Parenting Advice


This series started out as advice for my friend Roger who was having a late-in-life first baby (i.e., he was almost 40).  My daughter Stella was born a couple months before his daughter, so I talk more about Stan throughout this.  Stella wasn't around when I composed the bulk of these pearls of wisdom.  However, I've added quite a bit to this after the first few bits I sent Roger including some things I found in old emails such as discussing behaviorism with Val.  I have most of this arranged in a very loose chronological order.  Hopefully it will help anyone who happens across this page.



Before the baby arrives

Get a good camera.  Your phone is not a good camera.  It's barely a camera, actually.  You need something fast.  "Adorable" only lasts for a few seconds, which means it's gone in the time it takes to turn on your phone or cheap camera.  Get a proper SLR camera and learn to shoot faster than a gunfighter.  You also need to start getting good at archiving.  I have a whole system down for getting the files off the camera, renaming them with the date and labeling each with the kid's name (which is especially important with babies because you'll never remember who's in the shot if you have two that look alike as infants), then making sure they're all backed up (see here).  I do the latter religiously, and I don't do religion religiously.  Your kids are real though, and you care about them more than anyone else, so back up the pictures!

Don't tell anyone the name of your baby until you have the baby.  It's fine to tell the gender when you find out (though I would wait until the second ultrasound where it's doubly confirmed, just to be sure), but announcing the name is giving away the last detail short of baby pictures (and those are pretty terrible the first few days anyway).  Besides, you will have time to change your mind. 

Stan wasn't named until 26 hours after he was born, and we knew the gender for months before that.  We had a pretty good list of names, but "Stan" was only #3 on it.  When he was born, we looked at him and realized he didn't look like options #1 and #2 (don't ask me what those names even were; we have forgotten).  He looked like a Stan.  The third time the poor people at hospital records called up to our room asking if we had a name, we were like, "Uh..."  We settled on "Stan" and I called them back a few minutes later before they went home for the day.  That's how I remember exactly how long it was until he got a name (He was born at 2:32pm, and they called at 4:30pm the next day).

Don't tell anyone when the baby is born for the first 24 hours.  You're going to be exhausted.  I'm only the dad, and I was!  I had been up nearly the entire night (minus maybe a couple hours sleep on a cold leather couch in the pre-delivery room).  I hadn't eaten anything besides breakfast since supper the night before.  Stan wasn't delivered until 2:32pm after a whole night of labor and emergency C-section drama, and then there's all that rushing around getting him cleaned up before you can settle into your room and get a bite to eat.  Dani hadn't had anything at all to eat since the night before.  We just wanted to chill and rest and be with the new baby.

I remember some years ago when Julia Roberts had her first kid, she told the press the baby was due in, say, April.  Then she snuck off to the hospital and delivered her full-term baby in March, which was when the baby was actually due in the first place.  The paparazzi were covering other celebs and had their calendars marked for the wrong month.  Julia and baby got some peace.

Stan came early, so we never told anyone outside of immediate family that she was getting ready to deliver.  It wasn't until the next day (after we named our Stan) that we finally sent out the standard birth announcement texts and all that, and then there was a flood of people coming by to visit.  I've heard horror stories about friends being swamped with visiting relatives who overstay their welcome when the new mom needs some privacy to nurse the baby.  Both the parents and the baby feel overwhelmed.  No one would put up with a procession of visitors if they just passed a kidney stone, and we're talking about something a lot bigger.  So why not take a day to relax before debuting the baby?

Pick one brand of baby bottles and stick with them.  If you have more than one brand in the house, you'll spend all your time trying to assemble matching sets to make a bottle.  This isn't fun when there's the ever-present threat of a screaming, hungry baby at any moment, and you'll need a bottle in a hurry.  (I recommend Avent.  They have fewer parts than almost any other brand we tried, and they work at least as well as the competition.)

Read... early and often.  There is volumous research extolling the benefits of reading to your baby, even before birth.  I don't know that we started quite that early (maybe one or two books), but I certainly started buying books as early as possible.  Literally the first purchase I made for Stan (before we even knew his gender) was a bunch of Dr. Seuss and other books on eBay.  You can pick up bulk lots like 70 books for $200.  If you get classic titles like "The Cat in the Hat" and "Where the Wild Things Are," you'll more than get your money's worth out of them by reading them over and over for the next several years (and then again to the siblings that follow).

Don't buy any stuffed animals.  You won't need to.  These things will materialize out of thin air.  I've only bought a very few (a couple puppets: Grover and a turtle, and then there was a Picachu I won for Stan at Legoland), yet we have perhaps a hundred or more around the house.  Where did they come from?  I couldn't tell you.



