Raising self-sufficient kids

I suggest you start with a family meeting. Admit to your "mistakes." Say you want help, starting in small ways. Figure out good places to start together. Would they like to learn to cook? Help with the yard? Laundry and mending? Then work up. Regular family meetings is probably a good idea. An incentive of some kind is probably also a good idea. Maybe dessert or a small gift. Keep it positive. Lots of compliments. Celebrate successes. And don't rush.

Working together is often better. One person cuts up veggies while the other starts the noodles. One person sweeps the kitchen while another vacuums the living room. One person mows the lawn while another weeds the beds. Good luck!

I make chores a daily thing.  We have a big whiteboard calendar with everyone's schedule for the week.  The chores go on that whiteboard, along with appointments, practices,  meetings, etc.  I set up the schedule on Saturday for the upcoming week.  Depending on the chore, I'll ask them if they'd rather do it before school or after.  The chores are smaller than chores that I would take on myself.  Here are some examples:  scrub tub, vacuum stairs, sweep kitchen, sweep front porch, clean bathroom sink/mirror/toilet, clean microwave, mop kitchen, windex front door window.  They also do their own laundry.  I help them clean their room occasionally.  They do need reminders frequently and I will often leave them a note on the kitchen table if I'm at work that day.  

I'm in the same boat, and I've been working on this now that my 14 year old is stuck at home and I'm trying to work. Here are a few things that I've done.  At the beginning of the day, I do help him structure his day around the things that he needs to do, and am still doing substantial support for on-line schooling (he has learning disabilities and ADHD). However for the remainder of the day (the afternoon), he has a lot of down time and I'm working and really can't entertain him. I've been assigning him 1-2 self-help tasks per week that are new to him (and that he probably should have been doing for years).  For example, the first week of lock down, it was just making a sandwich for lunch.  I reminded him every day, but it was his job to make it--now that is a new habit and he does it without help or reminding. Next week, I had him take out the trash on trash night, then laundry. The first few weeks, it was with supervision and checking. Now he knows that it's his job and how to do it.  Same with laundry, etc... So more responsibility around the house, but gradually increasing and with support at first.  For entertaining himself, I let him know that I'm not available and that he needs to find something to do (but with screen time limits).  He sits on the couch doing nothing for some of that time, finds interesting projects for other times, and is entertaining himself.  I suggest things sometimes if I see or think of  something that he might like doing, but I'm not in charge of this time for him.  Limiting the screen time during these hours was important for our household--otherwise that would be the default.  But being bored has led to some good thinking time for him. I think it was important not to do this cold-turkey, so I did more structuring the first few weeks, but gradually relaxed my support.  Overall I think it's been helpful and good for both of us.  

I have 3 kids (22, 19, 14) who are reasonably cooperative and very independent/self-sufficient. For years I felt guilty that I didn't play with them enough! Recently I realized maybe I should stop feeling guilty, as they have turned out to be pretty great kids. The things I did that I think helped were:

assigned age-based chores (that were not compensated by allowance): mowing the lawn, setting the table, taking out trash etc. 

Starting in middle school they did their own laundry.

starting in high school, gave them yearly allowance, that I paid out in 6-month increments, that they used to pay for all their discretionary spending plus clothing (I bought all sports-related equipment and clothing plus jackets/fleeces/shoes). This taught them to budget and be smart shoppers, and stopped them begging for stuff. I let them spend it however they decided. 

Let them choose their classes/activities/sports. Was always supportive & encouraging. 

Had high expectations for behavior and academics, but never pushed, and expected (and witnessed!) lots of mistakes & learning from their mistakes as they went.

Lots of talking/tried to be as non-judgemental as possible.

I don't think it is too late for your 14 yo. I agree it will be harder than with a younger child, and you might get more resistance but I encourage you it's not too late and stick to your guns! I would talk to your child honestly about your thoughts and observations about the certain things you wish you had done differently with your older kids, and then give them a shortlist of your new expectations/rules. 

