The Attachment Point – SlackChat #6: What is the single most important thing you do to stay organized?

Welcome to The Attachment Point. This is our SlackChat content where volunteers on The Insurance Nerds Slack Channel (join here) discuss various topics. We do very little editing (so excuse the typos) and we try to keep it as conversational as possible. Enjoy!

Nick Lamparelli: For Slack Chat 6, the question for The Insurance Nerds members is, what is the single most important thing you do to stay organized?

Nick Lamparelli: READY?

Nick Lamparelli: GO!

Cara Carlone: Cara has joined the channel

Nick Lamparelli: I’ll kick this off. For me, the most important thing I can do is to write everything down and stay on top of it. If I do that, I can be incredibly organized. My biggest issue is writing everything down. I usually only follow through when I feel disorganized and stressed. I am trying to train myself to write everything down even when things are calm, and I have slack.

Cara Carlone: This sounds really lame, but I’m old school and need to write things down. I actually have a planner that I use to write down all my appointments, things that need to be done for that date, important phone calls, etc…I find it helps me stay organized with what needs to be done on any given day.

Cara Carlone: Hah! Great minds. 

Nick Lamparelli: Cara Great minds indeed! How do you stay on top of writing things down? That’s my biggest problem!

Cara Carlone: Well…this might not be a motivator for you, but I spend a decent amount of money on fancy planners. Erin Condron makes some really nice ones. I buy a pretty one at the end of every year and have it customized (and personalized) so I’m more apt to use it

Cara Carlone: I also carry it with me all the time and sometimes I have to physically take it out of my purse and keep it on my desk during the day, so I don’t forget to write in it

Nick Lamparelli: Cara Is there a slotted time where you examine and work on your calendar…AND ONLY DO THAT? I am thinking of doing that to force myself to spend allotted time. I am worried that I can’t be trusted to do that…

Cara Carlone: No, not usually. Anytime I have something important that has a specific deadline, I’ll mark it in there. I guess anytime I would normally update my work calendar, I make sure to also write it down in my planner.

Nick Lamparelli: Thanks Cara for your input. I’m glad I am not the only one going old school!

Cara Carlone: No prob! I definitely prefer the old school way of doing things.

Cara Carlone: *For the most part.

Nick Lamparelli: Old school is becoming vogue! We just had to wait it out Cara ?:

Cara Carlone: Hah!

Tony Canas: I’m congenitally disorganized, so this is a big challenge for me. I do keep multiple Google Calendars to organize my days, but for tasks that don’t have a specific time my to-do list lives on my Bullet Journal on a very nice moleskin that goes with me everywhere and serves as an almost outsourced memory kind of thing… Everything from the to-do list to random brainstorming and a list of articles I want to write go in it. If it didn’t go on my calendar I won’t show up, and if I didn’t write the to-do on my bullet journal it won’t get done.

Ryan Deeds: I built a little texting app for myself called “tomo” – I just text in the 3-4 things I want to get done tomorrow and if I complete the mIlet the system knows and it will give me a ratio of what I’ve completed, days I complete the most etc. – guess it’s the nerdy tech way of doing a planner.

Ryan Deeds: but I’m a chaotic mess and haven’t found a perfect system. I do think knowing what I want to accomplish for the day is awesome. The clarity helps feel like you are actually moving some stuff

Alan Godfrey: When I have a lot to do but both need to reduce the constant panic that I am not working on the right thing and need to motivate myself to make continual progress across a number of areas without actual short-term deadlines, I’ve had success putting tasks directly into my calendar to identify when I am going to do them. This requires me to upfront think about breaking a large task down into steps, being realistic about how long each will take and being honest about when I’ll do it. It helps me to know that what I am working on in that moment is the right thing to be giving my full attention to, forces me to think in advance about when I am more likely to be in the mood to have face-to-face meetings vs. head down in a spreadsheet (which I don’t always get right but will improve on over time) and can help me to say No to a new task if I am already fully committed. It does require effort to shuffle things around when life gets in the way, but I see that as a valuable part of the feedback process as well (i.e. losing half a day to an emergency project then forces you to think about what knock on impact it will actually have and whether anything now needs to be pushed back).

Alan Godfrey: For big projects, or when things get completely out of control, agile and constant review and refresh of paper notes / Notepad brain-dumps is the only way. I’ve resorted to 2D post-it notes (Importance vs. Deadline) before to get through tough periods – and I know things are serious if I have to add more dimensions (color etc.) in order to cope! ?

Nick Lamparelli: Thanks Alan G. Tony C. I used to have no issues with my Google Calendars but having two startups and a personal life, that creates 3 calendars to manage. Yes, I can line them all up, but it also means 3 emails systems, multiple Slack Channels and just a whole lot of managing technology, instead of managing my life.