0 to 6 months

Parenting instincts come factory-loaded but don't come on-line until the baby is in your hands.  Don't worry about it.  You will know what to do.  The stupidest people on Earth manage to keep their kids alive (unfortunately).  You can do at least that well on auto-pilot.

I never would have believed I had any parenting instincts until Stan was born.  I thought babies were interesting, but purely on an intellectual level; I never wanted to hold one.  In fact, we did the math after Stan was born, and I hadn't held a baby in four years before they handed him to me in the hospital.  My first thought when they said, "Take him over to mom now" after they cleaned him up was, "Wait.  I have to hold this thing?"  It was this realization that he was really mine now to take care of and not just an abstract concept.  Then I had to figure out what to do with the cameras I was manning in the operating room so I would have hands free to carry him!

Then I just immediately took to it.  I was changing diapers and feeding him, carrying him around, and it was no big deal.  It just came naturally.  My dad tells a similar story about how my mom was bathing me and then put me in a diaper.  He asked her, "How do you know how to do that?"  She said she was just doing what felt right.  If you're an intuitive type person (Look online to see what your MBTI is; I'm an ENTP), then you go with your instincts.  Pretty quick you'll be able to read what a cry means or gauge how long until you can put her down for a nap, and you won't even think about how you know that.

About the nursery: Don't worry too much about it.  Everyone stresses over putting together a nursery before the baby arrives, and you know what?  The baby will hardly spend any time in there until she's six months old.  I mean, we let Stan sleep with us until then (although you need to get them out by six months or you will never get rid of them!).  The nursery was just a storage area for baby-related things we weren't using.  We had it painted all pretty and kept everything neat, but we mostly kept the toys in the living room.  We hardly spent any time in there.

As of this writing, our baby girl will be here in less than two months, and we haven't even gotten her things out of the attic yet.  We're in the process of renovating the adjacent room, so everything that was in there is now in the baby's room.  It won't be out of there until we finish painting, then install the baseboards (including wiring the outlets in them) and maybe even put up some cabinets.  Only then will we have a nursery.  No big deal.  It's not like she's going to start telling us she "needs her space" or anything.

How to carry a baby: Babies have two parts: A head and everything else.  These are almost the same size and weight as one another.  Eventually a baby can carry his/her own head.  Until then, you have to carry both parts and keep them from getting separated.  Or if you want to view it another way, you either carry both parts of the baby, or you don't have a working baby anymore.

You can handle having a child because children come to you the size you can handle.  They don't start out as teenagers.  They start out as babies.  They do nothing for a while, just to see if you can keep them alive.  If you can do that (and almost everyone can), then they crawl around to see if you can child-proof the lowest eighteen inches of a room.  Then they learn to pull themselves up to see if you were stupid enough to leave anything within reach of a toddler.  Eventually they learn to go off in a car to test whether you brought them up with the life skills not to take anyone's life with a car or make any new lives in the back seat of it.

Babies are slugs until they are three months old.  They don't do anything except lie there and let Anne Geddes dress them up as fruit so she can make calendars for secretaries.  It isn't until babies are around three months old that they even laugh for the first time.  There's supposedly a Chinese tradition that they consider a baby's first birthday is the day he laughs for the first time.  As it happens, this is always around three months... which makes sense: 3 months + 9 months in the womb = 1 year = 1st birthday!  I remember how big a deal it was when Stan laughed for the first time.  We got out the camera and kept him laughing until he was out of breath.  Once they can laugh, you know you have a little human.  Before that, they're just slugs.

Do whatever works.  Whenever Stella would start crying, the one thing that seemed to work was to fly her around the room.  I'd hold her on her back and wave her around like Super Girl.  You find things like that, and you use them whenever you need to without caring who's watching.  And the same goes for what keeps you sane.  When Stan was a little over a year old, I once locked him in his room (i.e., behind a baby gate) and slept in my car.  I needed some sleep, and I was going to go crazy if I didn't get any.  Stan's room was childproof, naturally, so I locked the baby gate and got away from the crying for an hour.  If I hadn't, I would have likely gotten in a car wreck from sleep deprivation on my way to work or found myself in a psychotic state and hurt him.  Saying I locked him in his room sounds bad, but objectively speaking, it was the most sensible thing to do at that point.  Be objective and do whatever works.

Babies aren't as fragile as you think.  They'll survive a fall off the bed.  More parents have this story than you would imagine.  Both our kids have fallen off the bed at least once.  Dani fell asleep with Stella on her stomach only a couple weeks after we had her.  A short while later Stella hit the hard floor.  She survived just fine.