I don't think it is too late for you to start with your kids. Now, with everyone home all the time, is an especially good time to make changes. Call a family meeting and explain that you think they are ready for more responsibility. Many kids really care that things are fair, so also frame this as a fairness issue. Together, come up with a list of things around the house and let people volunteer for regular tasks. If they don't volunteer, put the tasks in a hat and have everyone draw tasks. You'll need to teach them how to do things - clean a bathroom, sort laundry - but do so and then expect them to do it. I wouldn't nag, and I wouldn't make allowance dependent on tasks either - you don't get paid for housework. Perhaps there could be a weekly family activity - movie night, baking cookies, frisbee golf in the back yard, etc. - and participation is dependent on getting tasks done. I think this can reinforce that all members of the family have to pitch in, and you all get to play together, too. (Do make sure the rules apply to adults, too!) And some tasks can be fun. Perhaps one of your children will discover a love of cooking; I remember that I liked sweeping as a kid because the cat liked to chase the broom.

Let them know, gently, that there are things for which you won't be responsible anymore. For example, if the person who finished the corn chips doesn't put them on the grocery list, there won't be corn chips on the next grocery run - even if they text you while you're at the store. If it is something they like having around (and you normally get for them anyway), give them the job of making sure it is available. If they've misplaced something, don't stop what you're doing to help them find it. And if they lose necessary items (keys, phones, jackets) make sure they understand that they will have to pay to replace them. You might front the money so they have a jacket, but they will have to repay you for that.

If they are relying on you to relieve boredom, you can tell them that you aren't available right then, but in half an hour you can do something with - not for - them. Or, invite them to help you with whatever you're doing, like weeding or sorting laundry. Or suggest they do something you haven't gotten to yet, like cleaning out the fridge. No? Then they will just have to entertain themself.

Losing their "servant" will be hard, and they will doubtless be angry at first, and tell you you're being mean. Roll with it.They will get over it. 

Admittedly, we started off parenting this way, as I shared your parents' reaction to you trying to be playmate, entertainer, and adult. Some other parents were dismayed that we didn't try to be everything for our kid, and doubtless thought we were bad parents. But the benefits were great for all of us, I think. Our kid never expected us to chauffeur them, and when we did play with them it was more fun and less of an obligation.We didn't  ignore our kid; we read together, went for walks, played cards, and conversed lots and lots. We often did homework side-by-side, we baked together and did other skill-building activities together as part of daily life. We expected them to be as self-sufficient as was age-appropriate; they learned to be responsible and were proud of the trust we placed in them. Try it - they will rise to your hopes and expectations!

-SF Mom 

I don't have much to say about turning around 14-year-olds--except teach them how to do their own laundry properly, if they don't already know--but I do want to express my agreement. Although my own family was dysfunctional in a number of ways (alcoholism, plus a raging narcissist of an eldest sibling), it was expected that I could usually figure out how to entertain myself, do my own homework, etc. Because I was good at such activities, they helped me feel competent, and I think that sense of competence is what leads to so-called self-esteem, not just constant repetition of "Good job, buddy!" for the simplest act.

Now I find myself watching the parents of young kids and wondering whether they're not more committed to being kindly friends with their children than to exercising a certain authority. My closest friends are my peers, not my daughter, much as I love her. (Perhaps one factor is the suspicion of authority so many of us felt during the '60s and '70s? But here's a real difference between being authoritarian and being authoritative.)

I think of it this way: my now-adult daughter's favorite teachers were the ones who were strict and consistent and loved their subjects. You listened to them or else, but they sometimes listened to you as well (when it was your turn!), and they knew when to be gentle. They were authoritative grown-ups, teaching children how to be competent.

P.S. Do your kids have regular chores that make them feel like useful members of the household? Meal planning, meal prep, cooking, gardening, recycling, that sort of thing? The planning part (during meal time?) is sometimes what gets them interested: think about meals, talk about the garden; how to make them better, healthier, more beautiful, more environmentally sound, etc. Let them do the research and make some decisions. Children usually enjoy planning and making decisions, like toddlers who love making objects move.

