The Devils In the Details: Over-Planning and How to Deal

As someone who is a planner to the core, working as a freelancer with no set schedule or routine can be a nightmare. Today, I even used the term "logistical fuckhole" to describe this current moment of my life to a friend. The inability to plan ahead (whether it be to book another job, or simply fit in basics like eating and doing laundry) can feel like more of a challenge than your actual job. On top of that, finding a way to just get your brain to shut up after getting all riled up strategizing can be an impossible feat. I have been known to go from prepping for a job, to staying up all night long, budgeting for major life investments like a wedding or houses, when I have exactly zero plans to act on either for a long time. Other times my pointless planning is slightly less pointless: working on budgeting to ensure I can cover my monthly bills, but this usually occurs when I've already done it...twice. For some it's anxiety manifesting, for others it's considered preparation, but for anyone freelancing, over-planning exists. It's not a part of life, it's how we live our lives (I mean, come ON, who else pays their taxes in advance?!). While these methodical traits can be seen as an exceptional skill, that big blessing can also be a major curse. How do you find peace with your future when you can't even plan it? You over-plan. That's how.

Don't get me wrong, skills are skills. This compulsive need to prepare can pay off big time in situations like prioritizing tasks while working multiple jobs - but can you turn it off? Can you stop planning and breathe when you need it? Learning to manage your planning powers in a way that promotes a healthy mental state is key. To any of you who stumble across this blog looking for "advice," or real-world perspectives on the life of a music industry freelancer, heed my warning: two of the most important skills in this industry are how to organize unorganized situations, and how to step back and breathe. We are so used to planning the minutiae that it can be difficult to stop when it goes from productive to pointless. More so, when things don't go according to plan, your ability to step back could decide if you have a breakdown or a good laugh. I implore anyone embarking on their own journey to discover their preferred method to keep organized and prepared, and find something that helps you avoid "over-planning" stress by releasing energies elsewhere. Here are a few tools that I've used in various ways over the years. What's your go-to: the notepad on your phone, or are you a Wunderlist die-hard? Do you relax with yoga, or YouTube?


1) A Planner
You're thinking "duh, Maddie, we like to plan, of course we love planners." It may seem like a no-brainer, but while many of us have planners, do we use them in efficient ways? Is your schedule condensed, or scattered across a page? Is your journal for personal thoughts also home to your to do list? Hosting both of those in the same place can easily lead to distractions and continual mind wandering, so split them up. Things like bullet journals have been a hit in the last year for organizing, but I found my favorite in a custom-designed planner from May Designs. With the ability to choose the right type of layout for you, as well as custom colors and patterns, your daily  lists have never been more fun. 

2) An App
Whether you believe in ye old faithful notepad on your iPhone (as does yours truly - 796 notes and counting), or you are a ride-or-die Wunderlist-er, apps are fantastic. That desire to cross things off your list is only heightened when you get a virtual, animated affirmation, am I right? If you're more of a traditionalist, Clear is a fantastic alternative to the built-in notepad. For a few more gadgets and gizmos (or a replacement now-defunct Wunderlist), see apps like Todoist or Things. For a business or team-setting, Asana is excellent for collaboration, and for all you students out there, I would have legitimately failed out of school if not for iStudiezPro.

3) Public Shaming
This header sounds ridiculous and bitter and like something no one should recommend, but as someone who's never had a proper workspace, I understand the struggle of finding comfortable locale that's not your couch, bed, or dinner table. If you work remotely and are prone to spending excess time being sidetracked by great "what-ifs" and worries rather than focusing on the task at hand, making yourself visually accountable by working in front of other people can be a mechanism to help peer pressure you into success. Finding a coffee shop with good energy and minimal frill, a library, or even a paid membership to a local co-working space can all help keep your brain focused on the "here and now." I'd also like to remind you that if you're planning on working in touring, your office will never be the same, you'll usually share it with 11 other people, and you have no choice but to get your shit done or the rock show won't happen - that's just not an option, is it? 

my daily office while on tour. No, I am not joking.

my daily office while on tour. No, I am not joking.


1) Exercise
Not only is exercise good for your body, but it's great for your mental health. When I get too caught up in my brain and its plans (or lack thereof), the easiest thing for me to do is hop on my bike, or head to the gym. Turn up your tunes, get lost in the music, and focus on your breathing. Whether your riding your favorite trail, or just panting on the treadmill like yours truly, this extra stimulus will suck your brainpower, turning off the over-planning, all while doing something healthy. 

2) Journal
Earlier I mentioned how it can be detrimental to keep your to-do lists in the same place as the rest of your thoughts. If you're anything like me, your daily questions, concerns, and personal struggles could fill up a novel. Why would you risk putting things you know are distracting in the same place as your to-do list? Get a journal (or a blog, or a word document) for all that word-vomit. It doesn't have to be a "Dear Diary" situation, but get those thoughts out of your head! Putting pen to paper stores ideas in a space you can re-visit later without cluttering your brain. I often find that taking the time to write my concerns down forces me to think about them on a deeper level, putting my worries to rest by realizing a solution, or at least better understanding my situation. 

3) Distract Your Brain
As Lil' Dicky tells us, "don't neglect the brain." Sometimes all it needs to shut the fuck up is something to shut it up. If you need a chill out from planning your next vacation...which only happens if you make enough on this next job...when is it due? (Could I squeak something else in this weekend before that tour starts? And did John pay me for that thing I finished? SEE. Bad, over-planning brain! Stop!) While I don't recommend Netflix binges because they lead to a lack of productivity, sometimes you need to switch gears to get back on track. Take an hour to watch that documentary you saw on Reddit, read a book, get lost on YouTube (which I do too often). Listen to a new album, go to sleep and come back to your work tomorrow, or just fall down the Instagram/Twitter/Pinterest hole for a bit. Force your mind to take a break by giving it a shiny object to steal it's attention. 

FOR EVERYTHING: Put It On A Calendar

Find yourself worried about something? Put every detail imaginable in your calendar. Catch yourself planning something? Add what you know on the right date. In the middle of working on something? Make sure it's on your calendar. Seeing a trend here? No, I'm not kidding. I use the notes section to list how much I'm supposed to be paid for each job. I use the notifications to remind me about things a week in advance, or bother me when something HAS to happen in the next hour and I'm sure I'm going to put it off. I have alerts tell me when I should leave so I can't run late, and I screenshot my emails and attach them to my calendar so I can reference stuff quickly on the go without digging through my inbox. My calendar is my true God, and you bet your ass I've got it backed up and exported in case of the apocalypse.  

There is no one way to keep yourself from sweating the small stuff and over-planning sometimes. As planners, our tenacious drive to create organizational bliss is first and foremost a skill, a talent, and something many do not have. We only succeed because of our ability to carve out details and complex life schedules, but unlike those with a 9-to-5, we are our own office, so it's a bit harder to put things down and simply "go home for the night." Did I miss any of your favorite organization tools, or quick tricks to shut your brain down? Share with me in the comments, and share if you like this style of blog! Decided to try something different today, so we'll see if they continue.