Money Monday: Make, Keep, Enjoy, Move — Week of September 14

Welcome back to Money Monday. Last week we kicked this off with one money-making opportunity, one deal, one lifestyle find, and one 10-minute assignment — and I think you’re here for it. So let’s keep it going.

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.

MAKE: 4 Real Ways to Make Money From Home

Last week we went deep on becoming a Virtual Assistant. This week, a roundup — because “work from home” is not one size fits all, and the right side hustle depends on your skills, your schedule, and how much energy you have left after your day job.

Here are four legitimate work-from-home options, with real pay ranges and where to start:

1. Freelance Writing ($20-50 per article to start)

Businesses need blog posts, product descriptions, newsletters, and website copy — and many would rather hire a freelance writer than do it themselves. You don’t need a journalism degree. You need to write clearly and meet deadlines.

Where to start: Upwork and Fiverr for your first clients; private Facebook groups for bloggers and small businesses often post writing gigs. Start with smaller assignments to build clips, then raise your rates with every few published pieces.

Watch out for: “Write for exposure” — exposure doesn’t pay bills. Also, content mills that pay $5 per article. Your starting rate should be at least $20-25.

2. Online Tutoring ($15-30/hour)

If you’re good at math, English, science — or literally anything students study — someone will pay you to explain it. Tutoring platforms let you set your schedule and teach from your kitchen table.

Where to start: Wyzant (you set your rate, they take a cut), Preply (you set your rate for language and subject tutoring), or Cambly if you just want to chat with English learners — no teaching credentials needed.

Watch out for: Platforms that want you to buy a “certification” before you can teach. Real tutoring platforms vet your skills, not your wallet.

3. AI Training and Data Annotation ($20-25/hour)

This is the newest one, and it’s real: companies building AI systems need humans to review, rate, and label content. It’s flexible, remote, and requires no experience — just attention to detail and solid writing.

Where to start: DataAnnotation and Outlier are the two most established platforms. You take a qualification test, and if you pass, you get assigned work you can complete anytime.

Watch out for: Volume varies — some weeks there’s tons of work, some weeks it’s slow. Treat it as a flexible income booster, not a guaranteed salary.

4. User Testing ($10 per 20-minute test)

Companies pay to watch real people use their websites and apps while thinking out loud. So you know all those times you were talking out loud and someone said huh and your reply was “nothing, just thinking out loud?” You can now make money at that. It’s the easiest entry on this list — no skills, no portfolio, just your honest reactions.

Where to start: UserTesting.com. Sign up, take a sample test, and you’re in the queue.

Watch out for: This is beer money, not rent money — most testers get a few tests per week, not a full-time income. Honest framing matters. But $30-60/week for talking out loud about websites? Not nothing. And sometimes a some extra cash for the weekend is all you need.

How to choose: Don’t pick the one with the highest headline rate. Pick the one that matches what you’re already good at. Your side hustle should feel like a lane change, not a personality transplant.

KEEP: Free Money From Bank Switch Bonuses (Read the Fine Print First)

This week’s KEEP is one of the most underrated money moves out there: checking account sign-up bonuses. Banks are so hungry for new customers that they’ll pay you $300-500 to open a checking account and set up direct deposit.

What’s on the table right now (offers verified this month):

• Chase Total Checking: $400 bonus for new customers with qualifying direct deposit — offer runs through mid-October
• Wells Fargo Everyday Checking: $325 bonus with qualifying direct deposits — ends October 13
• Bank of America: Up to $500 depending on your direct deposit amount — available through September 30

That’s real money for a task that takes about 20 minutes at your kitchen table.

How it works: You open the account online, update your direct deposit to point at the new bank, and wait for the requirement window (usually 90 days of qualifying deposits). The bonus hits your account once you qualify.

Who this is actually for: If you’ve been with your bank for years and they’ve been paying you 0.01% interest while charging you fees, this is your sign. Switching banks is a mild hassle — the bonus is your compensation for the hassle.

What to watch out for: This is why the fine print matters. Monthly maintenance fees (choose an account you can waive). Minimum direct deposit amounts (make sure your paycheck qualifies). And don’t churn accounts — banks track this, and opening/closing rapidly can affect your banking history. One strategic switch, done deliberately, is a money move. A new bank every three months is a part-time job with worse pay.

ENJOY: ResortPass — The Hotel Experience Without the Hotel Price

Here’s the concept that should’ve been obvious years ago: hotels have gorgeous pools, spas, and cabanas that sit half-empty most weekdays — and now you can book day access to them without booking a room.

ResortPass is a booking platform for hotel amenities by the day: rooftop pools, spa facilities, cabanas, fitness centers, even day-use hotel rooms. Day passes start at $25 and go up to about $250 depending on the property — a Four Seasons cabana and a boutique hotel pool chair are different line items, sis.

Why I love this for us:

It’s the luxury experience without the luxury commitment. A $200+ hotel night is a whole budget conversation. A $25-50 pool day is a line item — especially if you built your Self-Care line item from last week’s post (see what I did there).

How to use it: Enter your city and date, browse properties, book, and show your confirmation at the desk. No loyalty status, no check-in desk awkwardness. Weekdays are cheaper than weekends, and popular properties sell out — book ahead for anything specific.

The tie-ins that make this better:

• Money move: ResortPass earns 4% cashback through Rakuten right now (normally 2%) — so if you’re booking a spa day, activate your cashback first.
• Cruise day: If you’re joining us on the Suitcases and Vitamin Sea cruise, this is also a thing in port — cruise passengers use ResortPass in places like Miami for beach and pool days between arrival and departure. The $200 deposit for the 2027 cruise is still live, so there’s time to plan the shore day.

Your assignment, should you choose to accept it: look up your city on ResortPass and pick your reset spot. That’s your Selfcare September field trip.

MOVE: Your 10-Minute Money Assignment for the Week

This one directly feeds this week’s MAKE section. Set a timer for 10 minutes and do this:

1. Open a note (paper or phone, whatever you’ll actually revisit)
2. Write down five things you do at your job — or in your life — that someone would pay for. Not fancy skills. Real ones: you write clear emails, you explain things patiently, you organize information, you spot errors, you plan events.
3. Next to each one, write which of this week’s four opportunities it matches: writing, tutoring, AI annotation, or user testing.
4. Pick the best match and create the account tonight. Not “this week.” Tonight. Ten minutes of admin is the difference between “I should try that” and “I’m doing that.”

The hardest part of starting a side hustle is not the work. It’s the deciding. A 10-minute skills inventory decides for you — because the answer is already in your job description, you just never looked at it as a product.

Pynk Thoughts

Money Monday is two weeks old, and I want you to notice what we’re actually doing here: one MAKE (income), one KEEP (savings), one ENJOY (lifestyle), one MOVE (action). Earn, keep, enjoy, move. That’s the whole philosophy of this thing — money isn’t a grade you get, it’s a tool you maintain.

This week: pick one MAKE and create the account. Check if your bank is paying you $400 or $0.01. Put a ResortPass day on your calendar. And do the 10-minute skills inventory — I’m genuinely curious what you find. I bet you’re more marketable than you think.

Small moves, every week. That’s the whole secret.

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