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Jamie Rea


17 Questions To Ask Yourself Before You Pursue A Creative Career

So what you want to make a living being creative, do you?

Well you are about to sign up for a life of living hell. The lows are going to be low, extremely low in fact. You’re going to second-guess yourself. You will hate yourself. You will tell yourself how awful you are and how much you suck on a continuous basis. You will be your own worst enemy and you will constantly be riddled with insecurity and worthlessness. You will be broke, potentially your entire life. Those close to you will think you’re depressed, reclusive, stuck in a dreamy fog that prevents you from fully functioning in the real world. You will endure all of this, you must if this is the life you want for yourself. In fact, I beg that you go and do something non-creative, anything else, because that way you will be spared from the pain that this life will cause you.

But boy are you going to live. Sure the lows will be low, but the highs will be like ecstasy. You will think you’re invincible, incapable of doing no wrong. You will tell yourself how talented you are, how you have a unique voice that the world has yet to hear, a voice that the world desperately needs. You will be your biggest cheerleader and you will build yourself up and pat yourself on the back when you do good work. You will, because you must. You have to believe in yourself when nobody else will. You may become rich overnight, which is the beauty of the life you have chosen for yourself. You don’t need multiple degrees to reach income brackets, but rather, it’s all about the quality of your work and if what you end up creating has a mass market of people who will follow and appreciate it. Your friends working “normal” jobs will be envious of your passion and wish they had something they loved and enjoyed as much as you love what you do, or are trying to do. For the very fact you have a dream, a passion, you’re already walking a successful path. Remember what they say, “it’s better to be at the bottom of the right ladder, than at the top of the wrong one”.

You’re going to live a bi-polar existence, the good days will be amazing, and the bad days will be gut wrenching and horrible. This is why you must love the work. You must be addicted to the creative process, unwilling to defer your life to anything else. Creative work must be something that chooses you; it must be something you can’t control. You need the creative outlets to express and create the way your mind and soul crave in order to survive and flourish.

So whether you want to be a writer, an actor, a musician, a painter, a dancer, a creative entrepreneur, a designer, a comedian, whatever it may be…here are 17 important questions you must ask yourself before you pursue a creative career:

Why do you want to do it?

This is the most important question to ask. If you don’t know the answer to this question, then you’re just wasting your time.

When you want to become successful at anything, you first have to define your “why”. This way, when you remove all the potential bullshit and hardships you will face, it will always be clear why you want to achieve your goals. If you’re in the business you are in because you crave admiration, acknowledgement, fame, and money, then you are not walking the creative path for the right reasons. Sure you may achieve all those things if you become in the top 1% of your craft, but your motivation must always be because of how good the creative process makes you feel. Again, you must love whatever it is you’re doing. A writer writes because they’re in love with words and telling stories. An actor acts because they love to perform and walk in other people’s shoes. A musician makes music because the language of music is something they understand better than the language they speak. An entrepreneur creates businesses because they want to solve problems and the “entrepreneurial rush” is like crack to them.

Always before you pursue anything in life, establish your why. And that why for people who choose a creative path, is always because they love it and it’s their passion.

Are you prepared to fail over and over again and be bad at it for a very long time?

Nobody knows failure and rejection quite like creative people do. Creative people experience failure on a pretty much everyday basis and are constantly putting their egos on the line. This is because in order to get to the point where you start producing good work, you will have to be bad at it for a very long time. You will have to find a way to persist through those years, despite constant feelings of inadequacy, fear, insecurity, and rejection. Also, failure is a regular occurrence in creative work because you’re constantly taking risks and reinventing yourself — following your instincts and being pulled in different directions that take you out of your comfort zone and require you to stretch yourself further than you think you’re capable of.

Are you prepared to answer the question “So what is it you do again?” a million times over?

The “what do you do for a living?” question has an easy answer if you’re a lawyer or accountant, or something that is easily defined. But often people pursuing creative things, this answer can be much more complicated. Be prepared that people, particularly non-creative people, may not actually know what you do for money, or be confused when you to explain to them. It’s important that you come up with a quick couple of sentences, “I’m an actor, but I work as a bartender to help pay my bills, which gives me days off to go out and audition” in order to quickly counteract all these prying questions. You have to be ready to deal with the fact, that from an outsider’s perspective, it may not seem like you really doing anything with your life for a really long time. That is until you get a major break and people are able to see tangible success with their own eyes. IE. They see you in a movie or on a TV show.

Are you prepared to have your family and close friends continually ask you when you’re going to give up your hobby and get a “real job”?

Those closest to you will support you unconditionally, but that doesn’t mean it won’t be hard for them to see your success. As much as they may believe in you, they might see your odds as being no greater than that “one in a million” talk. So be prepared that while those in your closest circle will desperately hope for your success, they might just be biding the time until you finally cave in and go get a “real job” that guarantees you make a quality living for yourself. You have to remember that success is most often built behind closed doors, so while it may be tough for them to chart your progress, you know that every single day you’re doing the necessary things to bring yourself closer to success.