Patrick Wraight: I struggle with staying organized myself. The most important thing that I do to stay organized is to limit myself to 3-4 “a pile” items that I have to work on in a day. Once I set my limit, I work in focused chunks of time, rewarding myself with a walk, another cup of joe, or looking at slack. ? After my personal reward, I either jump back into what I was working on, or move to the next project.

Patrick Wraight: That’s also when I don’t forget and spend half my day wandering in and out of projects…

Nick Lamparelli: Thanks Patrick W. That is pretty much how I’ve been trying to structure my days as well. For me, the toughest part, is shutting everything off (email, phone, slack etc) to work on the desired task in the block I set. I am getting better at setting the time, but not at removing the distractions.

Tony Canas: Nick L., have you read “Deep Work”?

Patrick Wraight: That’s totally the truth. I have two mobile phones, a desk phone, and 7 open windows on my desktop. Always seems to be something that wants to distract me.

Carly Burnham: Carly B. has joined the channel

Ryan Deeds: I do find it to be extremely easy to lose the day to being busy and not getting what needed to get done. Meetings are the bane of my existence

Nick Lamparelli: Tony C. no. I’ve read “Be So Good hey Can’t Ignore You” by the same author. I follow Cal Newport. He is very big into minimizing technology. Patrick W. That book has got me thinking into removing more tech from my life. Not adding more. Not sure Ryan D. would go along with that ?

Ryan Deeds: Tech is here to stay – it’s like any tool though and it can definitely be more distracting. I find when coding I really have to turn everything off – if not physically then mentally – and just block out serious amounts of time to get through milestones

Jen Overhulse: Jen O. has joined the channel

Tony Canas: Deep Work entirely change the way I see getting stuff done, when it comes to in-depth work, a must read!

Patrick Wraight: Nick L. Look up the Building a Storybrand Podcast. He has a productivity worksheet that I use, too.

Taryn Haas: I use a paper planner – I was a proponent of the BuJo but setting it all up was too much for me. I’m using an Erin Condron planner which is very pretty haha, and I make it part of my self-care routine each Sunday to set it all up for the week. I use fun stickers and washi tape and it’s really relaxing for me to get prepared to the upcoming week. I also leave it open on my desk or at home depending on where I am, then I can just glance to see if I need to do anything. I vary in how specific I get with my tasks – if I want to make sure I practice an instrument a specific day, I’ll write t down, but I find if I get to specific with it it can be overwhelming. I’ll write general goals down as well for the week

Tony Canas: Productivity planning as self-care, very interesting!

Jen Overhulse: I eliminated Post-It Notes (which always get moved or covered up and are therefore lost forever) and now write everything down in a daily lined Leuchtturm 1917 notebook. I also consolidated conference calls onto Tuesdays and Thursdays ONLY. It makes for some pretty terrible Tuesdays, but it allows me to concentrate better on the other days and get more in-depth projects completed due to the focused productive/creative time.

Taryn Haas: Yup! It comes right after painting my nails hahaha. I do find it very helpful as it 1. Gets me to focus on what I can control and 2. Makes it so I don’t freak out over missing something I needed to do, so reducing anxiety

Alan Godfrey: Any one used the ‘4-hour work week’ approach and invested in a third-party PA to manage your emails / calendar etc. and prioritize it for you?

Tony Canas: I’m getting more and more tempted, especially my calendar which is a generalized disaster or work, insurance nerds, and personal stuff spread over one outlook and several G calendars

Alan Godfrey: I’ve not been in as extreme a position as some of you guys – for me it’s always been in the context of one job, which sets a more rigid framework than being self-employed, but I would suspect that it is something that I would consider if I was – PAing / Project Managing is a skill, and a full-time task at times, and surely not the most effective use of your time (if you can afford it)

Nick Lamparelli: Patrick W. thank you for this recommendation. I’ll check it out

Nick Lamparelli: Jen O. NO POST-IT NOTES??? Say it ain’t so! I do use them…but sparingly. I keep them in my daily planner for the tasks that I need to get done before a certain meeting. So if I have a meeting on Friday, I will put a small yellow sticky in the column for the day I need to have a task for meeting completed. Once complete, I remove the yellow sticky. I’m still feeling that out. I tried to do Sunday planning as Taryn H. described…but I’d get all panicky with dread.

So now I try not to do any planning on Sunday and hit it first thing Monday morning. I am not sure how well that will work.

Taryn Haas: Wow, why panicky? Are your weeks that insane?

Taryn Haas: You clearly need a prettier planner

Nick Lamparelli: Taryn H. yes..super anxious. I need you to teach me how to handle Sundays

Nick Lamparelli: Nick L. uploaded a file:

Taryn Haas: Haha. I’m guessing my weeks aren’t as packed as yours though.

