You Don’t Have to Quit Your Day Job

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Be an original and do things differently–but limit your risks.

This last week, I took a trip to Minnesota, and on the plane ride from California, I pulled out my Kindle and started reading “Originals” by Adam Grant. I had every intention of reading the entire flight, but I only made it past the first chapter before I was inspired to write this blog post.

I don’t want to talk about the actual book or the concept of”Originals” (though, it’s a good read so far!), but I do want to talk about something Grant said, and how doing something that doesn’t conform with the world around you involves taking risks–but not as many risks as you’d think.

When chasing creative success, a lot of people often have the idea that they need to go big or go home. Commit to the dream or inevitably fail. Grant wrote about notable cases of success over the years that involved original thinkers/non-comformists succeeding while still minimizing risks.

He wrote about well known originals like Bill Gates, Steve Wozniak, and the founders of Warby Parker who didn’t abandon their “safe” jobs and life plans to pursue their new concepts until momentum was already building.

Instead of quitting everything and jumping head first into their projects, they balanced both safety and risk until the risk became more stable. You don’t have to be a huge risk taker to be an original. In fact, those who minimize risks can find more success in their fields.

The Ultimate Creative Risk

So let’s talk about the biggest risk a creative person may deal with: Quitting your day job and depending on your creativity to pay the bills.

The desired outcome is to actually have enough money to pay the bills–the risk is having the math not work in your favor. I’ve had a lot of people tell me this is their goal. It’s a great goal to have–but does your day job need to be abandoned in the beginning of your journey? Or can you wait until you make enough progress with your dreams so that you can transition slowly from stable paycheck to dependable entrepreneurship?

Can you make the numbers work?

I love spreadsheets. To me, nothing is more comforting than seeing my life laid out in concrete numbers. I am risk averse. I do what’s safe and I calculate the pros and cons of just about every situation I enter. From career changes to driving in a snow storm. I don’t blindly jump into a situation I know nothing about.

If you are considering quitting your job to chase your creative dreams I want you to look at your life right now. What are your expenses? Do you have a family to take care of? Do you have a mortgage to pay for? Do you need healthcare? All of these things should be addressed before you even consider abandoning that stable paycheck to chase your dreams. It can all feel very overwhelming at first, but look at your expenses. Start calculating what areas you can cut down. Trim away anything that you don’t NEED. Compare your total expenses with your current income and savings.

Can you make the numbers work? Can you minimize the risks in your life?

You DOn’t Have to Do What Everyone Else Does: Make your own plan

I encourage you to make a plan. One of the scariest parts about abandoning your job is figuring out where your next payday will come from, but having a plan decreases risk.

How far along in your creative career are you? Do you have any sources of income that can grow? Include this in your spreadsheet. How many art shows can you do on the weekends? Do you have a savings built up that you can pull from as you progress? Do you have a partner or roommate that you can make a deal with?

Think of all of the possibilities of replacing your day job income and put it on your spreadsheet. How do the numbers look now? Probably still a little scary. Which is why I say: You don’t have to quit your day job.

You don’t have to go big or go home. You don’t have to focus all of your energy on your creativity. You can succeed creatively while still maintaining a sense of safety in your life.

Consider these 4 things before quitting your day job:

1. Balance your energy between creativity and income

When aspiring actors move to LA, they become waiters, bartenders, and fill other service positions. It’s not because they suck at acting or don’t have any other skills, it’s because they are balancing their energy/time output and their need to pay the bills.

If you want to pursue a creative career, how can you find a sense of safety while working on your dreams and still have enough energy to do creative work?

Maybe your current 9-5 job is too exhausting and leaves you with no energy to even think about your dreams when you get home. You don’t have to keep that job. Find something that gives you a paycheck and doesn’t sap your energy. There is no shame in working a service position or part-time gig. The only thing that matters is giving yourself a balance of time, energy, and money to pay the bills.

2. Don’t ask too much of your creativity

I have to point to another book here. “Big Magic” by Elizabeth Gilbert. I don’t remember where in the book, and I don’t remember the exact quotes, but Gilbert writes about how unfair it can be to put expectations on your creativity to make money.

