Chapter 2 (17 Years Old) - Making Time and Money Work for You

Time to Meet His Mentor

September seventeenth came quietly. The day he had been waiting two weeks.

The alarm still rang at 5:12 a.m.

Caleb’s hand moved before his mind did, silencing it in one practiced motion. Nothing about his mornings had changed just because he’d turned seventeen three days earlier. He still dressed in the dark. Still splashed cold water on his face. Still moved through the apartment as if sound itself cost money.

His mom had managed to get him a cake on his birthday. Chocolate, simple, slightly lopsided. They’d eaten it quietly at the kitchen table while his siblings laughed and argued over who got the bigger slice. It wasn’t much, but Caleb remembered it more clearly than most things. Not because of the cake—but because she’d tried.

This morning felt the same as every other.

By 5:30, lunches were packed. Shoes were tied. Backpacks were zipped. His brother yawned. His sister leaned against him, half-asleep. Caleb guided them through the routine like a system he could run even when exhausted.

Because it was a system. He just hadn’t called it that yet.

At school, the day passed in fragments—bells, lectures, notes scribbled faster than his mind wanted to move. After practice, muscles aching and mind fogged, Caleb didn’t go straight home.

He went to the church.

The building was quieter than usual in the late afternoon, sunlight slanting through narrow windows and pooling on the floor. The older man was already there, sitting at a small table with two chairs pulled out, a notebook open in front of him.

“You’re right on time,” the man said, glancing at his watch.

Caleb nodded and sat.

They didn’t start with advice. They started with paper.

“Walk me through your week,” the man said, sliding a pen across the table. “Not what you think you should be doing. What actually happens.”

Caleb hesitated, then began writing.

Wake up.Siblings.School.Practice.Work.Homework.Sleep—sometimes.

The page filled faster than he expected.

The man leaned in, studying it quietly. “You’re busy,” he said. “But busy isn’t the same as broken.”

He drew a line down the page.

“Here,” he said, tapping the left side. “These are fixed responsibilities. They don’t move. You don’t negotiate with them. Write them here.”

Wake time.School hours.Football practice.Work shifts.Family needs.

Then he tapped the right side. “This is flexible time. And right now, you’re letting chaos decide how it gets used.”

Caleb frowned. “I don’t really have extra time.”

“That’s not the problem,” the man said calmly. “The problem is that every decision costs you energy. And you’re making too many of them.”

They talked about time blocking—not squeezing more into the day, but giving each block a purpose so it stopped bleeding into the next. About decision reduction—why wearing the same kind of clothes, eating the same breakfasts, following the same routines actually freed the mind instead of trapping it.

“Chaos feels heavier than workload,” the man said. “Because chaos asks questions all day long. What’s next? What did I forget? What should I be doing right now?”

Caleb listened, skeptical but curious. “I don’t want to turn into a machine,” he said finally.

The man smiled. “Good. Then don’t. Structure isn’t about control—it’s about protection. Especially for sleep.”

That part landed.

They talked about recovery. About guarding rest the same way Caleb guarded Sundays. About how over-optimizing was just another form of panic if it ignored the body.

When they finished, Caleb’s notebook looked different. Not fuller—but clearer.

That Sunday came quietly, like always.

Church in the morning. His siblings on either side of him. No spending. No errands. No rushing from one thing to the next. The clock loosened its grip, just enough.

That night, before bed, Caleb sat on the edge of his mattress and whispered a short prayer. Nothing elaborate. Just thanks—for the cake, for the conversation, for the chance to breathe.

In the margin of his notebook, almost as an afterthought, he wrote one word: Grateful.

As he turned off the light, Caleb realized something that surprised him. The exhaustion wasn’t weakness. It was unmanaged structure.

And for the first time, that felt like something he could actually fix.

Learning to Track Every Dollar

(Mid-Fall — October) By October, the spiral notebook was full.

Not completely—there were still blank pages—but full in the way a tool becomes full once it has done its job. The corners were bent. The cover was creased. Ink bled faintly through thin paper where Caleb had pressed too hard, tired or frustrated or rushing.

It had taught him awareness. Now it was time for accuracy.

The shift happened quietly, the way most real changes did.

