Philosophy

The Five Questions That Change How You Parent

You don’t need a parenting book. You’ve probably read several and the pages are already blurring together.

You don’t need a system. Systems require bandwidth you don’t have at 7:15 AM when someone can’t find their shoes and someone else is crying about toast.

What you need is something that fits in your head. Something you can reach for in the exact moment when your default is to yell, fix, rescue, or manage. Five questions. That’s it.

These aren’t theory. They’re redirects. Each one interrupts a reactive pattern and replaces it with an actionary choice — in real time, under real pressure.

Question 1: “Can they do this themselves?”

This is the starting line. Before you jump in — before you tie the shoes, pack the bag, solve the problem, make the call — ask: can they do this themselves?

Not “can they do it as well as I would?” Not “can they do it as fast?” Can they do it at all?

If the answer is yes — even a messy, slow, imperfect yes — then your job is to step back. Your instinct will be to help. Your instinct is wrong. Every time you do something your kid can do, you’re teaching them they can’t.

The 5-year-old can pour their own cereal. It’ll spill. The 8-year-old can call to make the appointment. It’ll be awkward. The 12-year-old can handle the disagreement. It’ll be messy.

Messy, awkward, and slow are the price of capability. Pay it now or pay more later.

When to use it: Every time you’re about to do something for your kid. Pause. Ask the question. If they can do it — let them.

Question 2: “What am I teaching right now?”

Every moment with your kid teaches something. Not every moment is a lesson — most aren’t intentional. But your kid is always learning from what you do, what you tolerate, and what you prevent.

When you redo the dishes they loaded, you’re teaching: your work isn’t good enough. When you let them quit the thing that got hard, you’re teaching: hard things are optional. When you answer the question they could figure out themselves, you’re teaching: don’t bother trying.

You’re not trying to teach these things. But teaching is what happens, not what you intend.

This question forces you to look at the actual lesson — the one your kid is receiving, not the one you think you’re giving.

When to use it: When you notice yourself on autopilot. When you’re managing a situation without thinking. Stop and ask: what is my kid learning from how I’m handling this? If the answer makes you uncomfortable, change how you’re handling it.

Question 3: “Will this matter when they’re 25?”

This is the perspective question. It pulls you out of the moment and into the longer arc.

Your kid got a C on the science test. Will it matter when they’re 25? No. But whether they learned to manage their own studying — that matters.

Your kid’s room is a disaster. Will the mess matter when they’re 25? No. But whether they can maintain a living space — that matters.

Your kid had a fight with a friend. Will the fight matter when they’re 25? No. But whether they learned to navigate conflict — that matters enormously.

This question separates the urgent from the important. Most of what stresses you out about parenting is urgent but unimportant. The important stuff — the skills, the resilience, the independence — rarely feels urgent. It just quietly compounds.

When to use it: When you’re stressed about a parenting moment. When you’re about to escalate or intervene. Ask: does the specific outcome matter, or does how they handle it matter? Almost always, it’s the second one.

What skills actually matter at 25?

50 skills every kid should learn before they leave home — the ones that compound into a capable adult. Enter your number and we'll text it to you.

By entering your phone number, you agree to receive texts from Together Progress. Reply STOP to unsubscribe. Msg & data rates may apply.

Question 4: “Am I doing this for them or for me?”

This is the uncomfortable one.

You drive the forgotten homework to school. Is that for them — so they don’t get a zero? Or for you — so you don’t feel like a bad parent?

You redo the chore they did badly. Is that for them — so they learn to do it right? Or for you — so the kitchen looks the way you want?

You solve the social problem. Is that for them — so they don’t suffer? Or for you — so you don’t have to watch them suffer?

Most rescues are for the parent, not the child. Your anxiety becomes their limitation. You step in because your discomfort is harder to sit with than their struggle. But their struggle is building something. Your intervention is preventing it.

This question doesn’t mean you never help. It means you check your motivation. If you’re acting to relieve your own anxiety rather than to genuinely serve your kid’s growth — stop. Sit with the discomfort. Let them work through it.

When to use it: When you feel the urgent pull to fix, rescue, or smooth. That urgency is usually about you, not them. The question reveals which.

Question 5: “What’s one thing I can hand over this week?”

The first four questions are defensive — they interrupt bad patterns. This one is offensive. It creates progress.

Every week, pick one thing your kid doesn’t own yet and hand it over. Not five things. Not a speech about responsibility. One concrete handoff.

This week: they set their own alarm. Next week: they pack their own lunch. The week after: they manage their homework without a check-in.

Small transfers. Consistent. Permanent. You don’t take it back when they do it badly. You let them do it badly until they do it better.

Over a year, 52 handoffs. Over two years, more than a hundred. By the time they leave, they own their entire life — because you handed it to them piece by piece instead of all at once at 18.

When to use it: Sunday night. Every Sunday. “What am I going to hand over this week?” Write it down. Do it on Monday. Don’t take it back by Friday.

How to actually use these

You won’t remember all five in a crisis. You don’t need to. You need one.

Print them. Stick them on the fridge. Put them in your phone. Whatever it takes to get them into your line of sight when you need them most.

Over time, they’ll become automatic. The pause before the rescue. The check before the intervention. The handoff instead of the takeover.

That pause is the entire difference between reactive parenting and actionary parenting. Reactive parents act on instinct. Actionary parents act on intent. The five questions give you intent.

You’re not going to use them perfectly. You’ll forget. You’ll rescue when you should have let them struggle. You’ll manage when you should have stepped back. That’s fine. The questions aren’t about perfection. They’re about direction.

Ask them more often than you forget them, and you’ll be a different parent in six months. Not because you learned something new — because you stopped doing the things that weren’t working.


These five questions are the daily practice behind 50 essential skills. Forging Gumption gives you the full framework — or start mapping your progress for free.

Stop winging it. Start making progress.

Get the framework for raising kids with intention — not guesswork.

Get articles like this in your inbox

One email a week. Practical ideas for raising capable, independent kids.

Follow the journey

Real stories, practical guides, and behind-the-scenes of building a tool for intentional progress.

{% include landing-form-script.html %}