How asking so much of it can actually push it away. I can confirm in my own life that the moments where I need to produce something in order to make money are the least enjoyable creative exercises for me. The moments where my creativity wanes and the pressure to produce waxes can feel soul crushing.

Some people thrive under pressure, but many people like me crumble. In order to nurture your creativity, sometimes it’s best to take away the burden to make money. Take the pressure to create away.

If you quit your day job, how much pressure will that add to your creative process? How will that pressure change you and how much you enjoy what you do?

Maybe you will be the person who always has a day job. Maybe your creativity is there just for you. Maybe down the road it will take off and suddenly become your main source of income. There is no wrong way to be a creative person, but if you find that pressure to create makes you miserable and unproductive–then don’t quit your day job. Remove that burden from your creativity.

3. Life informs your Creativity

Another reason why you don’t need to quit your day job is that creativity needs fuel, and life is like gasoline.

If you are a writer, you may have noticed that you need to experience life to really flesh out what you write. Work places expose us to different people, situations, characters, and problems to solve. Sometimes a day job is exactly what we need to inspire and inform our creativity.

Instead of quitting your day job, look at how it can actually fuel you. This is the same for anyone considering quitting school to chase a dream. I may have quit the art program in college, but I shifted my focus to other areas that would still feed my creativity. How can you do the same?

4. Do you just need to rest?

You may be wondering why I’m encouraging you not to quit your day job to pursue a creative career, when I did that exact thing. I know I’ve mentioned this before, but when I quit my last full time job, it wasn’t because I so desperately wanted to just focus on my art. It was because I was deeply, dysfunctionally depressed. I started to have panic attacks at my work desk. I couldn’t focus on simple tasks. I was stressed and unhappy and I simply couldn’t be a productive employee much longer.

I used art as an excuse, but I knew I needed to just stay still for a moment–a week, a month, maybe even a year. I would tell people I was going to focus on art, and in a sense I did, but I didn’t have any real plan to make it a business. I just needed to make myself feel productive while I healed my mind, and so I painted and shared it with the world.

If you have dreams of quitting your job and working on art all day–is it because you are so fired up about your craft and you have a plan to make it into a business? Or, do you just need to rest (or maybe even find a new job)?

Mental health is talked about a lot these days, but not enough. There are so many of us that struggle with daily life. It’s perfectly fine to dream about an escape and to think about doing art all day. It might be exactly what you need. Just do yourself a favor and remove the pressure to make money from it. I can speak from experience that the pressure to make money while healing can just perpetuate the negative health state you’re already in.

If you need a rest, then take one. Truly. Use art as therapy until you feel whole again, and consider finding a new job that isn’t as mentally taxing if you aren’t financially able to take time off.


You don’t have to quit your day job in order to succeed as a creative person. Take a look inside of yourself and see what YOU need in order to take care of yourself and your creativity and carve your own path. Day job, side hustle, part time gig, or whatever–just do what’s right for you and take care of your responsibilities.

Please leave questions and comments below while commenting is open or reach out to me directly through Instagram or email. I’d love to hear from you! Make sure to sign up for my email list below to never miss a blog post. New posts are published every Tuesday. And if you’d like to see more content like this in the future, consider becoming a Patron of mine! (See details below.)


Do want to help me create more blog content? I want to keep providing content like this for free, but I need your help. If you enjoy my blog posts and gain any inspiration from the content I put out there, please consider becoming a Patron of Messy Ever After on Patreon. Pledging just $1 a month enables me to keep helping artists like you. Plus, you get extra little perks!

Further Reading:

How to Move Past Failure and Believe in Yourself

How I keep moving forward after my many many failures.

When I was a kid, I believed I could do anything. I would happily sing Spice Girls and imagine myself being equally famous some day. I ran around the yard and mixed potions out of collected rainwater and colorful leaves, dreaming of being a scientist–or a witch. Both were viable options. When I experimented with my own apple cinnamon muffin recipe when I was nine, I fully believed I could run my own bakery in the future.