Sometimes you find the only thing that soothes a kid is to pound on his (or her) back when you burp them.  You can't be gentle or it doesn't have enough of an effect.  Both my kids liked this as babies (albeit slightly different techniques: Stan liked karate chops; Stella preferred bongo drumming).  If I stopped or attenuated the intensity to what *I* thought was appropriate, the crying came back.  The only thing that was weird about it was that Dani would say, "Here, pound your daughter," and that just sounds wrong.

You don't need a diaper bag.  Parents (read: moms) pack things like they're going on a trip to Mars with a diabetic.  Babies aren't that complicated.  All you need are diapers, wipes, and a bottle.  I always kept two diapers and a zip-lock bag with some extra wipes in my glove compartment.  The bottle was in the baby's mouth.  Unless you're going somewhere without indoor plumbing, then you're going to be fine.

Screw the schedule!  A lot of parents try to rigidly adhere to a schedule with respect to eating and sleeping, but that ultimately causes more stress than it will ever reduce.  After all, how are you going to make a kid fall asleep like clockwork when (s)he's in the middle of a growth spurt?  What happens when (s)he wants to eat more often?  What happens when (s)he's been up all night because all four first-year molars came in at the same time, and then she is exhausted the whole next day?  (Yes, this is a thing.  It happened with Stan.  It was the reason why I locked him in his room that time.  That's where the sleep-deprivation came from.)  You think she's still going to take the same 90 minute nap she took last week after having a shitty time this week with a stomach bug?  That's bullshit. 

Do what your kid needs.  Feed the baby when (s)he's hungry.  Let the baby sleep when (s)he's tired, not when you are.  It's called needs-based parenting.  In other words, you're making decisions based on what the baby/toddler is indicating (s)he needs, not what the clock says.  Sure, you'll probably need a nap later.  The good news: Babies take naps.  Just go to sleep when the baby passes out.  They sleep something like 18 hours a day.  You'll manage.

And don't worry about monitoring things.  Every baby is different and every day they'll have different needs.  Don't get worried if (s)he doesn't eat much one day or sleeps too much or doesn't poop.  That's how kids are.  If they aren't acting sick, they probably aren't sick.  Stan went through a phase when he switched from taking hour-and-a-half naps to sleeping for five hours at a time for several days.  And babies sometimes don't poop for three days.  Enjoy the break.

Kick the baby out of bed when (s)he's a toddler.  Like I mentioned above, our limit was around 6 months.  If the kid can sleep through the night, then you are probably safe to make the transition.  The danger is that, the longer you wait, the harder it will be to get him (or her) out without a lot of crying.  They really don't care as much and are more adaptable when they're younger.  You might have to be firm about it if the kid gives you a hard time during the transition.  Consider it practice for everything that follows: Don't give in to a terrorist!

Get used to things breaking.  Every day something breaks.  Kids love to get ahold of things and crumple, rip, yank, etc.  I've had ceramic cereal bowls pulled off desktops before (both filled and empty; the bowl broke in the latter case).  As I write this, today Stan (at age 4) picked at a rotten spot on the wooden front porch until it was a gaping hole.  Toys break constantly, even if they're well-made.  Glasses in all forms will be broken: eyeglasses, sunglasses, toy glasses.  My balls, have been broken both literally and figuratively.  I mean, I've been punched or kicked in them repeatedly.  Note how their feet line up with your crotch while changing a diaper.  Same thing with the height of a toddler.



6 to 12 months

Late-bloomers do just fine.  There's a lot of research that says there is absolutely no correlation between success later in life and reaching milestones in the early years.  It's not a big deal if (s)he isn't the first in her preschool class to walk/talk/whatever.  In fact, bigger kids take longer to walk due less to maturity than the fact that they don't have the strength to stabilize their weight against gravity (In other words, sometimes being ahead in one race means falling behind in another), so it's a trade-off.  There are too many factors at play here for you to worry about developmental milestones unless there are serious delays.

Teach a kid to meet you halfway.  Soon they'll just go ahead and go the distance on their own.  Back when Stan was old enough to start pulling himself up at maybe 8 months (just guessing), I stopped picking him up out of the crib in the morning or after a nap.  I would come in if he was crying, and I would stand back about a foot from the crib.  I wouldn't pick him up until he pulled himself upright and effectively met me at the farthest point he could go on his own.  In later years I extended this approach in every way possible.  For example, if he wanted a drink, I'd tell him to get a cup, and I'd pour something into it.  And so on.  But start at this age.

