Chapter 1 of 6

The Surprise Bills

Most every family or individuals that want to keep track of their expenses have one thing in common. They have income. That is the starting point for The Getting Ahead Guidebook. If you didn’t have an income, you just wouldn’t have any money to organize.

I could lump this in and under the word budgeting. But it really isn’t budgeting as much as it is simply organizing what you have. Similar to a clothes closet. Clothes come in, go in their selected area. They get used (taken out) and then get washed and return back to the closet. If you have a varied wardrobe, you may have other closets that store your clothes for different seasons. You may add clothes to them when you see something you like, so you can wear it in another season. You look forward to it.

Let’s talk about a typical family. Tom and Diane Smith. We will keep it simple and just use a 2-person family.

Every month the Smiths spend money on things. They earn enough, what they buy really doesn’t cause them much concern. But, if they didn’t earn a substantial amount, wouldn’t it be nice if they organized what they bought so there were no surprises when any bills came in. Like the credit card invoice?

This is one of the bills that keeps surprising the Smiths every month. Can’t explain it, but the numbers are always not what they expect. And, if you think that shocks them, when the home or auto insurance bill shows up, it’s pure trauma. One day Mr. Smith had a brainstorm. “We only make so much money every month, how can we plan for the bills better?”

Chapter 2 of 6

Saturday Night at the Kitchen Table

One Saturday night when looking at his online bank statements Tom thought he would search for some type of application or software that may help him keep things in order. He was looking for something that was specifically designed for just knowing how to spend what they had. Somehow, he found The Getting Ahead Guidebook website.

He looked at the different pages and thought the logic actually spoke to him. They were a hard-working family, not rich, not in poverty, but he knew that they needed to know more about what happened to their money when they weren’t paying attention, and how to eliminate the surprises.

So Tom thought he would try the logic without the app, just the logic alone.

He grabbed a tablet — not a spreadsheet, because he could work the initial things out better with a pencil and paper.

The first thing he did was list as accurately as he could the money they had coming in every month. His paychecks from the grocery store he managed, and added his wife’s income from her teaching job. Although Diane had some great retirement benefits, and they had saved some money as well, he wasn’t worried about their future. He just wanted to control the present.

Tom now had the exact amount of take-home pay they had coming in each month. He felt like he had just made a major accomplishment, getting that handled. That act alone gave him more insight than he had ever had. Before, he was just assuming.

So Tom kept on the logic trail of The Getting Ahead Guidebook. He started thinking, “I have a clear understanding of our income, but what about those things we spend money on?” So he decided to gather some numbers and payees. He thought he would start with the ones that he saw (when he was paying attention) coming out of his bank account, or added to his credit card.

While he was making that list, he needed to clearly define the bank accounts and the credit cards that they used. So, on a separate piece of paper he made a list of each of the bank accounts and credit cards. They had only one credit card, and a checking account and a savings account.

The credit card was a cash-back type — paid back cash on total purchases — so Tom and Diane made a pledge to buy everything on the credit card. They really didn’t think about how much they would spend, or buy, just the fact that they were earning cash back sort of motivated them to buy more stuff. (Not sure that was the right motivation.)

Under each of those accounts, he went through the statements and highlighted the ones that were coming out each month. Once he had those noted and listed, he grouped the totals of each account and deducted that amount from the total amount of income that they brought home each month. These were just solid monthly bank account deductions, or credit card additions.

So Tom still had a decent amount of remaining income left. Now he needed to tackle the “sneaker” bills. Property taxes, home and auto insurance, and the rest. So, he then went through that same stack of statements and searched and noted the bills that they only paid twice a year, or annually.

He found a few that he had completely forgotten existed. The home insurance, paid every six months. The auto insurance, also every six months but on a different cycle. Property taxes that came due once a year, like a brick falling out of the sky. A roadside assistance membership that auto-renewed every December and always surprised them. Costco membership. Amazon Prime. The water company that billed quarterly. A subscription to the local newspaper that Diane liked having on Sundays.

He added them all up and divided each one by twelve to get a monthly amount. He didn’t have to PAY that amount every month — he just had to SET IT ASIDE every month so the money was there when each bill actually arrived.

That was the moment something clicked for Tom.

