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On leveling up and achieving your dreams: it’s not all its cracked up to be.

Into the Woods image via WSJ
Take it from Into the Woods – getting what you want isn’t a guaranteed recipe for happiness.

I haven’t seen the recent film adaptation of Into the Woods, but I’ve seen a couple of iterations of the stage version and mainlined the Original Broadway Cast recording enough times during the heyday of my Broadway geekdom to be familiar with the story’s themes. It’s easy to sum the story’s message up as, “Be careful what you wish for,” but I think it goes a little deeper than that. In this, the real world, where wishes aren’t magically granted after undergoing a quest through the dark and dangerous woods, a more relatable but no less true message is this: don’t pin your happiness on accomplishing your dreams.

I’m currently living one of my dreams. I’ve actually realized a few dreams in the last seven years or so. Back when I had a steady, safe job as a cubicle jockey, I dreamed of being a freelancer, and all of the apparent freedom that went with that. Freedom to set my own schedule, to write when I feel like writing, to decide who to work for and which jobs to take on, to not put on pants or makeup unless I just felt like it. It all seemed so awesome.

And then I got laid off during the lowest point of the Great Recession when there were no jobs to be had, and I turned to freelancing out of sheer desperation and survival (note: these are not ideal circumstances under which to begin a freelancing career. I really don’t recommend it if you can avoid it). And yes, I won’t lie: certain aspects of freelancing ARE awesome, like the aforementioned flexibility, and that whole pants and makeup thing.

But freelancing — especially doing it without a safety net — was fraught with its own set of problems, and it turned out to be very, very hard work, with long hours, and no benefits or job security.

Initially, I had dreamed of being a freelance editor. I had even started taking editing classes through Mediabistro right before I got hit with the layoff. I finished up the classes post-layoff, but I couldn’t get anyone to hire me as an editor. At the time, the only ones hiring freelance editors were mainly newspapers, magazines and websites, but thanks to budget cutbacks, they were turning more and more to having their writers edit their own work.

So instead I set myself up as a virtual assistant. I offered copy editing as part of my service package, and a few people took me up on it, but I also offered my HTML/CSS skills and that proved to be way more popular. It was also something I could charge more for, so after a while I moved the focus of my business to web design and development, even though that’s not something I ever really enjoyed doing as more than a hobby.

Still, business was good for a while, and I was living out my freelancing dream, so I tried not to complain. And then the web design business went belly-up and I went months–long, scary, stressful months–without being able to find work of any kind. I found a lifeboat in content mills, but I’ll tell you bluntly, writing for content mills sucks. It sucks your energy, it sucks your spirit, it sucks you in like quicksand and doesn’t want to let go. I don’t recommend that either.

Sometime in the midst of all of that I’d managed to realize another dream — to become a published author. I caved in and turned to self-publishing to make it happen, which at the time felt a little like cheating, but I no longer feel that way. It feels great to have my books out there, and I have no regrets about how I went about it. Another dream realized — and when dreams get realized, they become reality, and reality continues to be difficult. Self-publishing is a lot of hard work. There are a lot of ups and downs. It’s worth it, but it’s far from the easy path, if there is such a thing.

And now I’m finding that my initial dream of being a freelance editor is coming true. I took a very meandering path to get here, and  I’m very happy and grateful to have finally arrived. But it’s not all lounging in my PJs and reading all day. It is, again, a lot of hard work, and fraught with its own set of problems and difficulties.

You may see a pattern beginning to emerge here.

Ultimately, my big dream is to make a full-time living from writing and publishing my own novels — to have them sell well enough that I don’t need to have any kind of “day job,” freelance or otherwise. I like to daydream about it and in my daydreams I have all this free time on my hands. I only need to work a couple of hours a day to make my word count, after which I can be free to play around online and have a clean and orderly house and craft and read and watch TV and basically spend the rest of the day doing whatever the heck I feel like doing.

Of course I know that in reality, writing and producing quality books takes a lot of time and hard work. Selling books takes even more time and hard work. Once I’m making a living as a novelist, if that day ever comes, my days probably won’t look that much different than they do now. I’ll still be sitting here in my pajama pants, trying to balance my laptop precariously on a lap filled with furbabies, still wishing my house could be cleaner and fighting the temptation to watch last night’s episode of whatever and forcing myself to get work done, it’ll just be a slightly different type of work. But it will be work, and it will be fraught with its own set of problems and difficulties.

I’ve come to realize over the years that life is a lot more akin to a video game than to a storybook: reaching a goal or realizing a dream doesn’t mean achieving happily ever after. Rather, it means you level up to a whole new set of challenges.

Does that mean dreams aren’t worth pursuing? Of course not. As much as I fantasize about getting to take it easy, I subscribe to the notion that most things that are worth doing are hard. This looks kind of insane on paper, but I think most people are this flavor of insane. Things that require hard work are usually more rewarding than things that are easy.

I mean, sure, a Saturday afternoon spent lying on the couch mainlining your favorite show on Netflix is a reward unto itself. But after a whole week of that? Chances are, you’re going to start to feel like you’re wasting your life.

On the other hand, after a week of putting in hard work in the pursuit of something worthwhile, you’ll feel perfectly justified in spending that afternoon being a couch potato. You’ve earned a break, and knowing that lets you relax and enjoy it. Not so crazy after all.

I really think that even if your day-to-day life looked like a Corona commercial, you’d still have problems: sand in your shorts, having to worry about sunburn, plus eventually just sitting there sipping beer and staring out at the ocean is bound to get boring and you’re going to want to go somewhere and do something that involves having to put up with people and traffic and all of life’s little frustrations.

Problems and hardship are a constant part of life. Achieving your dreams won’t deliver you from having to deal with hard stuff. There will always be a new set of challenges and things to complain about. Which is why it’s a really bad idea to look to your dreams to make you happy. Contentment is a daily state of mind, and there’s joy to be found in the pursuit.

All of which is to remind myself to be grateful and enjoy finally being a freelance editor, and try not to complain too much about the new challenges it brings, or spend too much time daydreaming about being a full-time novelist, but to do what I need to to achieve that dream, too.

What do you think, dear reader? Do you agree or disagree? What dreams are you chasing, and how do you expect your life to change when you catch them? I’d love to hear your thoughts in the comments!

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