“I’m worried that my child just isn’t feeling confident.”
When parents share this confidence-related concern with me, it’s not without a whole lot of frustration, fear, and urgency. This is how we all start the micromanagement game where we try one college on for size, then another, convincing ourselves that the more we guide, support, and monitor our kids, the closer we will get to that holy grail college. It always makes me feel a little sad that when application season begins, parents can’t help but to try to solve all of our children’s problems for them.
We do the classic helicopter-parenting thing: hovering, reminding, and encouraging. We create spreadsheets for them, and schedule all the upcoming deadlines; we interview tutors and consultants. We start getting them to start thinking about the essay, floating ideas we think our kids should consider, then check in every so often on whether they’ve started writing that draft we outlined for them. What gets lost in all of it is this: confidence doesn’t just find its way into our kids; it’s earned, by doing things that seem hard initially, without us or our help, and doing it again and again until they realize they can do it on their own.
The hardest part of parenting for me (that also seeps into my work life) is resisting the temptation to help my kids too much. At work and at home, I won’t tell my students what to write, reorganize their paragraphs, hand them an outline, or solve a problem for them before they’ve had a chance to sit with it. Parents hire people like me for the same reason: watching your kid struggle feels miserable, and most of us have spent our parenting years sparing them from confronting difficulty. It’s uncomfortable, and genuinely painful, watching your kid stare at a blank screen and sit with their own frustration. But as counterintuitive as it feels, I have to say that I believe standing back and letting them confront difficulty may be the hardest work of parenting, but it’s also the only way that kids start earning their own confidence.
When Henry and I went on college visits together this spring, I made a point of standing back, literally letting him walk towards the front of the tour group. I didn’t ask questions like I normally do. I didn’t share what I noticed or point things out to him. I let him take it in on his own and share when something caught his attention: a specific major, a building, a question he wanted to ask the tour guide. For someone like me, who talks to everyone I meet and asks a lot of questions, it made me feel passive but it was the support my kid needed.
Confidence isn’t something we can just give our kids, it builds slowly, through action, trial, error, practice, and repetition. You don’t start believing in yourself just because someone believes in you. You start believing in yourself because you’ve faced something hard enough times that you start to gather the proof for yourself that you can do hard things. It happens the same way it happens when you fall off a horse. After you fall off, you get right back on, and stay on. You grapple with something, walk away from it, return to it and try again from a different angle until you finally get it. What accumulates from that proof that you can do something, is capability and that’s what confidence is built on. It isn’t a mindset so much as the result of a track record of success.
I’ve always hated the “fake it till you make it” mantra so many of my generation and the generation before me swore by; pretending isn’t practice. Confidence comes from doing something hard, badly at first, then less badly, until finally you’re doing it well enough top trust that you’re pretty good at it. Eventually you’ll feel comfortable knowing you’re achieving things you never thought you were capable of.
I’ve watched this play out with so many of my students. Kids struggle to write their own stories because writing one honestly requires space and the courage to sit with the uncomfortable stuff we’ve experienced in our lives. You have to stumble through the drafts you hate, conversations that initially don’t go anywhere helpful, real time spent with hard questions about who you are and why you’re here. Most adults don’t have tidy answers to those questions, let alone seventeen or eighteen year olds. These questions take time and deep reflection and it’s best done before the busy senior year fall semester.
I feel like I’ve shared what parents should avoid doing without actually giving some insights into what maybe we all should do more of on a regular basis. We don’t have to manage our kids but we can talk to them, we can be curious about what’s on their minds, what they’re grappling with. We can become sounding boards and safe spaces to help them process some of these big life questions. Talk to your kid. Tell them what matters to you, and listen when they tell you what matters to them.
You can also be helpful by sharing the load on the grunt work of the application, helping them with parts that have nothing to do with the writing itself. Sit with them while they fill out their Common App, so it feels a little less overwhelming or lonely. Help them format their resume. Capture deadlines on an application calendar, and help them populate spreadsheets that contain each school’s admissions criteria, relevant majors, acceptance rates, median test scores, and clubs. Help them as they organize every school’s supplemental prompts into one shared doc, sorted by deadline and word count. Dig into a school’s curriculum or research a specific program with them and talk through what you find. None of that requires writing a word of the essay or deciding what they should say about themselves. It just means showing up for the logistics and leaving the hard work to them.
My best advice, as a counselor and a parent both: resist solving their problems before they’ve had a real chance to sit with them. Every struggle you clear out of their path is one less thing they get to discover they are capable of doing themselves. This doesn’t change when our kids get older, long after college applications have been submitted, into job searches and summer courses and the first failed test in a class that was harder than they expected. As a mom, I’ve never asked whether they needed extra support; instead, I’ve waited for them to ask me. Mostly, I’ve encouraged my kids to see their teachers on their own, to work through it alongside classmates, and get to the bottom of it themselves.
My daughter went through her own version of this a few years ago, during the early decision stretch of her own process. After several early action responses and a deferral from Dartmouth, her first-choice and ED school, she had to decide whether to stick with the application plan and strategy we’d mapped out together or scrap it and “play the field”. Although it wasn’t the plan I would have chosen for her, she scrapped it, and while her outcome was different from what she’d expected, she landed exactly where she was supposed to. She hasn’t looked back since she enrolled that fall of her freshman year.
The strongest applicants were rarely confident from the get-go. They were the ones who felt stuck, and even stayed feeling that way for a while. They worked their way out of the stickiness, whether that meant by successfully completing an essay, a hard conversation, a revision, or weeks of a brainstorm that went nowhere before it suddenly crystallized into a brilliant personal statement.
So here’s the challenge I propose we rise to, as parents, educators, and advocates: ditch “fake it ‘til you make it.” Instead, work on helping them create the conditions to earn their own confidence. Handing them the keys without teaching them how to use them does nothing, but when a student believes in himself because he’s expended his own blood, sweat, and tears, they stop questioning whether they can be successful and realize they already are. They’ve learned that confidence is derived by trying, succeeding, and doing it again until the very practice of it feels like second nature. That’s when they have the confidence and knowledge that they are capable of doing anything, as long as they show up and do the work.
Action creates evidence which builds the kind of confidence our kids deserve to feel. Letting them struggle a little on the way is genuinely hard to watch, but you’ll be glad you did it the day they walk across that stage for that high school diploma, ready to confidently face whatever comes next.
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