He suddenly understood why every January felt like a punch in the face. Why every April was tense. Why August always seemed to wipe out anything they’d saved over the summer. It wasn’t bad luck. It wasn’t poor planning, exactly. It was that they were treating predictable expenses like surprises. They were paying full price every time, all at once, instead of spreading it out the way the bills actually accumulated in real life.

He looked at the total on his tablet. The monthly set-aside, for everything that wasn’t already auto-debiting from their accounts, came to $647 a month.

Six hundred and forty-seven dollars. Every month. Going somewhere they couldn’t track. No wonder they always felt strapped.

That night Tom didn’t sleep much. Not because he was anxious — because he was excited. For the first time in maybe twenty years of marriage, he was looking at their money instead of just hoping there’d be enough.

Chapter 3 of 6

The Brake Job

The next morning he made coffee and waited for Diane. She came downstairs in her robe, saw the papers spread across the kitchen table, and gave him the look she gave him whenever he was about to suggest something she’d have to be patient about.

“What are you doing?” she said.

“I think I figured something out.”

He walked her through it. The income. The accounts. The monthly bills they already knew about. And then, the part that surprised her most — the $647 a month they’d been ignoring.

“That’s not nothing,” Diane said.

“No,” Tom said. “It’s not.”

To Diane’s credit, she didn’t try to talk him out of it. She’d been the one mentioning, gently, for years, that something needed to change. They didn’t argue about money exactly — they avoided it, the way most couples do. But she’d watched the credit card balance creep up after Christmas every year. She’d watched the savings account stay roughly the same for the last decade. She’d noticed.

So when Tom said he wanted to try this — really try it — Diane was in.

That afternoon they made a decision. They’d open a second savings account at their credit union, separate from their main one, and they’d call it the “Reserves” account. Every payday, money would automatically transfer into it to cover the monthly portion of every sneaker bill Tom had identified. When the actual bill came due — property tax in November, insurance in March, Christmas in December — the money would already be there. They wouldn’t have to think about it. They wouldn’t have to scramble.

That was Saturday.

By Sunday night, Tom had also discovered something else: he wanted to actually try the app he’d found. The logic had worked on paper. He figured if it worked on paper, it would work better in something that did the math for him every month. Plus, he wouldn’t have to spread papers all over the kitchen table every time Diane wanted to make dinner.

So he downloaded The Getting Ahead Guidebook app on Sunday evening. It took him about twenty minutes to enter their income, their accounts, and their recurring monthly bills. The reserves he’d worked out on paper took maybe another fifteen minutes to add — one entry per “envelope,” with the monthly set-aside amount and the date the bill actually came due.

When he hit the dashboard for the first time and saw it all laid out, he felt the same feeling he’d had Saturday night — only stronger.

For the first time in his adult life, he could see, in one place, what his money was actually doing.

Three weeks later, the first real test came.

Diane’s car needed brakes. The estimate was $620. Normally that’s the kind of expense that would have triggered an argument — not at each other, but at the situation. Where’s the money supposed to come from? Should we put it on the credit card? Should we delay it? Should we pull from savings? Is the savings account actually for things like this, or are we supposed to be saving it for something else?

But Tom already had a reserve set up for car maintenance. He’d put $75 a month into it from the start. After three months and the lump sum he’d seeded it with from their main savings, there was $750 sitting in the reserve, untouched, waiting for exactly this.

He paid the brake shop with their debit card. No credit card. No conversation. No tension.

When he came home and told Diane, she stared at him for a second.

“That’s it?” she said. “You just paid it?”

“That’s it.”

She thought about it for a moment, then said, “I want to learn how to use the app too.”

That was the second click. The first had been for Tom. This one was for both of them.

Chapter 4 of 6

The Water Heater

The first hard month came in late spring.

They were six months into using the system. Things had been going beautifully. The credit card was being paid in full every month — for the first time ever, the cash-back rewards were actually rewards instead of a discount on interest charges. Reserves were filling up like little buckets under a steady rain. The forecast page in the app — the one that showed Tom what their bank balance would look like three weeks out, six weeks out, on the morning of Christmas Eve — had become his favorite thing to look at over coffee.

And then their water heater died.

The replacement, with installation, was $1,850. Their “Home Maintenance” reserve had $400 in it.

Old Tom, six months ago, would have put the rest on the credit card and spent the next eight months paying interest on it.