Are you prepared to be behind most of your friends and peers when it comes to “life timelines” and “life stages”?

When you decide to pursue a creative life, you’re committing yourself to a grind. Success is not going to come easy and it’s probably going to take you a very long time. This means that you probably won’t be able to have a family young, buy a house in the nice part of town, or be in a financial position to provide for anyone but yourself until later on in life. During this time you will have to be selfish; therefore, you may feel like your friends are all leaving you behind while they run off and get married and have babies, and get mortgages, while you’re still fighting to make rent in some rundown accommodation.

Are you prepared to operate with very little security in your life?

Lets face it; the creative lifestyle is a bit of a whimsical existence where there are no guarantees. Projects come together that seem promising, but die last minute. A lot of the time things will come up last minute and you’re constantly flying by the seat of your pants, so you need to have the flexibility to deal with the last minute nature of things. Also, one month or one year you may make really good money, but then not see any income again for months, so if you need the security that you always make X amount of dollars by X amount of time, then the creative field is probably not for you.

Are you self-motivated?

Most people in the business of creating things work for themselves, they’re entrepreneurs, sole proprietors of their craft. The great part about creative business is you often work for yourself and you can work and take time off as you please, but the downside is there is nobody to force you to do the work but you. Also, when you’re trying to build your skills in a particular craft, you will have to become your own inner authority figure and make sure you stay disciplined and do the work, even when you’re hungover and exhausted and it’s the last thing you want to do. So if you don’t have that burning ambition and desire to succeed inside yourself and are able to channel it easily and often, then you probably don’t have the self-motivation to build a successful career in the creative field.

Can you function productively with no work structure?

Some people need the work structure with a big office and multiple employees, or someone constantly telling them what the next project is. A big reason why people pursue creative endeavours is because they don’t like the structure of your typical 9-5; in fact, the mere thought of slaving away for 40 hours a week in some white-walled office space makes most creative types want to off themselves. It’s not a job; it’s a prison sentence. So if you find that you crave and desire the standard work structure that a corporate job gives you, then living the structure of a free-spirited artist may not be for you. You can also get a corporate job that requires you to use your creativity, such as in a marketing or advertising setting, or you can also build a home office and create normal work hours, if you have a hard time functioning using your couch as an office.

Are you prepared to have your work consume your life?

The truth is some people work jobs and then when they clock out at the end of the day, they live their lives. This basically means that for 40 hours of every week, which averages out to be 1,920 hours every single year people are just going to be working their “job” that they don’t really consider to be their “life”, anxiously waiting for the time to pass so they can start being happy again. These are the people that just work their job to look forward to the weekend, vacations, time spent with their friends and families, and time on the side to spend doing the things they really love (hobbies). The best part, and the worst part, about pursuing creative work (granted it’s what you love doing) is that you’re going to be spending that same amount of time doing something that you used to just consider your “hobby”, but because you worked hard at it, and you’re good at it, you managed to make a career out of it. Now the downside of spending your life being creative is that your work is never going to leave you, your brain is going to be constantly stimulated and your mind will often feel preoccupied. If you listen to Jerry Seinfeld talk about his comedy, he will tell you that he’s hardly ever there in the room with someone because he’s always thinking about his next joke. Now you can see how that would drive spouses and friends crazy, potentially making it more difficult to have healthy personal relationships. The blessing is that you love what you do, but the curse is that your work never leaves you and there is no clock you can punch at the end of the day to turn your brain off.

Are you prepared to pull all nighters, work odd hours, and sacrifice your personal health for your work?

Only issue that might arise when pursuing creative work is depletion in your personal health. You may not be getting restful sleep, you may start snacking and eating more junk, and you may drink one too many cups of coffee. Many creative types even turn to things like weed and alcohol to numb their brain and turn that switch off. As Johnny Depp says, “I drink to turn the circus off in my head”. This is also why you see so many famous celebrities overdosing and having addiction issues, they have a hard time shutting their minds off with natural remedies, and so they turn to synthetic options to escape their own minds. You can also be sure that you will have to work a lot of late nights, weekends, holidays, vacations, you name it. This means you will have to miss a lot of weekend trips away, holidays will require you to be in and out of your home office, and you will often have to sacrifice your own sleep and personal well-being just to make sure you get the job done on time. Larry David always talks about how he is writing and working on scripts every single year over the winter holidays. So if you want the type of job that only requires you to work, during the day, during the week, then you probably shouldn’t enter the creative industry.

Are you okay with truncating your friend circle and social life?

