When Should I Quit My Job to Pursue My Business?

How Do You Know When to Quit Your Job: The Breakdown to Full Time Entrepreneurship You Need

Note: This post may contain affiliate links.

After almost two full years of asking myself “When should I quit my job,” I am a full time entrepreneur (and I’m only 26). Woah. That feels almost surreal to say. Maybe because, as I start to write this, it is only day one of being able to say it. Why did I become a full time entrepreneur? For one, so I could have enough time to write this for you!

Table of Contents

My Backstory

I have been working since I was 12 years old. First with my dad in his hauling & moving business (so maybe I was predisposed to entrepreneurialism?). Then at my family farm milking cows and chucking hay.

Around 18, I transitioned from cows to dogs and started working in a doggie daycare. Then a pet store, and back to a doggie daycare again (What can I say, I love dogs; sue me). This love (and knowledge) of dogs helped me become Kennel Manager within 1 year and Doggie Daycare Manager within 2 years. I have been manager at my most recent job for the last 3 years.

Amidst handling the responsibility of managing someone else’s business, I continued owning my own while creating a second. These two passions work off of one another quite nicely. I started a dog sitting business in 2014 (when I first transitioned into the dog world) and a personal development blog in 2020 (amidst a global pandemic).

If one quote can sum up “becoming an entrepreneur,” it is this:

It takes 10 years to become an overnight success.

Today

This past year has catapulted my business, “Handful of Leashes,” to a new dimension (at least in comparison to all years that preceded it). So why not hit the gas?

Well, with the mind of an anxiety-ridden perfectionist, there are tons more thoughts centered around “Why I shouldn’t quit my job?” then “Why I should quit my job?”

I fought with the idea of quitting my job managing a doggie daycare for about a year or two before I actually did. I’m going to walk you step by step through:

What my biggest motivators were
What was holding me back
My reasons for finally making the jump
What you can do if you are struggling to know how & when you could do the same

Just for reference, yesterday was my last day at a job I have had for 5 years.

My Motivations to Quit

Before I jump into what was holding me back from making the jump, I thought it would make sense to start with what got me thinking it may be a plausible (and enticing) idea. Because if all I had were objections to the idea of me going full time, the question of when I should quit my job would have never surfaced.

So here are the reasons that started to really open me up to the daily, internal conversations of “Should I stay or should I go?”

Hustling Was Hurting My Health

I used to go to the gym 4-5x a week. I was the healthiest I had ever been. The more I went to the gym, the better I wanted to eat. The better I ate, the better I wanted to take care of myself. It was a snowball effect.

But that snowball can go down different hills and as my business was growing and I was still working my other job, something had to get cut.

The gym was the first thing on the chopping block.

I wanted more time for healthful decisions throughout the day (without having to always tackle a bootcamp before a 14 hour day between both jobs – which I did for about a week or so before I started then cutting back on sleep).

Hustle culture is detrimental to your health longterm and I knew I needed to find a way to work smarter, not harder.

Personal Life / Emotional Wellbeing Was Lacking

Some of my favorite activities include:

Journaling
Socializing
Getting dinner with friends
Going to Folk Festivals
Absorbing some vitamin D while laying on a trampoline
Walking around the farm
Reading

But I wasn’t getting much time, if any, to do these things. 3 months ago, before I really started questioning when I should quit my job, I wrote in my journal that all I want right now is “Peace” and “Balance.”

a journal entry from when I was questioning when I should quit my job

You cannot have balance if “work” is heavier than “rest.” I was sitting, heavy on a seesaw, while “rest” was on the raised seat ahead of me.

I needed to lose some “weight” to achieve that balance.

My Support System

Y’all, don’t underestimate the value of a kickass support system.

My Significant Other

For one, my boyfriend is a literal angel from above.

me and jack, my biggest supporter when I quit my job

When I ask him how much money he thinks I should be making in order to quit my job he’ll say $1,000. He knows I haven’t had a month lower than that in over a year. You see what he did there?

He doesn’t care about my money, he cares about my happiness. Disclaimer: I am better with money then he is so he may be downplaying the severity of needing money to be a functioning adult, but I find it endearing when it comes to him pushing me to purse my greater purpose.

