I have attention deficit disorder primarily inattentive, am a professor who travels a decent amount, and have trouble with being organized about submitting my receipts for reimbursement. I believe that it is caused by a combination of basic and deeper-rooted problems, and was wanting to know what you do to be organized about correctly getting reimbursed. This includes systems that you use to ensure that you have everything, where you keep receipts, what specific kinds of filing systems you might use while you're traveling so that nothing is lost, anything electronic (either hardware or an app), or even just the odd things that "just work for you".
Most of the following is only of interest if you find it interesting to hear how someone with ADD struggles to do basic tasks. I'm not sure you need the information to answer the question, in other words.
The longer explanation elaborates on "basic" and "deeper-rooted" things. Like I said, I have ADD-PI. Its manifestation for the narrow topic of submitting receipts is in the form of not remembering where I put receipts, failing to get the correct receipt from the vendor, and not having a system of submitting the receipts to our office manager. So I call this basic because I know it's just that something is breaking down between the time I make the payment to the vendor and the time that I'm to get my reimbursement forms to our office manager.
I should say that I don't travel a ton -- I probably take a 3 day trip (on average) every two months, and maybe one week-long trip once a year. It's almost always me traveling to another university to present research, though sometimes it's traveling to work with coauthors. I mention this because I think there are automated services that heavy travelers probably have access to that I can't justify, cost-wise. And I don't think it's necessary anyway -- these are solvable problems for me, and is just one example of many problems I have involving disorganization, impulsivity, and failing to properly connect the dots relating an action to outcomes over time.
All of this said (I'm already starting to ramble and failing to keep this post in check), I think that the deeper-rooted problems I historically had with regards to submitting reimbursements were connected to the overwhelming sense of embarrassment I felt about my problems with disorganization. I felt like such a failure that in combination with my own tendency to forget about submitting the receipts, and how disorganized I was with the receipts, I would just not turn them in and eat the costs myself. As flights and hotel accommodations rack up, and I'm not wealthy, this was itself another embarrassing problem as I now had to explain to my wife that I had "screwed up again", and so on.
Anyway, I'm doing better now. I'm medicated, I read extensively on ADD still, and have experimented with lifecoaches and therapists. I am more motivated to fix these historical problems, also, and so this is one I want to fix. We have an office manager, and so the first step was to come clean with her -- tell her that I was fighting a war inside my head and heart just to get the receipts to her, none of which made any sense if I verbalized it, and that any help she could give me was going to be disproportionally hugely valuable, no matter what it appeared like. She was (thankfully) awesome and has helped really fix this. (Things all went downhill once the department passed a new policy that reimbursements had to be in within X weeks of the travel. I still remember this wave of humiliation wash over me when I read that announcement, because it basically meant I was going to fail and badly. But things have gotten better since then, thankfully).
My workflow is much more organized than ever but merits a brief description. My workflow preferences seem to be simultaneously high(er) tech solutions and old fashioned solutions. So for instance, there's probably nothing I use more than Dropbox -- everything goes into Dropbox in fact. I am a heavy user and have upgraded to the 250GB. Best $200 I spent every year, and if something happened to Dropbox, I don't know what I'd do. I also use iOS devices a lot like my iPhone, iPad and Macbook. Since I keep losing receipts, I often will take photographs of the receipts immediately, and then move them to dropbox later. When I move them to dropbox, I move them to a "Reimbursement" folder and have organized subdirectories with the name of the trip and the date. I archive trips each year so that the subdirectory is clean. When I move pics into the folder, I will use that as an opportunity to read over the receipt, see if I can find the receipt, and rename the picture by the expenditure and its date. All of these seem to matter for reasons I don't fully understand -- but I think it has to do with my working memory struggles and how I've learned to direct my attention through hyperfocusing to correct for that. So simply going over the process of renaming the files seems to help me forget the embarrassment, and get excited about the process.
I also have opted to get a clean tan folder for every trip, attach several paperclips to the outside, write the name of my travel itinerary on the outside including the =arrival times, departure times, highlighter over the dates and times, and then store my receipts on the paper clips themselves. The problem is that there's several "moves" that are required to get the receipts to the paper clips -- like getting it out of my bag (which I may or may not have with me), and if I'm outside, trying to simultaneously put them in the clips without losing papers in the wind, etc. - and it's the fact that there's several moves that seems to be causing it to break down for me. So right now, I'm going over the receipts and I'm realizing that while this is the most receipts I've ever had (yay!), I'm missing several. And I remember it was because (a) I just forgot to ask for the receipt, (b) I asked for the wrong receipt [e.g., forgot to itemized receipts], and/or (c) I never put the receipt in here on the clips, probably because I didn't have my bag with me. Usually what I do is put the receipts in my wallet, and then TRY TO REMEMBER (Epic fail...) to put it in the folder later, but that just seems like I'm trying to fix a problem with another solution that has the same problem.
I feel like I need something like a folder that I really like -- something that I enjoy carrying around, in other words, and is attractive to me -- that is simple and functional. There's a simple place for my receipts, and that's it. Or I have some kind of tinier contraption, like a wallet just for receipts. I also sometimes take pics, but that makes me feel a little stupid when I am doing it in public, and I suspect my office manager will tell me they need the originals anyway.
So, that's it. What systems do you think I would respond well to? I think the answer is a simple "system" in other words, that may have a couple of purchases. But I think it's both, not either. That is, I have noticed that if I understand why I'm having these problems, then it helps address the humiliation I feel around the failures, and it helps me also come up with solutions that actually work. I've been gradually moving towards a solution on this, but still haven't figured it out, and so I thought I'd throw it out there to travelers, organizers, and so forth for advice.