Sam is 19, and when we started working together, his main financial strategy was texting his mom. (Sam isn’t his real name. We use pseudonyms for clients in the newsletter to protect their privacy.) Sam didn’t have a budget. He had his mom’s phone number.
At 15 it was small stuff: twenty bucks for Chipotle after practice, movie money, a “can you add to my lunch card” when the balance ran out (it always ran out). His parents said yes almost every time, which made asking feel about as serious as pressing an elevator button.
By 17 the button got more expensive, with his phone bill, gas, and a concert he’d already promised his friends he was going to before asking anyone (strategic, he admitted). By 19 it was groceries, a textbook he swears was real, and the occasional “I’ll pay you back,” which he fully believed every time he typed it.
When we asked why he continued asking for more and more money, his answer was honest: asking worked.
There was no set amount and no clear line between what his parents covered and what was supposed to be his, so every expense was technically open for negotiation. Planning a month of spending would have taken real effort, and sending a text took ten seconds. The ten second option won pretty much every time.
He gave another reason too. A quick “can you Venmo me $40” felt safe to Sam.
A real conversation about money felt like a trapdoor straight into questions about his grades, his job, and whether he had any plan for his life at all.
So he kept the asks small and frequent, which he described as “a very efficient way to never have the big talk.” He could tell his parents were getting annoyed. He felt guilty almost every time too, and he said asking for money constantly made him feel about twelve.
(If you’re a parent reading this and recognizing your own text thread, you’re in good company. Sam’s mom would like a word with all of you.)
Sam’s parents had actually tried a monthly allowance once before, when he was 17. It lasted about two weeks. He ran out, asked anyway, and when his mom said no, he asked his dad, who said yes. Then came a wave of “school expenses,” some of which were school expenses, some of which were not.
The second attempt looked similar on paper, with a set amount on the first of the month. His parents kept covering his phone, and food and going out came out of the monthly money.
What changed was everything around it. Sam helped pick the number. His parents agreed that any money request went to both of them and got one answer. They wrote down what counted as a real emergency (car repairs, medical stuff, required school costs), and anything on that list needed a receipt or a bill.
No receipt, no money.
For bigger costs, like the mechanic or a lab fee, his parents paid whoever was owed directly instead of sending Sam cash. When Sam asked for money for something that wasn’t an emergency, his parents waited until the next day to say yes or no. If he ran out, he could get one advance a month, taken out of the next month’s money. And they called the whole thing a three-month trial, with a sit-down at the end to adjust it together.
Sam told us the wait-a-day rule annoyed him the most, mostly because it worked. A lot of his asks were impulse buys, and by the next day half of them didn’t seem worth the text anymore.
It still didn’t go smoothly. The first month he ran out early again, used his advance immediately, ate a truly impressive amount of rice, and then texted his dad for “just $20” anyway. His dad forwarded the text to his mom, which Sam described as “a betrayal.” It turned into a real argument, and also the moment Sam realized the old workarounds were closed.
Month two went better until a friend’s birthday weekend ate half his budget in three days. By month four he was opening his banking app on purpose and had a rough idea of what a week of food cost him.
He still asks his parents for money sometimes, and some of those asks are fair (his car needed new brakes, and his parents paid the shop).
The asks come less often now, they come with an actual conversation about what the money is for, and everyone has a system to go back to when things go sideways.
If you’ve already tried an allowance and it fell apart, here are four things to try differently.
Pick the amount together and call it a trial. Agree on how much they get, when, and what it covers, and let them help choose the number. Teens and young adults are more likely to stick to an amount they had a say in. Try it for two or three months, then sit down and adjust it together. For a 15 year old, this might be $30 a week for food and fun. For a 22 year old, it might mean you cover rent and they pay for everything else.
Decide now what happens if they run out. Maybe they get one advance a month that comes out of the next payment, or maybe they wait. Either works. Settling it ahead of time means you won’t be deciding in the moment when they text you on the 19th.
Close the loopholes with a few clear rules. Every adult gives the same answer, so asking the other parent (or a grandparent) doesn’t work. Write down what counts as an emergency, and require a receipt or bill for anything on the list. Pay big costs directly to the school, doctor, or mechanic. For anything that isn’t an emergency, wait until the next day to say yes or no, which gives impulse requests time to fade. Keep the list short, because a long rulebook feels like a challenge to find the gap.
Keep money conversations separate from bigger conversations. Sam kept his asks small partly to avoid questions about school and his future. If a money request often turns into a talk about grades or plans, your teen may start asking in ways that avoid that talk. Bring up the bigger stuff at a separate time, when no money is involved.
Take some of the responsibility. Sam told us the change felt less personal once his mom said, “We never set this up clearly, and that’s on us too.” Owning your part of the old system makes the new one feel like a family fix rather than a verdict on your teen or young adults.
Any structure works as long as it’s predictable and everyone sticks to it, and one real conversation about it can save you a lot of Venmo notifications.
💙Announcements💙
We have exciting news!
There’s a free weekly support group for parents that we built with Other Parents Like Me.
It’s called Launching Young Adults, and it meets every Monday at 6pm PT / 9pm ET on Zoom.
OPLM is an online community where parents of teens and young adults support each other through the hardest stretches of raising them.
Their Peer Parents facilitate the group and our coaches won’t be in the room, so you’ll spend the hour with other parents who are going through the same thing, talking honestly about how it’s actually going at home.
Any parent can join and it’s free.
Registration takes about two minutes, so sign up now to save your spot.