Take kid classes for yourself.  You know: Swim class, music class, baby gymnastics, etc.  That's true for at least the first two years.  Most of those classes are for you.  Go into them knowing you'll get more out of them than the kid, and you'll have a better sense of whether you're getting your money's worth.  They're an opportunity to meet other parents and just get out of the house.  Sure, the kid benefits from them, but nowhere near as much as you will.

It isn't illegal to want to kill a baby.  Only the actual killing of a baby is illegal.  You are free to entertain thoughts of killing a kid... because you will be pushed to that point by all the screaming.  I never wanted to kill another human being in my life as badly as I wanted to kill Stan on days when he wouldn't shut up.  They say birth is a miracle.  I say their third birthday is, if they make it that far.  (Note: Moms who have thoughts of killing their baby probably ought to talk to someone about it other than Tom Cruise.  It's post-partum depression.  Unless your kid really is that big a pain in the ass.  However, dads get a free pass because we usually want to kill people who annoy us.  See various performances by Louis CK for further details and additional parenting advice based on years of field research.)  Stan was a perfect baby for the first 6 months.  For the next two years, I wanted to kill him on a daily basis.

Kids are suggestible = Anything you say is a suggestion.  I see this all the time when parents say something like, "She's going to be upset" or "That had to hurt."  Kids read these as cues from the director.  You need to avoid feeding your kid prompts to behaving in certain ways that are undesirable.  If you indicate that a fall was a bad one, to that kid it probably will be!  I never ask if the kid is okay.  I say, "You're fine," and tell them to get up.  If they're genuinely hurt, they'll let you know.

Develop repetoirs.  For every situation, you need to have tools, not just a "solution."  For example, infant is crying?  Here's a list of possible remedies that I might go through with Stella:
---Feed her.
---Stand her up (if she's lying down).
---Burp her (and hard, too; if she's crying then she needs it up quick).
---Your own version of hypnotism.  I don't know how to actually put a kid in a trance, but I used to whisper "sleepy" to my son, and it was a relaxing suggestion.  I had a version of this with Stella too.
---Change your tone of voice.  If you're speaking, then speak musically.  If you're being happy and upbeat, dial it down to a whisper (see above).
---Blow in her face.  This interrupts crying, but only for a second or two.  However, it's an opportunity to get her quiet long enough to try talking to her, which she couldn't hear over her own screaming.
---Mylicon.  Because maybe it's gas.
---Ibuprofen.  Because maybe it's a tooth coming in.
---Put her down for a nap.  And leave her there.  Sometimes they just need to cry it out until they pass out.  Stella went through that phase where crying meant that she just needed to be left alone to go to sleep, and sometimes that meant crying for 5 to 10 minutes first.

Coin one-word commands.
  It sounds very militaristic, but I found that when Stan was short on vocabulary, short, unambiguous commands get the message across much faster than all the explaining in the world.  In fact, you're wasting your time explaining anything to a kid under two.  They need to just do what you asked.  Here are some of the commands I had with Stan, many of which I used with Stella.


12 months through preschool

All toys should be one piece.  For example: If it's a boy: Trucks.  If it's a girl: Dolls.  It doesn't have to be that gender-stereotyped, but you get what I'm saying.  Stick with what's developmentally appropriate.  If a kid is going to lose essential pieces, then (s)he isn't ready for that toy yet.
A partial list of things to hide: To this day, I can't find these things around the house.  We used to have a dozen of each.  But somehow children find them when you aren't looking.
Get more baby gates than you need.  Children are animals that need to be caged.  They're worse than that even, like a fundamental force of destruction.  Think of your house like a submarine that's just been torpedoed.  Compartments are flooding, so hurry!  Every time you bring a child into that room, destruction follows.  You must seal off areas to contain the destruction before it can spread!  That's what baby gates are for: Cordoning off areas before the Tasmanian Devil can get to them.

Dads are always the bad guy.  You can tell the kid "No, you can't have any donuts until after supper" for several hours, then Mom will walk in and hand the kid a donut just as you're setting the table.  You're the one who will yell at the kid when (s)he won't listen.  On the other hand, you're the only one the kid will listen to.

Quit carrying him and make the kid walk.  It pays off.  For example, when I took Stan grocery shopping as a toddler, and I rarely had a problem with him.  Contrast with Dani, who at one point told me she couldn't take him to Wal-mart anymore because he was always giving her a hard time.  I'm like why, don't you put him in the cart?  She said she did but that he complained the whole time and kept trying to get out.  The next time I went to Wal-mart, I realized what I did differently.  I always made Stan walk with me across the parking lot.  Dani always carried him.  When she put him in the cart, he couldn't wait to get out and do something.  But when I took him, he was exhausted by the time I'd gotten him to the front of the store.  He couldn't wait to sit down and have someone push him around the store.  That little difference made a big difference.

