Good vs. Evil: Paper or Online Calendars?

Dear K & K: I think I’m an Organic Structure and use an electronic calendar on my Mac. But, I can’t quite cut the cord with my paper calendar yet because it no longer has the functionality for To Do items. Is there an online calendar you recommend so I can go fully digital? Signed, Annoyed in Annapolis.

Dear Annoyed: Technically, since you’re an Organic Structure — visual with your memory — the best thing for you is to use a paper calendar instead of a computer. That being said, we realize paper doesn’t have the functionality of inviting people to meetings and syncing calendars that makes life SO much easier to plan these days. And as two brilliant women once said, Life Should Be Easy. By the way, Apple’s move to get rid of the To Do list made no sense to either of us.

We’ve got two ideas for you. First, checkout would be Wunderlist because you can get it to sync up with everything do a bunch of lists and To Dos. It’s free but there are in app purchases. Also, Google’s schedulers pretty great and free. Finally, it’s okay to have paper and digital. Sometimes the act of writing helps some of us REMEMBER and that alone makes life easier. All our best: Katie & Kelly


Digitize Office Files

Dear K&K:  I currently work in my family’s real estate business … We have a lot of files (documents, leases, legal documents, etc.) that go back more than twenty years. I think we need to put all of these on the computer (digitize office files), and throw out what we can, though there are documents we do need to keep. Our office manager has scanned some documents and filed them onto external memory sticks, but I feel like that is inefficient. I think the main obstacle is that the office has been run the same way for the last 30+ years and while there is a recognition and desire to get more organized we do not know where to start. Any tips, advice, suggestions would be appreciated. Thank you! Documents in Detroit

Dear Documents: What you should keep in mind is that at its core, organization is about retrieval. Can you find something when you need it at a moment’s notice without stressing out? If you can, your company’s paper & digital systems are basically organized. If you can’t? You’re not really organized and potentially losing value to inefficiencies because of it.

Yes, there are more efficient ways to digitally store older documents. We’d suggest hiring a firm to digitize documents and then set you up with an electronic data management system. This way employees can search for saved documents at their computers without wasting time figuring out which memory stick it might be on. The latter method is more time-consuming. There is a reason for that saying, time is money. It’s true. The more time people waste trying to find a document that’s been digitized, the less time they have to work on things that actually produce value. All our best! Katie & Kelly

Data management companies: SAS or Iron Mountain

Organize Your Way

Dear K&K: Loved hearing you on NPR, and to hear about personality based organization. My sister and I were just talking about how difficult it is to organize and create systems to stay organized. Recently, I’ve realized how stressful it is for me not to able to control clutter in all aspects of my life. I’ve recently started a new job, for which I work out of my house, hence why I’ve been more aware of wasted time trying to get organized.

Of course, my job doesn’t generate enough income to be able to hire an organization consultant. However, I feel that having a good organization system would make me more productive, and generate more income and satisfaction with time. Looking forward to some words of wisdom. Sincerely: Interested in Illinois

Dear Interested: Well, technically the best bang for your buck would be to buy our book, Organize Your Way. BUT, you can also go on our website and take our quiz for free, then read about your type and some of our tips for each type.

The two things that are integral to making systems work no matter what your personality type: (1) Room to grow!! Set up a system that has room to grow, i.e., leave empty space and/or bins. Clutter always multiples over time. If a system fits your clutter after a purge, we can guarantee it’ll eventually overflow out of control one day. (2) Reduce organizing systems as close to one step as you can. Fewer steps mean easier, which translates to more adherence. The definition of what’s easy depends on who you are. If you’re an Organic Freedom it means setting up a coat rack instead of expecting yourself to hang up all your coats on hangers. It means taking off the lid of a hamper to make it easier to dump clothes in there and not on top of a lid.

Hope that helps!!

All our best,

Katie & Kelly

Book Trailer:

Your Boss on Facebook


Dear Katie & Kelly: My boss just asked me to be his Facebook friend. We have a great rapport but I want to keep my work separate from my home life. Is it okay to turn him down or is that a dumb move career wise?


Signed: Flummoxed in Florida

Dear Flummoxed: Of course, it’s okay to turn him down. You are not obligated to accept anybody’s Facebook friend request, even your bosses. We would, however, counsel you to turn down your boss a little more diplomatically than some weirdo you barely know. As you said, you have a great rapport, he could simply think his request is just another extension of said rapport but it technically could also qualify as harassment. Simply tell him that you don’t ever mix social media with work — “It’s a bad cocktail, man!” It’s nothing personal, just business. But before you do anything, make sure you truly keep work separate from home and you’re not Facebook friends with other colleagues. If you are, it in no way changes our advice about your boss’s request. But, we’re betting it might change how he sees your rejection of his request since your whole “I don’t mix social media with work” is actually B.S. in that case. You might want to consider being consistent with your stand across the board.

Good luck! K & K 

Make Uncomfortable Work Talks Less So


Dear Katie & Kelly: I’m a full time nanny taking care of two school age children whom I’ve known their whole lives. They’re now in second and fourth grade. When they started school full time I figured I would have to find a different job because part time isn’t enough money for me. But my employer reluctantly agreed to keep me on full time even though the children are gone most of the day. I do a little light cleaning but it’s not enough to really occupy me or make me worth my salary. Obviously, I know I’m lucky, my worry is how long can this arrangement last given her reluctance? I keep meaning to ask my employer but I put it off as I hate conflict and don’t want to give the impression I’m unhappy or want to leave. I just hate not knowing. I’m pretty sure that I’m an Organic Structure.

