How To Start Over As A Middle Aged Person With Nothing But The Clothes On Your Back

Recently, a friend in need asked, “How do you start over as a middle aged person….?” The clock was ticking. Her house payment was coming due, she was out of work and recently divorced from a deadbeat Dad. “How do you do it?”

Though I had no idea whether it would help or not, I gave her an example.

Dateline: Portland, Oregon, summer, 1984. Shades of George Orwell. Toughest city I ever survived, and barely at that.

My third ex-wife was in Montana, not doubting me but scratching her head, wondering how it was I couldn’t find meaningful work when I’d never had that problem before. She had $200 per month of child support to worry about, and I wasn’t paying a dime at the moment. Not by choice, but because I didn’t have a dime. I was, in fact, one tiny toehold from becoming homeless.

How did it happen that I was down to the clothes on my back?

Simple enough: My current lady and I had decided I needed to rip up a few of the roots from my past by throwing everything I owned into a local dumpster. Not that she’d consider doing such a thing with her stuff, you understand, but me? Yeah, I should go ahead and do that.

So I did.

The purging wasn’t quite complete; I held onto my novel manuscripts…but not much else. The dumpster lid yawned wide, happily gobbling down my high school yearbook, the hand-colored 10″ x 14″ photo of my best and most famous bull ride ever, the padded vest with the Million Mile Safety Award from Halliburton, even my baby pictures.


Oh, I’d hung onto the guitar…for a little while. But the stress between my baby and me was getting harder on her, culminating in a black and white movie we watched on her 13″ TV one evening. The heroine suddenly had blood gushing from her nose, spooky stuff, no logical reason. I looked at my woman–and she had blood gushing from her nose, just like the TV gal.

We both knew. Number Four and I could read the signs; we were pretty equally skilled that way. It was her apartment, and time for me to get out.

The guitar left my life that same night, swapped to a younger couple for a week’s use of their living room couch. It was not a comfortable arrangement. I’d met these people the previous year in northern Montana when I’d been the social worker who’d yanked their 13 year old daughter from their home. The girl had plenty of bruises to back up her story…and now I was their house guest?

Top that one if you can. (Except you, Dusty; I know you can.)

At that time, both of them were well advanced in the study of Kung Fu while I had only a few of the fighting skills I possess today. The feeling in their home was not one of great safety.

Portland had already been kicking my butt considerably, ever since my arrival in mid-February. Work! I needed a job!

Got one, just before it was time for the couch rent to come due. Commercial wood cutter, classified ad. I’d grown up with an axe in my hands; how tough could this be?

Don was a 55 year old bachelor, big man, with a place outside of town and a vicious dog. Nobody came in there without the boss telling the pooch to wait for his kibble instead of taking a bite out of the visitor. But I was a cut above the other hands, someone who could talk Don’s language. The heck with the mancamp; he decided to put me up in the spare bedroom across the hall from his own.

In like Flynn, as they say.

Sort of.

Turned out Don’s woodcutting and delivering business was totally legit…but also a hardcore scramble for survival every single day. He had plenty of dead timber to cut, obtained by bidding on parcels at Forest Service auctions designed for the purpose. On that score, he was well ahead of the game.

But it went downhill from there, and rapidly so.

The other men he hired had a turnover rate you wouldn’t believe. They came to him the same way I had, through his little classified ads in the newspapers, but they were mostly…”the dregs of society” comes to mind as a description. Not lazy per se, the ones I met, but easily defeated, and none too thrilled to be doing what they were doing.

The hills were steep, and Hell on the wood truck, a Chevy with no jake brake and a tendency to wear out engine after engine.

At best, the money was barely enough to survive without paying for my own shelter. Heck, Don even fed me–I remember a big ham sandwich on white bread, one evening after a fourteen hour day–and I still couldn’t save a dime.

Things came to a head one Saturday when I took the wood truck out alone, determined to bring in one more load for the week. Don would deliver it on Sunday. The two men at the work camp refused to load the truck–no way to get it done before the midafternoon deadline, when USFS fire regulations shut down the forest for the rest of the day due to the risk of wildfire. I’d started loading the hard way, alone without them, moving like a bat out of Hell. Shamed them into helping after all, got the load out on time, down the hill, going to be a hero.

Blew the engine. In my rush, I’d forgotten to double check the oil before diving downhill. That engine was so worn, it sometimes took as much as a gallon in either direction.

My bad. My very, very bad.

Didn’t know it till Sunday morning. Thought everything was cool. I was back at my bloody-nose girlfriend’s place. She’d picked me up late Saturday evening; we were talking hopefully about maybe patching things up.