Teach independence by allowing it to happen.  I think some kids are independent by nature, but you can certainly encourage it in any kid.  For example, we always put kid food (e.g., fruit snacks, juice boxes, etc.) down low on the kitchen shelves so that Stan could get to them when he was hungry.  Had Stan been the kind of kid who was gluttonous, I would have modified that strategy, but he was reasonable with food, and that made things easy on me as well as creating an opportunity that encouraged independent action on his part.

Make them work for it.  On a related note, whenever Stan asked me for something like his juice cup, I wouldn't point to it; I'd just say it's in the room.  I'd give him vague directions so that he would find it for himself.  The result was that he learned to help himself when he wanted something to eat.  We created the aforementioned shelf in the kitchen so that he had access to fruit snacks, peanut butter, etc.  I still had to get him more juice (because he was still too clumsy to pour from a heavy bottle effectively and not strong enough to get the top off the sippy cups anyway), but he could do a lot of things for himself if he made the effort, and food was a good way to encourage that.

Make them think they're doing it... and soon they will!  When we went to the park when Stan was smaller/weaker, he used to struggle to climb up the slick surface of the slides.  I wouldn't lift him to help him up them.  Instead I put my hands beneath each foot as he set it down.  He thought he was getting a lot better traction than he was.  As a result, he didn't ask me to pick him up; he just worked at it as hard as he could.

I still do things like that at the park.  He's to the point where he can do most things, but there are still some bits that he can't climb without a lot of effort.  He'll try to give up, but I keep telling him "You can do it,  you can do it," over and over.  I'm constantly after him to finish the task, but I won't do it for him.  I'll maybe take the weight off him, and I'll always have an arm under him or along side so that he can't fall, but I won't give him a free ride.

It paid off.  I was at the aforementioned park in my neighborhood at one point when he was still pretty small.  He was walking and could climb the stairs on the playground to get up to the top.  I was talking to another dad who was there with his 4 year-old daughter.  I really wasn't paying that much attention to Stan when she said, "That little boy can do anything!"  I looked over where she was pointing, and Stan was all the way at the top of the really big spiral slide.  At that point he'd been down it before, but only when I brought him up there.  I was like, "Okay, then.  Come on," and he came down it.  He was fairly confident about things like that.  If he thinks he can reach it, he'll go for it.  If he doesn't, I try to get him as close as possible before I step in and help him bridge the difference.  There's only so much influence parents have on their kids' personality, but I'd like to think I instilled some of that in him beyond whatever was already there.

Get memberships.  Look for what's fun and interesting in your area that involves a lot of walking.  For example, we have a zoo and a science museum that are big and convenient.  If you get a membership, then you can drop in for a couple hours, then go home to put the kid down for a nap.  If you paid full price every visit, you know you'd feel like you wasted money if you left early.  Kids this age are only good for about an hour or two some days.  Bonus: Most memberships allow you to bring guests either for a discounted rate or free, so it's good to have a membership if you want to bring friends or play groups.


Please and Thank you.  These are two of the most important phrases in the English language (or their eqivalents in any other language).  When Stan was barely talking, these words were required for any elective transaction.  If he wanted a cookie, he had to say "Please" before I would even make a move to get him one.  Once it was in my hand, I would hold it out but not release it until I received a "Thank you."  Once he said "Thank you" I would then let go.  This was before he could even put together a full sentence.  In fact, I used this process to chain together words to form a sentence.  Originally he'd say "Cookie."  I'd ask, "What do you say?" and he'd give me a "Please."  Over time I added words.  "Please what?"  Him: "Please can have cookie?"  I always thought it was funny that the words he left out were the shortest ones: "I" and "a" but he eventually got the whole thing: "Please can I have a cookie?"

Learn to speak in code.  When parents talk, they have to avoid letting the kid in on what they're saying a lot of the time.  For example, Stan will want to take a bath if either of us are going to bathe or shower, so we say things like, "Are you going to cleanse?"  We change it up every time and avoid pairing the synonym with the actual meaning so that the kids never pick up on what we're really saying.

Practice reverse psychology.  Everyone thinks they know how to do this, but it's like seeing a couple moves ahead in chess.  You can't start with the move you want to do; you have to make the move that sets things up for what you need to happen.  For example, Stan would refuse to answer questions if he knew I was quizzing him.  However, he would freely argue with me.  So instead of asking, "What's this a picture of?", I would tell him, "Look at this picture of a butterfly."  He would look at it and say, "That's not a butterfly; that's a lion!"  I got him to answer me without asking the question he wouldn't have answered.