Take, for instance, me starting my blog. Because I was working my job, while running my own business every week, he knew Saturdays were a big morning for me to work on my blog. He started waking up at 6 AM to do our grocery food shopping and would come home with a Wawa coffee fit for me to sip while blogging as soon as I woke up. He made it almost impossible to not love every minute of what being an entrepreneur is all about.

I am eternally grateful for all his support, kind words (“I am so proud of you.” “Your business is doing amazing.” “That’s so cool that you learned how to do all this; it looks so good.”), and bragging to his mom, coworkers, and friends. He has helped me believe in my own business, capabilities, and potential.

My Friends / Family

For two, my friends and family are the absolute best.

They have always made sure I knew what a hardworking person I am and that if I wanted to do this, there’s no holding me back.

One of my friends recounted: “You’re going to do big things. You want to know how I know? Because you are Heather F-ing Garges.”

Seriously, if you don’t have a circle that is centered around building each other up, find a new circle. It is one of my biggest flexes.

3 best friends supporting one another as one quits her job

Manifestation Was Working

For anyone who doesn’t know what Manifestation is, I have a JUMBO blog post on it called: “What is Manifestation? Your Ultimate Resource.” Give that a peek and then read on, friend.

But yes, my manifestations were working.

When it comes to manifestation, you need to leave space for things to grow. In my case, I was leaving Fridays – Sundays off from my other job. I left it available to dog sitting clients (since Friday – Sunday is primarily when owners go away for little weekend trips).

a red SUV driving towards mountains on a sunny day

When my dog training really started to take off, I knew I needed to make space to tell my subconscious mind “I believe my business is popular and ever-growing.” I added Wednesday as another day off.

Almost instantly, I started getting new clients.

It became clear that it was only a matter of time before I would have to pull back another day. This thought became a motivator in potentially quitting my job.

I Was Hitting Almost All My 1, 3, 5 Visions

In August of 2020, I wrote up my 1, 3, 5 Visions (another manifestation practice I love). It is the practice of writing down goals you would have liked to accomplish in the next 1 year, 3 years, and 5 years, somewhat stacking off of one another.

goals are easiest to write out 3-5 years into the future

You write them knowing that they may change as you grow. However, in this moment, this is what you would love to see for yourself in those 3 time frames.

This was what mine looked like in August 2020:

my goals I wrote last year before quitting my job

This is what mine looks like now in May 2021:

my goals I hope to consistently keep hitting even when I quit my job

As stated above, goals change. I ended up going with Laser Hair Removal as opposed to electrolysis and the idea of having a child in the next 3 years doesn’t seem as much a “goal” now that my business has been so fulfilling and I haven’t worked out a schedule to where I could balance mom life / business owning at this point. I’m pleased with the things that have already received a green check mark in the last 9 months.

Only 9 months? Yes, I am not even at year 1 and I have hit things in my year 5 range. This is why writing down your goals and taking aligned action towards each one is so important. It expedites the process.

I thought to myself “If I could hit so many goals this fast, while working two jobs, imagine if I quit my job and I put all my energy into one.”

My mind was telling me it may be time to hyper focus and double down.

I Have Too Much Potential

… to stay locked into a comfort zone. Because that’s what my job was: steady income, fun dogs, same people every day. I was comfortable there, but no one grows in comfort zones.

If change was comfortable, everyone would be doing it. Everyone would be quitting their job. Everyone would pick up a hobby and make it into a career. But not often do you see it done in practice… because it’s unconventional and potentially unsteady.

I also knew if anyone could do it, it’s me.

I wanted to see how much my potential was still untapped.

I'm going to reach my full potential when I quit

My Business Was Being Stunted

By having another job, I felt obligated to keep my efforts in my own business at bay. If I were to start making advancements to get tons of bookings or inquiries, where would I be able to fit them into my schedule?

I knew I would get unnecessarily stressed if I started receiving calls, emails, and dates and couldn’t fulfill them. So I remained quiet. Letting my business coast on by when there was so much more it was capable of.

By not quitting my job, it was becoming evident I was choosing security over inevitable growth. I didn’t like that.

Didn’t Like Asking for Financial Growth, I Wanted to Create it Myself

When you work any job, the amount of which you get paid isn’t in your hands. Sure, you can make efforts that highlight your strengths and (hope) that grants you a nice dollar or two validation. Even still, you are only getting a piece of your own pie. If your efforts make $25, you get $2. That’s just how it works.

