What’s It Really Like To Quit Your Day Job?

I walked into my boss’ office on a snowy winter morning, knowing my life was about to change. I’d never been so excited, so sure of anything before.

I was going to quit my job.

I think he knew what I was about to say when I knocked on the frame of his open door. The conversation was underway before I had a chance to think twice. There was no turning back. Plane tickets were booked.

It was time to jump…

If you’re anything like me, you’ve daydreamed about this moment yourself.

You might have read books about how to escape the corporate grind and followed the blogs of those successfully pulling it off.

You’re not alone if you’ve wondered “is it really possible to quit your job and live life on your own terms?”

And the answer, of course…

…is an anticlimactic maybe.

It’s entirely up to you.

I know, I know. You’d prefer a definitive answer so you could either turn in your notice or go hit up co-workers for lunch plans.

But let’s get real, writers! No one is going to give you permission to live your life. You’ve got to be your own advocate, and yes—if you want to quit your job and start calling the shots, you’ve also got to be a little bit audacious.

Here’s the truth: if you have WiFi and a dream, your fate lies in your hands.

I quit my job this year to become a location independent freelance writer.

We’ll get into my story in a second, but I was freelance right out of school, and in the intro above, I was on the verge of quitting my first (and so far, last) day job to go back to being my own boss.

I wasn’t going full-blown nomad, but travel was a huge part of my motivation, along with nixing alarm clocks, spending time with family, and writing in aromatic cafes instead of stuffy offices.

(You know, real life.)

I’m going to give you my honest rundown of what happened, and I hope you can extract some useful insight from it all.

Warning: Large dose of realness ahead.

Why quit your job in the first place?

Let’s get this out of the way first.

Not a week goes by that I don’t run into the “Are you insane? You should be grateful to be employed!” argument when I’m talking to people about the Day Job Optional lifestyle.

Of course, employment is a blessing, and this is a valid comment.

There are plenty of people out there who would give a limb to get a job, and the idea of quitting yours can feel like an ungrateful move.

But seriously, this is the wrong way to program your brain if you’re aiming for a life that actually makes you happy.

You’ll never achieve happiness by limiting yourself to what other people do—or don’t—have.

It’s true that life doesn’t deal a good hand for everyone.

We know this!

Some people seem to have all the luck (wealth, health, privilege, etc), while others can never catch a break.

You may even feel, from time to time, like you’ve been dealt a crappy hand.

We all have something like that in the back of our minds.

Life just isn’t fair.

But you’re not doing anyone any favors by sitting in your office chair at a job you hate or forcing yourself to feel grateful for something that makes you miserable.

Please, please, please, writer friends: cut the martyr routine. Start taking ownership of your potential. Do you really think “appreciating” a bad situation because “at least you have it” is going to help other people? Or make you feel fulfilled?

Or help the world in any capacity? No.

But wait…

Does everyone hate their job?

Definitely not!

And if you actually love yours, don’t worry about this whole movement of liberation from fluorescent lighting and water cooler small talk.

This isn’t Day Jobs Are Evil, after all. It’s Day Job Optional.

But there’s a reason we toss around cliches about “the rat race” and make jokes about how awful Mondays are.

There’s a reason we read about a woman literally dying at her desk and have nightmares about the same thing would happen to us if we kicked off by Friday EOD.

If there’s a better route, why not pursue it with all you’ve got?

Why settle?

Settling only reinforces the behavior most of us have been taught since birth: sit down, shut up, and follow the rules.

Still having second thoughts? It helps to get a liiittle morbid, sometimes.

We’re all going to die.

Yep, it’s going to happen! Could be today, even. We don’t have any way of knowing when or how.

But if you know that it’s inevitable, do you think you’ll look back on your life and feel good about how you’re spending the majority of it right now?

That’s not rhetorical, by the way. Answer it in your own head, and then chew on this:

Of the top five things people say on their death bed when asked what they regret about their lives, one of the most common answers is “I wish I’d had the courage to live a life true to myself, not the life others expected of me.”

(You can check out the rest here.)

Is the life you really want waiting for you in your cubicle Monday morning?

