When I was about 12, my parents sat me down and informed me in no uncertain terms that when I hit 18, I had three choices:
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Go to college (which I was expected to organize payment for through my efforts, they would “help if they could”, but considerable discussion about scholarships and loans was also had). This was my parents’ strongly preferred option.
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Join the armed service of my choice.
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Begin paying $500 per month rent beginning June 1, 1993 (the first month following my expected high school graduation date). Failure to pay this rent would result in the locks being changed and me being officially on my own, ready or not.
This was the initial conversation. From that point forward, my parents incorporated the notion that one day I would be handling things on my own without guidance from them in every possible way they could. Protest about chores? “You’ll have to do this for yourself soon enough - might as well learn now.” Broke and wanted a CD or a treat or new book? “How are you planning to pay for that? Someday you’ll have to pay all your own bills.”
Conversations about what I intended to do with myself once I turned 18 started happening - whether or not I wanted them to - routinely and frequently. It’s pretty clear in retrospect that my parents were as much trying to help me figure out what I wanted to do as they were helping me plan how to accomplish it.
I know for a fact that my brother had a functionally identical conversation with them when he was about 12 - I was there. Feeling slightly smug because I - like a dipshit - thought that this meant their attention on future planning would now be split and I would hear less about it. God, was I wrong about that. The older I got, the larger a portion of my interaction with my parents turned into a discussion of how I intended to manage my future. (It turns out this topic of conversation was basically a bell curve, peaking about the time I graduated from high school.) It was the same deal with my brother.
Me? I selected Option 1 with a quickness, busted my ass in high school to earn scholarship dollars and build savings, and ultimately had about 80% of my undergraduate college education planned and payment arranged (mostly scholarship money) by Christmas break in my senior year.
My brother attempted to select “none of the above” through the strategy of avoiding the conversation as much as possible and being as vague as possible when my parents cornered him. As a result, on June 1, 1994 (the first day of the month after his high school graduation), having still not made a call on his future plans, my mom woke him up at 7:00 in the morning and said “Okay, I’ll take that 500 bucks now. If I don’t have it in my hand by June 5, we’re changing the locks. I already called the locksmith and made an appointment.” I remain certain she’d have done it. She wouldn’t have been happy about it, but my brother needed a pretty firm kick to get him launched out of the nest and she was well-aware of that.
He did, in fact, panic like a mofo. My mother, however, had already anticipated both his attempt to be a lazy bastard about this, and calculated his probable ultimate decision, and she and the guidance counselor at our high school had some last minute options available for him when he called the counselor in a freaking panic on June 4. He ended up in a tiny random community college (who accepted him as a late admission) and racked up more student debt than he otherwise might have, but he also ultimately went with Option 1. He admits these days that if my mom hadn’t taken that tactic with him, it is entirely possible he would still be living in their basement working part-time at the hardware store for beer money to this very day.
At no point with either of us did my parents ever let up on the theme of “you’ll have to do this on your own at some point” from the date of the initial conversation until the day we actually left home for college. Which is a fact that I remain deeply grateful for - and my gratefulness dates from my first week of college, when I realized that I already had basically a full suite of tools available to be a freaking adult and a goodly number of my classmates had no such thing. By the time we graduated from high school, my parents had carefully made sure that we had a baseline level of knowledge to function as adults (basic budgeting and accounting, basic cooking, cleaning, mending, at least some work experience, basic child care, basic appliance maintenance, scheduling, etc.) and at least some practical experience to go with it.