This is something I have learned first-hand through my experience with creative work — It’s unbelievably difficult to maintain and nurture a large friend group when you’re slogging through the trenches of the creative process. Again, your mind is constantly occupied and you’re so consumed with your own ideas and thoughts that it can make it difficult to think about anyone else. Truth is you just don’t have enough energy to put towards an abundance of personal relationships when you’re really in the “creative zone”. It’s exhausting and you only have the ability to expend so much energy before you body breaks down. So if you aren’t prepared to cut most of your fringe friends lose, then maybe you should pick a job that won’t require every single ounce of your mind and energy to get the job done. You need to now think about the quality of your personal relationships and who actually really supports your endeavours, instead of concentrating on the amount of friends you have.

Are you willing to say goodbye to most of your hobbies?

Hopefully in creative work, your hobby is what will eventually become your job. But in order to get really good at creative work, you need to train those muscles religiously. This means there is going to be a lot less time for you to play pick-up basketball with your friends or take a class that has nothing to do with your industry. I always say you have time for one hobby outside of your craft. For me, that’s going to be gym to stay fit. Anything outside of that time should be put into your craft.

How important is passion in your life?

Creative people are passionate people. It’s why they decided to go against the grain and pursue something a little non-conventional because they place a high priority on loving what it is they do for a living. Most creative types value passion and inspiration in a career more than they do financial security. So if you find that you aren’t burning with this passion inside of yourself to do the work, or you would rather have the security of money than be inspired in your work, then you probably aren’t meant for something creative.

Are you prepared to be broke while all of your friends are making money?

This is one of the hardest parts. You may even begin to lose some friends over this — your friends in corporate jobs may start to earn great money, while you struggle make ends meat, which means they may begin to congregate to people that earn salary in the same income bracket. For you, there is going to be a lot of “no sorry I can’t come out, I have to watch my money” going on, while your friends are going out and doing awesome and fun things. So if you aren’t prepared to say “no” to most things because you won’t be able to afford them, then you probably should sign your soul away and go get a corporate job somewhere.

Are you prepared to work a shitty job on the side that gives you the flexibility to pursue your dream?

Larry David was a cab driver. Comedian JJ Smooth sold fire extinguishers. George Clooney was a shoe salesman. Clooney also lived in his friend’s closet. There is no way you will be able to begin pursuing something creative and instantly be making enough money that you don’t need to work a day job, or another part-time job. So many actors work as bartenders and waiters so they can audition during the day, and so many musicians teach lessons to kids so they can play shows at night and on the weekends. They manage to survive these horrible jobs because they have their eye on the prize. They know that if they went out on got an actual career job, that they would be sub-consciously admitting to their failure and giving up on their dream. They want to keep the dream alive, so they work shitty jobs that allow them the flexibility to get rid of shifts or take off on a day’s notice if book a big gig with their creative work.

Are you prepared to be plagued by fear but continue anyway?

The best fruits are at the end of the branch. You can’t get to the other side of the shore without leaving the dock. We all know those types of sayings. There is inevitably going to be a long stretch of time where you future and success is uncertain. During this time you will be all consumed with fear and insecurity that you’re going to fail and you have made some huge mistake. In order to succeed, you are going to have to continue to push even while you still feel all these awful things. They say the stand-up comedian that makes it is the guy that gets up every single morning knowing that he’s a terrible comic, but still, he goes on stage and performs every single night, knowing very well that he is probably going to face complete and utter humiliation. Now try and wrap your head around that? As long as you have the drive and you believe you have a natural instinct for what you’re going after, then you must trust that everything will come together eventually.

Are you prepared to put in your 10,000 hours?

Now here’s the big kicker. Are you prepared to put in this amount of time? If you want success to be a quick fix, then you’re in the wrong industry. They say it takes 20 years to make an overnight success. Louis C.K. (considered to be the funniest person in the world right now) didn’t start to become big until his 40’s. You can’t cheat success in the creative industry. Sure there are the rare one in a million stories where the person achieves massive success in their first three years, but those stories are few and far between. Even if you do achieve huge success early, you won’t be able to sustain it because you didn’t put in the necessary amount of time to build your skills to a level that can produce that quality of work on a consistent basis. You have to prepare yourself for a lengthy battle of attrition. If you aren’t prepared to outwork and outlast everybody around you, bide your time and work your ass off, then you shouldn’t even start.

So do you still want to pursue something creative?

While you’re signing yourself up for a difficult life, one full of nasty twist and turns, as well as massive failure, rejection, and disappointment. It can sure be a rewarding life. There is no better feeling in the world than when your ideas and creativity touch people and move them in ways that change their life. For that reason alone, please don’t rob the world of your creative talents. Take the leap, go for it, do what you love. Chances are, if you’re reading this then you consider yourself to be a creative person. The only thing holding you back now is fear. We only get one shot at life; you’d be crazy not to pursue your Plan A.

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