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Overplanning and Stressing Over Failure


My original plan for this Sunday was to be lazy. It’s been awhile since I had a day off, and then I was reminded how in this grind we don’t get days off. At best we can find moments. I wanted to follow up on the topic of planning since I wrote my 10 steps to better planning blog. I’ve done a terrible job thus have insight to share. 


The quick update is I have failed to make time to regularly plan. As a result things have been chaotic for me and I’ve been constantly playing catchup with my regular set of duties. Now while things have moved along, what I didn’t do correctly was leave space for the unexpected. 


My calendar looks full and I barely feel like I am working on the right things at the right time. I have been overplanning and the result of this is a failure to live up to my plan when I face it. Especially when I failed to anticipate life events.


You must leave some extra time for the unexpected


Last night I was driving some Uber Passengers on highway 20 in the South Shore. The next thing I knew my tire was flat and I was on the ground in the mud putting my spare tire on. Today I found myself trekking over to Montreal Nord to find this open tire repair store. Then since I was out I did a bit of Uber to make up for the money I didn’t make after my tire failed me.


Overall Uber was slow this week. I found both Friday and Saturday night to be lacking ride requests and really bad for money. I was so disorganized in my head I found it really difficult to focus on anything between rides. There’s only certain kinds of work you can really do when you are out and about on the road given you never know when the next ride will come. 


When you fill your calendar to the brim you are relying on yourself to be perfect. This is not likely going to happen. Whether you get distracted because a lot of dice appear in Monopoly Go or you get caught up in some family situations, there are going to be things you cannot plan for. Knowing this, you need to make sure there is time leftover in your calendar.


I also really underestimate how much sleep I’ll need. For some reason I assume I always plan for a certain amount, but then I end up going to bed late for whatever reason. This means I wake up late and it throws off the entire day. Now I’ve been working real hard on being as disciplined as possible but sometimes playing catchup on podcast releases has you finishing at 11:30 PM instead of 10 PM as expected.


That is what life will be. Delays and hurdles that throw off your timeline. Now if you know that will happen you can be a lot smarter on how you divide up your week.


Focus on only doing a few things in a week


The truth is, when you add a gajillion things to do at once, you still only get a few things done. It’d be better to have a clear plan focused on what can be done. To achieve this you need to figure out how much “extra time” you have leftover when all your regular life work is done.


I’ll give you an example of regular things I need to do each week:

  • Sleep (49 Hours)

  • Shower/Groom/Choose Clothes (7 Hours)

  • Cook/Eat (7 Hours)

  • Work at the food promo gig (35 hours)

  • Do Uber Drive (25-30 Hours)

  • Write Blog (9 Hours)

  • Miscellaneous Chores (3-4 hours)

  • PRSPCTVS Podcast (4-5 Hours)

  • Trainman Report (4 Hours)

  • Read (3.5 Hours)

  • Exercise (3 Hours)


Now this is assuming I only sleep 7 hours. I ballparked some numbers. I can probably do the blog in about 7 hours across the week, but sometimes they take longer than an hour because I either get distracted or the topic requires some research. Uber is super fickle, if it’s popping I can hit my money goal in 20 hours. When it is not popping it takes 30. That’s a huge variability.


Within Uber time I can do some chores and combine some grunt work, but realistically that is my “whirlwind”. The regular chores I get done each week. I did the math for you. That is 152.5 hours of my 168 hours in a week.


Within the remaining 15.5 hours I need to fit additional meetings, recreation and time with Bonnie. It becomes really clear when I put it like this I don’t have as much time to move things along as I’d like. Keep in mind I’m on this board of directors and that has some additional projects as well. 


I’ve been really stressed and feeling like I’m failing, but when I list out how much I actually get done in a week, it makes a lot more sense. I can maybe do 2-3 extra things a week for now. 


Plans are fickle and nothing is set in stone


A lot of time what ends up happening is I make these opportunity cost choices. In the morning if I wake up late, I can either read or exercise. There is not actually time for both unless I start cutting into work time. 


In a lot of ways my schedule is not allowing me to be an artist like I wish I could. However you’ll see I'm out there working a good 60+ hours a week at the moment. Making money is a big priority for me so I can set myself up to have more time later on. 


Now you need to really be aware of how long everything takes you to do. Those numbers I listed in the last section are the result of me trying to maintain my calendar and keep track of how long it takes me to get shit done. Over time I will shift them and rebalance. 


I clearly have an ambitious amount of regular projects in play. No one told me to throw myself into two podcasts while writing a blog every day. I just know these activities will help me get closer to my goals. The day will come when I will throw myself into music. When I have the resources I will be able to release hundreds of songs a year. For now I need to focus on getting those resources.


As my regular plan is forcing me to basically remain in overclocked mode, I need to accept I cannot actually achieve it every single week. There are real life things that happen. There are moments you need to say fuck it and do something recreational. I have never been good at planning realistically, but mapping out what I have to do in a week is showing me that I really don’t have as much time as I’d like for things like recording new songs.


When I can I will, for now we grind.


Live Long and Prosper Everyone





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