As I was parking last week, I noticed a dime and a penny on the ground near some teenagers. I asked the kids if they had dropped it and a girl explained as she climbed into the car that the change wasn’t hers.

“Don’t you want it?”

“No,” she said breezily, “it’s just 11 cents.”

They were gone before she could hear me say that big money is a long slog.

If a journey of a thousand miles begins with a single step, then the trek to $1,000 or even lifetime wealth begins with a single penny or dollar.

I’d complain that kids don’t know the value of a buck these days, but the truth is that we’re all a bit confused about the value of a dollar right now. Inflation running at 40-year highs and wildly changing prices at the pump and in the supermarket will do that.

Complaining about how costs are adding up doesn’t help; making our savings and spending go farther does.



Last week, I detailed five of my favorite savings and spending challenges to make basic financial tasks more fun, more like a game. This week, I’m offering five more options.

Each of these efforts can help restore balance and order and a sense of progress to your financial life. Personalize these challenges, make them your own, turn them into a game, involve family members, track them as best you can, but know that there is no downside to failing at them because the more you know about your financial habits and feelings, the better off you will be.

Step-Up Savings Challenge: There are many ways to do this, but I prefer variations that don’t feel like a burden and that raise a bit of cash quickly, whether to seed an emergency fund, substitute for a holiday-spending account or come up with the money to pay for a splurge.

For the short, fast version, set aside one dollar for each date in the month. You save a buck on the first of the month, two dollars on the second, 15 on the 15th and so forth.

If successful, you end the month with $465 saved, despite never setting aside more than $30 at once.

This exercise helps with budgeting, because it’s easy to save the first five days of the month – when the set-aside is just $15 – but the struggle can be real when numbers get bigger and you have to come up with $140 over the last five days.


A longer version of this challenge takes a year, and it starts with $1 per week, and adds a buck every week. You’ll only save $10 over the first four weeks, but you save over $200 in the final four weeks and your tally for an entire year will be roughly $1,375.

Free entertainment challenge: Entertainment spending is a guilty pleasure and an indulgence for many people, it is clearly on the “want” side of the ledger, even though it is often treated like a “need.” It’s also where many people splurge.

This is not a specialized “no-spend challenge.” This starts with answering “What can I do that is free to me?”

That doesn’t just mean going to the public library, it means finding out if the library has free passes to get you into the regional zoo or aquarium or historic site or museum. It doesn’t relegate you to simply taking a hike or going for a bike ride: You can have a game night, have friends over for brunch or host a pot-luck supper.

Use up gift cards, cash in loyalty/rewards points and get big savings with coupon deals. Those things have real value, but Americans have billions of dollars in gift certificates and frequent-flyer rewards that they haven’t redeemed. You make the most of those credits by cashing them; consider them “free entertainment” for the purposes of this challenge.

A free/low-cost entertainment weekend every other week can help you splurge on the things you most want the rest of the time.


The $5 bill challenge: There are many variations of this, but it boils down to saving every $5 bill you get. I have done this since 2020 and have saved roughly $1,325 since.

Whether it’s “fun money” or the start of some savings objective, this adds up reasonably quickly, especially if you force yourself to pay cash on small-dollar transactions.

Personally, I save everything under $10 bills, so I set aside the fives, singles and coins; the smaller money has amounted to another $1,075 since the start of 2020.

Spring-cleaning challenge: There are many ways to do this, but my favorite is to go through your home and come up with one item each day for a month that you no longer want or need that you can try to sell. If you find a lot of extra items along the way — and if you get rid of things that don’t have any re-sale value — that’s all good, but the idea is to keep things simple and manageable.

Surveys have shown that the average homeowner has somewhere north of $3,000 in items they’re not using but that they could sell with ease. For those who question whether the juice is worth the squeeze, this is the challenge where you find out.

Value it by the pound challenge: This is a twist on spring cleaning, but it’s a great one for organizing your home for the long haul.


Someday, if you leave your current home and take your belongings to your next place, a moving company will come in to size up the cost of helping you make the transfer. Once they get through the big, tricky items – moving the piano or big sofa – they ultimately will be charging you by the pound.

In this challenge, look at the stuff in your life — even the most organized people have clutter — and think about whether you would pay to move it; if it’s not worth 50 cents to a dollar per pound to move it, maybe it can go now.

If there’s value in selling that stuff now, do it. If the value comes from simply eliminating clutter, that’s also a win.