Nick Lamparelli: look at those pretty colors!

Taryn Haas: Haha very nice! If only you could get some animal shapes in there….

Nick Lamparelli: Haha!

Tony Canas: I use sticky notes around my monitor for detail-oriented things I can’t forget “Remember to copy X on every Y” kind of thing

Taryn Haas: Do you write in the good/exciting events as well?

Taryn Haas: I tend to emphasize those

Taryn Haas: So, if there’s crappier stuff, I have that jumping out at me

Jen Overhulse: Nick L. Post-It Notes were invented by the Devil! I can always picture the note in my head on a green, yellow, or blue note, but then I have no idea where the piece of paper I stuck the note to has gone! Evil! My Leuchtturm 1917 is my own special version of a planner. I set time to write out my to-dos every morning, or I won’t do it. It’s like exercise. If I don’t run in the morning, I don’t run at all.

Jen Overhulse: Jen O. uploaded a file:

 Taryn Haas: I wonder if putting in some more personal stuff would help Nick L. ? I can’t read what you have right now, but a lot of what I find relaxing is noting what I’m going to work on for the week and what I’m thankful for

Taryn Haas: Oooh I like yours Jen O.!

Ryan Deeds:  like a beautiful mind and what not

Jen Overhulse: Taryn H. thanks. Ryan D. more what not…?

Nick Lamparelli: Jen O. top notch! May we use the picture for the blog article that this conversation will become?

Jen Overhulse: Nick L. knock yourself out!

Taryn Haas: Taryn H. uploaded a file:

Jen Overhulse: Taryn H. I’m now envious of what looks like a clean desk.

Taryn Haas: Sometimes my stickers are a bit silly but they make me smile so

Taryn Haas: Hahaha well I just started here 3 weeks ago

Nick Lamparelli: Taryn H. may I share that picture?

Taryn Haas: Sure!

Taryn Haas: It’s not the most comprehensive lol

Taryn Haas: Sometimes they get crazy

Cara Carlone: I do this too! It’s the grown-up version of writing notes on my hands. Which, I used to do in school. ?

Nick Lamparelli: I bet it’s like exercise. It’s a drag early on. But at some point, you start to accept the discomfort. Further on, you seek it out and feel let down if you don’t feel the discomfort. I hope to enjoy planning and being/staying organized someday.

Taryn Haas: Yup! That’s a very lovely way of putting it

Tony Canas: I still do that, but as little as possible ?

Nick Lamparelli: Taryn H. & Jen O. you two are my mentors now…question…as I think about my organizational problems, I think they manifest mostly with tasks. I can’t fit tasks on my calendar. How should I try to manage my tasks given I am trying to keep everything organized in my calendar? When you are thinking days ahead…what’s your secret to making sure the right tasks get done at the right time?

Taryn Haas: Nick L. I split my day into 3 categories, mostly due to how my planner is set up. First block is set events happening in personal life, second is work goals/events, and the last is goals (so things I will ideally get done but more of a guideline for me than a push from the outside world). I keep everything set weeks/months out on the month page and put those in first when I’m looking at my week. From there I fill in with anything set, putting it on the corresponding block, and then if I have other goals that just need to be done by the end of the week, no specific day, I put them either at the bottom or in the lined space to the side.

Taryn Haas: And if I don’t complete something I had set for that day, I cross it out and move it to the next

Taryn Haas: Is that helpful?

Jen Overhulse: Nick L. I mentally break projects down into tasks, and tasks down into more bite size “pieces.” I enter pieces into each day at a rate which will accomplish my overall tasks and project, sometimes projecting out as far as a week. I decide on a project deadline date and then back into tasks and pieces from there. I also enter the final deadline date at the end of the line where each smaller piece or task is recorded. Similar to Taryn H. I migrate those that did not get accomplished to the next day…

Taryn Haas: Yea that’s a good point Jen O.! Breaking things down is key

Nick Lamparelli: ok, real example. I have a podcast recording later in the week. I try to have an agenda sent to them a few days before hand. The recording is on my calendar. The agenda falls through the cracks often and I don’t get to it until the night before or the day of. I dislike that very much. I thought about penciling in a 15-minute slot during my day…but if something comes up, I forget to move it. Its these small tasks which are important but not urgent that end up causing me the most anxiety.

Taryn Haas: Are you fitting everything within specific times?