Don called, ticked off. He’d found the engine all seized up when he went out to start the truck. Insisted I had to come back to work immediately, help him change out the engine.

Nope. Not gonna do it. My day off.

Easy enough to read that writing on the wall. While Don was out working on his truck, I had my girl drive me in her Datsun B210 (well used) over to his place. She parked on the shoulder above the gravel driveway; I dashed down the steep grade, right through the vegetation, bluffed my way past the killer dog–who wasn’t real sure about it–grabbed my stuff out of the bedroom, and split.

Now I was back in “her” place…but still, owned nothing but the clothes on my back.

What next?

What next?

What next?

Long story short: Temp job here, temp job there, finally hired by General Electric to clean out PCB-contaminated transformers, ugly enough job but a job, and we two off-and-on lovebirds got married. But we had a deal: I gave her every dime of my paycheck.

I still owned nothing but the clothes on my back.

Come December, my new wife, an expert in the bedroom but a control freak everywhere, financed my flight to San Diego to look for work. No luck. Flew back and, in her words, we moved to San Diego by car (with most of her stuff following via friend plus trailer) and, “took the city by storm”.

The storm was mostly in her savings account, which was dwindling. Again, temp work, temp work, finally longer term temp work, riding to work on a 650 Suzuki behind a really big bisexual guy who happened to be my Supervisor and admired my pecs.

Still nothing but the clothes on my back, and those were wearing out at a pretty fair clip.

Great American Insurance, classified ad. Interviewed, got hired at the bottom rung: Clerical work in the Underwriting Department. I’d been a lead Home Offfice Underwriter, but my past was, as they say, checkered. I was probably a flake, but at clerical wages, they could take a chance.

At this point, the fecal matter hits the fan blades. Wifey bangs neighbor, tells me the following day by phone when I’m at work. Writing on wall getting pretty clear. One month after that, give or take, she hauls off and kicks me in the shin because I brushed past her on the way to the trash can with a paper plate after supper. I promptly kick her back, then inform her it’s time for me to go. If I’m starting to lose control, firing back like that, I’m outa there.

She freaks. Wants her $6,500 savings account, which is now down by several thou, fully refurbished. I agree, at such and such a percentage of my paycheck for however long it takes.

Divorce is so expensive because it’s worth it.

Now, counting the child support debt to wife #3 and the settlement agreement to wife #4, I have less than the clothes on my back.

But the tide is turning. I’m still in a sublet bedroom of a cockroach-ridden two-bedroom apartment when my boss at the insurance company gets hired away to become Assistant Vice President of a regional insurance outfit headquartered in La Jolla. I’ve done good work for her at Great American, straightening out a clerical mess in the Workers Compensation department and getting promoted up a step to Assistant Underwriter. She promises to “bring me with” if and when she possibly can.

It takes her a few months, but she gets the job done, bringing me over to Insurance Company of the West (ICW) as a full Underwriter. In time, I straighten out another mess for her at that company (in this case, the Assigned Risk pool) and move up the ladder. I’m a Supervisor, making $30,000 annually, almost enough to live on.

I get a small bike, a 200 cc Kawasaki KZ…then an old leaky Pinto…then a guitar…up to a worn Ford Granada…then, finally, a brand new Ford Escort GT. Ford, Ford, Ford, three in a row.

My newest woman, who will one day become wife #5, is awesome. We buy a house together, and eventually start a multilevel marketing business that grosses a couple million bucks over a 20 year period before finally fizzling out.

And that, dear readers, is one example of how I started over with nothing but the clothes on my back.

Do not try this at home.

15 thoughts on “How To Start Over As A Middle Aged Person With Nothing But The Clothes On Your Back

  1. Hi.
    Kinda speechless.
    I lived a parallel life. Going on hubby #2 though. Always hoping. Chin up.
    Can’t kick this dog when I am down. I pay child support too because of a fat ass ex who refuses to get a job and lives off American tax money….clincher,..we have joint custody.
    Thanks for sharing your story.
    Shows me that no matter what, there are people out there that are struggling or have had struggles that make them who they are.
    Sometimes in this world the struggle is what causes us to revert inside ourselves when it should be something that draws us together.
    Take care.
    I will keep reading on occasion.

  2. Thanks for commenting, Jen, and you’re welcome. The struggles definitely make us who we are, even if we’d rather have done without the experiences. 🙂 And you’re also right about the struggle sometimes driving a given individual down the survival scale instead of up; it can go either way.

