Maybe it’s a function of feeling like you’ve reached the three quarter mark, the back nine, the fall season, mid-life plus, whatever….but have you found yourself second guessing some of the turns you made at critical junctures in your life?

It might be just a few “what-ifs” or an entire catalog of them, but I sense that many baby boomers could be wondering how their lives might have turned out had they taken a different path. How would life be different if you majored in accounting instead of physical education? Where would you be now if you married Alice instead of Denise? Clown school may have been the worst idea you ever came up with. Sorry that you only had one child or sorry you had any children at all. Was the third marriage your biggest mistake?

Most of us can identify some crossroad where a choice was made that changed the course of our lives forever. Choice of a mate would certainly top the list but a first job or career choice would be right up there in the critical crossroad category. So let’s say you didn’t marry Alice and instead followed Denise to Oregon to join that commune. That would most likely mean you never went to medical school but instead ended up selling farm equipment in Iowa.

The geography choices alone can be critical determinants in the turns your life takes. Settling in the Pine Barrens of New Jersey seemed like a good idea in the halcyon days of 1970…not so much now. Las Vegas turned out to be a bad locale for someone who realized he was a compulsive gambler.

At some point we just have to come to terms with the choices we’ve made and by that I don’t mean we settle. Life turned out the way life turned out and while it may be interesting to ruminate about how it could have been different, you’re better off just marveling that you made it to this point at all.

Besides, you still have crossroads and choices ahead and if you don’t pay attention you could miss your turn all together.

Jay Harrison is a graphic designer and writer whose work can be seen at DesignConcept. His mystery novel, Head Above Water, is available on Amazon and Kindle. You can also visit his author page here.

I forgot my iPad was under my coat when I went to order coffee at Starbucks. I didn’t realize it was missing until I got home. No worries. I was sure someone would find it and turn it in. But just to be safe, I used a Find My iPhone app to locate it. That’s weird. Apparently my iPad was now in a beauty salon a few stores down from Starbucks. I drove back to the salon to retrieve it, but it wasn’t there.

In fact, according to my trusty app, my iPad was now in a pizza parlor ten miles down the street. I was pretty sure I’d never see it again.

That afternoon, I got an email from someone at a car dealership who said he mysteriously found my iPad in his office. The next morning when I reached the man who’d found my iPad, he was terribly apologetic. “I’m so sorry,” he said. “God, I can’t believe what I did!”

“What’ja do,” I asked.

Yesterday, I interviewed a guy for a job at my dealership and after the interview, the guy came back two hours later. So I asked him, ” Michael, what are doing back here?”

“I came back to pick up my iPad. I left it here.”

“I insisted, it couldn’t be his,” the sales manager said. “I traced it to a man named Jack Goldenberg.”

“I know,” said the thief. “Jack’s my best friend. He loaned it to me. I’m so glad you found it. Jack would have been pissed if I lost it.”

“Do you happen to have his phone number and address?” I asked.

“Sure. He was here for a job interview. I have all that. His name is Michael, but his friends call him Mikey.” Then he gave me his cell phone number.

I wasn’t sure what to do next. Should I rat on Mikey and call the police? Nah, too drastic.

Should I ring his doorbell and confront him? Nope, too dangerous.

So instead, I called him early the next morning. I was pretty sure I woke him up. “Mikey, hi, it’s Jack Goldenberg. (The fact I knew his nickname must have startled him!) You’re my angel, Mikey. I understand you found my iPad. Thank you so much for being such a good Samaritan.”

“So glad I could help out,” Mikey said. “Would you like to come to my house to pick it up?” Right! And be shot dead when he answered the door? No way.

So instead, we agreed to meet at a McDonald’s in my neighborhood. When I left my house to meet him, my wife asked me where I was going. “I can’t tell you,” I said, “but if I don’t come back, you’re gonna need a new iPad.”

Anyway, long story even longer. I got my iPad back from the thief who stole it. To this day, I bet he still wonders how I tracked him down. Guess he never heard of angels.

Jack Goldenberg is a prolific Copywriter, innovative Creative Director at Einstein, da Vinci & Goldenberg, and consummate, strategic marketer. Read his blog at  10 minutes of brilliance. With all he’s done, he still believes his best efforts are ahead of him.

My mother and I used to go for long walks, usually ending up at one of the strip malls that punctuated our southern California town. As we stood on the front porch ready to go, she’d lock the door, check it and recheck it before turning to me to share her time-honored parental advice: Remember. Look for money.

Seriously. Mom’s thing was to look for money as we walked, I guess because there was never enough. And the funny thing is – we usually found it! Scattered coins in the sidewalk cracks, a dollar blowing in the breeze. Once we found two $5 bills, and it was as though we’d won the lottery.

Sometimes we’d celebrate with a bite to eat at the dime store lunch counter. Was it J.J. Newberry or Woolworth’s? I can’t remember, and they’re both gone now. Mom got Jello because it wasn’t fattening. Grilled cheese for me because it was cheap.

Money was in short supply at our house, and perhaps that is why I grew up obsessed with making sure I had enough. And with this mindset, it’s easy to believe there will never be enough. No sacrifice to great, no cushion to thick – more money always wins.

Some baby boomers are reluctant to retire, in part because they haven’t saved enough and in part because they can’t give it up. Boomers say it’s the work they can’t give up, and I get that, because what we do for a living is part of our identity. But I also wonder if it’s the need to make money and the habit of spending money we can’t quite quit.

Only in the last few years did I begin to reconsider my relationship with money. I had a nice nest egg from years of saving, and that helped. But as I closed in on the concept of retirement, it occurred to me I could feel more secure with that nest egg if I spent less. You don’t need as much stuff as you think.

It is scary when the regular paychecks stop. I’m not super-frugal, and I’m not a financial whiz. Preparing for retirement was more about changing my mindset … believing I could live differently and gain back what we used to call a life. Time to sleep late, read, write and cook from scratch. Meet with friends, volunteer, maybe a little side hustle just in case.

I still love my long walks, and now I have time for them. Sometimes I enjoy a mindless loop, and other times I like walking toward a destination. There’s a little strip mall at the bottom of the hill, and I often think about stopping for a bite to eat. For now, I just keep going, occasionally scanning the grass that lines the sidewalk, looking for money.

Donna Pekar is an aging badass (for real) who lives in California and writes Retirement Confidential.