Taryn Haas: Cause for me, that would go in the 3rd column. It’s something short and I can knock it out easily, has no set time, and I would just like to cross it off that day as opposed to another

Taryn Haas: So, I would view as something that I want to be aware of for that day but fit it in as my day unfolds

Bill Wilson: Bill W. has joined the channel

Bill Wilson: In December, I create a Word document that is my annual To Do list. I spend the better part of a day entering planned travel, meetings, etc. I also decide tentatively on major tasks I want to accomplish for the year, from refinishing the front door on my home to writing a book. I consider these “commitments” and schedule and block time for them as if they were recurring appointments or tasks. It’s a living document and changes constantly throughout the year.

Nick Lamparelli: Taryn H. There is no room in my planner for anything except time-related events. So if you look at the picture I took above of my calendar, I added sticky notes to move day-to-day to keep track of tasks and the day I want to do them. So far, that’s worked, but I am afraid it won’t keep working. I guess I don’t trust myself.

Tony Canas: Bill W., you are amazing at sticking to deadlines and getting stuff done. You pretty much were ahead of the deadline at each step of the book writing process. We were blown away. How do make time and create space for that kind of deep work?

Bill Wilson: One of my book projects for this year is one on my seminar “The 7 Maxims of Time Management.” I try to incorporate those maxims on a daily basis to get and stay organized, schedule goal-focused activities, make sure to balance my time among work, family, community, etc. Here is a Slideshare of 7 maxims: <>

7 Maxims of Time Management

Bill Wilson: Here’s an article I wrote: <>

Virtual University – The 7 Maxims of Time Management

Tony Canas: Insurance genius, time management guru, famous quotes chronicler, and guitar playing rockstar. Is there anything you don’t rock at? It is perplexing!

Nick Lamparelli: Bill W. How do you handle small tasks, perhaps unforeseen in your initial planning but that at some point need to get some?

Bill Wilson: There’s a RoughNotes magazine article written by one of their contributors who attended my seminar: <>

A GUIDE TO TIME MANAGEMENT – The Rough Notes Company Inc.


Nick Lamparelli: Thanks Bill W.!

Nick Lamparelli: lots of gems in those articles!

Jen Overhulse: Nick L. I have found with tasks such as your podcast agenda that those things do not get done unless I do them immediately. So, let’s face it, you likely have in mind what you will talk about on the podcast, or you wouldn’t be doing it in the first place. That said, you have also likely held MANY of these planning calls. So, you know what this agenda should look like and what you want to talk about. When you set up the call, create the agenda IN THE INVITATION ITSELF. Take the extra 5-10 minutes it will take to do it right at that moment, even if it will need polishing up later. You can always amend it, or add detail later, but you won’t be starting from scratch. And, if you create the rough/outline agenda right when you send the invitation for the call, it will all be pretty fresh in your mind. My two cents. It works for me. Might not work for you.

Jen Overhulse: Nick L. It is also those kinds of small, perhaps unforeseen, tasks, which never make it to the daily to-do list. Unless I need to feel good about myself and I go back at the end of the day and add them in there. (But, who has time for that when one could be having a nice glass of Layer Cake Malbec instead?)

Nick Lamparelli: Haha! Jen O. thank you! You are correct. The agenda can almost be templated with fill-in-the-blanks.

Jen Overhulse: Nick L. That’s another organizational tool for those using a PC and gmail…there’s an app called Boomerang. It’s a lifesaver when it comes to scheduling emails which need to be sent at a later date. I loved it. Now I use a Mac and they don’t have an app for that…:-)

Nick Lamparelli: Jen O. thank you. I have a mac and use an app called Kiwi for email. I have 3 gmail accounts and that app allows me to easily toggle between my 3 google accounts. Boomerang works in Kiwi. I use it and I agree, it’s great

Cara Carlone: I’ve never used it personally, but my coworker swears by Evernote to stay organized. That’s an idea too!

Nick Lamparelli: Cara I’ve tried Evernote. I could never make it work for me. Maybe I didn’t try hard enough because so many people use it.

Tony Canas: I love Evernote, I use it for business cards and for notes when I worked in sales for a carrier that didn’t have a CRM system

Jen Overhulse: Nick L. you and I are living under the same rock again…never could make Evernote a thing.

Nick Lamparelli: For those that are reading this, I use an app called Pocket. It’s sort of like Evernote, but I find it easier to use. <>



Nick Lamparelli: @channel, thank you all so much for participating in this quick SlackChat. I am going to close it off now. We will edit and post on the blog in the next week or so

Taryn Haas: Thanks for starting it Nick L.!


About Nick Lamparelli

Nick Lamparelli is a 20+ year veteran of the insurance wars. He has a unique vantage point on the insurance industry. From selling home & auto insurance, helping companies with commercial insurance, to being an underwriter with an excess & surplus lines wholesaler to catastrophe modeling Nick has wide experience in the industry. Over past 10 years, Nick has been focused on the insurance analytics of natural catastrophes and big data. Nick serves as our Chief Evangelist.

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