One afternoon after school, instead of heading straight home or to work, Caleb stopped by the public library. The building smelled like dust and printer ink, the air cooler than the outside fall heat. Rows of computers lined one wall, most of them occupied by students pretending to research and adults filling out applications.

Caleb logged into a free computer and stared at the screen longer than he expected.

Spreadsheets felt intimidating at first—too official, too precise. Boxes and formulas didn’t leave much room for excuses. But once he started typing, something clicked.

Income went in first.

Hours worked.Pay rate.Gross pay.

Then came the second column.

Actual usable money.

Taxes.Bus fare.Gas.

The few dollars that never really belonged to him because they always ended up in his mom’s hand.

The difference startled him. He’d always known the numbers were smaller than they looked—but seeing the gap laid out in clean rows made it real. It wasn’t discouraging. It was clarifying.

His mentor’s words echoed quietly in his mind: Awareness before ambition.

As the spreadsheet grew, Caleb began to notice patterns. The big expenses—the ones he worried about—were predictable. Shoes. School supplies. Transportation.

The real damage came from the small leaks.

A snack here.A convenience there.A rushed decision made because he was tired.

Individually, they barely registered. Together, they erased progress.

That lesson stuck.

A week later, the mentor introduced him to the envelope method. Physical cash. Real boundaries. Money assigned a purpose before it ever had the chance to disappear.

Groceries.Transportation.Emergency

“Emergency isn’t a goal,” the man said. “It’s peace.”

Caleb liked that.

He treated the envelopes the way he treated football drills. Repetition. Discipline. No shortcuts. Budgeting stopped feeling abstract and started feeling physical—like reps in the weight room. You didn’t argue with the process. You showed up and did it again.

Sundays made it easier. The boundary held, even as fall brought more invitations. Texts came in late Saturday afternoons.

“You coming out?”“We’re grabbing food.”“Just this once?”

Caleb declined without drama.

“Can’t,” he’d say. “Sunday.”

At first, people pushed. Then they stopped. Not because they were offended—but because consistency trained expectation. No pressure. No arguments.

He noticed something else, too. Sundays weren’t just saving him money.

They were quieting his mind. No impulse spending. No rushed decisions. No background anxiety about what he should be doing. Just space.

By the end of October, Caleb sat at the library computer again, scrolling through rows of numbers that finally made sense. Money wasn’t abundant. It wasn’t impressive.

But it was measurable.

And for the first time, it wasn’t mysterious. That alone felt like progress.

Side Hustles Don’t Look Like Hustle Culture

(Late Fall — November)

November arrived with shorter days and sharper air, the kind that made breath visible and time feel tighter.

Caleb’s mornings hadn’t changed.

The alarm still rang at 5:12 a.m. Shoes were still tied in the dark. Lunches still packed quietly. His brother still dragged his feet. His sister still leaned against him while half asleep. His mom still slept through the day after long nights of work.

But, even his mom was seeing a difference in him. She saw the relief in his face and eyes. She would ask him a few questions about what had changed, but he wasn’t willing to share. Not yet.

Structure held. That mattered.

When Caleb met with his mentor mid-month, the conversation shifted—subtly, but deliberately.

“You’re doing well where you are,” the man said, flipping through Caleb’s notebook. “Now let’s talk about growth without grind.”

Caleb looked up. “I can pick up more shifts.”

“You could,” the man agreed. “But let me ask you something. Why work extra hours at twelve dollars an hour when you could make twenty mowing lawns—or fifteen refereeing games?”

The question sat there. No pressure. No push. Just logic.

They talked about controlled expansion. About choosing work that paid better per hour instead of work that demanded more hours from an already full week. About protecting energy, the way Caleb protected Sundays.

Caleb started small.

On Saturdays, he offered yard cleanup to neighbors—raking leaves, trimming edges, hauling debris. He learned to quote prices out loud, not apologetically. Learned that confidence mattered as much as effort.

Twenty dollars for a small yard. More if it took longer.

He added basic car detailing—nothing fancy. Vacuuming, wiping down interiors, washing exteriors. Word spread quietly, the way it always did when someone did solid work and didn’t cut corners.

