Supporting your structure-and-planning-resistant kid while honoring their autonomy and values
Estimated read time: 15 mins
"My free-spirited kid is very resistant to planning things out, doing any more than the bare minimum, or even attending class regularly because it goes against her life philosophy (she doesn't like structure and wants to live in the moment). She values being out and about in the community, experiencing life as it comes. In fact, she wants to graduate early so she can travel the world and live a more spontaneous life - but she’s in for a rude awakening if she doesn’t put in the work at school. There's a disconnect between her dreams and her actions, and I don’t want to have to clean up the mess when she crashes and burns. How can I help?" - Anon
Hey anon. Your kid’s values and dreams aren’t wrong, and you also aren’t wrong for feeling scared for her future – it’s hard to live a free-spirited lifestyle while dealing with the realities of late-stage capitalism, climate collapse, a pandemic that won’t quit, and folks in power who are doing their darndest to make life a living hell for the majority of us.
Earning good grades and a diploma, cultivating marketable skills, and securing a well-paying job can feel like necessary life rafts to cling onto as we try to navigate the turbulent waters of new adulthood. Money means stability. Stability makes things easier. Putting energy into doing well at school feels like a reasonable path to earning enough money to live a life of relatively minimized suffering.
When we see our kids struggling to engage with school, or straight up not caring about it, it can feel scary. We don’t want them to suffer as adults. Many of us are operating from a perspective of scarcity and trauma – we’ve seen how bad it can get. We carry lived experience of immigration, financial hardship, systemic inequity, or other factors that have shown us plainly – to survive, it’s necessary to follow a certain path.
I first want to say: your perspective and experience matter. Your fears matter.
And, there are many things that could be happening here, some of which may be hard truths to accept:
Your kid may not value the allure of stability as much as you do, at this current stage in her life, or ever.
She may have a greater tolerance for risk.
She may not fully comprehend the consequences of her choices. I say this neutrally, not with judgment. She literally may not realize the barriers and challenges involved in making certain choices over others.
She may have thought a lot about those consequences, and chosen to pursue her own path anyway.
She may not see engagement with school as the path to the life she wants, or the only path.
The life she wants may be different than the kind of life you value.
It makes a lot of sense that your kid doesn't see the value in the things you mentioned (planning things out, attending class), given that rigidity conflicts with how she wants to spend her time. It can be hard to help our kids find a happy balance between working toward their long-term goals (e.g. a spontaneous life of fun and travel) and their short-term wants (e.g. the freedom to hang out with friends on short notice).
While you are her caregiver and loving supporter, ultimately, this is your kid’s life. There are many ways to live a good and valuable life; people have been doing so since the beginning of time. Life involves some compromise, drudgery, and delayed gratification, but there’s also a lot of wiggle room around how she does life while also attending to the Really Important Responsibilities. People have also been messing up and making mistakes since the beginning of time; if your kid regrets her choices at some point, it won’t be the end of the world. She can lean on her inner strengths, her community, and all of the coping-and-problem-solving skills she’s learned from you and other folks in her life.
There is a lot of peace that comes with relinquishing the idea that we have control over another human being.
That said – relinquishing the idea that we can control our kids’ futures doesn’t mean not having boundaries with them, or that we shouldn’t talk to them about their options. You mentioned not wanting to have to “clean up her mess” if her choices end up not working out. That’s a valid concern, and with it comes another possibly hard-to-stomach truth:
Our role as caregivers, parents, and trusted adults does not require us to clean up our kids’ messes for them.
We can support them, teach them to problem-solve, problem-solve with them, and cheer them on with unconditional love. But we do not have to jump in and save the day. In fact, doing so can be detrimental to our kids’ growth and ability to build self-trust. Allowing them to struggle while also providing a listening ear and a soft place to land will help them a lot more in the long run rather than taking responsibility for their life paths.
A bonus of adopting this approach is that we get to model clear boundaries to our kids, which benefits both of us.
Here are some suggestions for things to ask when having a conversation with your kid about her choices:
What things do you value and how do those things shape your choices?
How do you see your current actions aligning with your long-term goals?
What potential risks and benefits do you see in your current approach to school, short-term and long-term?
Have you thought about what you might do if things don’t go as planned? What’s your backup plan? Would you like help creating one?
Who are the people and resources you can turn to for support when you face challenges?
What small steps can you take now to prepare for your future goals without compromising your current values?
What skills do you think will help you achieve your dreams? How can you start developing these skills while still in school?
What kind of support would you like from me?
Take these conversations slow. Approach from a place of curiosity and non-judgment.
And, consider when it makes sense to communicate boundaries with your kid around their actions:
Ask yourself: Are your kid’s choices putting her life or well-being in danger? Are they putting other people at risk? If so, this could indicate a place to set a boundary. Here’s an example:
You: "I'm really worried when you skip school and I don’t know where you are. It’s important for your safety and my peace of mind."
Kid: "I just need a break sometimes, but I don’t want to ask for permission because I’m afraid you’ll say no."