What if, instead of submitting to the grind and spending your life working for other people, you decided to be brave as hell and see what great things you can do with this life?

What if you decided to launch an online writing career? What if you decided that anything is possible, and went for it?

Now, more than ever, is the time to pursue that thing you’ve always wanted to do. That thing you know you’d be amazing at. That thing you’re so freaking passionate about.

Not everyone is miserable at their day job… but if you’ve read this far, I’m willing to bet you feel like there’s a better future out there waiting for you to grab it with both hands.

Sound like you? If so… you’ve just identified your “why” for quitting.

Don’t let anyone talk you into playing it safe when you know you were meant for more.

(Woah, how did this soapbox appear beneath my feet? Ha! Moving on.)

Above: Me, the night after I quite my job at a high fashion menswear label and packed my bags for a warmer climate.

Day job vs. No day job? Let’s get real

Pay attention, because there are more than two sides to this coin.

If you think quitting your job means running straight from the office into a bohemian clothing store to stock up on harem pants and incense while your S.O. searches spiritual retreats and plane tickets, take a step back.

I mean, hell, that’s one way to do it—and it seems to be the trend if you’re looking at the #DigitalNomad hashtag on Instagram!—but it’s not the only way to enjoy location independence.

Some people get disillusioned by this idea that you’re supposed to become a backpacking nomad when you turn in your corporate ID, but that’s why the DJO lifestyle itself gets a bad rap.

Check the comments on any “I quit my job to travel the world!” article and by many, this life-altering choice is considered irresponsible, irrational and ridiculous.

The nerve!

Seriously, though…

It’s not stifling skyscraper or beach bonfire with no happy medium.

While my examples above are vain attempts at humor, the point I’m trying to make is this: in your mind, quitting your job shouldn’t be some insane, irrational thing you’re daring to do that will officially make you an outcast from society.

In fact, when you lay it all out, it could be the most rational choice you ever make.

After all, remote and freelance jobs are on the rise, and humans are exponentially being replaced by really smart robots in the workforce.

A skill set someone spends their entire lives perfecting in a day job could be obsolete by the time they’re thinking about retiring, which means a layoff, not the “someday” scenario they were waiting for.

The point of opting out of day jobs? It’s to design your life the way you want it.

To build something great. To realize a passion. To work a schedule you feel good about.

Once you’re a happier, healthier, more inspired version of yourself, you’ll literally be making the world a better place just by existing.

Why?

Because aside from the product, service or experience you share, creativity, happiness, and passion spread like wildfire.

Even better if your freelance career is somehow heart-centered, helps people, or contributes proceeds to worthy causes—things you have no control over as a 9-5 employee.

Once you understand what your post-9-5 life could look like, you’ll have a mental picture to fuel your dreams and start working toward them, hardcore!

Let’s try a little exercise:

If you’re reading this at the office right now or you’re dreading to go to work this Monday, take a minute to imagine what you’d do if you suddenly got a whole week off.

And yes, it’s a paid week off.

What time would you wake up? What would you eat? Who would you make plans with? What would you get done? Or not get done…?

Now, imagine that you get a call saying you have a paid month off.

What would you plan? Where would you go? What project would you finally finish? Who would you spend more time with?

Now, do the same thing for a year off.

Get the picture?

These questions can help you paint a picture of your specific, unique reasons for leaving a job you don’t love and taking control of your own life.

When we imagine having time off from work, our hearts literally fill with joy and our minds spin with the things we want to do.

Shouldn’t life… just be like that?

Shouldn’t we be able to work hard and enjoy being alive more than two days per week and two weeks per year?

And here’s something else to chew on…

Job security has ridden off into the sunset, and experts say it’s not coming back anytime soon.

And let me ask this: what is so seemingly secure to you about putting all of your eggs in one corporate basket in the first place? If that basket drops, you’re toast!

Some people are trying to robot-proof their jobs, which basically equates to doing a ton of kiss-ass-y stuff that’s unrelated to your job so people “like” you and may feel less likely to ax you when lay off time rolls around.

I call bullshit.