Youth sports refereeing came next. Weekday evenings. Saturday mornings. Clear rules. Defined time blocks. Fifteen dollars an hour to stay alert and make quick decisions.

It fit.

He learned another skill, too.

Saying no.

Not every opportunity was a good one. Not every dollar was worth the cost. When time didn’t allow, he declined without explanation. No excuses. No guilt.

Sundays remained untouched. Even when neighbors offered extra cash.

“I don’t work Sundays,” Caleb said.

That was it. No defense. No justification.

People accepted it—or didn’t—but the boundary held.

Late one afternoon, Caleb stopped by the library again, spreadsheets open on the screen, updating numbers that were slowly—but unmistakably—changing. Income lines rose without chaos spreading into the rest of his life.

That’s when he noticed her.

She sat two rows over, head bent slightly, hair pulled back, focused in the way people were when they were actually there. When she looked up, their eyes met briefly.

Just long enough to register.

No smile. No wave. Just recognition.

Caleb looked back at his screen, pulse a little quicker than before. When he glanced up again, she was gone.

The moment passed—but not entirely.

Walking home later, hands in his pockets, Caleb realized something else had changed.

More money hadn’t taken control from him. It had given him options.

And somewhere between yard work, spreadsheets, and a quiet glance in the library, the future felt a little wider than it had before.

The Bottle Stops Here

(Early Winter — December) December arrived with colder air and louder invitations.

Holiday music played everywhere—school hallways, grocery stores, car radios turned up too loud. The year felt like it was rushing toward something, and people around Caleb seemed determined to celebrate their way through it.

That’s when the pressure showed up. Not all at once. Quietly. Casually.

A few friends started carrying coffee everywhere—iced, flavored, oversized cups that cost more than Caleb spent on lunches in a day. Others had moved on to vaping, ducking behind buildings or into bathrooms between classes, laughing like it was harmless.

Caleb noticed everything.

He didn’t say much. He didn’t need to.

He’d seen addiction up close. Not in movies or lectures—but in living rooms, family gatherings, and phone calls that stopped coming. He’d watched relatives lose jobs, relationships, and time to bottles and pills. Watched potential rot into regret.

It never started loud. It always started casual.

Caleb had made the decision years ago, though he’d never announced it.

He wouldn’t start.

Because if he never started, he’d never have to stop.

He drank water. Almost exclusively. It was free. It was simple. It didn’t ask for anything back.

Milk was for cereal. That was it.

The money his friends poured into coffee or vaping—daily habits they joked about being “addicted” to—went instead to shoes that fit, groceries that lasted, and an emergency fund that gave him quiet peace. He watched friends complain about being broke while holding cups that cost five dollars each.

The vaping bothered him more.

It wasn’t just that it was addicting. It wasn’t even just the health risks.

It was control.

Anything that made you rearrange your life to get more of it—anything that threatened football, school, or freedom—that became a master. And Caleb refused to be owned by something that didn’t care about his future. Marijuana fell into the same category.

He wasn’t interested. There was more out there than this.

Mid-month, Caleb attended one school dance.

Just one.

He budgeted for it carefully. Ticket. Shirt. Nothing extra. He arrived on time, stood near the edges, watched more than he moved. Observed the noise, the energy, the way people chased moments they wouldn’t remember.

He planned to leave early. But then she arrived.

The girl from the library.

Their eyes met again—this time long enough to hold.

She stood near the refreshment table, scanning the room like she was deciding whether to stay. Caleb hesitated, then crossed the space between them before he could overthink it.

“Hey,” he said.

She smiled. “Hey.”

“I think we keep running into each other at the library.”

She laughed softly. “Yeah. I was hoping that wasn’t just in my head.”

“I’m Caleb.”

“Brianna.”

The name settled easily.

They talked briefly—about classes, about how loud the music was, about how neither of them stayed late at things like this. Nothing dramatic. Nothing rushed. They both enjoyed the time talking.

Soon, she had to leave, and so Caleb walked her out to her parent’s car. He didn’t leave as early as he was hoping, but not late. And, it was all worth the extra time.

Walking home through the cold, hands tucked into his pockets, he realized something had in life had shifted again.

Everything he did was intentional. Saying no—to drinks, to pressure, to habits that consumed people—wasn’t about restriction. It was about correction.

