I was well aware of the risks involved, and I knew success was not a guarantee.

Fortunately, I was one of the lucky ones.

Within a few short months, I had already more than replaced that old income with revenue generated from my new freelance business. Today, my business ventures are producing more than $300,000 in annual revenue, mostly from freelance graphic design, and they’re on track to hit $400,000 in 2021.

Today, reflecting on my decision to walk away from a job that no longer made me happy seems like a no-brainer. But at the time, it was terrifying.

So terrifying, in fact, that it took me months to work up the courage.

My husband had actually pleaded with me to walk away years prior to my leaving because he saw potential in me that I wasn’t able to see in myself. In fact, that disagreement even led to one of the biggest fights we’ve ever had as a married couple. He was tired of me complaining about my job, and knew I would be happier-and likely wealthier-if I just did my own thing.

My husband had already been a self-employed contractor for years, and we were used to relying on my corporate-sponsored health insurance.

So as one might imagine, at the time, I thought he was nuts.

If only I had a crystal ball.

Perhaps that’s why I am frequently asked, as a converted believer in self-employment, how I knew it was finally time to cut the cord and what I did to prepare for the transition.

In this article, I’ll share how I knew I was ready to cut the cord and quit my job-and how I prepared for that transition. Hopefully, my story can help others who want to do the same.

1. Job dissatisfaction was taking a toll on my quality of life

Four years ago, I was working in a fast-paced, high-stress corporate environment.

I was suffering the effects of unpredictable hours, office politics, and intimidation. I was regularly denied raises, advancements, and opportunities. I lived in daily fear of losing my job.

I rarely saw my family. I worked nearly every holiday and every weekend. We weren’t even allowed to take scheduled vacations through something my employer called the “blackout period,” which ran from November-January. That made seasonal travel impossible. If I wanted to see my family and friends during the holidays, they had to come to me.

I had no life outside of work and woke up each day in a horrible mood.

I once read that the average person will spend 90,000 hours at work over a lifetime, which equates to approximately one-third of your life.

While that might seem like a sobering statistic on its own, it doesn’t even take into account time getting ready in the morning, commuting back and forth, or thinking about work when you’re off the clock.

Studies have shown that job satisfaction is one of the top factors in an employee’s overall life satisfaction, ranking it even higher than family, leisure time, health, finance, and social activities.
And I can certainly say that statistic was true for me.

So, I asked myself: What made this job so important that it was worth so much sacrifice and stress?

While I don’t think hating your job is a necessity for change, for me, it was certainly a motivating factor.

2. I could clearly envision a different path for myself

If you want to achieve a goal, you have to clearly picture that goal in your mind. You need to take what seems like a pipe dream and make it seem obtainable.

Throughout my adult life, I’ve always freelanced to some degree, but mostly as a side hustle to earn a bit of extra cash here and there.

But I knew quitting my job and turning that side hustle into a full-time freelance career would be a major adjustment, and I often wondered what that kind of life would even look like-or if it would bring me the satisfaction I so desperately desired.

So I began reading success stories from other freelancers and challenged myself to envision what it might be like to follow in their footsteps.

According to Psychology Today, visualization has a direct impact on motivation, confidence, and even performance.

One study published in the National Library of Medicine even suggests mental exercises are nearly as effective as physical exercise.

The study compared results from people who did strength-training exercises in their heads to people who actually physically performed the exercises in real life. As expected, those who physically performed the exercises saw a 53% increase in strength, but surprisingly, the group who performed the workouts in their heads saw a 35% increase after two to four weeks.

With that in mind, I tried to imagine what it would be like to work for myself, and how empowering it would feel to take control over that aspect of my life.

As I commuted to work in the dark on rainy early mornings, I imagined what it might be like to ditch the commute. Or even better yet, ditch the alarm clock altogether.

I saw myself no longer being limited by a salary, which was an important shift in mindset. I went from seeing my salary as something that protected me to something that was stifling my potential.

When my husband would go out with friends while I had to go back to work for an overnight shift, I would imagine the alternate fringe universe where I might be able to tag along instead.

It was like a vision board in my head. And as silly as it sounds, it made my dreams tangible and gave me the courage to actively pursue them.

