Transitioning from making a living to making a life...without stripping your gears?

Maybe the lines were more clearly drawn when our grandparents were living their timeline. They went to school. Then they went to work.  Maybe they changed jobs once. Then they gave their all to their chosen profession for a certain number of years, after which someone made a nice speech, cut some cake, gave them a watch, smacked them on the butt & declared them 'retirees.'  At which point they had paid off their mortgages & launched into their 'golden years' with enough saved to travel a bit, fill a couple of albums with pics of those trips & their grand kids.  Then they died, & had also saved enough to pay for their final funereal wishes, & leave a little or a lot to their progeny. The end. 

Our story arcs are no longer that clear cut or linear (if an arc can be linear?).  School can overlap work. Some of us will die never having chosen a major. We careen through careers, changing direction like socks, location like nomads, & focus like a room full of caffeinated preschoolers. Some of us choose to forego having kids. Some of us simply run out of biological time. We upsize, downsize, live in McMansions or tiny houses no bigger than an Airstream. We travel for work, telecommute, staycation, turn our hobbies into careers & our careers into contract work, then we blog about all that. 

(My workspace--representing working from home & completion of a hairbrained, put off project that finally came to fruition & worked better than anticipated--the big blue porch table)

The lines between work & leisure are so blurred they are virtually nonexistent, & we live so long & mistrust Social Security & our investments so much that a lot of us jam our fingers in our ears & babble 'LALALALALALALALALALALALA, I CAN'T HEAR YOU LALALALALA' when anyone dares utter 'retirement' in our presence. 

At this point, I think the most any of us dare hope is for a shifting (at some point, or gradually) of the emphasis from making a living to making a life. To that end, & despite appearances of seemingly random scrambling, I think I must have always had an 'unplan' churning away in the back of my head, kind of like an unsung background program while I focused on a more pressing foreground ap. 

I have a lot in common with Henny Penny, chiefly that my friends poked fun at my over-the-top emphasis on toil. They would jab that I was trying to pay off my mortgage last week. Sometimes, after a few sleepless nights spent making jewelry & ornaments during high season, I questioned my sanity too.  

        (Best coworker in the world--Mu)

An aside:  a lot of their apparent jibes were just their way of trying to convince me that I am human & in fact need sleep. My friends & my Mom know I am beyond bullheaded & that humor is really the only way to change my behavior. That, or making me believe it is my idea. Also, there is ABSOLUTELY NO WAY I could have worked like I did without an unseen army of support from Mom & my friends. From seemingly random drop bys just when I was setting up, lugging, or taking down, to food, beverages, laughs, supplies, opinions, ideas, & actual financial support (thanks Mom!), I get by with a lot of help from my Mom & my friends. They have been integral in any life- or financial-goals met.  

   (View of landscape change--realized by decidedly UN-glamorous labor of friends + solar)

So now what?  When you've rushed headlong at one goal for several years, once met, how do you put on the brakes instead of running off the edge into thin air, a la Wiley Coyote?  

I'm just starting to answer that for myself. Not pretending this is a good template for everybody, mine looks more like a shift from 'plan it for someday' to 'WHY NOT NOW?  It doesn't sound like a big deal & thus far I'm not talking about huge life changes, but it requires a fundamental brain retrain, even for the smaller stuff. Most of mine is about arty & construction projects. And it is about stomping down some fear. Drowning by doing that damnable voice of doubt (mine sounds like Bush saying 'wouldn't be prudent').