An inheritance didn’t have to be money.

Sometimes it was a choice. And tonight, between water cups and quiet conversation, Caleb felt certain of one thing: The bottle stopped with him.

Winter Is for Endurance

(Mid-Winter — January–February) Winter didn’t arrive all at once.

It crept in through the cracks—longer nights, colder mornings, breath turning visible before the sun even thought about rising. By January, the alarm at 5:12 a.m. felt heavier, as if the cold itself were pressing down on Caleb’s chest when he swung his legs out of bed.

It was cold. They kept the thermostat down until 5 a.m., while they slept and then it kicked on before anyone woke up.

He was very conscience about life and that even though it may sometime be hard, his routine stayed.

Shoes tied in the dark. Lunches packed quietly. His brother still complained about the cold. His sister still leaned against him, stealing warmth. His mom still slept after night shifts, and Caleb still guarded that rest like it mattered—because it did.

Football season was over but team workouts continued and he attended when he could. His coach knew of his situation and taking care of his siblings and that was more important. He knew Caleb was dedicated.

No more Friday nights to burn off stress. He did that in the weightroom when he could attend.

That was when discipline became personal. Most of his workouts were outside of team work hours.

There was no whistle anymore. No scoreboard. No one clapping if he showed up tired and did the work anyway. Habit had to replace adrenaline. Routine had to carry him when motivation didn’t show up.

His hustles shifted with the weather.

Yard work disappeared under frost and snow. In its place came shovels—driveways cleared before sunrise, sidewalks scraped clean while the world was still asleep. On the days the snow was melted away, Caleb would be up on his neighbor’s roofs cleaning out the gutters. Youth refereeing picked up again, weekend games in cold gyms with echoing whistles, noisy players, and restless parents.

The income continued to increase though. With more intention in life and work, the more it grew. And the systems held.

Mid-January, he met with, Mr. Evans, his mentor, again.

They didn’t start with numbers.

“Tell me what you’re saving,” Mr. Evans said.

Caleb talked about money—emergency funds, envelopes, spreadsheets—but the man nodded and leaned back. He was thinking of starting up a savings account at the local bank but hadn’t had the time.

Mr. Evans asked, “didn’t have the time?”

“You’re right, I didn’t make it a priority to do so.” Caleb replied and Mr. Evans smiled.

“Now tell me what you’re saving emotionally.”

That question took longer.

They talked about savings accounts that didn’t show up on paper. About relationships that replenished instead of drained. About rest, solitude, faith, and boundaries as reserves—not indulgences.

“Winter drains people,” the man said. “The ones who survive don’t spend everything they have.”

Sundays became essential.

Long naps stretched into the afternoon. Meals stayed simple—nothing fancy, nothing rushed. Church felt quieter in winter, voices lower, movements slower. Caleb liked it that way.

Faith anchored him—not loudly, not dramatically—but steadily.

A short prayer before sleep. Gratitude written once a day in the margin of a notebook. Silence allowed to do its work.

By February, Caleb noticed changes he hadn’t been looking for.

Less anxiety.Fewer emotional swings.More clarity.

He still woke tired—but not frantic. Still worked hard—but without panic. Recovery wasn’t something that happened when he collapsed.

It was intentional.

Winter didn’t make him stronger by force.

It taught him how to endure.

And as the days slowly began to lengthen, Caleb realized something important:

He hadn’t survived winter by pushing harder. He’d thrived by being intentional and resting better.

Social Life, But Small

(Early Spring — March–April) Spring didn’t arrive with a dramatic announcement.

It showed up quietly—in longer afternoons, in jackets worn open instead of zipped tight, in the way the air stopped biting back when Caleb stepped outside before sunrise. The alarm still rang at 5:12 a.m., but the mornings felt lighter, even when the routine stayed the same.

By March, Caleb’s world had narrowed—and somehow, expanded at the same time.

He didn’t have many people around him.

But the ones who were there mattered.

His circle stayed small: a few teammates who understood exhaustion without explanation, one or two friends from school who didn’t ask why he declined certain things, who simply accepted it. There were no parties on his calendar, no late nights he’d regret the next morning.

Team meals replaced everything else.

