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Money Monday: Make, Keep, Enjoy, Move — Week of September 7

Welcome to Money Monday. This is your weekly breakdown of one money-making opportunity, one deal worth knowing about, one lifestyle or travel deal that caught my eye, and one 10-minute money assignment.

The goal isn’t to obsess over money. It’s to make your money support the life you’re building. Four quick sections. Let’s go.

If you can manage an inbox, schedule appointments, and stay organized, businesses will pay you $15-35/hour to do it remotely as a Virtual Assistant (VA).

You get to use what you already know to make an income. No MLM. No inventory to store in your guest bedroom. This is real work for real companies — and the demand is growing as more businesses go remote and realize they don’t need a full-time in-office assistant.

What a VA actually does:

  • Email and calendar management
  • Scheduling appointments and coordinating meetings
  • Data entry and basic bookkeeping
  • Social media scheduling (not creating — just scheduling)
  • Research and organizing information
  • Customer service responses

Where to find VA jobs right now:

  • Upwork — the largest freelance platform. Search “virtual assistant” and filter by hourly rate. You’ll see hundreds of postings. Create a free profile, highlight your organizational skills, and start with smaller jobs to build reviews.
  • FlexJobs — hand-screened remote and flexible jobs. There’s a small monthly fee, but the listings are higher quality and scam-free.
  • Freelancer.com — similar to Upwork, good for building a portfolio

How to start without experience:

  1. Identify 3-5 things you already do at your day job that are VA tasks — inbox management, scheduling, organizing spreadsheets, handling customer emails
  2. Create a profile on Upwork (free) and list those skills
  3. Apply to 5 entry-level VA jobs (don’t worry about rate — your goal is first review, not top dollar)
  4. Start with 5-10 hours/week around your day job
  5. After 3-5 completed jobs with good reviews, raise your rate

What to watch out for: Anyone asking you to pay a fee to “get started.” Real VA jobs don’t require startup fees. If someone wants you to buy a training package, handle their personal banking, or receive and re-ship packages — that’s a scam, not a job.

Realistic income expectation: Starting at $15-20/hour for basic tasks, scaling to $30-35/hour as you specialize (social media management, bookkeeping, or real estate VA work). At 10 hours/week and $20/hour, that’s $800/month extra — before you adjust anything about your day job.

This week’s KEEP is a two-parter because both are worth knowing about.

Part 1: Rakuten Labor Day Boosted Cashback

Rakuten is a free cashback platform — you shop through their links or activate their browser extension, and you earn a percentage of your purchase back as cash. This Labor Day week, they’ve boosted rates at dozens of stores. A few standouts:

  • Under Armour: 10% cashback (normally 2%)
  • Dyson: 10% cashback (normally 1%)
  • Zappos: 10% cashback (normally 2%)
  • Viator (tours & experiences): 15% cashback (normally 2%)
  • CVS: 5% in-store cashback (normally 2.5%)
  • Macy’s: 4% cashback (normally 2%)
  • Expedia: Up to 6% cashback (normally 3%)

How to use this: If you were already planning to shop Labor Day sales, going through Rakuten first means you stack the sale price AND earn cashback on top. That’s double-dipping and it’s completely free.

What to watch out for: Cashback rates change. What’s boosted this week goes back to normal next week. Don’t buy something just because the cashback is high — that’s spending money to “save” money, which is just spending money.

Part 2: Ibotta for Grocery Cashback

If you’re not using Ibotta yet, this is your sign. It’s a free app that gives you cashback on groceries — both in-store and online. You browse offers before you shop, buy the items, scan your receipt, and earn cash back.

It’s not coupon-clipping. It’s more like getting paid for groceries you were buying anyway. The key: only use it for things already on your list. Don’t add items to your cart just because there’s an offer. I just got $1.10 back for my receipt. I didn’t even purchase any of the deals that were available.

This one’s super personal because it’s a group cruise with my travel community. I am a travel advisor, as is my sister, and we have collaborated to create Suitcases and Vitamin Sea, specializing in hosting group trips. I would love for the Pynk Collar Girls to be a part of the group and join us on the open sea.

The trip: 3-night cruise on Royal Caribbean’s Wonder of the Seas — one of the largest cruise ships in the world. Departs from Miami, stops at Coco Cay (Royal Caribbean’s private island) and Nassau, Bahamas. Memorial Day weekend 2027.

Why this is a Money Monday ENJOY: Because travel is a lifestyle goal, not a luxury — and this trip is designed to be affordable. The $200 per person deposit locks in your spot and gives you until March 12, 2027, to pay the balance. That’s 6 months to spread out payments. How many times have you wanted to go somewhere but didn’t because of cost?

What’s included: Cabin accommodations, gratuities, taxes and fees, and all included dining (not specialty restaurants). Once you’re on the ship, your food is covered.

What’s not included: Roundtrip airfare, hotel before/after the cruise, transportation to the Miami port, and shore excursions. Budget separately for these.

The money move here: If you’ve been saying “I want to travel more” but haven’t committed to anything, this is your sign. $200 to lock in a real trip — not a “someday” trip, not a “maybe” trip. A trip with a date, a ship, and a community. Check the full details and book your spot here.

This is the easiest one. It takes 10 minutes and it’s the highest ROI thing you’ll do all week.

  1. Open your bank app or credit card statement right now
  2. Look at your recurring charges — subscriptions, memberships, apps, services
  3. Find ONE you forgot about or don’t use anymore
  4. Cancel it
  5. Set up an automated transfer to savings for that exact amount

That’s it. You just redirected money from something you don’t care about to something that builds your future. If that subscription was $15/month, you’re now saving $180/year without changing anything about your lifestyle.

The average person has 2-4 forgotten subscriptions draining $20-40/month. That’s $240-480/year in ghost charges. Killing one subscription and redirecting that money is the financial equivalent of finding money in a coat pocket — except you can do it on purpose. I do love when I find money I forgot about.

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Money Monday isn’t about doing everything at once. It’s about doing ONE thing this week. Pick one section — MAKE, KEEP, ENJOY, or MOVE — and take action. Just one.

Start the Upwork profile. Activate Rakuten before your next purchase. Put down the cruise deposit. Cancel that subscription. One action, this week, and your money situation is already better than it was last Monday.

Next Monday, we do it again. Small moves, every week, compound into something big. That’s how you build a life your money actually supports.

This post contains affiliate links. If you sign up through one of my links, I may earn a small commission at no extra cost to you. I only recommend things I actually use or believe in. See my full Affiliate Disclosure for details.

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