Other people are getting resourceful by getting ahead of this major shift in the workforce.

They’re upgrading their skills on websites like Udemy and Lynda.

They’re seeking out remote jobs, asking for days to work from home to show their bosses the increase in productivity when they’re not crammed in a cubicle.

They’re starting consulting companies and freelance services on the side.

They’re planting the seeds for something that can’t be ripped out from under them like virtually every day job in existence.

When you quit your job and start out on your own as a freelancer, you’re taking the power back from a company that could wreck your life—and any future goals you’ve been basing on employment—with one sheet of paper.

You’re making yourself the central source of value. You’re calling the shots.

You’re deciding what your profit goals are, how many hours you want to work, when to hire a team, and even how often to check your email!

Which sounds better to you? The employee life, or one you can fully design?

My first (and last) 9-5

If it was 2014 right now, I wouldn’t be able to write a post about quitting your job with confidence. This past year was one of many firsts—including securing and quitting my first day job.

Creative people have a very hard time sitting still, and I’m one of them.

If you’re like me, you’ve spent wistful hours dreaming of faraway places, outlining creative projects and feeling an ache that somehow, you are meant for more than spreadsheets and small talk.

I couldn’t rationalize spending the healthiest and strongest years of my life in a swivel chair… and that’s why I started off as a freelancer right out of school.

I quickly realized that by freelancing, I had way more freedom than my friends with day jobs.

I took extra days off to go seashell hunting on New England beaches, flew to San Francisco to photograph rows of pastel houses, and roamed various cities in Peru for a solid month. I also dedicated ample time to side projects like my blog, which landed me some exciting partnerships and opportunities.

I quickly learned how to work with clients remotely. I also learned that they couldn’t have cared less where I was in the world as long as I made deadlines! Most importantly, there was no way I would have had the energy or time to keep up with all of my passions and projects if I was a 9-5er.

While many remote workers start off in the day job grind and escape, I started off with that taste of location independent freedom… and took it for granted. I was enticed by a day job as a copywriter in the fashion industry, and I went for it.

After all, I’ve always learned best by experiencing things first hand! I was curious whether the dreaded day job life would really be as bad as I thought.

I was a stellar full-time employee for a year. I was excited to get the job in the beginning… because it was a good job! There are far worse, more boring roles to take on than the one I was offered.

Also, it feels good to be chosen.

My ego wanted me to put in the time and impress everyone at work. There were a lot of candidates gunning for the copywriting position I scored with a designer fashion brand, and I was the “winner”.

I dove into the company culture, working with a large team and multiple departments, conceptualizing, project managing and submitting hundreds of copy deliveries. I even got eye fatigue, so I felt pretty legit! #officelife

With benefits, friends at the office, and a sweet stable paycheck, things felt pretty good…

I still had that nagging feeling, though, especially on slower days. Being obligated to sit in an office chair just felt wrong and bizarre.

I started the job during the harsh month of March when it was cold and nasty.

I knew the company had a small office in LA, and I devised a plan to get transferred there to avoid any further snowy winter commutes.

By the time summer rolled around, though, I was less worried about LA and more focused on building Day Job Optional, which had been born in between.

It didn’t have a name yet—it was mostly ideas scrawled in a spiral notebook during brainstorming sessions with Krystal.

We spent the spring excitedly brainstorming and figure out how our new project would take shape.

Something that would offer resources, inspiration, and community to writers hoping to get out of the corporate grind.

Everywhere I looked I found a story of someone leaving the rat race. I became fixated on the Screw the 9-5 Podcast and Etsy’s Quit Your Day Job series.

After literally days of back and forth about our new website’s name, I sent a text to Krystal while riding the M train…

“Day Job Optional” was born

“YES!” she replied.

After so many names, we’d finally touched on the one.

And so, DJO came into being. It went from a dream to a thrilling reality quickly. I felt brave for creating it, because it wasn’t just a website. It was my promise to myself that I would leave my job and walk the walk.

I would personally embark on this lifestyle I was so enamored with, and document it along the way.

The point of the content here has evolved since then—we were once less about writing and more about just being free!—but that was where it all began.