When I started skateboarding when I was thirteen I imagined becoming pro. Same with snowboarding. Never mind the fact that I had few skills and a very VERY low pain tolerance. (I’ve still got a scar on my hip from a graceful belly flop onto a sidewalk…)

I dreamed about all of the different lives I could choose for myself. I didn’t see obstacles. I didn’t see limitations. I saw a thing that I enjoyed doing, and a vision for what life would look like if I pursued it. I was also having a fantastic time.

I believed in myself. And–

Believing in yourself is the most important thing you can do to move past failures.

I didn’t succeed at any of those dreams (yet). You could say I failed at every one of them if you look at the definition of failure as a lack of success. You could even say that I’m failing at my current dreams depending on how you look at it. A few recent failures prompted me to write this post. I found myself looking at job listings online, because maybe, just maybe I should explore other non-creative career options.

But that lasted all of ten minutes, before I started giving myself this pep talk and turned it into a blog post.

Many of us fear failure, as if it defines us or is a permanent state, but I define failure as accepting an unexpected outcome without further action. So if I applied for a job for someone else and gave up on this whole creative pursuit of mine–then that would be failure.

You’re going to fail many times in life. A lack of success happens over and over again. The important thing is what you do after each failure and how you convince yourself to keep moving forward.

And that’s where the belief in yourself comes in.

Three Reasons Why You Need to Believe in Yourself:

  1. Belief fuels you to continue moving forward.
  2. Belief makes the present moment more enjoyable and worthwhile.
  3. Belief turns failure into opportunity.

Belief is a catalyst. If you belief you can do something, you are pushed to pursue it. You are charged up by the pursuit of a possibility. It doesn’t really matter what exactly you believe you can accomplish, and it doesn’t matter if you ever reach your end goal. Just having belief that the future will look the way you want can make every mundane and arduous task ahead of you seem more enjoyable.

Believing in yourself assigns you a purpose. It makes everything you do have meaning.

What happens when you don’t believe in yourself:

  1. You don’t move forward (because what’s the point, right?)
  2. You may depend on others to hold you up and encourage you.
  3. You abandon your dreams before you even try to reach them.
  4. You don’t enjoy the present moment.
  5. You internalize failure.
  6. You become a pessimist.

If belief in yourself is a catalyst that moves you forward, a lack of belief will hold you right where you are. Look at all those unpleasant side effects of not believing in yourself. Are you ready to believe?

How to Believe in Yourself Right Now and Move Past Failure

I spent a long time not believing in myself. I lost the thirteen year old skater punk, and the nine year old baker and became a pessimist for years. For the last three years, I have been rewiring my brain and have worked hard at reclaiming my belief in myself. Now, I’ll share with you how I’ve done it.

1. Challenge your negative confirmation bias.

When I was a pessimist, I was always looking for proof that I sucked. Proof I couldn’t succeed. Total confirmation bias on my part. I believed I couldn’t succeed, so I found evidence that supported that belief everywhere I looked.

I had to turn off this thought pattern. The first step was recognizing when my brain latched onto a negative belief, and then saying “Whoa there, Kelly. You don’t have to think this thought.” or “Whoa there, Kelly, why are you searching for jobs that you know won’t fulfill you?!”

Recognize when you are following this thought pattern and stop it in its tracks. Overtime, you can replace this with a positive thought pattern and train your confirmation bias to work in your favor.

If I tell you to notice the color red, you’ll start picking it out in the environment around you. If I tell you to see all the areas where you are succeeding, you’ll do the same. Don’t tell your brain to see all of your failures.

2. Realize you don’t need proof to believe in yourself.

You don’t need to know you will succeed to believe you can succeed. Knowing and believing are two different things. Belief needs no evidence.


You don’t need anyone to tell you what you’re capable or incapable of doing. Though, if you meet someone who excitedly encourages you to do the things you love and makes you feel like you can take on any obstacle in your way, keep them around. Those people are the best. Just don’t depend on them to replace your inner belief.

3. Do what a person who believes would do.

Remember when I said a lack of belief holds you back and belief moves you forward? Belief may be a catalyst, but you can still move forward without consciously believing in yourself. It just takes a little more work.