Invent a bedtime routine (and stick with it for as long as it works).  The current bedtime routine (which I've been doing since he was about three) goes as follows: I read him two storybooks.  At the end of the first one I say, "Okay, goodnight."  He protests and says, "One more!"  "Then what?" I ask.  "Sleepytime."  Sometimes I ask when "What next?" after the first book, and he says, "One more book then sleepytime."  I read the second book to him, then put it down, and there's a four item sequence that I always do in order:
1. Me: "Give me a hug."  Stan gives me a hug.
2. Me: "Give me a kiss."  Stan gives me a kiss.
3. Me: "I love you."  Stan: "I love you too."  (The hardest part was getting him to understand the concept of "too."  Even when he was almost four years-old, he would still say, "I love you too" before I say "I love you.")
4. Me: "Goodnight."  Stan: "Goodnight."
I turn out the light, and he goes to sleep.

When he was younger and wouldn't pay attention to the books, I used to do a puppet show with all the stuffed animals in the room.  They did variations on what they were good at.  Grover told a few bad jokes.  Tigger jumped around going "Boing, boing!"  And so on.  When we ran out of animals, it was time to leave and turn off the light.  He usually wouldn't protest because we had done everything there was to do.

You know what helped a lot?  Earplugs.  One of the hardest things to deal with during Stan's early years was all the screaming.  The constant assault was lessened when I finally discovered earplugs.  Get a pair of soft silicon earplugs.  Search for swimmers earplugs in particular.  Those are far better than the foam or putty variety.  I keep pairs of these everywhere through the house and then some: Next to my bed, on my desk, even in my car.  Because when a child has a meltdown in a confined space, you don't get to escape from them.

You know what else helped a lot?  Blood pressure medication.  I have always had borderline high blood pressure, but it's even worse during a "fight or flight" moment that my body perceives as a crisis.  A crying child is a routine event for any parent, but it always sounds like a crisis to me.  Beta blockers in particular are a class of medication that attenuate the physiological response to stress.  Actrors and musicians frequently employ them to reduce the feeling of anxiety (i.e., "stage fright") before a show.  Parents are expected to perform all day long, so these can help quite a bit at keeping you level.

Toddlers hate shoes.  I have no recollection of exactly when this starts*, and as of this writing I'm still waiting for it to end (He's 3.5 years old).  I'd put him in the car seat fully shoed when we left, then arrive and have to spend another couple minutes crouching beside the car in the rain looking for where he threw them when he pulled them and, inevitably, his socks while I was driving.  I've finally broken him of peeling them off in the car, but if we're indoors, that's sufficient reason to shed them, like we're in a very, very casual Japanese setting, one where you can strip to a diaper even.  I've put his shoes on him, and in the time it takes me to fill a sippy cup and return to collect him on the way out the door, the shoes (and, yes, socks too) are off again.  *Update: Stella's doing it now, and I think it started around age 1.5, but I guess it depends on whether the shoes have velcro or not).

Where possible, let natural consequences deliver the lesson.  When Stan was around three years old, he was leaning off the edge of playground equipment.  I knew he was going to fall.  I could have yelled at him, but I knew if he fell he wasn't going to be hurt too badly.  So I let him.  He leaned too far and tipped over onto the playground mulch.  Didn't hurt anything except his pride.  If I had preemptively admonished him, I would have had to do it again and again.  Instead, I did nothing, and he only fell off once.  Sometimes holding back and letting a lesson teach itself is faster than actively "teaching" the same thing.

Keep a box or two of toys out of sight.  We have "new" toys hidden all over the house so that we can pull them out for rewards or special occasions (xmas, birthdays, etc.).  For example:
Make lists of presents.  This overlaps with the above item, depending on how you apply it.  Sometimes you'll see something you want to get him/her, but they just aren't ready for it yet.  If it's a steal and/or one-of-a-kind, then buy it and hide it in one of the aforementioned boxes.  Otherwise, write it down.  You can make a master list to consult for all the major events: birthdays, xmas, graduation, whatever.  See also the "Birthdays" and "Christmas" sections below.

