On Difficult Ages.

By: Jen Shoop

Do you think that there are certain childhood ages that are categorically more difficult to parent than others? This is not to say that we can’t still enjoy and celebrate each age, or that we don’t still absolutely adore our children with reckless abandon through the more difficult phases, but — #realtalk. Is this the case?!

Over dinner a few weeks ago, friends of ours said: “They tell you to brace yourself for the terrible twos, but we weren’t prepared the difficulty of the threenager phase. Three was way more difficult for us than two.” This was the third or fourth set of parents who had shared the same observation on the twos versus the threes independently of one one another in recent memory.

I have to agree with this mounting and informal consensus. Three really rocked our world. It was full of big emotions, boundary-testing, what felt like endless reinforcement of the same set of rules, meltdowns, struggles to get through even highly routine steps in our daily regimen. I can’t tell you how many nights we spent troubleshooting as parents: “But what if we tried…?” and “Maybe she needs more one-on-one time…?” and “We just need to be consistent on…” I was frankly shell-shocked by the sassiness and the dawn of emotionally manipulative comments and the shocking volume of her feelings around needing a specific cup, or specific pajamas, or what have you. There was also the daunting reality of being physically outmatched: at two, my daughter could be lifted out of a dangerous situation; at three, my daughter could often out-run and out-wrangle me.

Then again. We were parenting a child through a pandemic; I feel as though she was still processing the addition of a new sibling (“he’s permanent?!”); she is our first and therefore this was our inaugural interaction with the threenager phase; and the period is also fresh in our memories, whereas, for example, newborn days feel like a distant blur (time does sand down the edges, doesn’t it?). Is it possible that when micro hits this age, we will be seasoned enough to “come ready” and feel less throttled by the Big Emotions of a three year old? Do some children lean into “the threes” more than others? Will gender play a role? Is two with micro going to be more difficult for us than three with him simply because he is who he is? (I already feel as though micro at two is far more physical, fearless, and adventurous than mini was at the same age, though…am I just forgetting? Or was it a little bit easier because there were two parents to one child versus now two on two, and we are therefore necessarily stretched thin this go around?) Does it all vary by child anyhow, regardless of how many you have or what’s going on with the world? (I say this with particular attentiveness because the OK-to-wake clock we bought for our daughter was a game-changer for us — but it does not work for every family. I was discussing this with a mom friend who had no luck with the clock, and I observed: “Well, you know, mini is something of a rule-follower — like me! I think it worked because of that. She tends to like things with discernible signals, logic, etc. I would have also probably reacted well to it as a child.”)

That is to say, there are so many dynamics, inputs, idiosyncrasies, and conditions to contend with that I feel hesitant to categorically say “three was more difficult than two.” However. It truly felt that way, at least with mini. Corroborating this perception: it seems as though mini turned four and a switch flipped. Gone are the protracted conversations and outbursts when leaving the playground, or a playdate, or any interesting activity. She can be reasoned with. She can be relied upon to uphold and even remind us of the rules (“no talking with your mouth full, mama!”). She is downright helpful with her brother, alerting us when he is getting into something he shouldn’t and a serving as a fountain of knowledge for new sitters (“he only drinks milk out of these cups”; “he needs to be wearing a bib”; etc.). She may push back or whine or pout when she does not get her way, but I cannot remember her last tantrum (!). What a relief just writing that! I know, of course, that four will have its own trials and tribulations. I worry, for example, about whether children will be more judgmental about her eye patch as she heads towards five, and I think a lot more about the children she pals around with. I have seen her bring home new phrases and awarenesses that give me pause. A whole new world to contend with. I am already anticipating feedback along the lines of “but Kennedy is allowed to do this!” Still, for anyone struggling through the threes, let me be your ray of hope for the day: parenting my four-year-old daughter feels about ten times easier than parenting her when she was three.

When my children were very young, my mother had a habit of reminding me that, with infants, it’s often two steps forward, one step back, especially with sleep and feeding patterns. I have never been able to pause this fast and inconsistent footwork, even well beyond the newborn phase: some days feel easy, and others feel impossible. We make strides in one area — let’s say, table etiquette — and then all of the sudden mini is licking butter off her noodles one by one, with her feet propped up against the table, the very picture of defiance. (!?!) I look at her blinkingly, and I wonder whether any of the three trillion and ten reminders and rejoinders I have issued around the subject of table manners have been all for naught? We move from a relatively calm week where micro tampers with nothing in the apartment to a weekend where he cannot keep his fingers from any electrical cord in the unit. Then it’s back to neutral. Then it’s climbing tables. Then back to neutral. We remain, it seems, smack dab in the middle of that two-step-one-step tango.

In other words, everything is, truly, a phase and there are sub-phases and recursions and regressions within phases to boot. Raising my children feels anything but linear. So I suppose it remains to be seen whether three will prove to be one of the most challenging ages we will face with mini. Perhaps we will encounter a new bumpy patch at four and a half, or seven will be tricky, and God help me come the teenage years. I know enough from watching my parents gray while raising five teenagers to know that it is not an easy road. Beyond that, I have a hunch that by the time my girl is in her 20s, I will have all but forgotten the travails of threenagerdom, remembering instead her willingness to hold my hand; her wonderment at space and bugs and tiny little toys; the way she shrieked with joy while running through the splash pads of New York City; her obsession with blue; the flick of her ponytails as she sprinted ahead of us down the city sidewalks of Manhattan.

