If the thought answering one more client phone call makes you want to weep and you’re so overworked that you just realized you’ve been walking around all day with your sports bra on backwards then it might be time to take a step back. This stuff is supposed to be fun, remember?

Things not being fun anymore is a good sign that you’re tired of work and life and receiving those spam emails from pushy web designers advising you that they “checked out your website and noticed that you could be getting a lot more hits.”

It’s time to tell the real world to piss off for a while. It’s time to go on vacation.

You Still Need Vacation Time

Once I read in a book on freelancing that a good way to plan out your yearly income goals is to decide how much you can produce in a week and then multiply that corresponding monetary value by 48 to account for 4 weeks of vacation. Then I laughed, laughed, laughed all the way to the bank while resolving to work year-round, pounding my chest, and shouting to myself that “I’m no sissy!” and that “I’ll show this very successful freelancer who knows more than me who’s boss!” Mo’ work hours, mo’ money, is what my past-self would tell you.

Except I didn’t laugh my way to the bank, and my past self can be a damn fool sometimes. I couldn’t work year-round, and mo’ work hours does not equal mo’ money when your brain is more fried than a very fried, over-cooked egg. (Weak-ass metaphors are another sign you might need a vacation.)

It’s easy to forget to take vacation when you’re working for yourself. Don’t be like past me. She’s worn down, has bags under her eyes, and smells like fried chicken when she decides that stopping by Church’s is easier than cooking her own dinner. While I’ll admit there’s nothing sexier than a greasy, sweatpant-wearing swamp creature, I still think you should start planning some vacation time before it’s too late.

Planning For Vacation Time

I find the easiest way to build in vacation time is to plan your career by quarters. Designate the last week of the last month of each quarter as vacation time and you’re good to go. Simple as that.

Following through will be hard sometimes. You’re going to want to work through it. Or you’ll promise yourself that you’ll “just finish this one thing on Monday” and start your vacation right after. You’ll get an inquiry from a promising prospect, or you’ll convince yourself that you don’t really need the time off.

But you’ve got to stick to your guns, partner. The work will be there when you return. That prospect can wait for your proposal. Not taking time for yourself is a mistake that affects your health and your business.

Vacation time–whether you’re staying home or traveling far away–is like hitting the reset button. And oh man, does it feel good. It’s a chance to restart, refresh, and take a step back from work and life. It’s a time to make plans for the next quarter and even re-chart your course if you feel like it’s time to take things in a new direction. Vacation time every quarter is an excellent way to build natural transition points into your career plan.

Don’t make the prep work more complicated than it needs to be. About a month out, start making plans to free up that last week. Don’t schedule client work for that week and don’t schedule too much the weeks before or after, either. Let clients know 2-3 weeks out when you’ll be unavailable and work with them now to make sure it’ll affect them as little as possible.

If you’re traveling during this time, then obviously you should make those plans too. But I’ve found that my best, most affordable vacations consist of me staying in my home town having fun at home, out with friends, or at the beach.

This works just fine for me because I have the house to myself most of the time, live close to the ocean, and live in one of the best cities on earth. (I also find that out-of-town trip planning can be pretty stressful. And personally, saving money while I’m still getting settled into my career is always a plus.) But you might feel that it’s a must for you to get out of your hometown to really enjoy your time off, and that’s fine too.

Things You Should Do On Your Time Off

What’s your vacation week look like? Mine’s kind of half-work, half-pure relaxation. I only do work that’s 100% fun or necessary, like reading a book on writing or planning out the next quarter–but absolutely no client work and never work that I don’t really feel like doing. Save that stuff for next week.

This is the stuff I do all day on Monday and Tuesday.

Then the party starts on Wednesday and all hell break looks. If hell looks like sleeping in, hitting the cafe and getting caught up on my reading list.

My vacation time can be pretty productive because I like it that way. It doesn’t feel forced–I actually like planning, brainstorming, reading, catching up on to-do list stuff, and learning new things. Your vacation time might look a lot different, and that’s cool too. Now’s not the time to feel guilty about how you really want to spend your time. Now’s the time to do whatever the hell you want and enjoy every single bit of it.

Here are some things you might want to do on your time off.

Things that have been on your to-do list for way too long.

Perhaps you’ve been meaning to:

  • Get a new passport
  • Catch up on your favorite email newsletter
  • Get some of those cute little cacti to add a bit of green to your office
  • Make that recipe you’ve been wanting to try
  • Clean out/organize Evernote
  • Get a haircut

But be careful not to fill up your whole week with stuff like this! Do what you gotta do and be done with it. Early on. So you can get to sippin’ coconuts.

Work that doesn’t feel like work–but sparingly.

This might look like:

  • Planning your next quarter, setting career goals
  • Changing your direction if you’re unhappy with your current situation
  • Taking a course that’ll help you grow more skilled at what you do
  • Reading a book relevant to your profession
  • Brainstorming marketing campaigns

I once read somewhere that people like planning so much because it gives the illusory feeling of productivity. Oh well, who cares. I freakin’ love it. That’s how you should feel about any “work” work you do during this time–FUN STUFF ONLY.

Dream job stuff.


  • Focusing on creative writing projects
  • Reading a book on comedy writing
  • Reading a book on selling your paintings
  • Taking a photography course
  • Actually writing, painting, and taking photographs
  • Making a website to showcase your work
  • Going to local artist’s events

Fun fun. Another area to watch out for, though. If it feels like work, then stop it, you.


What are you going to cross off your TBR and watch lists? I’m going to:

  • Continue watching 30 Rock and Always Sunny all the way through
  • Check out the TV show and book series Outlander
  • Finally watch the second season of True Detective
  • Finish The Martian and read The Foxfire Book
  • Watch Inside Llewyn Davis, Sicario, and A Girl Walks Home Alone at Night

This is the shit I LIVE for. Ah, vacation time. This is why we do it.

Go live a little.

Sometimes I forget to leave my house. But there’s some pretty cool stuff out there, y’know? Try:

  • Eating at a restaurant alone
  • Going out with friends
  • Being a tourist in your own city
  • Going to the beach or pool
  • Going hiking or camping
  • Taking a yoga class
  • Doing something super weird that you wouldn’t normally do, like open mic night poetry

And lastly:

Be 100% comfortable.

Do you. This ain’t the time for diets, regrets, or self-judgment. Or hanging out with negative-ass people you don’t really like.

  • Rock them eating pants, homegirl/boy.
  • Drive across town for doughnuts
  • Skip showering for a day (I guess this is a big deal for some people)
  • Lay out and tan that bod
  • Take a bath and light a jillion candles
  • Sleep in and stay up late
  • Spend time with those you can be yourself with.

Things You Shouldn’t Do On Your Time Off

Anything that feels like trying.

Simple, right? You can do that. Like mentioned above, too much of one thing is what you shouldn’t be doing, like too much career planning, to-do listing, or “personal project”-ing. I know we’ve all got this intrinsic guilt at not spending every single second productively, but you can let that go just for one week, right?

You sure can my friend. I’m going to do it next week, and you can do it too. When will you take your next vacation? The beach and the book at the top of your TBR pile are waiting for you.

Heads up: no blog post next week because…well, duh! It’s all in the post. I’ll be spending some quality time with books, my cats, and strong margaritas. This happens every quarter, but don’t worry–I’ll be as fresh as something that’s very fresh when I return in a couple weeks.