New Tom pulled $1,450 from their main savings — money that, in fairness, used to disappear into mystery anyway. He paid the plumber. Then he sat down with Diane that evening and they did something they’d never done before in twenty years of marriage:

They had a money meeting on purpose.

Not a fight. Not a crisis conversation. A planning conversation.

“The home maintenance reserve needs more in it,” Tom said. “We’ve been putting in $100 a month. That clearly isn’t enough.”

Diane thought about it. “What about $200?”

“That works. We’d have to come up with the extra $100 somewhere.”

They looked at the dashboard together. They could see — visually, plainly, in front of both of them — that their “eating out” line had been quietly creeping up. Not dramatically. Just enough. Nobody was tracking it, so nobody was thinking about it.

“What if we cut eating out by $100?” Diane said.

“Done.”

That was the entire conversation. Sixty seconds. No tension. No defensiveness. Just two adults looking at the same set of numbers and making one small adjustment together.

Tom would remember that conversation later as one of the most peaceful moments of their marriage. Not because it was romantic. Because nothing was hidden.

Chapter 5 of 6

Christmas Without Dread

Six months later, it was Christmas.

Diane had been quietly putting $80 a month into the Christmas reserve since the app went live. By December 1st, she had $960 sitting in it. They’d never had Christmas money set aside in advance before — not once in twenty years. The closest they’d come was the year Diane’s aunt slipped them a check in November.

They went shopping the first Saturday in December. They didn’t worry about it. They bought what they wanted to buy for their daughter, for their grandkids, for each other, and for the small handful of friends they exchanged with. They came home, wrapped everything, and felt — for maybe the first Christmas in their adult lives — that the holiday was a gift to enjoy, not a debt to manage.

On December 26th, Tom checked the credit card balance. The total Christmas spend, including the groceries for the dinner, came to $940. Twenty dollars under what they’d saved.

He looked at Diane and said, “We’re going to feel this in February.”

“How?” she said.

“That’s the thing,” he said. “We’re not.”

January came. The credit card bill arrived. They paid it in full from the Christmas reserve, like it was any other bill. No interest. No regret. The reserve emptied out, did its job, and started filling back up again on January 5th when Tom’s paycheck hit.

That year — for the first time in two decades of marriage — January was just another month.

Chapter 6 of 6

The Barbecue

A full year after Tom first stayed up late at the kitchen table with a tablet and a pencil, he sat down at the same table and looked at the numbers again.

Their savings had grown by $4,200 — not because they’d earned more, but because they’d stopped leaking money into surprise bills.

Their credit card balance was zero. It hadn’t carried a balance once all year. The cash-back rewards added up to $487 — actual money in their pocket.

The reserves were full. Every single one. Property tax: there. Insurance: there. Christmas: there, refilling for the next year already. Car maintenance: there. Home maintenance: there, and topped up after the water heater incident. Even the small ones — Amazon Prime, Costco membership, the newspaper subscription — every one of them had money waiting for the day the bill arrived.

But the thing that surprised Tom most wasn’t on the dashboard. It was something he couldn’t quite put into a number.

He and Diane didn’t fight about money. They didn’t avoid the conversation. They didn’t lie awake at 3 AM running through the credit card balance in their heads. They didn’t dread the mailbox.

They knew where their money was. They knew where it was going. They knew what was coming.

That was the whole change.

Same income. Same bills. Same life.

But now, instead of money happening TO them, it was something they were quietly, calmly in charge of.

A few weeks later, Tom was at a barbecue at his brother’s place. His brother — the one who’d built the multi-location business, the one who’d always had more money than Tom — mentioned in passing that he was stressed about a tax bill that was coming up.

Tom didn’t say anything for a minute. Then he said:

“Can I show you something?”

He pulled out his phone and opened the app.

His brother watched, asked a couple of questions, then asked another.

By the end of the conversation, his brother had downloaded it too.

That was when Tom realized something. The closet metaphor he’d held in his head all along — the clothes coming in, going to their right place, getting used, getting cleaned, going back where they belonged — was never really about clothes. It was about everything.

A well-organized life isn’t about having more. It’s about knowing what you have and where it goes.

That, Tom thought, finally putting his phone away and going back to the barbecue, is the whole thing.