Having Krystal by my side as an accountability partner, editor and cheerleader also helped the whole project feel real.

Soon after, the URL was registered, the logo was designed and a site was built.

To be fair, I knew I had successfully freelanced before, and I knew I could do it again. Still, a year in unfamiliar waters made it all feel a bit scary.

More than anything, I felt increasingly tired of working toward someone else’s dream. I had my new passion project waiting for my on my laptop, and I bolted home every day to work on it. The muse was alive in well, and I had to strike while the iron was hot.

“Omg, you quit your job?”

Friends and peers have asked me whether it was nerve-wracking to quit.

Here’s the thing: I tend to stress about little things, but glide through the bigger decisions based on instinct. I know, not everyone is like that. Sometimes I think it should be reverse!

Each time I’ve taken a leap after feeling it was the right choice in my heart, the road has risen to meet me, like the old Irish proverb. This was one of those times.

After a year at my full time job I had more inspiration than I could hold in my head, a new website that I went to bed and woke up excited about, a partner to embark on the journey with, and experience as a freelancer to hit the ground running.

I took a solid week of PTO to think it over, and then went back to work to give my boss the news.

Oh… and I didn’t have a backup plan. You might want one!

Everyone is different, from mental blocks to support networks to obligations. If I give myself too much cushioning, I know I’m less likely to follow through with drastic changes in life. You’ve got to think this through and decide what’s best for you.

For instance, I don’t have kids or a family to feed. I had rent, student loans, and basic living expenses to cover, as well as a online business training to pay for.

To be completely transparent, Day Job Optional was not part of my income plan when mapping out my escape. My plan was to do freelance writing projects remotely, make my own schedule (and travel!), creating ample time to work on the site. I wanted to give it a chance to grow.

So, this is the part where you have to be honest with yourself about the numbers.

I recommend putting it all on paper and deciding what kind of income you need to generate to maintain the lifestyle you want. Plenty of people start their side hustle and build up to that number before they quit, which I think is incredibly smart.

At the very least, you should have some leads for client work or savings in order not to wind up in a very stressful situation.

Bottom line? Quitting your job is a bold thing to do… but you have to be smart about it if you’re going to look back and say “that was the right decision”.

Resigning the right way

Ultimately, when I made my decision, I wanted to leave on a good note. Part of the quitting plan? To avoid leaving anyone hanging or hurting the workflow with my departure.

Again, I liked my job! It wasn’t awful, but it had proven my theory: that I’m not fit for an office chair and a 9-5 schedule.

In one year I’d gained weight, developed major eye strain and couldn’t walk into the office without sighing sadly, knowing there was something else I’d rather be working on.

When I sat in front of my boss on that fateful morning, he said very little until he heard my story. I was transparent about my intentions: I didn’t have another job lined up. In fact, I had simply decided for a multitude of reasons that it was time for me to break back into freelance writing, see more of the world, and launch a website.

I was completely honest.

(Another good thing to note? My boss was super cool, forward-thinking and supportive in general.)

I gave him a month’s notice because as the only copywriter in the company, I would have left a pretty sizable hole if I’d just jumped ship. Dramatic exits are pretty hard to justify, even if you’re excited about leaving.

Instead, I hung around, buttoned-up projects, and did as much advance work as I could to set them up for a smooth transition.

Fast forward a few weeks? I opened my phone and found an email from my boss while sitting in an airport waiting to fly to Mexico. He was asking if I’d be up for remote freelance work.

Let me tell you…

Those words sparkled and shimmered on my phone like a godsend.

I used that income paired with other projects I’d secured to travel, upgrade my tech, and invest in DJO. I then received a few one-off freelance projects from the company in the year following my departure and was invited back to train their new copywriter.

So yeah, it went pretty well!

Not only had I left on a good note, but they were supportive and trusted me enough to turn around projects from other countries and give their new recruit the lay of the land.

It felt good.

I knew I had made the right decision, and the universe (and my professional network) was supporting me.

My story vs. yours

Everyone’s quitting story is unique.