This internal dialogue wasn’t serving me and I wanted a bigger piece of the pie (especially if it’s pumpkin). I want my earnings to greatly reflect the:

Type of person I am
My hard work
My reliability
How personable I am
Strengths in all things dog, personal development, organization, and resourcefulness

I felt it was time to stop asking for money and simply attract it.

a pumpkin pie because I want more of the pie when I quit

What Was Holding Me Back?

Funny enough, even with tons of motivators, I was frozen in time for 1 to 2 years. And even with so much confidence in my ability to create wealth, find fulfillment, and let go of my old comforts, they were also some of the biggest factors holding me back.

Money

Am I Making Enough to Quit?

I think this is everyone’s most popular roadblock in ANY big decision, so let’s start here.

I asked 20 of my closest friends and family: “How much money would you need to make in your own business a month in order to quit your current job and go full time?” Essentially I was slyly asking them “When should I quit my job?”

Almost all of them said either “$1,000 a week” or “$4,000 a month.” (You can tell which of my friends are good listeners and heard the question as it was asked). I told each of them, “Yeah, that’s around where I thought to.”

a graph showing how much money I would need to make a month after I quit my job to live in each state — How much money you need to make a month to afford rent in every state

I said that to all but one friend, the one who said: “Probably $10,000.” I lashed back “What? That’s what you would need to make in your business to know you should quit your job? Are you worried you don’t have what it takes on your own?” He then proceeded to say “If I owned my own business, I would need a shop and very expensive insurance.” He was referring to opening a mechanic shop. Lots of overhead. I understood his point of view. His response, that originally sped up my heart rate, ended in a sigh of relief: “I don’t have nearly as much overhead in my business.”

Okay, so now I have an average of what I “should” be making to quit my job (omitting the outlier of $10k).

What Was I Making?

Okay, time to get super transparent. If I only base my income off the year I made the decision to go full time, this was my monthly gross income (before business expenses):

Month	$	% of AVG ($4,000)	Fraction of AVG ($4000)
Jan	$1400	35%	1/3
Feb	$1900	48%	1/2
Mar	$3200	80%	3/4
Apr	$2600	65%	5/8

I have never once hit the goal of the most popular answer of when I should quit my job: $4000 / month.

This was something holding me back.

What If I Can’t Afford to Move Out?

I am 26 years old. I live at home with my parents. Before you go judging me (which is mean *sticks out tongue*), I live with my whole dad’s side of the family on my 236 acre family farm in PA surrounded by beautiful animals and nature. We do everything together and I love them dearly… oh, and money. Money is a big part too.

I know what you’re thinking: “You still live at home, and you seem like you got a good head on your shoulders, which means you’re probably a saver.” Although it is wrong to make assumptions, you are right. I do all the “right” things, I:

Put money into my savings every month
Invested a pretty penny into Bitcoin when it was only at $8,000 a coin
Am a pretty frugal spender (fetching most of my clothes from thrift shops and entertainment from nature – which is thankfully free)

But it’s still not enough.

You know the quote: “Give a man to fish, feed him once. Teach a man to fish, feed him forever.”

I think that is where my hang up is.

I want to be self reliant after I quit my job

By having a lot of money in savings, but not a lot of money coming in each month, it emulates getting given a fish but not knowing how to consistently and abundantly receive fish / money each month to sustain a life outside of my orange, Christmas-light-lined bedroom in my parent’s house.

This was an extension of my fear of not making enough money in my own business to quit my job.

This was something that was holding me back.

a man's hand next to 6 fish on his tailgate

What if Everyone Stopped Using Me / My Services After I Quit?

Let’s face it, dog sitting businesses have highs and lows.

Highs – Holidays, summer weekends, and the occasional fall wedding
Lows – Post-Holidays, most of fall

If I were to bank on dog sitting services alone to carry me through, I would be a nervous wreck. There is no consistency and that’s why I was so thankful when Covid-19 yielded so many puppies.

The training portion of my business, which I’ve had for 3 1/2 years at the point of writing this, blew up. I have worked with so many adorable pups working through leash manners, crate training, overexcitement at doorways, etc. You may be thinking, “That awesome, Heather. Doesn’t this solve your problem of inconsistent income?”

Yes and no (there’s always got to be a catch). Yes, because now I can see my families once or twice a week on a weekly basis, but the whole goal of training is to train a well-behaved dog. Meaning, at some point, the goal is to not need to see me every week.

