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July Contest: Who has the messiest desk or office?

How would you like to be eligible to win a prize for sending me a photo of a messy desk or office?

Intrigued? I’ll get to the two contests I’m running this month in a second. Hang in there.

First, let’s talk about the lazy days of summer. Now that gloriously hot weather has arrived (at least in Ottawa), it’s tempting to pull your foot off your financial gas pedal and take it easy for a bit. ‘Tis the season to relax and enjoy, right?

I’m going to suggest, instead, that July is the perfect time to breathe a breath of fresh air into your finances.


By tackling an often-overlooked area: your financial back end. That is, your office, or wherever you keep your financial records. We’ll leave the cognitive heavy lifting for another day and turn our attention to the way you organize your financial system.

“Doris, why bother? I’ve got better things to do,” you might insist.

Here’s a little tidbit I’ve noticed over the years: The way you set up and maintain your system affects how you feel about your finances. It also plays a role in what you can accomplish. 

Sue’s story

I once worked with a woman we’ll call Sue. Sue kept her office tidy and diligently kept every piece of paper that was relevant to her finances. From the outside, everything looked good.

The problem lay inside the filing cabinet and inside the boxes in her office. They contained a heap of files of past years’ paperwork, receipts, and tax filings.

When I asked Sue about the contents, she stated the obvious: “It’s all my records and receipts.”

I looked inside the cabinet for a moment. “What story would they tell if they could talk?” I asked her.

She shrugged. “I don’t know.”

“Do you know what the numbers are for each year?” I asked, taking a different tack.

“No,” she replied, clearly uncomfortable.

When I asked Sue about her process, she told me that as soon as paperwork (i.e. bills, statements, Notices of Assessment, etc) comes in, she doesn’t look at it. Bills get paid without reconciliation. All documents then go straight into the files.

After a few more questions, Sue realized that this is a form of avoidance.

The illusion of order

Sue had convinced herself that she was being financially responsible by paying her bills on time and keeping all receipts, but she never took the time to look at the numbers, determine if her system is serving her well, and make adjustments.

She admitted that she is embarrassed by her situation. She doesn’t really want to know how little she earns and how much she spends. By hiding the evidence as quickly as possible, she avoids any unpleasantness.

“Does it work?” I asked. “Do you feel good about your finances? Is this working for you?”

“No, ” she admitted. “I’m pretty stressed all the time and I don’t know what to do about it.”

We put a plan in place and Sue started to dig through her paperwork. Her shredder got one hell of a workout! It took a while to go through all the boxes, but with persistence, doing small bits of work at a time, she made it.

In the process, she discovered a number of self-defeating patterns at play in her life. “I had no idea,” she told me. “This pattern of under-earning and overspending is coming to an end right now.”

And that’s when things changed substantially for Sue.

When you clean out the “dirt”, you gain clarity and you can create a positive plan that gives you a renewed sense of purpose. You can then consciously create a financial system that serves your values and goals.

Look for the signs

Sue is not alone. I’ve seen many variations of systems in disarray:

– Bills stuffed in a drawer, unopened.
– Receipts scattered around in purses, cars, in booklets, and on counter tops.
– Boxes stacked in every possible corner.
– Piles of paper on every surface.
– No receipts kept for anything, so no clutter. No records, either.

I’ve also seen the flip side of this, where an office was impeccably clean and all files were super tidy – bills organized, files colour-coded, everything alphabetized. There was just one problem: Organizing, sorting, and prettying up were used as a procrastination mechanism to avoid the hard work of figuring out the next financial steps.

We’ve all done this – filled up hours with busy work, while essential work sits ignored, all because it feels super productive to be busy. It’s also a lot easier than sitting down and tackling a chunky problem. We’ll do that later, when we’ve had more sleep or coffee, or when the office has been tidied.

As Kate Beeders aptly says, “There is no time on the clock or calendar called “later.” Later never happens.”

So yes, your back-end system makes a big difference to your outcomes. Organizing it is Step #1. 

Whose job is it?

As I introduce a contest to help you clean things up, as it were, I want to ask an important question: Whose job is it to tidy up the books and the files? Since I know that many of my readers are women, I don’t for a moment want to suggest that this job should land solely on your lap.

We know from research that women already carry a huge cognitive load when it comes to the management of their households. In this article, author Lisa Wade shares an eye-opening study by sociologist Susan Walzer:

Walzer found that women do more of the intellectual, mental, and emotional work of childcare and household maintenance. They do more of the learning and information processing (like researching pediatricians).