You: "I understand needing a break, and I’m open to you taking mental health days. But we need a system in place. From now on, if you feel like you need a day off, I want you to tell me in advance. You can ‘call in sick’ and I will support you in taking that day off. But it’s important that you let me know exactly where you’ll be so I know you’re safe."
Kid: "What if I just don’t want to go to school last minute?"
You: "If it’s a last-minute decision, you need to call or text me before school starts. We can agree on a place where you’ll spend the day, whether it’s at home or another safe location we both know about."
You: “If you don’t communicate with me, I’m going to take steps to ensure your safety, which might include calling your school or reaching out to (emergency contacts).”
You: “Because I’m your caregiver, I’m responsible for your well-being. If you continue skipping school without communicating with me where you’ll be, I will start driving you to school in the mornings, rather than letting you walk with your friends, so that I know you’re at a safe place.”
If a negative consequence happens (e.g. a failed class), what do you (as the adult) have capacity to step in and help with? Communicate what you will do and what you won’t do, so there are clear expectations. For example, you might say:
“If you fail a class, I will always be here to listen and offer emotional support. We can talk about how you're feeling and what you want to do next."
"I can help you come up with a plan to retake the class or find alternative ways to earn the credit you need."
"I will help you find resources, like tutoring or study groups that can help you raise your grade.”
"However, I won't do your work for you.
“I can cover the cost of retaking a class once, but if it becomes a recurring issue, we’ll need to have a discussion about how to handle additional expenses."
Now, I want to share some validation and insight around what your kid may be experiencing, and how to support her during and after those hard conversations:
First, let's get some perspective:
You and your kid may come to the conclusion that she wants more balance; maybe there are skills or practices she can cultivate now to prepare her for her future goals without compromising her current values.
That said, your kid is not the kind of person who can be tricked into changing her ways ala the "covering the gross broccoli in tasty cheese" method. Nor do we want to coerce or manipulate our kids into changing. She may have some pretty deep neural pathways developed around her (valid) disdain for the systems and tools that have been pushed on her, as well as the narrative she has built around her identity as a free-spirited person. That means it will take lots of practice and trust to build new pathways if she hopes to see these tools as more of a neutral option.
She needs someone to validate that what she's experiencing is true (e.g. planners don't work for her; many of her school assignments are boring busywork) and also to help her find a way through the difficult stuff so she can reach the goals *she* cares about.
We don't always know the full story of what our kids are going through. Many kids have had negative school experiences, have tension with the adults in their lives around academics that leads them to dig their heels in harder, or simply value other things. Regardless of her reasons for feeling this way, part of our role is to work with our kids where they're at.
So, what are some good next steps?
Don't push solutions on her, and lean into the relationship you’ve built. She may agree that some planning is useful but have a negative association with planning tools because they haven't been used to further her own goals but rather the goals of someone else -- her adults at home, teachers, etc.
Give it some time; make sure she feels safe with you and knows that you are there as an ally in helping her feel less overwhelmed, more equipped to handle school, and more prepared to start her adult life on her own terms -- not to force her to conform to the mold of a perfectly organized person.
Sometimes we are able to develop a different relationship with a subject, tool, or class we hate through reframing, mindfulness, adding personal motivators like novelty and creativity, accountability, and community support (i.e. you, friends, family, classmates) -- and sometimes not.
It can be hard to build trust in just a few conversations, especially if you or other adults in her life have tended to push back against what she finds important (freedom, doing things her way, not using systems, keeping things flexible).
Try honing in on the things she says she wants for her future (and present). Talk about what barriers she's facing and how those barriers make her feel (e.g. stressed, pressured, unheard, undervalued). Ask her what her goals are and how she thinks she can achieve them. Find out what motivates her.
Then, you can brainstorm together how she might begin to address those things, and what tools she might use.
Example:
Goal: be able to connect authentically and spontaneously connect with different kinds of people during her post-high-school travels
Step: increase her fluency in Spanish
Why: be able to make meaningful friendships in Spanish-speaking countries, order food from restaurants, get a job more easily to fund her travels, and generally be more independent during her travels
Make it her own: attend and participate in Spanish class more, but also take it a step further by not limiting herself to just passively attending class; make a plan to engage with her community weekly in some way where she is speaking Spanish (e.g. attending a dance class in a Spanish-speaking neighborhood, ordering food in Spanish, or cooking a recipe with her friend's Spanish-speaking parent)
Why this works: she has agency to choose how she spends her time (with the structure being that it's something in service of her bigger goal); she's able to connect with friends and community (things she values); grades don't factor in at all as a motivator, but better grades may be a natural consequence
Example 2:
Goal: communicate more clearly and more often with teachers about challenges
- Why: get her parents and teachers off her back about missing assignments, less stress, build better relationships with adults in her life, feel more independent by communicating directly and proactively with adultsStep: each week, while hanging out with her accountability partner at their favorite park, she will check her school portal on her phone to see if there's anything that needs addressing and reach out to teachers if so (Side note: this is easier said than done. Paid subscribers get access to my favorite resources for effective email communication as well as my favorite resources for actually following through on a multi-step, possibly activating, possibly challenging task like this.)
