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100 Envelope Challenge: How to Save Thousands in Just 100 Days

Kickstart your savings with the 100 Envelope Challenge! Learn how to save $5,050 in 100 days and discover expert tips to make saving easier.


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In today's unstable economy, very few people enjoy saving money. 

However, since saving is essential, many individuals have come up with a variety of methods, such as the 100 envelope challenge. 

This challenge provides a fun way to save thousands of dollars in just over three months through cash stuffing. The trend has gained popularity worldwide, helping people achieve their savings goals. 

In this article, you'll learn how the challenge and savings goals work and how to implement them in your financial planning. Additionally, you'll find book recommendations from Headway for further insights on saving and incorporating the challenge into your long-term financial strategy.

Understanding the magic of the 100 day envelope challenge

The 100 envelope challenge is a simple yet powerful savings technique. 

Here's how it works: 

You take 100 envelopes and label each with a number from 1 to 100, corresponding to dollar amounts. Over the course of one hundred days or weeks, you pick an envelope at random and stash away the amount of cash written. You're in for a delightful mix of excitement and suspense each time you draw an envelope. 

By the end of the challenge, you'll have an impressive $5,050 to top up your debit card, invest, or buy something you've wanted for a while. 

The key attraction of the challenge comes from its clear and organized nature and the rewarding feeling you get when you can actually see your savings increase over time.

Pros and cons of the 100 envelope challenge

Starting to save money can be an exciting adventure. 

However, the 100 envelope challenge, though fun and organized, comes with its own set of ups and downs. Look at both lists before deciding if this challenge fits your money-saving goals.

Pros and benefits:

  • Structured savings: This challenge gives you a solid framework to guide your saving journey. With clear goals, you'll find it easier to stay on track and watch your savings grow.

  • Gamification: Who says saving can't be fun? The thrill of chance and visually tracking your progress turns saving into an exciting game

  • Building a habit: Setting aside a specific time each day or week to review finances and savings accounts promotes mindfulness about spending. It also empowers you to develop consistent saving habits, ultimately leading to a healthier financial future.

  • Remarkable savings ahead: Tackling this challenge may result in significant savings accumulating over time, showcasing the tangible benefits of careful financial management.

Cons and considerations:

  • Cash handling: Safety is critical yet difficult to maintain when handling large amounts of cash. Store the envelopes in a safe location to ease any security worries.

  • Budgetary limits: Daily contributions might be tough if you are on a low budget and the economy is unstable. Why not tweak the challenge to a weekly or less frequent schedule? This slight adjustment could make the process more manageable and enjoyable.

  • Consistency: Success is all about consistency, which is highly conditional on keeping up under the pressure of modern times. Keeping things steady will help you stay engaged and committed to the challenge.

Step-by-step guide for the 100 envelope challenge

Step 1: Tailor the challenge to yourself. What’s your financial goal?

The 100 envelope challenge goal is to make savings work for you, so feel free to customize it. You may pick multiple envelopes at once or extend the timeframe to fit your routine better. Don't hesitate to adjust the amounts on the envelopes to align with your budget. If the total of $5,050 seems a bit much, consider a smaller sum. 

If you're up for a bigger challenge, dare to select higher denominations to boost your savings! Think about going digital: while the classic envelope method has its charm, modernizing the challenge is just as easy. You can use a spreadsheet or a savings app to track your progress — ideal for those who prefer to keep things cashless!  

Step 2. Label the envelopes

Prepare 100 envelopes, ensuring they are of uniform size and design for a cohesive look. Carefully label each envelope with a distinct number from 1 to 100, using a permanent marker or label maker for clarity. Make sure to write the numbers clearly on the front of each envelope for easy identification. Consider organizing the envelopes in a sturdy saving challenge box or holder to keep them neat and accessible.

Step 3: Select your amount

To maintain an element of surprise and excitement, randomly select an envelope each day (or weekly, if you prefer a more relaxed pace). This approach adds a fun twist to the process, making it feel less routine. You may find "a random number generator" app helpful. By entering the total number of envelopes, you quickly generate a random number that corresponds to the envelope you should choose. Include additional elements like lighting a candle or playing music to make the selection process fun.

