From Broke to $10,100: How the 100 Envelopes Challenge Changed My Finances

From Constantly Broke to Finally in Control

For years, I felt like I was living paycheck to paycheck even though, on paper, my salary should have been enough.

By the time the month ended, I’d be asking myself the same question over and over: “Where did all my money go?”

Starbucks runs, quick Target trips, late-night McDonald’s meals, and endless Amazon “just one more item” checkouts were silently draining my wallet.

Saving money felt impossible. 

Every time I thought about building an emergency fund, I’d give up before I even started.

Then one night, scrolling through Pinterest, I stumbled upon the 100 Envelopes Challenge.

The idea looked so simple it was almost silly: take 100 envelopes, number them, and fill them with the matching amount of cash.

Do this consistently, and you’ll end up with $10,100.

At first, I laughed it off. “Yeah right, like I’m going to save ten grand with envelopes.” But deep down, something clicked.

What if this could be the system I’d been missing? Spoiler: it was. And it completely changed my finances.

Here’s the full story of how I went from broke and anxious about money to finally saving $10,100 with the 100 Envelopes Challenge—and why you should consider doing it too.

What is the 100 Envelopes Challenge?

The rules are ridiculously simple, and that’s why it works.

• Grab 100 envelopes.
• Number them from 1 to 100.
• Each day (or week), pick an envelope and put in the amount of cash.
• Keep going until all 100 envelopes are filled.

At the end, you’ll have $10,100.

It’s almost like turning saving into a game. Instead of boring spreadsheets, you get this visual, tangible progress.

You seethe envelopes piling up, and every time you seal one shut, it feels like leveling up in a video game.

And that fun factor? That’s what kept me going when I usually would’ve quit.

My Rock Bottom with Money

Before I found the challenge, my financial life was chaos.

Every morning, I’d grab a Starbucks latte and breakfast sandwich. That’s around $6 a day, $180 a month—$2,160 a year, just on coffee.

Add in random McDonald’s cravings at midnight (another $60–$80 a month), and my “fun” Amazon orders (“oh, it’s only $20”) that always ballooned into $200 carts… it added up fast.

But I didn’t realize it until my checking account constantly hovered near zero. Bills stressed me out.

I was embarrassed when friends asked me to go out because I wasn’t sure if I could afford it.

The worst part wasn’t just being broke—it was feeling out of control.

I didn’t even know where my money was going. That’s when I knew something had to change.

Starting the 100 Envelopes Challenge

On January 1st, I bought a cheap pack of envelopes from Walmart, grabbed a marker, and started numbering.

It felt silly at first—like a school project.

Day 1, I picked envelope #3. Easy. Dropped $6 inside.
Day 2, I picked envelope #97. My heart sank.

$196 in one go? That was almost my entire grocery budget. I almost quit right then.

But instead of giving up, I got creative.

I skipped Starbucks for two weeks, cooked at home more often, and managed to make it work. 

And that envelope? It ended up motivating me more than anything.

Here are a few things that helped me stay consistent:

• Random Draw Method: Picking envelopes at random kept it exciting.
• Saving Box: I bought a cute storage box to keep them safe. Watching it fill up was incredibly satisfying.
• Printable Tracker: I also used a printable 100 Envelopes Challenge Tracker. Coloring in each number felt like checking off progress in a journal.

The first 30 envelopes were tough, but once I got into the rhythm, it became addictive.

Lessons I Learned Along the Way

Every single envelope I sealed taught me something new—not just about money, but about myself.

Saving wasn’t just about building a pile of cash. 

It was about reshaping my habits, confronting my weaknesses, and celebrating small wins.

Here are the 17 biggest lessons I walked away with after completing the 100 Envelopes Challenge:

1. Small amounts add up fast.
   At first, putting $5 or $10 in an envelope felt like nothing. But when I looked at my tracker after a few weeks, I realized those little bills stacked up to hundreds. It was proof that consistency beats size.
2. Skipping Starbucks won’t kill you.
   For years, I told myself I “needed” my daily latte. But skipping Starbucks a few days a week saved me $60+ monthly. Surprisingly, I didn’t miss it—and I started making better coffee at home.
3. Patience pays off.
   The challenge taught me that not everything needs to be instant. Waiting to fill all 100 envelopes was hard, but it reminded me that slow progress is still progress.
4. Gamification works.
   Turning savings into a game kept me hooked. Picking envelopes at random was exciting—like playing bingo but with my financial future at stake.
5. My money anxiety dropped.
   Before, checking my bank balance gave me stress. But once I saw those envelopes stacking up, my anxiety was replaced with confidence. I finally felt like I had a plan.
6. Involving family helps.
   One night, my partner asked what the envelopes were for. Instead of laughing at me, they joined in—sometimes even slipping in extra cash. It became our shared project, which made it more fun.
7. Mindful spending matters.
   I started questioning every purchase: “Do I really need this, or do I just want it right now?” That pause was enough to kill a lot of impulse buys.
8. Cash is powerful.
   Swiping a card never hurt, but handing over physical bills did. The envelopes reminded me that money is tangible—and that every dollar has weight.
9. Grocery planning saves money.
   I used to shop without a list, throwing random things in my cart. By meal planning and budgeting, I cut my grocery bill by almost $100 a month. That extra went straight into envelopes.
10. Amazon isn’t urgent.
    The “Buy Now” button used to be my weakness. But during the challenge, I started leaving things in my cart for a week. Most of the time, I’d forget about them. That alone probably saved me $500.
11. FOMO isn’t worth it.
    I skipped a few brunches and movie nights, worried my friends would be upset. They weren’t. Turns out, real friends don’t care if you’re saving money—they cheer you on.
12. Gratitude grows.
    Every time I sealed an envelope, I felt grateful. Even on weeks when I could only fill small numbers, I reminded myself: this is progress. That mindset shift changed everything.
13. Confidence builds.
    The more envelopes I filled, the more capable I felt. By the halfway point, I wasn’t just saving money—I was proving to myself that I could stick to something.
14. Goals motivate.
    The number $10,100 became my obsession. Every time I wanted to give up, I pictured what it would feel like to hold that much cash. That vision pushed me forward.
15. Saving is self-care.
    I used to think “treating myself” meant spending. Now I realize the best form of self-care is peace of mind. Having savings felt like wrapping myself in a warm blanket.
16. I learned patience with shopping.
    I started giving myself a “waiting period” before buying anything over $50. More than half the time, I ended up not buying at all.
17. I broke the broke cycle.
    By the time I filled the last envelope, I didn’t see myself as “bad with money” anymore. For the first time, I felt in control of my financial story—and that’s priceless.