Make it her own: she can use this as practice for directly and confidently self-advocating for her needs and wants (an extension, an accountability partner, an alternate assignment) and learning the nuances of persuasive communication -- something that benefits her in life, not just school
Why this works: by choosing a friend as an accountability partner who also wants support with their own stuff, it's mutually beneficial -- your kid and her friend help each other stick to their goals. Building this habit into existing hang-out time means she's not sacrificing friend time; the email check in routine feels more "natural" because it's happening as part of a bigger picture of mutual support and community time
This sort of collaborative brainstorming is important to encourage her to take ownership of her education and time rather than tell her what to do, so she can be empowered to make decisions in alignment with her goals.
Okay. So. You and your kid have talked. She’s relatively on board. She wants more balance in her life and wants to take some next steps. Here are some concrete strategies to help her pass her classes without giving up her sense of agency, freedom, and spontaneity:
1. Passing her classes requires some engagement with annoying systems, but there's room to engage in her own way. To set the vibe for your exploration into this goal, you can browse through the Functioning resources doc (available to paid subscribers) together, which has links to a lot of (neurodivergent, anti-capitalist) content creators who push back against productivity norms and structures that cater to neurotypical ways of doing things. Find some people who resonate with her, share her values, and are thriving. Get ideas from them.
Here are a couple to start with:
Dr. Devon Price (white trans Autistic author of Laziness Does Not Exist (written to be accessible to neurodivergent people, available for free on Hoopla/Libby)
Tricia Hersey / The Nap Ministry (Black artist, theologian, and community organizer who promotes the radical power of rest as resistance against capitalism and white supremacy)
Divergent Design Studios (neurodivergent, white, queer, disabled person who educates on ADHD and other neurodivergence esp. from perspective of shame)
Getting started is the hardest part: a visual graphic e-book from Marta Rose of DD Studios
Understanding neurodivergent Spiral Time and how it liberates
2. Help her find some systems that allow her to reduce her cognitive load (the mental post-it note, her working memory) while also keeping things loose and flexible:
"Rhythms instead of schedules" visual aide and more details on how to use it
Rather than making super strict planned-out schedules, have her make a big brain-dump of everything on her plate, then turn that into a checklist of things she can choose from
Resources like Habitica, Asana, MindMeister, Jamboard, and Remember the Milk can be good tools for this, or she can use her Notes app, a piece of paper, a vision board, colorful post-it notes on her wall, or a blank page in a notebook that she picked out for herself. Whatever feels less icky.
Help her decide how she'll use this list.
Maybe she wants to prioritize one big task, and then choose 2 more small things each day
Maybe she wants to sort her list into categories (school, chores, hobbies, self care) and pick one thing from each category each day
Maybe she wants to decide what she'll do depending on how much energy she has or what mood she's in
Here, Caroline Hardin gives some examples of menus for "high" vs. "low" energy days, "BS" days, priorities with consequences, self care, visible affirmations, etc. And here's another 1-minute clip explaining how to choose what goes on the menus.
Download Caroline's menus for free (or pay-what-you-can) here
Prioritize completing assignments that feel "useful" to her rather than doing all of the busywork; making a point to try to find something new she can glean from each assignment
Find ways to make assignments less tedious/faster
e.g. use the wealth of tech tools at her disposal, like speech-to-text, or dictating to a supportive friend or family member while they type out her thoughts for her
collaborate with classmates to divide tasks, share resources, and brainstorm ideas
use automation tools for repetitive tasks
estimate how much time and effort it will take her to complete assignments vs. what she'll gain from doing them. Prioritize strategically and be intentional about what she'll do vs. drop.
Have her communicate with her teachers about alternative assignment options where she is able to engage her interests, feel challenged, and try new things rather than complete the same task or worksheet
For Big Stuff That Matters, ask herself "How can I introduce more novelty, more challenge, and more of my personal motivators into the task at hand?"
Final thoughts:
There are a lot of adults who don't work a traditional 9-to-5, don’t use traditional calendars and planners, and sacrifice some stability in order to live a more carefree life. Plenty of people do that and manage fine -- but yes, sometimes not having a planning system or understanding how to organize your life or manage your responsibilities can lead to unpleasant consequences when things inevitably get forgotten or overdue -- missed opportunities, bills and late fees, strained relationships, etc. There can be a happy medium.
Make sure every system you try out is in service of your kid’s values and the life she wants to live post-high school (traveling requires some planning to be safe and have fun; funding her travels requires having and keeping jobs), and see if the ideas from these systems can come from either herself or vetted by other people who aren't her caregivers or teachers.
As you continue to strengthen your relationship, you may be able to get to the core of why certain tools and structures have a negative association for your kid. Often, there are deeper things happening -- shame, overwhelm, fear. Our job isn't to fix those things but to acknowledge that they're there, and be mindful of how they influence our kid. Ultimately, it's up to her to figure out what kind of relationship she wants to build with school so she can have balance in her life and reach the goals that matter to her.