Step 4. Deposit the cash

Place the exact amount of cash specified on your selected envelope inside it. Choosing the envelope marked "37" means you should put exactly $37 in cash into that envelope. Ensure that the amount is accurate and that the money is neatly folded or stacked to fit comfortably within the envelope without causing damage.  

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Step 5. Track your progress

Keep a record of the envelopes you've filled out using different tracking methods. One simple way is to make a list where you can check off each envelope as you complete it. You could also use a spreadsheet, which allows you to organize and see how much you've accomplished easily. 

If you prefer a more visual method, consider making a chart that shows your progress; it can motivate you as you see how far you've come. These techniques can help you avoid mixing up which envelopes you've already filled and relive a sense of achievement each time you see progress.

Expert tips to make the most out of the 100 envelope challenge

With all the steps revealed and after tailoring your challenge, how about taking your savings dynamics to the next level? The 100 envelope challenge gets even better when you blend it with the personal finance classics wisdom. A few relatable insights from Headway-recommended bestsellers will deepen your financial knowledge and maximize your personal growth journey.

1. 'Rich Dad Poor Dad' by Robert Kiyosaki: A mindset shift

In 'Rich Dad Poor Dad,' Kiyosaki emphasizes the life-changing impact of embracing a "rich dad" mentality. A winner's mindset will redirect your energy toward discovering valuable assets and seizing income-generating opportunities to secure a sustainable financial future.

"Winners are not afraid of losing. But losers are. Failure is part of the process of success. People who avoid failure also avoid success."

While doing the challenge, think about how the $5,050 (or your adjusted goal) can be a stepping stone towards acquiring income-generating assets rather than just a one-time contribution.

"You're only poor if you give up. The most important thing is that you did something. Most people only talk and dream of getting rich. You've done something."

Kiyosaki emphasizes the importance of understanding money to make informed financial decisions. He encourages readers to see failures and challenges as opportunities to learn and grow as investors and personal finance managers. Facing and overcoming challenges will boost your confidence and economic reasoning.

2. 'The Richest Man in Babylon' by Charles Conrad: To donate, save

At the heart of 'The Richest Man in Babylon' by Charles Conrad lies a powerful mantra: stay consistent in setting aside a part of your income. The 100 envelope challenge can be your creative approach of "paying yourself first" with parts of this income to build vital financial habits. Conrad advises learning and following the "six laws of wealth" to create habits in your character:

"The First Law of Wealth: Keep a part of all you earn. Save at least 10% of your income. The Second Law of Wealth: Put your savings to work for you. Invest it so that it will multiply. The Third Law of Wealth: Avoid debt. The poor pay interest, while the rich earn interest. The Fourth Law of Wealth: Don't speculate in get-rich-quick schemes. Invest in solid businesses that you understand. The Fifth Law of Wealth: Invest in yourself. Gain knowledge and skills to increase your earning power. The Sixth Law of Wealth: Safeguard your growing fortune with diversification and insurance."

The core of the message here is to live below your means: spend less than you earn and put the difference into savings and investments. Practicing such a disciplined lifestyle will nurture a mindset hardwired to financial security.  

3. 'The Total Money Makeover' by Dave Ramsey: Be ready for emergencies

In 'The Total Money Makeover,' Dave Ramsey emphasizes the importance of an emergency fund to prevent falling deep into debt, even if it feels like you have no way around it.

"Debt is so ingrained into our culture that most Americans cannot even envision a car without a payment, a house without a mortgage, a student without a loan, and credit without a card."

The 100 envelope challenge can help you start filling the fund. Make weaving a crisis safety net your top mission to stay motivated to save.

"Savings without a mission is garbage. Your money needs to work for you, not lie around you."

Ramsey continues this thought by giving precise advice like "never to take more than a fifteen-year fixed-rate loan, and never have a payment of over 25 percent of your take-home pay." Ramsey then recommends "a debt snowball" post-challenge tool to repay all your debts, beginning with the smallest one and slowly gaining momentum as you progress toward a debt-free status.    

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4. 'The Financial Diet' by Chelsea Fagan and Lauren Ver Hage: Budgeting as a fresh start

'The Financial Diet' by Chelsea Fagan and Lauren Ver Hage is packed with down-to-earth advice that resonates with everyday life. Here's what they want you to remember to rock the 100 envelope challenge:

  • Be realistic: Set practical and achievable goals. Feel free to adjust the amounts and timeframe to fit your financial situation. Simplify the challenge to make it inspire you. It is all about your wellness, not the rules.

