Welcome to reThinkable, a weekly newsletter where I share actionable ideas to upgrade your money and life.

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Read time: 2 minutes and 56 seconds

I hated the holidays.

Don't get me wrong — I have great childhood memories but…

Nowadays, “holidays” seem to go hand-in-hand with “expensive obligations” — gifts here, gifts there, gifts everywhere.

And I’m not alone: 40% of Americans stress during the holiday season about spending too much or not having enough.

Thankfully, I now know how to optimize every single dollar when I shop.

Sit back, relax, and pour yourself a glass of eggnog (or your favorite bev) cause I’m sharing my 5 shopping hacks.

I used to subscribe to every store’s email list to get their welcome discounts and latest deals.

I thought I was saving money but then I realized I always felt the urge to buy something every time they sent me an email.

That abandoned cart? Another reminder. That item you browsed? "On sale!" That wishlist? "Last chance!"

Before you know it, you're buying your 28th pair of underwear.

Here's how I took back control: I created a separate email address I used just for shopping promotions (for instance: [email protected]).

Now YOU decide when you want to look for deals. So when you’re ready to buy something, check that email inbox for discounts.

Rakuten is one of my favorite free shopping extensions since it has some of the best cashback deals. They partner with thousands of retailers like Apple, Best Buy, and Target, letting you earn anywhere from 1% to 40% cashback.

Cashback is like getting a refund on everything you buy.

If I spent $1,000 on some speakers at Best Buy and applied Rakuten's 10% cashback, that means Rakuten will give me $100 back, so the speakers only cost me $900.

If you’re interested, if you sign up for Rakuten with my link, you’ll get a $30 cash bonus when you spend $30.

Black Friday used to be simple — ONE big day of sales.

Nowadays, it's an exhausting marathon stretching from October to December.

With so many different sales, it can get overwhelming to keep up.

Instead, I wait for the best sales to pop up on Slickdeals. It’s a free site where people crowdsource their favorite deals, coupons, and discounts across the internet.

There are times when I don’t know what to get people so I just get them gift cards.

Pepper lets you buy gift cards at a discount (typically 2-20%) from hundreds of top brands, including Amazon, Best Buy, Airbnb and more.

Last year, I used Pepper to get my friend a $100 Target gift card for $90. Plus, I earned reward points that I used in the future to buy other things on the platform.

If you’re a new user you get $20 after spending $200 in your first 15 days with a referral code at sign up (mine is 621776).

If you have a big family or friend group, it can get expensive fast to get individual gifts for each person.

That’s why for larger groups, I always propose doing a White Elephant or Secret Santa gift exchange. It’s a fun way for everyone to get a fun gift without any big financial pressures.

I'm gonna experiment with different newsletter content styles in the coming weeks and would love to hear your thoughts on what you like and what you don’t like.

Tell me what’s on your mind here (don’t worry, I have thick skin)

Thanks in advance!

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