Simplifying the Holidays: Rocks in a Jar

holiday-gift.JPGI adore Melissa Massello, not only because she’s super creative and fun (plus, we share bonds over figure skating, fashion, shredding, and all things writerly), but because I’ve seen her jump from traditional employment to fulfilling her dream of launching the online magazine Shoestring Magazine, which focuses on tips for achieving the good life for less. As the first in my Simplifying the Holidays guest blog series, today Melissa shares a strategy for prioritizing and planning holiday gifting that can result in major bargains, meaningful finds, and less stress.

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From Melisssa:

As much as it pains me to see the displays on store shelves, the white snowflakes printed on red Starbucks cups, and the wintry wonderland of TV commercials in late October/early November, the truth is, I've always done my holiday shopping before Thanksgiving. The hard part is keeping my finds a secret until December.

Why? Well, for a bunch of reasons, some of which might only make sense to me, but they save me time, money, and most of all, stress -- that is, when I can contain my enthusiasm for my finds. Here’s how I go about my shopping:

The Bucket List

Whether due to being sentimental or simply caught up in the spirit of the season, I tend to completely overdo it this time of year. That is, unless I make a concerted effort to distance myself, setting realistic expectations about events and making an objective, uber-organized list for gift-giving -- which I review at least three or four times over a period of weeks. I use a practice my dad calls Rocks in a Jar:

Put the Rocks (family members) in first, the Pebbles (friends, close colleagues, extended family) in second, and the Sand in last (co-workers, obligatory nice gestures). If you take the hour or two to do this, you'll absolutely have room for everything -- both financially and emotionally -- no matter your budget or busy schedule. Assign realistic dollar values for each of the three buckets and then make each of those dollars count.

A wise editor friend in NYC once told me to actually take out the cash for my entire holiday shopping budget, then stash a few notes for each present in separate, labeled envelopes, then spend no more than that amount – for example, one envelope marked Mom with $50, one for Husband with $100, etc. This tactic works incredibly well for mall shopping, but for online shopping or a combination of resources, my secret weapon is a $1 iPhone app called Better Christmas List. A good, old-fashioned list (in whatever form lists work best for you) will do, too.

If you start early enough, you can focus on finding one or two "perfect" presents each week until the holidays, as well as hunt down the best deals and best value products through a combination of sales, customer reviews, and retail coupons. It all feels a lot less overwhelming mentally, and a much smaller burden on the weekly paycheck, to break it up over time. You might even find, as I do, that you ENJOY it and get to share in the magic of the season, not just the materialism of it. You might even find you have time to bake cookies and pet treats from scratch, the byproduct of being organized that I found most memorable last year -- and which make great, cost-effective gifts for the people on your list in any Bucket.

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Melissa Massello is co-founder and Stealfinder-in-Chief at Shoestring Magazine, where she brings bargainista tips with new media tricks to the masses online. You can follow Shoestring on Twitter at @shoestring or fan Shoestring on Facebook.

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