Signed: Nervous in Nevada

Dear Nervous: The best approach given your procrastination is just to ask your employer about their vision for your future employment when it seems organic or at your year-end review or whenever you have your discussion about annual compensation. If you don’t have this sort of annual discussion, you should ask if it’s possible to have one going forward. Doing so should not create conflict as it’s pretty standard with almost all professional jobs. Just because you work in a home doesn’t mean you’re not a professional doing a job deserving of feedback and this way you have a guaranteed time when you and your employer both can bring up any issues. This way the conversation isn’t a big deal. It’s simply part of an annual ritual.

All our best: K & K


How to Deal with Competitive Colleagues


Dear Katie & Kelly: My firm just hired this new guy who is at my level. He’s working insanely long hours and making me look practically lazy in comparison. I work in finance and I’m a Classic so I’m used to hard work and long hours. No problem. But, this guy is too much. He’s a brown noser to the core and I don’t trust him. I don’t want to complain to my boss because I’ll sound like I’m whining. Any advice on dealing with his nauseating behavior.

Signed: Classic in California

Dear Classic: Keep your friends close but your enemies closer. Attempt to befriend him first. This sounds Machiavellian but it’s not. Just wise. Classics can get stuck in the details of the present and need to take a step back and look at the bigger picture. Chances are this person is semi normal and just new and trying to make a good impression. Someone might’ve seen you in this same light when you first started. When Kelly was working at a hedge fund, this new gal started and seemed like a total annoying eager beaver. Low and behold she was just new and instead of acting like a bitch to her, Kelly befriended her and she remains one of her closest friends. But this isn’t always the case and in the world of high finance never dumb to keep your guard up.

If you temporarily suspend judgment and still find this guy to be an untrustworthy brown noser, focus on you. Make sure he’s not impacting your trajectory. Regularly check-in with your higher ups to make sure everything you’re doing is on target. Run your own race while keeping an eye on what the rest of the field is doing, including the new annoying guy, and continue to keep him even closer once you’ve confirmed he’ll never be an actual friend.

Take care: K & K

Sharing a Desk Stinks


Dear Katie & Kelly

I share a desk with a colleague. We work part time and keep different hours. We both leave a few personal items on the desk. I never touch her things. But recently, I’ve noticed she keeps moving my things around so that I have trouble even finding things and can’t seem to find a pair of my gloves that I left one day and I swear she’s eating my lifesavers. Would it be rude to leave a note asking her not to move my things?


Annoyed in Annapolis

Dear Annoyed,

Umm, no, leaving a note like that is never a good idea UNLESS you’re spoiling for a fight. Hear us out. Kelly once left an anonymous note in her sorority’s house fridge asking people not to eat other people’s food. It seemed a perfectly normal request because somebody had repeatedly eaten her various leftovers in the fridge without asking. Rude! Whoa nelly. Her note sparked a firestorm the focus wasn’t on the food stealer but the rude note author.

In review, a note is fine if you want to sour your relationship with this person and risk her doing something very naughty to your lifesavers and then putting them back in your drawer. The other solution would be to ask your supervisor for a desk with two separate locks to drawers so you can put your things away at day’s end and not worry about anyone disturbing them.

All our best,


Coming Home

Illustration by BreckWorks

Illustration by BreckWorks

Dear Katie & Kelly,

I’m a working mom with young children. Some days I love being at work doing my own thing. Others, I miss them terribly. Regardless, when I come home from work, I’m exhausted and it’s almost too much when I arrive home and relieve the nanny. I go from being swamped at the office to being swamped by dinner, baths, bedtime, arguments. It leaves me constantly stressed and I am often short with the kids. Then I feel guilty because I should relish my time with them. Any ideas?


Exhausted in Edgemont


Dear Exhausted,

No matter what your personality type, when you get home from work, most of us need to decompress, especially introverts. You’re not a bad mom, you’re human. Upon your return, carve out 15-20 minutes doing something alone that rejuvenates you — don’t relieve the nanny until you’re done. Make this part of your daily routine. Our introverted Smart Structure father would come home from work everyday, go into his study, have a drink and read for 20 minutes. Sometimes he’d even take a 20 minute nap and then we’d all have dinner together. Recharging your battery first will help you be your best self.

All our best,

Katie & Kelly

Lazy Leader

Dear Katie & Kelly,

I’m working on a project with a co-worker. I don’t know his personality type but he’s driving me crazy. He is supposed to be the lead on the project but barely does anything unless I initiate it. He ignores his deadlines which makes it difficult for me to get my parts done. I’m about to ask to be reassigned. Do you have any ideas?

Angry in Arizona.


Dear Angry,

Since we don’t know his personality type, this reply is a shot in the dark. Our bet is the person is a Fun, Organic Freedom or Smart Freedom. They’re the only types that don’t sweat blowing through deadlines unless they’re real deadlines. We assume they’re suggested deadlines because if they’d blown through real deadlines, someone higher up would’ve already noticed. The problem with working with the above personality types if you are not one of them is that they work to real deadlines. Other types — Classics, Organic Structures, and Smart Structures — tend to steadily work toward completing them all. Sit down with your co-worker and tell him how you prefer to work. Work out a timeline together. If he can’t respect it or you can’t find a workable compromise then as a last resort ask to be reassigned. But, frankly if I was your boss I’d wonder why you two couldn’t figure it out. Besides, if you try our approach, chances are he’ll work with you.

Hope that helps,
Katie & Kelly