Cheers to anyone who is sitting there gobsmacked by a new phase. Sometimes it helps to be reminded that “this, too, shall pass” (as noted earlier, I can state with confidence that four feels much easier than three so far!) and sometimes you want to know that other people’s children lick butter off their noodles and tamper with electrical outlets, too. In either case: tonight at five p.m., I’ll be toasting to you in solidarity.

In the meantime, curious to know what you think about the idea that certain phases are just trickier than others as a parent? What say you?


+More thoughts on parenting through challenging times.

+Practical thoughts on welcoming a second child.

+Do you think the transition from 0-1 children was more difficult than the transition from 1-2?

+9 things that surprised me about having a c-section.

+High and low: love both these $13 shades and these $400 ones.

+Lusting after this gorgeous dress.

+These lobster cover-up pants (under $100) are SO good. Sad I missed them in my size!

+More chic cover-ups here.

+Striking wedding guest dress option. (More here!)

+Just discovered that Minted has adorable personalized labels for school gear! (These ones for boys!)

+Have gotten a lot of wear out of these distressed pull-on jeans. They wear like sweatpants but look like denim!

+Have received a number of questions about Baptism/Christening gifts. I love these personalized crosses (also have ones with Biblical quotes on them for less, and I also love the slightly more whimsical styles from Tricia Lowenfeld); a simple white Bible; and this children’s Bible and book of prayers bundle, which I think I have given to about six babies at this point.

+A couple of gifts to give to godchildren as they grow older that have a religious theme:







+These popular $10 gingham swim trunks for boys are still available in nearly all sizes!

+My next Reformation acquisition.

+How great is this red-and-white striped maxi?!

+The price on this 49-piece set of cutlery is absolutely shocking…would be great for al fresco dining! Love the mint and pink colorways.

+I really want this entire look, head to toe: white trousers, white pleated top, raffia clutch. 100 100 100 100!

+More great woven bags for summer here.

+This bandana print one-piece…!

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18 thoughts on “On Difficult Ages.

  1. Oh yes, difficult ages. And the interesting thing is that it varies for everyone. Such a balance/combination of what age-related behaviors are most grating for the parent and what is just a challenging spot for the child. Some of my friends have loathed the 2s, while my sister is adamant that 4 is the hardest. I only realize a difficult phase once it’s over, because I think I just push to survive them and it’s definitely gotten easier as my son has gotten older. He’s 4 now, and I often think “now THIS is the best age.” I can see now that 2 was a whole year of challenges and 3 brought the constant barrage of questions and boundary pushing. 4 feels just right today, and when he turns 5, I bet I’ll like that too — but certainly I’ll remember 4 for something difficult I can’t quite see today while I’m living through it.

    1. Hi Jen – Such interesting points! I have the same suspicion around the proximity of “the threes” — will, in a few years, I look back and think “nah, that wasn’t particularly hard, it just stood out at the time because it was fresh in my mind”? Maybe, too, three (or two, for some people) feels difficult because it’s the first brush with a different kind of parenting? I mean, newborns/infants/babies require so much hands-on care and nurture, but it’s when my children started talking and testing boundaries, I felt as though I was graduating to a different sort of parenting. Maybe that’s also why three felt so challenging. I was learning to flex a new set of parenting muscles that involved repeated rule-setting, lots of conversations, boundary reinforcements, care with language, etc. It felt as though it was much more intellectually exhausting. But again, maybe it’s just that it feels so close in the rear view mirror.

      Anyway, thanks for the note and the reminders that a) the parenting experience is different for everyone and b) there are always going to be challenges and gifts at every age.


  2. My children are now 4.5 and 6 years old. Last night at the dinner table, I looked across at my partner as he mouthed “kids are annoying.” Our little ones are definitely moving out of the toddler phase and becoming kids. Bathroom humor (where do they learn this??!), fighting, and the occasional hurtful words to us and each other. And yet they still reach for my hand when we’re out, love to snuggle when we read books, and would love nothing more than for me to lay with them every night until they fall asleep. As we all prepare for them to head into the classroom in person this fall, my heart is full of excitement at all they will learn and the friends they will make, as well as dread for the mean comments they will likely endure at some point.

    I was speaking with a neighbor mom of teenagers recently that had just gotten their driver’s licenses. She told them that their health and safety were the most important things to her. I’ve tried to keep that in mind when daily annoyances creep in with my own children. Yes, I want them to be kind and polite (so very important), but most of all I want them to be safe and healthy, especially as they become more and more independent as they get older.

    1. Such good perspective, Erica, on all fronts. I totally understand your mixed emotions about being excited for and nervous about the upcoming year of in-person schooling, too. My parenting emotions can be so intense and contradictory!!