Although irrational, my thoughts went to “But what if all my clients get what they need, love their results, stop booking, and no one calls to fill those spots?”

This was something that was holding me back.

“When should I quit my job” turned into “When there is absolutely no opened ended questions in how many clients I would have at any given time.”

fear I wouldn't have clients after I quit

Losing Steady, Predictable Income

When it comes to my own business, as stated before, income fluctuates depending on a myriad of things.

When it comes to working for someone else you get paid an hourly wage multiplied by the amount of hours you work and get paid every two weeks.

Predictable.

Steady.

Comfortable.

If I want more money, I work more hours. If I want more time, I work less hours. But you can never seem to have both.

Cue “Entrepreneurism” stage left. If you play your cards right, you can have both money and time but, as stated earlier, this takes time & money to build a foundation which you can stand alone on.

Fear of not having enough STEADY money was keeping me locked into a comfort zone, afraid to quit my job.

This was something that was holding me back.

a game of jenga with coins stacked on top of the game

Structure

I Am Going to Go Nutty Without the Structure

You remember, March 11, 2020, the day the world shut down (and ironically also my 25th birthday). Ahh, if I had known that day of bar hopping with my family would be the last, I really would have breathed it all in (maskless and unafraid).

That was the last day of uninterrupted human interaction. From that point on (for me at least), I was completely locked in and locked down. The global pandemic that had affected each and every one of us was a joy to me… at first.

My job was closed for 3 months. I spent the first 1 ½ months doing something I had been dreaming of for the last 5 years. I started a personal development blog. That’s how I’m talking with you right now, cool right?

I taught myself how to use WordPress, how to make edits using both HTML and CSS, and made sure to have at least 6 hearty blog posts written and posted before “going live.”

The Proof is in The Pandemic

And then hysteria set in. Okay, that sounds a little intense, but that’s pretty much what it felt like.

I could sleep in every day and there was no consequence.

Eat ice cream at 1 PM on a Tuesday while binging dog movies that make me cry and there was no consequence.

I could play Animal Crossing for 9 ½ hours straight and no one would bat an eye… because they were all doing the same thing.

I started craving normalcy. I felt structureless, which, in turn, made me feel purposeless. So much of my self-proclaimed identity has been centered around how much I accomplish and strive for on a daily basis and there was no need for it because, again, there was no consequence for not doing anything.

SpongeBob meme of not knowing what to do during quarantine

This mid-quarantine crisis gave birth to “33 Intentional Ways to Utilize Free Time During Self-Isolation.” I didn’t want anyone to feel the way I did during this time and, honestly, if you use this guide post-quarantine I really think there is still so much to gain.

Despite this fun feet, I was excited when certain restrictions were lifted and I could go back to work.

The fear of re-enacting the loss of structure during a time I was away from the clock in / clock out lifestyle was anxiety-provoking for me.

This was something that was holding me back.

What If I Become a Lazy Entrepreneur After Quitting?

I don’t know if that’s even a thing and I don’t think it should be because there is so much background noise the average business owner has to muddle through. However, I still couldn’t help but feel like “… But what if I’m the first person it applies to?”

a girl laying on her couch after quitting her job

I feel like the allure of being an entrepreneur is fierce:

I’ll have time to go to the gym each day
I could grab a bite to eat with a friend around lunch time in the middle of the week
I’m going to get to see my live-in god daughter so much more throughout the week
I’m going to buy a bike and start to do more of that. (Which I did, this is the one I bought)
I won’t have to rush to shower after a 14 hour day and could take baths any day I please
I could read after breakfast, lunch, and dinner

Doesn’t this all sound nice?

But doesn’t it make you wonder “Well, when the hell does the entrepreneur actually work?”

My thoughts exactly!

I was fearful that “What if the allure of being an entrepreneur sucked me down a rabbit hole of just having extra time to sit around or socialize.” This thought process caused me to think “Well, if I’m just going to be sitting around anyways, might as well keep managing my doggie daycare to keep making money while growing my business.”

This was something that was holding me back.

a girl yawning while holding a computer mouse

Where Would I Even Work?

You’re probably thinking: “Your room?” And I understand why. When you live at home with your parents, your room is your bedroom, living room, office all in one… unless your boyfriend is a night shift diesel mechanic.

