How to make your taxes easier? Go paper-less!

Paperless Tax Time

As a professional organizer specializing in home office and small business organizing, one of the most frequent requests I get this time of year is to help my clients prepare tax documents for their accountants. I prefer a paper-less tax environment — notice I say paper-LESS, not paper-free, as I like to keep some of my tax backup in paper for 3 years before shredding it. But it is important to have permanent electronic copies of tax records, as you never know when you’re going to need to produce a W-2 from a former job or some other piece of information for a bank loan application. I find it’s much easier to store and retrieve this kind of data digitally than in paper format.

As I help my clients plan for tax season, here are the main steps that I advise them to take if they are interested in taking the paper-less route:

  • Create an electronic folder on your computer called Taxes (Year) and a corresponding paper file folder.  Keep both in an easy-to-find place (such as your computer desktop for electronic records and a standing file on your desk for your physical file) during the height of tax season.
  • As your tax documents start to arrive in the mail in January and February, first scan them (using either a document scanner or one of the many great phone scanning apps that are available) and save them directly into the Taxes folder you have designated for that year. Then put the paper copy in the paper Taxes folder.  Keep them all in one place – don’t let them stray around your home!
  • If you are a small business owner, you’ll probably need to file a Schedule C which itemizes your business income and expenses.  You can use something fairly simple like the free app Everlance to keep track of these items throughout the year, or a more comprehensive system like Quickbooks or GoDaddy Bookkeeping.  Make sure also to keep track of the miles you drive for business, as those are deductible as well.
  • If you are self-employed, scan all your business expense receipts throughout the year, and save them directly into a electronic folder called something like “Business Expenses (Year)”. You do not need to keep paper copies of your receipts – the IRS accepts scanned versions.  I shred mine as soon as I have scanned them.
    • I like to subdivide my business expenses into folders following the categories used by the IRS on a Schedule C, such as Meals/Entertainment, Supplies, Parking, Contractors, etc.
    •  If you have email receipts for business expenses, save these as PDFs into the same folders using the same categorization method.
  • As you make charitable contributions throughout the year, scan and save mailed gift acknowledgements immediately into a subfolder of Taxes called Contributions.  If you get email acknowledgements, just save these as PDFs directly into that folder.  (See how to print to PDF on a Mac.)
  • If your tax preparer is paper-less too, share your Taxes folder with them on a secure online cloud system like Dropbox or Box – no need to send in shoe boxes of receipts! He or she can only see the data that you have shared with them and nothing else.
That’s it! During the coming year, just make sure to stay on top of any tax deductible expenditures (business expenses, charitable contributions, etc.), and save them directly into your Taxes folder for that year.  You’ll be one step ahead of the game come next tax season!

How to be a Productive Freelancer When Cabin Fever Sets In


Penny Catterall was thrilled to contribute to this blog from Insureon, a small business insurance provider, about what freelancers can do to stay productive during the long days of winter. You can read the post below, or click here to read it on the Insureon website. 

The perks of working at home as a freelancer mean you can typically set your own hours, work in your pajamas, and take a walk in the sunshine. But what happens when cabin fever strikes during the darkest throes of winter?

If you don’t want your efficiency to take a nosedive, try these five expert cabin fever cures that can help you stay productive.

Freelancer Malady #1: Household Chores & Errands

What Ails You: An endless parade of chores and errands takes your attention away from work.

Maura Thomas (@mnthomas), founder of management and productivity training companyRegain Your Time, says working from home presents personal procrastination temptations.

“You think, ‘Let me just empty the dishwasher. That’s a good use of my time,’” Thomas says. “But then you end up frittering the day away doing things around the house.”

The Cure: Use personal chores and errands as breaks, Thomas suggests. “If you’re doing brain-heavy work – spreadsheets, videos, computer work, etc. – mundane chores are a really great way to take a break,” she says. “Physical activity gives your brain time to relax and to switch things up.”

Freelancer Malady #2: Multitasking Mayhem

What Ails You: Multiple projects are vying for your attention.

You’ve got several deadlines looming, but working on them simultaneously won’t get the work done any quicker. If anything, it might take longer. A Stanford University study found that multitasking is less productive than completing a single task at a time.

The Cure: Try the Pomodoro Technique. Professional organizer and productivity consultant Penny Catterall, owner and founder of Order Your Life (@OrderYourLife), advocates this technique to help complete work in set blocks of time, complemented by short scheduled breaks.

There are many free apps and downloads that follow the principles of the Pomodoro Technique. Catterall recommends Focus Booster for its visual representation of your time.

Freelancer Malady #3: Digital Distractions

What Ails You: Technology notifications and incessant emails plague your working hours.

Technology connects your business to clients and helps you complete your work, but it’s just as efficient at distracting you from it. Productivity consultant Lori Vande Krol (@lvandekrol), CPES and president of Life Made Simple, says anything that pulls you from your plan is a potential distraction.

“Ask yourself if the phone call, new email, or Facebook notification is worth time away from your defined plan and priorities,” Vande Krol says.

The Cure: Turn off all notifications (e.g., phone, email, social media, etc.) for a set amount of time, Vande Krol suggests. Don’t give into temptations to peek – it will still be there when you’re done working.

Freelancer Malady #4: Kids & Pets Underfoot

What Ails You: A whirlwind of kids and pets compete for your attention.

Whether they are too young for school or they’re on break, children often pose a distraction for freelancer parents working from home. And don’t forget Fido – he needs to eat and go for a walk. Technology may be the simpler distraction to thwart of the two.