It looks like you haven't gotten any responses yet, but maybe they just haven't been posted. There is no one right way to raise kids. Hopefully you did it the way you wanted to and enjoyed. And hopefully you have good relationships with them. It's never too late to change behaviors. It can be hard, but at 14 they are old enough to understand that they are not a child anymore and they need to do more for themselves. For me, the main thing is respect. Do they demand things from you instead of asking politely? Do they shout from another room and expect you to go to them? These are the first things I would put a stop to. Learning how to do chores and take care of themselves more is something they can definitely do. 

Here's my different perspective. My self-sufficient daughter is just finished her junior year at college.  At her apartment, she cleans and cooks healthy meals for herself.  She keeps to her budget.  In college, she is on track to graduate magna cum laude, is on a sports team, and helps run two clubs.  I never made her do chores around the house.  Why?  Because I felt the other things in her daily schedule were more important, including sleep.  Here's a typical day of high school:

6:30  Wake, dress, breakfast, gather school things
7:00  Leave for school
3:45 home from school, snack. an hour of homework
5:00 Sports practice
7:30 Dinner
8-10:30 Homework
10:30-11 Shower, get ready for bed
This kind of time allocation was typical for a student trying to get into a selective college. She could have spent an hour cleaning a bathroom or preparing dinner on a regular basis, but which hour?  Things are different during a pandemic, and maybe as a society, we won't go back to the grueling routine necessary for a high school student to get into a UC, but I don't regret not assigning chores.

I have thought about this for several weeks since you posted the question.  I think you can hit reset, especially if you do with humor and a message that with additional freedom comes additional responsibility.

Like you, other than insisting my kids clear their plates after dinner from an early age, I didn't involve them in the business of running the house when they were young; I did that on the side, after work, after entertaining them.  My husband too.  A mistake, not doubt, but not terminal.  

I had an "aha" moment when one son, then 12 or 13, was eating at the counter and asked me "can you get me some water?"  He was literally two steps from the cabinet with glasses, another step or two from the sink.  I was across the room.  WTF?  I said to him (not nastily, but with humor) "you really need servant girl to get you water?  You have legs."  It became a joke -- so much so that I found a servant bell in a bric-a-brac store and gave it to him as a gift.  (It still lives on the counter, and he gleefully rings it when he visits.)  But he started getting his own water.  In middle school, the chauffeur service ended.  One son went to school a couple of miles away; he rode his bike.  The other was in school through the tunnel.   We expected him to take BART and either walk home from BART (a couple of miles) or cool his heels at the library or Peet's until we could get him after work.  It took several dry runs walking from his middle school to the 19th Street BART station, and taking the train to Orinda.  But he gained the confidence and then did it himself every day  The kids started taking out the garbage and bringing the cans down and back up the hill on trash pickup day.  Not without protest and reminding, but they did it.  They could make whatever they wanted in the kitchen, but had to clean up so there was no evidence of their culinary activities. Again, we sometimes had different standards for what constituted cleaning up.  But they mostly did it. There were a lot of these lessons.  We parents had a mantra:  "The role of parent is one of planned obsolescence.  If we are not obsolete by the time you are 18, we haven't done our jobs.  Not that we won't be there as support -- we will.  But you shouldn't need us for the mechanics of life."  When they were teens, we reeled out both freedom and responsibility -- as much of each as they could handle.  My husband also started talking to them about finances -- money management, markets and compounding, consumer debt.   They sometimes balked, and I was human scourge for my older son's high school years.  But eventually, the lessons took.  My kids are now 28 and 24, and are fully independent -- self-supporting, managing their own households (one solo, one with roommmates) and affairs.  Both cook, keep reasonably tidy kitchens, pay their bills on time, even occasionally vacuum.  :)   And my older son likes me.

So courage, my friend.  Kids are smart and resilient.  They can accept change, especially if it is done with love and humor instead of anger, and is a reflection of (and quid pro quo for) their increasing ability to manage their own affairs.