"Saving money isn't about depriving yourself. It's about deciding you love Future You as much as you love Today You."

  • Connect to the challenge: Reflect on your habits and identify unnecessary purchases. Cutting these out can help you save money for your envelopes and master budgeting as the foundation for mindful spending.

  • Keep it fun: Personal finance can be enjoyable. Make your budget binder DIY and colorful! Decorate your envelopes, use an app for random number selection, and celebrate each milestone. Involving friends or family might be an extra boost to the sense of belonging and community.

"As I've said before, money doesn't buy you happiness, but it buys you the Lego kit of happiness. It buys you comfort, security, and options, even if you still have to build your happiness on top of it."

  • Play a long game: Consider this challenge a step up your financial journey ladder. After saving, follow a pre-agreed plan for your money — whether paying off debt, investing, or building an emergency fund.

  • Continue learning: Let the challenge inspire you to learn. Read more books, listen to podcasts, and explore blogs on saving and investing to make informed decisions.

These tips from 'The Financial Diet' will make the 100 envelope challenge more engaging while you proceed with your savings goals. See each envelope as a tangible reminder of why it is worth it to stay committed.

Integrate the 100 envelope challenge into your long-term financial planning

The 100 envelope challenge is a creative way to supercharge your financial goals. However, to truly unlock this money-saving challenge potential, you need to weave it into a larger, strategic financial plan. Consider these suggestions to make saving money enjoyable while keeping your bigger financial picture in focus:

1. Define your "why" and set SMART goals

Consider why you want to achieve your goal as an alternative to fixating on the $5,050 (or whatever amount of money you're aiming for). Are you saving for a down payment, something you dream about, or an emergency fund? Having a clear "why" feeds lasting motivation. A classic SMART framework might be of great use to you:

  • Specific: Clearly state how much money you want to save and an end date.

  • Measurable: Track your progress using a savings tracker or budget book.

  • Achievable: Set a realistic amount and a feasible timeframe for reaching your goal.

  • Relevant: Ensure your goal aligns with your overall financial objectives.

  • Time-bound: Set a deadline, such as 100 days, or adjust the timeline as needed.

2. Treat budgeting as a priority habit

A budget planner or cash budget system can help you better understand your income and expenses. It can highlight areas to cut back, like digital subscriptions or Amazon's instant checkout, freeing up cash for the envelope savings challenge. This tool also allows you to evaluate how this challenge impacts your long-term financial goals. If paying off your credit card debt is a priority, use the savings from the 100 envelope challenge to maintain a good score. Plus, don't forget your emergency funds to reassure yourself when making riskier investments.

3. Share your experience:

Share your savings journey on social media, like Facebook, TikTok, or Instagram, to keep yourself accountable and discover extra tips from others. Use popular hashtags related to saving challenges to connect with more people. Make your savings tracker personal to express yourself. Compliment yourself when you reach new goals. Consider putting together a "challenge kit" that includes everything you need, like envelopes, stickers, and some little goodies to celebrate your milestones.

4. Go beyond the 100 Days

The 100 envelope challenge might be an entertaining and straightforward way to quickly save money, but what comes next? Once you've completed the challenge, keep that saving spirit going! Try out savings challenge boxes, savings challenge books, or any appealing saving games to keep improving how you manage your budget. Think of the challenge as just the start phase of a long-term plan.

5. Keep the big picture in mind

Incorporating the 100 envelope challenge into a well-rounded financial strategy facilitates money accumulation and fosters new habits. By committing to this challenge, you'll systematically set aside money, which leads to greater financial discipline and awareness.

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Use Headway summaries to improve your savings habits

Are you ready to join a group of responsible and successful savers? Try Headway as your go-to for quick summaries of personal finance books, helping you grasp key concepts and take action on your day-by-day savings financial journey.

Take with you the memorable words of 'The Richest Man' author:

"The best investment you can make is in yourself... seek out wisdom, adding new skills and experiences that will make you more valuable." 

With Headway, you can expand your financial knowledge while tackling the fun and effective 100 envelope challenge. By combining it with expert insights, you'll be on track to achieve your financial goals. Let's get saving!


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