As Charlie Gilkey (@CharlieGilkey), author and business adviser of Productive Flourishing, says, “Facebook doesn’t come banging on the door, but your kids might.”

The Cure: Gilkey says work can be more challenging with children and pets, so there may be times you need to work from coffee shops or offices. “To do so, you obviously might need to coordinate childcare and possibly speak with your partner about budgeting for it,” he says.

Penny Catterall says you don’t need to feel responsible for your kids 100 percent of the time. “On random snow days with the kids stuck at home, find a neighborhood teen to watch your kids for a few dollars,” she recommends.

Freelancer Malady #5: Overflow of Inspiration

What Ails You: An outpouring of ideas and an overwhelming list of tasks occupy all your time.

Productivity speaker and consultant Nicole Chamblin, owner of Visions Productivity Solutions(@visionsps), says she’s often distracted by all the great ideas floating around her head for classes, blogs, and solutions for clients.

Fortunately, Chamblin says there are many cloud-based tools that can “make a freelancer kick their productivity into high gear.”

The Cure: Try mind mapping – Chamblin says she uses this technique to help empty her brain and flesh out her ideas. To stay focused, she recommends using a master planning calendar to track your workload.

Additionally, Chamblin recommends tools like 17hats or Trello to set up workflows, reminders, and tasks.

Staying Productive Means Staying Proactive

Staying productive may also be your best form of risk management. While we love talking about insurance for freelancers and independent contractors, we realize most freelancers don’t think about making that purchase until they can maintain a steady stream of work. The more productive you are, the steadier your workflow and revenue stream will be, making it easier to afford smart risk management investments like small business insurance.

Scanning photos on a snowy weekend


If you live in the Mid Atlantic, you probably were snowed in last weekend by “Snowzilla.” As an organizer and therefore a Type A person, I couldn’t face the prospect of being stuck inside for several days without a major project to keep me occupied. I figured this would be the perfect opportunity to catch up on scanning the boxes of photos that have been sitting in my basement for the past 10 years.

I wanted to tackle this for a couple of reasons — primarily because I noticed that many of my older photos had started to deteriorate and I wanted to get them digitized before they got any worse. And secondly because I finally realized that I was never going to make any more physical photo albums (I am not a scrapbooking kind of person). With all those photos in boxes in the basement, I had completely forgotten the parts of my life they represented. I grew up overseas as the daughter of a US Foreign Service officer, so we have some pretty incredible pictures of places that most Westerners have never traveled to! The best way to bring those memories back to life was to scan them and have them on my computer, where I can choose my favorites and use them as a screensavers. More importantly, I can make digital albums out of them. With the impending snowstorm arriving over the weekend, I thought this would be the perfect time to get this done! Here are the steps I used to accomplish it.

Back It Up

Since I had been thinking about doing this for while, I was already somewhat prepared. I had purchased two 2 TB WD Elements external hard drives – one to store all my photos on, and one as an extra backup. No matter where you end up keeping your digital photos — whether on your computer hard drive, Adobe Lightroom, Google Photos, Apple Photos or the myriad other photo organizing options out there — BE SURE TO BACK THEM UP!

Start Small

I started by going through the pictures, one box at a time. If I looked at all the boxes at once, I got overwhelmed.  I just took it a little at a time.  Fortunately, I am neurotic enough that I had already organized them by year, month and event.

Box of photos ready to be scanned.

Scan It With a ScanSnap

I am also already the happy owner of a Fujitsu iX500 ScanSnap, without which this entire project would not be possible. The most important thing I needed was for the power not to go out — fortunately, it did not.  It’s incredibly easy and fast to scan photos with the ScanSnap iX500 — see here for a more detailed explanation.  Here’s my ScanSnap, ready to scan with about 30 pictures in it.

ScanSnap iX500 great for photo scanning

Organize It

I scanned my photos directly to the external hard drive, into a folder structure laid out by year, month and event, similar to how I had them categorized in my physical photo boxes. For my kind of brain, a very ordered structure like this makes the most sense, but you can set it up any way you want.

How to organized scanned photos on an external hard drive

Once I am done scanning, I can decide which ones I want to use to make albums by creating specific folders with those photos and importing them directly into Apple Photos. I ended up trashing most of the actual photos (sacrilege, I know), but I did keep those that held really special memories or were of excellent quality. I was able to reduce the number of photo boxes from 6 to 2 — was a real accomplishment for me.

 “Ah Ha!” Moments

I realized a lot of important things as I was going through this process.

  • First, I remembered how in the 80’s and 90’s, when we ordered photos from places like Ritz and Kodak, they often came with free duplicates for us to give our friends and families. Most of the time, at least for me, those duplicates ended up sitting in the photo boxes just taking up space. And they were duplicates of pretty bad photos too! During this project, I tossed them all out.
  • Second, a lot of these photos were just terrible! They were out of focus, or I didn’t remember who was in them, or they were just of some generic landscape with no people in them. If they didn’t have a significant memory attached to them, I tossed them too.
  • Third, I had a wonderful trip down memory lane, remembering people, places, and events that I had completely forgotten about. It made me put my life in perspective, and now I want to get in touch with people I haven’t seen or talked to for a long time.

While this was a very time consuming project, it also was extremely rewarding; once I had a system down for how I wanted to scan photos in, it went pretty fast. The snow stopped and eventually I had to get back to my real work, but I am about 90% done with my photo scanning at this point. Hopefully it won’t take another snowstorm for me to get finished!

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