3. I had a small financial safety net

I knew I would need a little financial safety net if I was serious about quitting my job and launching my own business just to be on the safe side.

Experts often suggest putting away at least three to six months’ worth of expenses in an easy-to-access emergency fund. It’s important to factor in things like family size and other financial obligations when determining exactly what that amount should be.

Luckily, I have always maintained a three-month emergency fund, and as a married woman with no kids and a low mortgage payment, I knew it would likely be enough to fall back on if needed.

I was also prepared to live lean if necessary. To me, a short-term sacrifice was worth long-term gain.

I never planned on actually dipping into that emergency fund-just as a tightrope walker doesn’t plan on falling into the net below. But it should be there just in case.

I realize building an emergency fund isn’t always an easy task with 80% of Americans living paycheck to paycheck and 57% having less than $1,000 in their bank account. However, the bigger the cushion you’re able to give yourself, the better off you’ll be.

And I always suggest for those who have no cushion to consider a more gradual transition. Building a new business as a part-time side hustle in addition to working a full-time job can be a great way to earn a little extra income in the interim.

That being said, I would also warn against over-planning and procrastination.

I have friends who have supposedly been working up to quitting their jobs for years with talks of pursuing their dreams “one day” when they are “more prepared.”

If you don’t give yourself a deadline, perpetual procrastination will likely take over and “one day” may never come.

4. I tested the viability of my pursuits and knew my chance for success was high

This is probably the most important step for any would-be freelancer or aspiring business owner to take when making the leap.

I knew I’d have to learn to walk before I could run and leave as little as possible to chance.

So I began ramping up my freelancing efforts long before I actually cut the cord to prove viability and sustainability.

I started by revamping my website and updating my portfolio. I then began applying for new freelance jobs, sending out proposals, and making my existing clients aware of my intentions.

I pushed myself to take on as much work as I could handle while still maintaining my full-time job.

If I failed in those efforts, it would have been a sign that the business might not be viable on a larger scale.

Luckily, my efforts were quite fruitful.

The increased workflow not only proved that there was potential in my plan, but it also allowed me to save up a bit of extra cash for that previously mentioned financial safety net.

By the time I quit my job, I was already clearing nearly $4,000 per month in just freelance income alone, which made the transition much easier.

5. I made a plan and gave myself a deadline

This is the “do as I say, not as I do” part of my story.

My husband and I agreed that we would renovate our home to give us the option to sell once I quit my job to give us flexibility. And so we gave ourselves a six-month deadline.

One month into the renovations, I ended up rage quitting instead.

I remember that moment vividly as it was in the middle of a previously scheduled meeting with my boss. I was tired and frustrated, and I knew I didn’t have it in me to stay another day. I told her my heart wasn’t in it anymore, and I walked out.

I returned home that afternoon to a gutted bathroom and a husband who was confused over what had happened to our well-laid-out plan.

Fortunately, due to my efforts in the months prior, I already had a financial safety net ready to go and a decent amount of freelance work already coming in.

While it was enthralling to quit in such an unexpected fashion, and it makes for a great story today, it was the riskiest part of my journey. I don’t necessarily recommend following in my footsteps unless you know you are really ready to go.

Make a plan, and actually stick to it if at all possible.

Whether you are still deliberating on whether or not to quit your job or have already made plans to do so, it’s important to remember that no two paths are going to be exactly alike. While I hope that at least part of my planning process is helpful or applicable to your situation, it’s important that you follow your own gut instincts as they will rarely lead you astray.

Morgan Overholt

Tennessee native Morgan Overholt is a freelance graphic designer, owner of Morgan Media LLC and co-founder of Morgan and her team have worked with nationally recognized clientele from all over the world, including the Centers for Disease Control Foundation (CDCF), Kimberly-Clark, and Stanley Black & Decker.

Morgan transitioned into the role of freelancer and small business owner after spending nearly a decade in the traditional corporate world left her feeling unsatisfied and unfulfilled. Today, Morgan is passionate about sharing her story with other hopeful entrepreneurs who hope to follow in her footsteps. She has been featured on, Refinery29, and Business Insider.

Originally published at on October 27, 2020.



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Morgan Overholt

Morgan Overholt is a freelance graphic designer and owner of Morgan Media LLC. She is also a contributor for Business Insider and Collective.