Our brains are big and powerful, but sometimes our conscious mind is a little slow to pick up on the benefits of positive habits. You don’t have to think “I can do it!” You don’t have to have mantras or sticky notes on your mirror with affirmations. You don’t have to gush positivity. You can start by simply taking the same step that a person who does believe in themselves would take. It’s a little “fake it ’til you make it”, but I stand by it.

If you want to run a marathon, but don’t believe you can, what would people who believe in themselves do? Get out of bed early and run? Do that.

What would a painter who believes they can make a living from their art do? Find the person doing what you want to do and mimic their actions. Let their belief carry you until yours develops.

4. Take power away from “success”.

Success isn’t everything. One way to prevent the sting of failure is to take the power away from success. Don’t hold tightly to your expectations. For example, if you want to learn how to draw hyper-realistic portraits, start by learning the basics. Break your goal down into the smallest tasks you can and build incremental success. Don’t expect to achieve your main goal right away.

Sharpen a pencil. Get out a pad of paper. Find a reference photo. Put the pencil to paper. Draw a single line. Draw another line. Shade over here. Shade over there. Don’t psych yourself out by thinking you have to draw technically perfect portraits right away, or even at all. Focus on the actions you can complete right now and don’t focus on your expectation for the end.

Recognize each task as a moment for success. Sharpen a pencil=Success. Draw a line=success.


Alright, I’m feeling sufficiently pepped, and all job hunting browser tabs have been closed. I hope you enjoyed this post and found a little encouragement to believe in yourself as well! What’s the worst that could happen? 😉

Please leave questions and comments below while commenting is open or reach out to me directly through Instagram or email. I’d love to hear from you! Make sure to sign up for my email list below to never miss a blog post. New posts are published every Tuesday. And if you’d like to see more content like this in the future, consider becoming a Patron of mine! (See details below.)


Do want to help me create more blog content? I want to keep providing content like this for free, but I need your help. If you enjoy my blog posts and gain any inspiration from the content I put out there, please consider becoming a Patron of Messy Ever After on Patreon. Pledging just $1 a month enables me to keep helping artists like you. Plus, you get extra little perks!

Further Reading:

Why You Need to Embrace Boredom as a Creator

Do we waste our boredom on technology?

Last night, I was mindlessly scrolling through Facebook and I saw a post about a public art installation. Funny enough, the installation was a sculpture that criticized our dependence on technology. As I stared at a screen, I couldn’t help by giggle. I’m sure you’ve heard countless people say that we are addicted to digital screens and that it’s a problem.

Well, I say we are addicted to curing boredom and digital screens are just an easy remedy.

Whenever I sit down to do a boring task, I feel an itch to look at my phone. Have to respond to emails? Let’s check Instagram instead. A new blog post needs to be edited? Facebook time! Need to edit photos and add inventory to my shop? Hey, I wonder what external hard drives on Amazon run for these days…

Boredom isn’t something new. People have been bored for over a millennia. Our current addiction to technology is just another way to end the discomfort. Just like reading books or playing sports and board games do. Our brains want to be stimulated and distracted, because boredom is really uncomfortable. I remember going to my mom as a kid and complaining I was bored, just like I would complain I was hungry. The feeling was unpleasant and I wanted it to end.

Boredom feels like mental hunger, and we want to consume anything we can to feel satiated, but I’m here to tell you that boredom is a fricken super power for creative people, and a little discipline with boredom can unlock a wealth of creativity.

Boredom is a catalyst for creativity.

If you were alone in a room with white walls, white ceiling, white floor, a white table, a white chair, and a phone with WiFi–what would you do? Sit there quietly with your thoughts? Maybe for a bit, but you’d eventually pick up the phone and cure your inevitable boredom, right?

If you were in the same room, but replaced the phone with a green marker and permission to use it on any surface in the room, what would you do? Again, sit there quietly with your thoughts? Or would you take that marker and go to town on all the surfaces available?

When I was in school, I doodled on my notes in class. I didn’t have a phone, so drawing was my next best distraction. Eventually, those doodles would turn into an idea for a new piece of art, and then I found myself drawing even when I wasn’t forced to sit in class.

When you are bored, your brain is going to latch onto the fastest and easiest method to end the torture. This just happens to be our phone most of the time. Though, if you learn to use new tools to end your boredom, you can jump start your creativity instead of just mindlessly scrolling through the same three social media apps for hours.