I had an advantage with years of freelancing under my belt before I took that day job, but all you really need is a little bit of audacity.

My boss’s reaction? Also pretty unique!

What I hope you’ll get from my story is that, with a little planning, setting dreams into motion will cause the universe to respond.

If you believe it, if you want it? You can start your new life—one free of the soul-sucking day job you dread going to.

There’s no punchline here that I am now a millionaire or that I just got a call from Oprah.

But I’m still doing the freelance thing, working on DJO, and living life on my own terms.

Each year I try to set the bar higher, and each year I get a little more inspired.

So… about your story!

What do you need to consider to embark on this path? I’d say just get real about the reasons you’re doing it.

There’s no wrong answer except the one that doesn’t work for you.

Not everyone wants to be a hostel-haunting hippie or a full-time traveler. The whole point of taking back your life is being able to design it yourself.

You can design a life that works for you, and you owe it to yourself to do so.

Quitting is exciting… but what’s next?

Once you quit your job, expect a multitude of emotions.

Let me try to break it down for you, as I remember it:

You may feel a sense of freedom when you put in your notice and walk out of your boss’s office.

You’ll probably feel some urge to stand on your desk and shriek with joy!

Soon to follow, you’ll notice a mix of resentment and “senioritis” when you still have to show up to work for a few weeks.

Push through, work hard, and finish up on a good note. Still, you won’t be out of the woods just yet.

During your first days of freedom, you’ll be on fire—at least mentally.

It’s all new, it’s all fresh. The world is your oyster!

You’ll want to dive into your new projects and plan your new life, but resistance will pounce, and you’ll end up watching Netflix.

(That’s okay.)

Without structure, if you’re not used to not having a boss peering over your shoulder, you may experience uncertainty and anxiety. You may second-guess your every move.

Again, that’s totally normal.

Don’t assume you made a bad choice when you’re suddenly not as excited the week after you leave your job.

Stick with your instincts. The excitement will come and go in waves because you’re doing something life-changing.

If it was easy, everyone would do it.

If you’re feeling overwhelmed, ease up on the reins and talk it out with supportive friends, family, and mentors.

Rest assured that you’ll get back on track. Give yourself time to freak out! It’s a big deal.

You’re living your truth now.

Also? Don’t push yourself when you have those initial waves of panic. You can get back to the hustling when you’re centered again.

My secret weapon?

The DJO facebook group! A community of writers who are living life on their own terms. We talk each other through writer’s block, share ideas and keep one another motivated.

Manifesting a new life

Whew! This post has been exhausting to write (and to read, I’m sure—thanks for sticking with me!).

Before I wrap this up, I’ll impart some straightforward actionables you can tackle to start making your dream life a reality:

First, commit! Set a quitting date and let yourself get hyped up. Make collages of the places you want to travel to. Build yourself a website. Chase down some client leads. Take some online courses to sharpen your skills. Mark the occasion of this epic decision with something special and meaningful to you.
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Tell other people. This is where accountability comes in. You can think about it all day and even blog about it, but until you say it aloud, it’s still an idea. It became real for me when I told my mom. She was hesitant but she believed in me, and that made it very real!
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Re-write your online bios to reflect your new career goals and lifestyle. I’m creating a separate post to guide you through this, but updating my Linkedin and other “about” pages from to reflect my new title and niche was liberating and hugely motivating. Don’t stress about this—you can always modify it further later!
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Get connected with YOUR people. A.k.a., people who are in the thick of the lifestyle you’re aiming for. I joined an exclusive club for digital nomads and anti-day job peeps who I talk shop with all week long. We share our projects, ask questions, solve problems and build connections. It’s accountability and inspiration galore! Also, gotta drop the link to the DJO community once more! *wink*
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Get real about your needs. This isn’t the exciting part, but it’s essential. Figure out how you’re going to take care of #1 when the security of a day job is gone. Know what numbers you need to hit, and have a plan for getting there.

So that’s my story, babes.

I truly hope this post helps you and inspires you—and you get a gold star for making it all the way through! I’ll have more to share as I progress on my own path. This story is ever-evolving. For, now I would love to hear about your experience!

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