Cheap food after practice. Sitting around tables littered with napkins and half-finished fries. Laughter that didn’t require pretending. The kind of connection that came from shared effort, not shared chaos.

When invitations came—and they still did—Caleb declined Sundays without hesitation.

“No Sundays,” he’d say.

And no one argued anymore.

The boundary had become part of who he was, not a rule he had to defend.

One afternoon, walking with his mentor after a meeting, Caleb mentioned it—how his social life felt smaller than everyone else’s, but steadier.

The man nodded. “Longevity beats popularity,” he said. “Every time.”

That stuck.

Caleb noticed something else, too.

He wasn’t anxious walking into rooms anymore. He didn’t feel like he was missing out when he went home early or skipped events altogether. The quiet didn’t feel empty.

It felt chosen.

He spent more time studying with people who showed up. More time talking with Brianna—brief conversations at the library, a few shared laughs, nothing rushed. Enough to feel human without feeling pulled apart.

By April, Caleb realized something that surprised him. He wasn’t choosing discipline over connection anymore.

He was choosing it for connection.

And for the first time, that balance felt sustainable.

What the Numbers Say Now

(Late Spring / Early Summer — May–June) By late May, the year no longer felt like something Caleb was surviving.

It felt like something he had shaped.

Sunday evening settled over the apartment the way it always did—quiet, unhurried, dependable. The kids were already winding down, backpacks on a hook by the door, lunches half-prepped for the morning rush. His mom rested on the couch, one arm draped over her eyes, gathering strength before another long night shift.

Caleb sat at the kitchen table with a spreadsheet, that he printed at the library, laid in front of him. He reviewed the numbers slowly, deliberately—not because they were impressive, but because they were honest.

Total income: just about $10,000Emergency fund: fully establishedSavings: right around $4,000

He didn’t lean back in his chair or shake his head in disbelief. There was no rush of pride, no urge to tell anyone.

The numbers weren’t a trophy. They were proof.

When he met with Mr. Evans that week, Caleb laid everything out—yard work, refereeing, savings, envelopes, spreadsheets. Mr. Evans listened, nodding, letting Caleb finish before speaking.

“You’ve done well,” he said. “But now I want you to think bigger without working harder.”

Caleb frowned slightly.

Mr. Evans leaned forward. “You mow lawns for thirty dollars now, right?”

Caleb nodded.

“And how much were you making last year?”

“About twenty.”

Mr. Evans smiled. “Then why not let someone else mow for twenty—and you keep ten?”

The idea landed softly but firmly.

“You find the jobs,” Mr. Evans continued. “You schedule, you collect, you pay. You’re not cutting corners—you’re multiplying time.” He waited for it to sink in. “There are plenty of students who would like to earn $20 per hour mowing lawns, they just can’t find the work. And, if they don’t show up, you will do it for them and make the full $30.

Caleb sat with it, uneasy at first. It felt strange—like cheating effort. But the math was clean. Ethical. Honest.

By June, he tried it.

He needed another mower.

He needed help.

What he didn’t realize was that the first kid he hired, James—recommended casually by a friend— come to find out was Brianna’s younger brother.

He didn’t find out right away. One day he was standing in a driveway, handing James the lawn mower and explaining his expectations: show up on time, do clean work, finish strong.

Then from the corner of his eye he noticed a figure walking towards them. It was Brianna walking by, probably checking on her younger brother. She laughed—not at Caleb, but in admiration.

“That’s actually really smart,” she said. “And… kind of nice. You didn’t even know he was my brother.”

She turned to James and started into him, “Now you listen to him and you may learn some things.”

She whispered to Caleb as she walked by “Thank you”. Her bright red lipstick caught his eys.

Caleb shrugged. “Work’s work.”

But it mattered more than he let on.

That Sunday evening, after everything was settled, Caleb closed his budget spreadsheet, set his alarm for 5:12 a.m., and stood for a moment looking around the apartment.

Nothing sparkled. Nothing looked impressive from the outside. But everything was in place.

Mr. Evans’ words echoed quietly in his mind: You bought time. You bought options.

Caleb turned off the light, knowing the morning would come early—but also knowing that, for the first time, the future didn’t feel rushed.

It felt steady. And steady was enough to build on.