The Moment I Hit $10,100

I’ll never forget the day I sealed the last envelope. My box was full, heavy, and beautiful.

I counted it all out, and for the first time in my life, I had five figures in savings.

That I wasn’t destined to always be broke.

Here’s what I did with the money:

• Paid off my lingering credit card balance.
• Built a $3,000 emergency fund.
• Set aside some for a vacation (because rewarding yourself matters!).
• Kept momentum by starting other savings challenges.

How You Can Start Your Own Challenge

If you’re ready to try it, here’s a simple guide:

1. Grab 100 envelopes or print a 100 Envelopes Challenge Tracker.
2. Number them 1–100.
3. Decide on your pace: daily, every other day, or weekly.
4. Pick envelopes randomly or in order.
5. Store them somewhere safe.
6. Stay consistent—even if you have to adjust some days.

Pro tip: Use a printable like the Saved $10,100 in 100 Envelopes Challenge. It keeps everything organized and makes the process fun and colorful.

Frequently Asked Questions About the 100 Envelopes Challenge

1. What if I can’t afford the bigger envelope numbers like 95 or 100?

You’re not alone—I panicked too when I first pulled envelope #97 early in the challenge.

Here’s what I did: I broke it down. Instead of putting in $97 all at once, I filled it in smaller amounts over a week until it was complete.

Remember, the challenge is flexible. It’s not about perfection—it’s about consistency.

2. Do I have to do it daily?

Not at all. Some people fill an envelope every day, but I chose a weekly schedule to make it more manageable.

You can even do it twice a week, or whenever you have extra cash. The key is progress, not speed.

3. Can I use digital money instead of cash?

Yes! If you’re more of a digital person, you can transfer the amounts into a separate savings account.

Some people even create “digital envelopes” with apps or spreadsheets.

Personally, I liked the physical envelopes because they gave me something tangible to see and touch.

4. What if I already live paycheck to paycheck?

That’s exactly why this challenge works. You don’t need to put in huge amounts right away. Start with smaller envelopes first—$1, $5, $10—and build confidence.

Over time, you’ll find little ways to cut costs (like skipping one fast-food meal or canceling a forgotten subscription) and redirect that money into envelopes.

5. Do I have to complete all 100 envelopes to succeed?

Nope. Even if you only fill 50 envelopes, that’s still thousands saved—money you wouldn’t have had otherwise.

Don’t focus on “failure.” Celebrate every bit of progress.

6. How do I keep myself motivated for months?

This was my biggest struggle too. Here are a few tips that helped me stay on track:

• Use a printable tracker so you can color in each number.
• Keep your envelopes in a visible spot—it’s a daily reminder.
• Share your progress with a friend or partner for accountability.
• Reward yourself for milestones (for example, treat yourself when you hit $1,000 saved).

7. What should I do with the money once I finish?

Great question!

When I completed the challenge, I used part of the money to pay off credit card debt, built an emergency fund, and set aside a little for a reward trip. 

Think about your priorities: do you want to clear debt, save for a home, or create a rainy-day fund?

Having a plan before you start makes the finish line even sweeter.

8. Can kids or teens do this challenge?

Absolutely!

You can scale it down by numbering envelopes 1–50 or 1–20.

It’s a fantastic way to teach younger people about the value of saving and delayed gratification.

9. Do I have to use envelopes?

No—there are plenty of creative alternatives.

Some people use mason jars, others use a binder system, and many (like me) use a printable 100 Envelopes Challenge Tracker.

The important thing is that you have a system you enjoy and stick to.

10. Is the $10,100 version too hard for beginners?

It can feel intimidating, but here’s my take: start with the $5,050 version first.

If you finish it, you’ll already have proof that you can do it.

Then, if you want to go bigger, try the $10,100 challenge. Either way, you’re winning.

Related Articles:

• Money Disappearing After Payday? Here’s a Pretty Little Fix
• How to Make a Lot of Money Fast
• 35+ Clever Hacks to Save More Money
• How to Save Money Fast on a Low Income
• Where Did All My Money Go?! This Tracker Knows

Conclusion

I started this challenge as someone who could barely hold $100 in savings.

I ended it with $10,100 and, more importantly, a completely new relationship with money.

The 100 Envelopes Challenge isn’t just about envelopes—it’s about building confidence, discipline, and freedom.

If you’ve ever felt broke, overwhelmed, or hopeless about saving, I promise this challenge can change your life too.

So grab your envelopes (or your printable tracker), and take the first step today. Your future self will thank you.