5. Can You Get Affordable Health Insurance?

This is one of the main obstacles that can get in the way of you becoming a full-time writer. It’s also one of those things most people don’t think about when they are imagining their dream job. But if you’re a resident of the USA, this is a major issue that needs your attention.

If you’re like me and have a pre-existing condition/illness which requires a constant dose of medicine or medical procedures, it can be almost impossible to afford these medical expenses without good health insurance. The same can be said if you have a family who you’re responsible for taking care of. Getting insurance independently can be on the pricey side—if not downright impossible. So really think and plan this part out thoroughly before making any life changing decisions.

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6. Are You Ready To Be An Entrepreneur?

It’s kind of funny to think of yourself as an entrepreneur when you’re a writer, but that’s kind of what you are. You have to be ready to sell yourself and your work any way you can. Or at the very least try to find paying work from other sources to move your career along. Again, this won’t be an easy process. If it were, every aspiring writer would do it.

Many writers have trouble marketing themselves. They even think that if they can score that elusive book deal with one of the big name publishers, they won’t have to worry about the marketing. Unfortunately, that’s 100% incorrect. In fact, many big publishers want to see your self-marketing plan before you sign a book deal. To be blunt, you’ll be doing the bitch work when it comes to selling your work. So you better come up with a plan on how to market yourself effectively before you quit your job to become a writer.

7. Where Will You Get Your Human Interaction From?

For some, this can be a big deal. For others, not so much. But on average, we all need some kind of human interaction to keep us sane. This interaction usually comes from your day job. I’m sure you never really thought about this being an issue, but many of us get most of our personal interaction from work.

The life of a writer can be lonely. Even to the point that it’s a common cliché in TV and movies. This is because while you spend most of your time writing by yourself, everyone else is working with other people. And when they get done working, many people just want to be alone for a while. But you’ll be the opposite since you already spent your whole day alone. Long story short, it will be hard to connect with people as easily. You’ll actually have to go out into the real work to meet people.

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8. Do You Have The Discipline To Work Independently?

It’s one thing to get work accomplished when you have an overbearing boss breathing down your neck and barking orders at you until you get things done. It’s another thing entirely when it’s YOU trying to tell YOURSELF what to do and when to get it done by.

Far too often writers who simply try to will themselves to get work done end up putting the work off over and over for some later time. AKA procrastination. You can’t have that. You must hold yourself accountable and make sure you get your work done on time. Yes on time. Meaning schedule your writing ahead of time and keep daily, weekly, and monthly writing goals. Hit these goals regularly and things will go a lot smoother for you in the long run.

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9. Do You Have Supportive Family And Friends?

As I stated many times previously, if you’re going to quit your day job, you need to make sure you have certain things set up to make that a possibility. A lot of that can come from your friends and family. Hopefully they will be able to support you in your time of need if you decide to go this route.

Obviously, you don’t want to rely on other people to support or help you out. Unfortunately, things can go south sometimes. And that’s when the people you are closest with may be there to bail you out of a bad situation. Again, this isn’t ideal by any means. But just knowing you aren’t going into this new world alone can be a big confidence boost.

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10. What Is Your Backup Plan If Things Don’t Work Out?

Now, I don’t want to be that guy, but if you do decide to quit your day job you must have some kind of backup plan. We already went over the need for having money saved up in case things don’t go as planned. But it doesn’t hurt to have a possible regular job lined up just in case you find things aren’t working out well at all.

This isn’t saying things won’t work out for you. It’s just wise to have a backup plan on the off-chance you find yourself in an unsatisfactory situation. Hopefully you’ll never have to use your backup plan. But it’s good to know it’s there as a fail-safe. The last thing you want to do is bet all your money on hitting it big as a writer, only to find out you have years of rejection and being poor ahead of you first. In the writing game you don’t have to play it safe, but you do need to play it smart.


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