They do more worrying (like wondering if their child is hitting his developmental milestones). And they do more organizing and delegating (like deciding when the mattress needs to be flipped or what to cook for dinner).

That’s certainly true in my household, and I’m married to a terrific guy who does a ton around the house. Still, I’m the one who remembers to book dental appointments for our girls, buy them clothes because they grew out of their pants in the blink of an eye, and plan our social calendar, to name just a few small examples. (When I’m grumpy, I ask him if he’d like me to list the items alphabetically or in order of importance.)

So, the last thing I want to do is suggest that this is a job for women to tackle, unless you happen to be a gal living alone or you’re in a lesbian relationship. Then it definitely is a woman’s work!

For everyone else, I suggest you take a teamwork approach to the job. This is a case where two minds, and two sets of hands, are better than one.

Time for a Contest (or two)!

It’s time to have some fun and do some good at the same time. This month, I’m running a contest: Who’s got the Biggest Disaster Zone? Send me your photos and I will share them with my community, anonymized of course. (I take your privacy seriously. Remember that I’m the gal who creates a safe zone for every meeting and/or presentation.)

Does your desk look like this?

If so, congrats! It might just win you a prize. Take a pic and email it to me at

At the end of the month, I will give the winner of the messiest desk or office a $20 gift card to Bridgehead or Starbucks – you choose.

Contest #2

There’s a second part to this contest: I’m also giving an award to the person with the best Before & After pics! Same giveaway as Contest #1.

Hell, if you have the worst mess and you manage to pull off the best transformation, you could win both gift cards! And don’t worry, I won’t name names (unless you want me to).

The idea, this month, is to look at your office, your files, your desk or wherever you maintain your financial system. Ask yourself the following questions:

  • Do I feel good when I look at this area?
  • Is everything easily accessible and organized in a way that makes sense to me?
  • Have I kept everything that is important for my financial system?
  • Is there anything I can get rid of?
  • What story does my paperwork tell about my earnings, spending, savings, and investing patterns?
  • What improvements could I make to ensure the system serves me more effectively?

Just one thing

Take a snapshot of where you’re at today. Literally – take a photo. Document it so that you have a baseline for comparison. Then, write down one thing that you can do to improve the situation. Just one thing. That’s all you can focus on, anyway.

I strongly recommend that you start with something small, like “Open all the bills” or “Sort bills by type: credit card statements, utilities, taxes…” or even “Shred stuff I don’t need from one file.” Make it something manageable that you can accomplish relatively quickly.

By the way, shredding feels really good.

If you start with a monster task like “Go through all the boxes on the floor”, you’ll soon be overwhelmed into a state of paralysis, or reaching for a wine bottle. Keep the first steps really small to secure quick wins.

Once you’ve identified your first step, get to work on that one thing, whether it’s opening all your bills, organizing your documents, shredding old files, etc.

Just. One. Thing. Yes you can. The big picture is probably overwhelming, but one step is not. Focus on small, bite-sized chunks.

What happens when you do this

If you’re like several of my Women’s Money Group members, this process will likely create momentum for you. It’s amazing what happens when you get in the driver’s seat of your finances.

Have fun with this and pleasepleaseplease send me photos! Lots of photos! Don’t be shy; this is all anonymous.

If your space looks like it could be an exhibit in a museum, take a pic and send it to me. I want to see that, too!


I will email you every single week this month to check in and provide encouragement. I’m also going to share photos. So a) get on my mailing list if you’re not already there. You can join our community of cool people rocking their finances, right here on my website. Look up, WAAAAAAAYYYYYYY up to the purple band at the top of this blog post and hop on to get weekly money tips plus updates on this month’s contest. 

And b) start doing a little bit every day. Yes, even Saturday and Sunday. Shred something (seriously, it’s so damned therapeutic), file something, look at something you haven’t looked at before, or sit quietly and think about what a good set up would look like for you.

In the coming weeks, I’ll also share what my system looks like, but only if you’re on my mailing list. That’s where the nitty gritty, inside scoop stuff happens.

On July 31st, I’ll announce the winners.

Why pics?

Here’s why I want to share photos of disaster areas and messy files/desks/whatever: to let you know that you are not alone. There are heaps of people who are struggling with the same issues.

We are all in this together. We are a community of people who support one another.

I look forward to hearing from you!

Reach out if you need guidance, inspiration, or a shredder.

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