A Freelancers' Guide To Ending Summer

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I am, to say the least, an incredibly lucky man. In addition to running a small digital media company I have the pleasure of being the father of two amazing children that I get to take care of full time and I get to be husband to an incredibly loving and talented and powerful woman. Because my wife owns her own business and both of us are self-employed, we’re able to create a summer schedule for our family that allows us to spend about half of our summer on vacation.

But summer is almost over.

I mean, it’s not really almost over but at the same time, there are a finite number of beach days left and I’m left realizing that I need a plan of attack when the beach is closed and I’m back to real work. What I’ve learned, over the past several years of self-employed life is that planning is the absolute key to everything, so I thought I’d share with you some steps that I’ve used to help me enjoy my summer and not be distraught when the coolers are emptied and the beach shorts go away.

I Started A While Ago

This one PROBABLY isn’t going to help you much this year but one of the reasons that my return to work is easier for me than it is for most is that I have a general plan in place months before.

I had written and produced almost all of the content I would need for entire summer and for the first couple of weeks of fall before the first week of June. While there are a few posts here or there, mostly time sensitive posts related to Pokemon Go, that I’ve been working on, but for the most part, I’ve made sure that everything I CAN do in advance, I HAVE done in advance. This means that when client needs pop up or I get several new projects, nothing goes on the back burner and as such, nothing gets left behind.

Most people look at things that can wait and think, “well…that can wait.” Because…it can. Things that can wait, CAN wait. But if you want to enjoy your summer and want an easy transition when work or school is back in full force, handle the things that CAN wait when you HAVE time. I know, I know, it’s important that you keep up with Peaky Blinders and Game of Thrones and there are ONLY 162 baseball games in a season but when you’ve got a chance to get ahead of yourself, get ahead of yourself.


In The Words of Soccer Announcers Everywhere, GOOOOOOOOOOAAAAAALS!

Have goals. And I’m not talking about really vague, “I want to be a better person and have more money” goals. I’m talking about straight up, “I’m going to write 9 ebooks this year” goals. I’m sure you know all about SMART goals but let me give you the ultra high-speed recap just in case you don’t.

Goals should be specific things that you want to do, there should be a way to measure whether or not you’ve succeeded, it should be possible to actually reach these goals, the goals should make sense and be aligned with your actual life purpose and there HAS to be a deadline.

Back in April, I set some pretty audacious goals for myself. I was going to write a specific number of blogs, ebooks and ACTUAL books (that last one is looking less and less like it’s going to happen), I was going to devote myself to a certain number of educational endeavors and when it was all said and done I would have a specific number of clients/projects completed.

My year, from a goal perspective, is all planned out. I know what I want to do, I worked hard to determine why I wanted to do it (I dropped a few of my goals and changed others on the advice of some respected people), how I was going to complete those goals and when I’d complete them by. I don’t leave things to chance. In the words of Chief Bogo from Zootopia, a film I’ve watched/listened to more times than I can count this summer thanks to the desires of a certain four-year-old boy;

“Life isn’t some cartoon musical where you sing a little song and all your insipid dreams magically come true.”

If you don’t have goals, either get goals or quit.

Endless Summer

This last point is a little more philosophical than practical. This whole post has been about what happens when summer ends and you’ve got to head back to the dread and drudge of work or school. Except, and you may have noticed this, I didn’t once talk about going back to work being anything other than enjoyable.

You see, the end of summer is unfortunate in that the weather isn’t as nice, and the water isn’t as warm and my office hours expand rather dramatically, but I love what I do. This isn’t about going from good to bad but rather about a change in schedule. My purpose in this post is to give you some tools to make your summer more enjoyable and your autumn a little more manageable. But if you hate what you do, I can’t help. If you’re dreading going back to school or you would rather jump off a cliff than see your coworkers again, this post isn’t going to help you too much.

I love my job. Love it. I do things I love to do for clients I (ALMOST always) love to work with. So for me, heading back to work isn’t the end of the world, it’s just a change in schedule. If the same can’t be said for you, you need a slightly bigger change.

How has your summer been? How do you balance work obligations with the desire for some sunshine? Do you have a plan for when the days grow colder and the nights grow longer?

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