  3. My dad asked his grandmother this question and she responded without missing a bear, “the 60s have been incredibly difficult” which is such a great reminder that you are ALWAYS a parent no matter what stage of life your child is in…the ultimate privilege but not without its challenges

    1. What great perspective! Thanks for sharing. I was reminded of this recently when I decided not to share a little stressful detail related to our move with my parents — I thought, “Why stress them?” When everything was sorted out, I did mention the mix-up and my parents said: “Oh…I’m so glad you didn’t tell us. We would have been so anxious!” I was reminded that my parents are still my doting parents, even as I turn 37! They carry all of my worries and stresses, too, even now! xxx

  4. Omigosh 500% YES. Age three has been harder for us than two, for sure. The NO’s, the testing of limits, the big big BIG emotions… whew. It all makes sense though because I remember reading that at roughly 3 is when they go through “individuation” – in which they realize they are their own person, with their own wants separate from their parent, and want to exercise free will. Looking back, at age two she was still more of a relatively pleasant people-pleaser. I feel more exhausted — emotionally — at the end of the day with this age than two. I feel like I use all the tricks I know: age appropriate choices, preparation for changes/transitions, phrasing instructions in the affirmative, limiting “no” and “stop” to safety issues, (I ask myself, what’s the worst that could happen if I say yes to xyz request?) etc. and yet we still encounter so many challenges. The changes you’re describing at age 4 are giving me hope! I hope mine turns a corner around that time too.

    And yes to that entire outfit on Moda: white hot!!! Love the sculptural shape of that top. I’d love to renew my marriage vows in something like this for a milestone anniversary!

    1. For sure on ALL of these things. They all resonate! Parenting when mini was three felt…ineffectual? futile? at times. It was so disheartening! I remember tuning in to some of the Montessori programming about parenting at this age and it always sounds so simple (and calm) in theory. Fingers crossed you turn a similar corner at four. It really feels like night and day!

      Hang in there!


  5. I definitely agree that some phases are trickier than others. We are entering the adolescent years (pray for us!) and recently ran across this article, which I found so reassuring as we’re in the throes of major eye rolling and backtalk:

    Lots of food for thought there! I do think that the past year-plus has been uniquely challenging for all of us, children included — they’ve absorbed a lot of the fear and anxiety, and I think it is often expressed in different ways than in adults. Here’s hoping that as things continue to improve, kids (and all of us!) will be able to rebound from this most challenging time!


    1. So true, MK, on the point of everyone in the family absorbing and reacting to stress/anxiety in different ways. On a totally different tack, our dog (Tilly) gets super anxious any time she sees boxes or suitcases. She knows what’s happening and starts acting out! It’s always a reminder to me that “little rabbits have big ears.” Children and pets alike pick up on SO much!


  6. Has anyone out there found 12-15 months to be challenging?? My son went from being the happiest, smiliest, easiest baby (truly– the first year of his life was shockingly calm/straightforward/strife-free. My husband and I routinely looked at each other in wide-eyed wonder that newborn/infant life could be so breezy.) to a little boy with OPINIONS and an inclination towards frustration right around his first birthday. I feel like we are *maybe* inching our way out of it around 16 months as he’s now a bit more able to communicate with us, but the whole thing has me on edge because no one talks about that age as a tricky one. What are we in for with 2, 3, teenage years, etc??

    The motto that got me through some of the rough moments was “survive and advance, survive and advance, survive and advance.” Ha!

    Glad you’re through one tough phase with Mini and hope that Micro’s on the other side of this developmental leap soon too!

    1. Hi! Thank you so much for your vulnerability here! Solidarity! I remember a similarly challenging period around that time, when my son really started walking everywhere and getting into everything. I felt like my world was caving in. How was I ever going to get anything done?!

      Survive and advance, amen!


    2. Hi HH! That was certainly a tough time for me and my son, especially because he was very mobile and exploratory but not (in any way) stable so I felt I had to be within arm’s reach at all times, and when I tried to get him to independently play he would stand in his play pen and shriek! Ha!

      You’ve likely already done this, but sign language helped. Teaching him “more” and “all done” specifically made mealtime smoother. Then we added “help” to the mix which naturally he used for everything (especially “take me out of my play pen”) but was preferable to shrieks. (To be clear, he still shrieked, just less.)

      He also really loved musical toys he could turn on.

      I think in general that time can be tough because they’re kind of transitioning from baby to toddler — so, at least for my son, he was physically way too big for any baby stuff (like a bouncer or even a baby carrier for my back’s sake) but too small to do some go-to toddler things (like crayons or walking beside me on the sidewalk while holding my hand — we are still working on those two at 20 months).

      Hang in there and try not to project into the future too much. (Easier said than done.) Xo.

      1. Thanks for chiming in, Joyce! Always such practical and calming input from you! I love the note “try not to project into the future too much.” A good reminder for me, too. xx

    3. Thank you, Joyce and Jen!

      Joyce, your son sounds very similar to mine. “More” and “all done” have helped tremendously. I appreciate the encouragement and knowing that I’m not alone!

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