Invest in milk crates.  They're cheap and durable and great for organizing kid stuff.  Buy more than you think you need because you'll probably need them.  At the very least, you can always use them in your garage.  I picked up about 25 of them, and we use all of them for Stan.  Incidentally, mine were all $2.50 a piece from a guy on Craigslist.  They were $10 at the Container Store.  Sure, mine were all black instead of an assortment of bright colors, but I think mine were sturdier in addition to being a quarter of the price.  We made labels for them according to general categories of toys*, and that kept the chaos down to "barely tolerable."
*Note: Our categories include Cars, Hot Wheels Track, Action Figures, Wood toys, Alphablocks, Letters, Food (plastic kitchen stuff), Wood blocks, Legos, Hats, Guns, Stand-alone (toys that don't have more than one part like "Simon"), Bike helmets, Dress-up, Sports, and Musical toys.  Later we generalized still further and made a whole row of just "Dress-up" crates which incorporated Hats, Guns, and other weapons, capes, masks, vests, etc. that he had gotten more into.  I also made a couple bigger bins for outside toys (sporting goods and cars, swimming pool toys, etc.) and put them on the front porch.

Consistency is key.  The biggest failing I see in parenting is backing down from the first thing you said.  If you said, "No, you can't do that," then there's no reason to negotiate or modify.  Take a reasonable position from the start and hold it.  Don't say, "No, you can't have any cookies" and then say, "Here, just have one to hold you until supper" because you're tired of the whining.  All that cookie did was reinforce the whining.  The whining will never go away if you give a kid a cookie every time (s)he whines for one.

Give them tasks to create responsibility.  For example, as soon as Stan was able to sort silverware, we made him put away the forks and spoons.  I pulled out the knives and odd cooking utentils, then gave him the drawer liner to put them all into.  He whined and complained, but the task was tangibly right in front of him, and he wasn't allowed to move onto anything else until he completed it.  Over time he realized that complaining and delaying were simply counter-productive.  When given a task, the fastest route is through it.

Use something objective as the bad guy.  The iPhone is a perfect choice.  Check out the timer function under the standard clock app.  This works great for potty training, transitioning between tasks such as the end of playtime, etc.  Say "five more minutes," and set the clock.  When it goes off, hold up the phone with the alarm going off.  After a certain age, kids recognize objective boundaries such as this.  They'll argue with you, but they can't argue with the 4th dimension.  (Low tech alternative: The sun.  For example, I tell Stan he can do something "when it gets dark."  I don't have to deal with pestering; I just point to the window.)

Colored pencils.  These were probably the best investment I made.  Screw crayons.  They're messy and imprecise.  Colored pencils are more robust: they don't break.  They're basically just pencils, so skills acquired using them to color will transfer over to basic drawing/writing skills they'll need later.  They're also very nuanced, so you can teach a young child to do mixing and shading (i.e., pressing lightly = light color vs. harder = darker) at a very young age.  After coloring with Stan for a couple weeks, his ability to write letters jumped more without practice than with all the practice combined up to that point.

Let kids get dirty.  Let them play in mud.  Let them splash in the rain.  They're only kids once, for fuck's sake.  The clothes will wash.  If they don't, fuck it.  They were about to outgrow them anyway.  I hate parents who think dirt is a boundary rather than a badge.

Build a bookshelf.  I couldn't find any that met my needs, so I built one with the following characteristics:

Take lots of pictures.  This goes two-fold.  First, yes, take lots of pictures of your kid(s).  Don't let a week go by without some pictures.  Keep a camera within reach or at least put the camera icon somewhere on the main page of your phone.  Second, take a lot of pictures in a row.  Kids are notoriously unpredictable photographic subjects, so be prepared to shoot three or more shots where you'd normally shoot just once.  These don't have to be in rapid succession like you're trying to catch a sprinter, but shoot several times before the kid moves away.  Only one of those will be a great shot, sure, but you can delete the rest and look like you were always prepared to catch that perfect moment.  Everyone takes lots of pictures of the baby, but then it starts to tapper off.  I'm saying it again: Keep taking pictures.

Pre-event acclimation.  Just to get Stan more comfortable with a new place or activity, I always take him there once or twice before any formal event he is scheduled to attend.  For example, if he's going to a classmate's birthday party at a skating rink, I'll take him skating at that same rink once or twice first.  That gets him over the hump of worrying about being on skates for the first time in front of his peers.  If he's going to Putt Putt with his friends later, maybe we'll go once by ourselves.  Then, when he goes there socially sometime later, he can concentrate on the social aspect of the interaction rather than acclimating to the sport or the venue.  Not every kid needs this, but mine did, and I think it helps the majority of them get a leg up even if it isn't a necessity.