  3. Um…thanks? Nothing in this post was intended to be funny, though. It’s all 100% true and didn’t feel “hilarious” as it was being experienced, anyway. On the other hand, if it made you smile (or laugh), that’s definitely a good thing.:)

  4. Hell no it ain’t funny..
    Ahhh, but ya did make me feel better. Just knowing Imnot the only one who took some lumps! Thank you for sharing!
    Btw….I think your amazing! Write a book and make another million or two! Ill get it at the sale price, but I’ll throw in my dime on it!
    I hope you may retire with enough, if not in luxury, at least enough for some chips with your ham sandwich!

  5. Hi, Amber–and thanks for commenting. It’s the feedback that keeps us writers going.

    I have actually written a book–several of them over the years–but don’t figure to do a full blown autobiography, simply because I seriously doubt I’m skilled enough to “tell all” without hurting somebody along the way, and that’s not worth any price. (I do that on occasion, but accidentally, not deliberately.) On the other hand, I do have plenty of fiction material available. Most of it’s only here, on this website (under the various fiction Indexes near the top of the page), but one western fiction volume, Tam the Tall Tale Teller, is available on Amazon, either as a paperback or an e-book.

    Whenever I get around to publishing the two sequels (Tam is part of a trilogy), it’ll probably be only as an e-book. Printing costs have gotten ridiculous.

    As for “retirement,” I’m theoretically retired now, will turn 73 shortly, but am busier than ever. Start with a deeply disabled but still feisty redheaded spouse (wife #7, 20 years together), add a bit of writing, songwriting and singing/guitar practice nightly, mix well with living off grid in a home I built single handed in 2010, etc…all in all, doing just fine. Might have to hunt around for the ham to make a ham sandwich, but got a bag of Lay’s potato chips right here! 🙂

  6. The dynamics of the personalities and outcomes reflect that which I have become accustomed to. I was the hero throughout my youth surviving abuse yet losing a mother who didn’t have the help she needed, then being dragged through hell by fathers divorces and all the moving, emotions and separations of genetically engineered love for kin that kept me focused on achieving a higher education. Those I supported condemned me and though I believed in repayed me in persecution. A few auto injuries back to back “as a passenger” going to or from school or work left me, well ….limited in my personality. I lost my beloved talents of golf and guitar, and was kicked at a low vulnerable point. Yet your attitude in your story never gave room for dealing with your circumstance a moments delay. I felt better knowing that hey, shit happens but things do change and sometimes it’s not a diaper, but the weather and you can really see the world is a bit bigger then your imaginative canvas. Great job on keeping at your job for the kids. Thank you for your testimony also

  7. Thanks for commenting, Giancarlo. Your remarks remind me of the old adage, “No good deed goes unpunished.” As for my attitude “never giving room” for a moment’s delay in dealing with circumstances, I hadn’t thought about that as being all that “different”–but it has been a lifetime approach, something I’ve worked on for many, many years. As I’ve seen it, I usually didn’t feel I had any time to waste.

  8. I’ve been living through hell for two years with no end in sight. I only hope to keep my mind and my heart as I’ve lost everything else. I never in my wildest dreams imagined this would happen to me. Thanks for sharing. Be well.

  9. Just read your story, loved it. It was very informative of the struggle some will never face. I’m currently facing eviction of my apartment. I decided to go back home with nothing but the clothes I own, and let Oklahoma become a memory. I have a goal. Family land back home that no one wanted can’t see if I can’t information on it, crash at the lake I got my bug out box ready for my journey. Just wanna thank you cause if not for people like you- people like me would not find hope. God bless you friend.

  10. There you go. I’m guessing you may already have bugged out, but just in case you do get to read my response: Go for it, and may the blessings be. Pam and I have now moved back to my home stomping grounds in Montana (from Arizona). It was a complex challenge…but nothing like the pure survival situation you’re going through at the moment.

  11. thanks so much brother, i have been through some great challenges too and still kicking on. This story makes me believe in God and a bright future. ones more thank you so much…

  12. Appreciate the comment, Louis. It’s feedback like yours that makes a post like this worth writing.

  13. Your story was very rough. Glad to see your doing amazing now. I’ve also been married , going thru second divorce now. Husband after 13 years turned out to be gay, and a drug addict. I just turned 45 and have 7 year old parents died so no family to go home too. Working temp jobs here and there but still hard to make ends meet. I pray it gets better because ive got nothing left but my self respect and my son. God bless

Leave a Reply

Your email address will not be published.