Jasper works from 7 PM to 9 AM five days a week. Which means he sleeps in our bed from 11 AM to 7 PM, with the lights off, black out curtains drawn, and a desire to not share a room with the literal energizer bunny (me).

I’ve tried to manage the situation: spent an entire 3 day weekend scrubbing and reorganizing my bathroom top to bottom and setting up a pop-up desk in there on an “as needed basis.” I felt like Jeff Bezos, creator of Amazon, in the early days. That lasted a day. An 8 person household tends to yield a lot of bathroom breaks (and toilet paper).

Jeff Bezos working in his rickety amazon office years ago when he quit his job

I thought “What is the point in quitting a job to have more time to work on my QuickBooks management, doing virtual training lessons in the AM, and creating content for both Handful of Heather (hello) and Handful of Leashes, if I don’t even have a place I can do so?”

I put the plausibility of me leaving my job into my boyfriend’s hands: “Maybe I’ll just wait until you find a day shift job before leaving?”

This was something that was holding me back.

My Business Isn’t Ready to Go Full Time

When you think of any business you think of their logo, their color scheme, their tagline, their uniforms, etc.

Guess who doesn’t have any of those just yet?

*Raises hand*

I have business cards, a social media presence, and a website (with no blog posts on it yet).

We’ve all heard it (or in my case, said it): “Start before your ready” … and I did. But did they say to quit your job and go full time while still at the perceived “starting line?”

This was something that was holding me back.

Emotions

I’m Going to Miss My Job / The Dogs / My Coworkers

For anyone who doesn’t know, a doggie daycare is a space (usually indoor and outdoor) that houses anywhere from 30-60 dogs of varying breeds, sizes, colors, and play styles… And you get to play with all of them, all day, without their owners. If this sounds like heaven on Earth, I bet you now understand my hesitation in putting in the notice of my leave.

Yes, there are rough days:

Barking (bless Bridie’s heart)
Emotional drain (you are dealing with 30+ living creatures)
Temperament balancing (not all humans like one another; we can’t expect the same from dogs)
Difficult phone calls (yes, some dogs do get kicked out of daycare)
Preventative Management (keeping staff safe, preventing dog bites, teaching dog psychology)

BUT, you can’t help but overlook most of those pitfalls when you get to spend your days in a pile of thee most loving creatures on this planet (don’t fight me on that).

The idea of leaving them to seek higher fulfillment in my own business seemed filthy or selfish.

Plus, my best friend Dory worked with me and given our schedules only lined up to work on Mondays, those Mondays were cherished. How could I leave her behind without her trustee manager and friend (this is where she would probably interject and say she was “going to miss her friend” part way more).

This was something that was holding me back.

I’m Going to Lose Trust / Credibility When I Quit

I not only work at a doggie daycare, I manage one. I am the head honcho at a dog based business outside of my own. This raises dog owners’ trust in my love of dogs and consistent immersion in their psychology.

I feared that quitting my job and “just” being a business owner of a dog based business would lower my credibility.

I feared that without that backbone of a “real” job that my job would fall short of trust.

This was something that was holding me back.

I Quit Anyways

On April 5, 2021, I gave my notice that I would be leaving my job and becoming a full-time entrepreneur. For anyone who remembered what my last day was earlier in this post (which, honestly, if you remembered that, I’m surprised), it was May 3rd.

I gave a month’s notice. In that month, I helped hire and train the new doggie daycare teachers, set up the new manager to take on the role I’ve had for years, and gave my boss plenty of extra time to straighten out anything he may have needed. I was generous because this was a hard decision and I think I needed the time to process the “loss” of who I was for the last 5 years: a staple of a business that added to my identity as a dog based business owner.

What Changed?

My mindset… and the weather (honestly, sunny weather truly is the physical representation of a mindset shift).

I had started working with a life coach, Hailey Curtis, and I brain dumped all of the doubts I just shared with y’all onto her (don’t worry, it’s her job and she gets paid nicely for her services). We spent the next 2 calls breaking down each doubt, finding questions to debunk their validity, and then came up with a range of dates that would be best suitable to give my notice.

I knew if I would have waited until after the summer (the most fun time to work at a doggie daycare and the busiest point in a dog sitting business) to quit, I would have bargained with myself: “I’ll just work one more winter since I’m slow anyways, and then quit before next summer.”

But I knew it would have been my third year in a row doing that and mama, don’t like to give 3 chances for the same wrongdoing. That’s the definition of insanity.