Bonus: Tips for Holidays and Other Occasions
Organize for holidays and parties.  We have several storage tubs in the attic dedicated each to specific holidays/events: Easter, birthday parties, etc.  It makes it convenient to be able to pull out a sort of a kit to assemble the holiday, especially the things that have to get set up the night before like eggs for the Easter egg hunt.

Birthdays

Get presents in advance.  If you see it on sale, get it.  I don't care whether she's too young still; if you know she'll want one in a year or two, it's that much less you have to shop around for when he birthday is closer.  Obviously you can't anticipate changing tastes like how one year a kid's into Star Wars and the next it's Spiderman, but some toys are independent of preferences or are better than anything a kid might dream up for their wish list, like a baseball pitching machine, something Stan never even knew existed before Santa put it under the tree.

Make your invites way in advance.
  I'm not saying you need to print them out and deliver them, but at least write up the text.  Even after the parties are over, save a copy of the invitations somewhere you'll always find them so you can reuse the text with minor modifications and not have to re-write everything every year.  There's simply too much else you'll be busy with.


Don't open the presents at the party.
  I know that's a typical thing, but I always feel like it's a big waste of time.  Let the kids enjoy the party and socialize instead of making them watch the birthday boy or girl unwrap presents no one will have time to play with before the party is over.  Speaking of which...


Make the presents last!
  Here's what you do instead: The birthday kid gets to open only one present a day.  Not only does this make the birthday last a week or two, it also allows the kid to focus on each present, to spend time reading the instructions, putting the decals on properly, playing all the levels, putting all the pieces of the puzzle together, etc.  It basically turns a birthday into Hanukkah!


Easter

Have an Easter egg hunt.  It's a tradition.  Plan for it.  I packed a bunch of eggs and hid them the night before.

Not just candy.
  Here are some ideas for things for their baskets: Hot Wheels cars, Legos, etc.  Any toys you can fit in the eggs or a small basket will do.


Hit the after-holiday sales!
  This is always a good idea for getting stocked up early for next year.


Halloween

Have the Halloween party early!  It avoids scheduling conflicts if you push Halloween back to an earlier date.

Have activities and conversation pieces.
  See my list of Halloween party activities and conversation pieces here.


Hit the after-holiday sales!
  As always, you'll be ready with decorations and whatnot.  Also, if your kid loves costumes, this is the best time to stock up on Batman masks and fairy wings.


Christmas

One present the night before.  It seems like most familes have this tradition already, but think about which present is best for the occasion.  I usually go with the one present that requires concentration and reading the instructions.  For example, last year I gave Stan a magic trick that required watching a dvd of the performance of the trick, reading the instructions, and practicing it.  Had I given it to him on Xmas morning, it would have gotten lost in the shuffle of all the action figures and everything else that was more about playing.

Elves are magic.
  One of the things I used to do when Stan was younger was to set out Rudolph figures on the mantle, one or two every night leading up to Xmas.  First there would just be young Rudolph, then Hermie the elf, then other characters, and eventually we'd work up to the gang meeting Bumble, and so on.


Have traditions.
  Some examples include:

Hit the after-holiday sales!  Again, decorations are half-off or less, plus you might pick up presents for the next birthday (or for one of their friend's party).


Bonus: General advice
How do you prepare the kid for a younger sibling?  Here's what you tell them over and over: Babies do two things: cry a lot and sleep.  Sure, babies do a lot more than that (for example, there's a lot of poop and feedings, but as far as they're concerned, that's it: crying and sleeping.  Many parents make the mistake of pointing out toddlers and say, "You're going to have a brother (or sister) soon!"  Wrong.  They will expect a playmate when, really, they're just going to have something that is alternately a 90 decible* malfunctioning fire alarm or, honestly, a slug.

*Yes, really.  A motorcycle is 85 dB.  A jet airplane is 95 dB.  A crying baby falls somewhere between the two.  See the advice about earplugs (above).

Bonus: Teaching

Stuff to teach (and roughly in what order):
Learning to read.  This is a long process.  Here are some steps along the way.
The way I introduced the ABCs.  First thing I did was to download a "hollow" font (i.e., not a solid one) so that 1) I could color it and 2) it wouldn't waste all my printer ink.  I printed out the whole alphabet (one letter per page) and colored in insides of each letter.  I used different colors, but there was a system to it.  For example, R was red, G was green, and so on.  Even L was yellow because that's a salient sound when you say the word "yellow."  I introduced one letter every day or two so that Stan didn't get them jumbled.  Once they were all up on the wall in the living room, the colors allowed us to play games like, "List all the blue letters."  From there we were able to move on to making the sounds of the letters using a similar approach and games to reinforce it.


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