Boredom is only temporary.

Boredom sucks. I know, but it doesn’t last long. Imagine the white room again. How many seconds would it take before you picked up your phone? And if you didn’t have your phone and only had that green marker, how many seconds until you uncapped that beast and started drawing on something?

I bet you’d do it in less than two minutes. That’s only 120 seconds of discomfort before your brain finds something to end the boredom.

Anytime I walk into an office to wait for an appointment, I always check in at the front desk, and then right after I sit down in the waiting room I have my phone out–probably within 15 seconds of sitting.

My brain: I’m bored. Oooo, phone!

And the boredom is gone–but so is my potential to create in that moment.

I want you to be bored and I want you to be intentional with your boredom. The discomfort won’t last long and if you point your boredom at creativity, the benefits will be amazing! I’ll show you how I do it.

How to Jump start Creativity with Boredom

1. Create an environment for creativity.

Remember, your brain wants the easiest and fastest way out of boredom, so you need to control your environment and make sure you give yourself productive boredom-ending tools.

This means you need to create a space in your house, your studio, or in your office that includes as many creative tools as possible. Create a space with all of the art supplies you love using. Have a shelf full of your supplies so you can easily look at them and grab what speaks to you.

Most importantly, this space shouldn’t include the tools and devices that easily distract you and aren’t in the creative realm. Put your laptop in a drawer and hide your phone. If you remove those items from your sight, your brain only has the option to grab a creative tool to end boredom.

2. Schedule time for it.

Boredom should be scheduled like sleep, exercise, and meals. Consider the discomfort of boredom as creative self-care and put it on your calendar. It’s not going to be pleasant at first. If you don’t feel inspired to create and you force yourself to sit in a room with just your art supplies, it’s going to suck, but I promise it will be completely worth it.

3. Fight the urge to find an easy distraction.

Remember my itch to look at my phone? As I’ve been writing this blog post I have been tempted by many easy distractions: An email notification. A FedEx delivery from Blick Art Materials (OMG, I can’t wait to unbox all of the new supplies I ordered!), the hunger in my belly for lunch, and the Amazon tab I have open just to the left of this tab.

Creative work is hard work. The things that easily distract us are not. It’s completely reasonable that we’d want to choose the easy things to occupy our time, but we must fight the urges. For me, I use the easy distractions as a reward for completing the creative work. Once I hit publish on this post, I’m going to stuff my face with food and then open ALL THE BOXES! But not until the moment I’m done.

Fight the urge. Do the hard work first.

4. Disconnect from your devices completely.

Technology is so addictive, because it cures boredom instantly. You open up your phone and you have notifications popping left and right. You have access to social media, games, news, weather, dating apps, and more within seconds.

Give yourself more power over the distractions. Turn off push notifications for your most common time wasters. Give yourself blocks of time where you turn on “Do Not Disturb” or leave your devices in another room.

If you work on digital art, or have a lot of tasks to complete on your devices that are creatively motivated, then clean up your digital work space. Close all programs that aren’t related to creativity and definitely turn off ALL notifications.


I hope this post was helpful and maybe made you look at boredom in a new light. I admit that I am addicted to technology, but it’s not as bad as people make it out to be. If you get rid of technology, we are still going to crave mental stimulation. All I want you to do is use that to your advantage to help unleash your creativity.

What kind of creative messes could you get yourself into if you stuck yourself in a room with only your art supplies? You’d be surprised just how much creative noise your brain can make after a couple of minutes of boredom.

Please leave questions and comments below while commenting is open or reach out to me directly through Instagram or email. I’d love to hear from you! Make sure to sign up for my email list below to never miss a blog post. New posts are published every Tuesday. And if you’d like to see more content like this in the future, consider become a Patron of mine! (See details below.)


Do want to help me create more blog content? I want to keep providing content like this for free, but I need your help. If you enjoy my blog posts and gain any inspiration from the content I put out there, please consider becoming a Patron of Messy Ever After on Patreon. Pledging just $1 a month enables me to keep helping artists like you. Plus, you get extra little perks!

Further Reading: