About 8 blocks from the office where I worked for 26 years, there’s a small park that I nicknamed, “The Crying Park.” I call it that because whenever work got just too much to bear, and I felt like I needed to cry, I’d go there. It was just far enough away that I probably wouldn’t run into anyone there from work who might see me crying, tell me to suck it up – or worse, offer comfort.

Looking back now, does it seem funny that I had no problem crying in front of fellow New Yorkers – but dreaded the idea of being vulnerable in front of my colleagues?

I knew it was a lie, but I still felt it

There was one particular day, when I was hurrying home through this park, frantically dialing my therapist who I had been seeing for over 20 years and had never called between appointments. When she answered, I collapsed on a bench, babbled at her what had happened, and finished up by screaming into the phone. “He said I was a failure! A failure! I’m a failure! I’m a failure…”

“He” was my new VP. He had told me that afternoon that he was replacing me. I didn’t mind that – I had outgrown the job and had been planning to leave for a year. My latest excuse was that I wanted to hand my job off to someone who would care for the people I served with as much love and care as I did. When he said her name, I thought she would do this this, and that was a relief.

And I knew that this was his MO whenever he took a new job: scare his new team into submission by firing a top woman. In my case, he didn’t fire me, he had offered me a scut job, a job with no agency, where I would take commands from others.

Because, he said, it was clear that I wasn’t qualified to do my job. That I was a failure at my job. My job that I had been doing successfully for 8 years.

But something about that word, Failure, really pressed my buttons. It reduced me to a raving madwoman in a New York park, screaming “Failure, Failure, Failure” into a smartphone.

And it gave me the fire to leave that company, the people I had served for 31 years. To start a journey of figuring out who I was without that company.

Sometimes you can’t even see it

I took a job at a start-up. Then a job at a H&W company, what I called a “re-start-up.”

When I found myself back on the job market in 2025, amongst hundreds of thousands of other white collar professionals, mostly older women, I began to notice something as I networked. As the GenX women that I met at events told me their stories, I wanted to do something to help them think through their next steps, to figure out what was next, or to have the confidence to believe that they could.

I began conducting more formal interviews, asking 10 simple questions. Questions like:

• What are your thoughts on Career?
• Retirement?
• Purpose?
• How do you think about Success?
• How do you think about Failure?

And I learned something from these interviews – but it wasn’t what I thought I would learn. I thought I would hear a pattern in their answers that would help me figure out how to help them. And I did.

But it was their answers to my question about Failure that got me thinking. Because they all said kinda the same thing: Failure is how you learn. Yeah, it sucks when it happens – no one likes feeling that way – but you learn from it and you go on.

Every single person said something like this. The first person, I think, yeah, she’s covering up what we really feel about Failure. Two people, three, in denial, yeah?

But every single person…?

I began to think maybe the person who was the outlier about Failure, was me…

Mistakes vs Failures

Don’t get me wrong – I’ve made plenty of mistakes throughout my career. I’m generally not afraid to try new things and I get out over my ski’s, and things don’t always work out, and I have egg on my face and have to backtrack. Or I do something dumb, hear what I want to hear.

Like the time that I closed a store by mistake.

I thought I heard Real Estate say that the lease wouldn’t be renewed. So I put the merchandise on deep discount, sold the fixtures, scheduled the signs to be removed, and told HR they could lay off the staff.

Boy, was that mall manager surprised when they walked by that empty storefront the next week. They were actually still negotiating with us. We were the only reason anyone still went to that mall. We ended up with a rent-free lease, but had to spend a couple million to rebuild the store, ship in new stock, and rehire the staff after giving them severance.

For over 10 years, whenever I saw that store number or ran into that manager at a conference, my soul shriveled up inside me. It was a horrible mistake to make, that had a devastating effect on 15 employees, and I still regret it.

But I don’t think of that as a Failure. That’s a mistake that you learn from. And I did.

As I began to work more on my community for GenX Women, I realized how anxious I was about it. Anxious?

I was terrified! I couldn’t make myself push the button to get it going – I had plenty of excuses: I needed to interview more women. I needed research. I needed a new laptop.

And what was I terrified of?

Failure.

Not the idea that it wouldn’t work out. That I’d schedule walks and end up walking by myself. Or that I’d schedule workshops and no one would sign up. That I’d sink a bunch of money planning a retreat that no one attended.

Those are normal growing problems – you do something, it doesn’t work out, you figure out why and pivot.

What terrified me was the idea that someone would tell me I was a failure. That a past friend or colleague would see my very public inability to make it work, and think “she’s just an old failure now.” Or that family would see that I wasn’t able to make it work and say, “I told you so.”

I told you so.

So where did my fear stem from?

When I was a child, the worst thing my mother could say was, “I’m so ashamed of you.” And my mother said it a lot. Don’t know your times tables in 3rd grade? “I’m so ashamed of you.” Dye your hair hot pink? “I’m so ashamed.” Secretly apply to drama school instead of law school? “Ashamed.”

And it applied whether my action drove the shaming incident. When I discovered I needed glasses in high school, my mother accused me of wanting them to make myself the center of attention. I argued that I wanted to be able to see things across the room. Eventually what came out of her mouth was – say it with me – “boys don’t make passes at girls who wear glasses.” In 1982. The truth was, she felt ashamed that boys weren’t asking me out, that her daughter didn’t fit her definition of popularity. When I finally got a boyfriend, she was ashamed that I had chosen that specific guy. In retrospect, so am I, but I was Learning. And that was a Learning lesson.

When I confided in my mother a few years before she died that the reason I had fought, tooth and nail, at age 12 not to be left at home with the teenage son of a houseguest while our parents went out to dinner, was not because I wanted to go out to dinner. It was because, on our only previous encounter, he had handcuffed me to the foot of a bed and reveled in my increasing panic. And I had a bad feeling about being left alone with him. A fear that proved valid that night, when he attacked me.

My mom’s reaction: Oh, I’m a bad mother. I’m so ashamed!

This is the legacy that my mother left me. She wasn’t an abusive parent. Just consumed with shame.

What a sad way to live.

And she passed that shame on to me.

Don’t be vulnerable in front of them. Don’t ask for help. Don’t do anything that might cause people to say bad things about you.

When my mother died in 2022, my need to protect her from shame didn’t die with her. Instead of releasing me, it became even more a part of me, the demon sitting on my shoulder telling me not to do things, that they won’t work out, that it will just prove the nay-sayers right: that I am a Failure.

Looking at it objectively, people I care about would not say I was a failure, even if my career takes an unexpected bend.

I have a healthy savings, a good home, a loving husband, caring friends, a full social life. I’ve done good work, putting things in place to make it easier for people to enjoy their jobs. People I work with talk about how they enjoyed working with me; the difference I made at the organizations I worked for. I can call just about every executive I worked with and they’ll give me a recommendation without hesitation. That says something to me.

Some of my favorite moments are when people I managed reach out to me from my past to tell me how something I said or did helped them see a path forward that they hadn’t seen before. Or how they find themselves telling someone else something that I had once said to them.

One of my younger cousins – a JAG – sent me a holiday card in which she wrote, “Change the world for the better – just is your nature.”

I know that in my head. And still Failure haunts me.

What failure is not

A friend who had recently lost his mother after a long illness told me that he felt like he had failed her: if he had just done something different, made different decisions, maybe she would have continued living.

I shared that I had also lost my mother after a long illness, at the end of which, my sisters and I decided to remove her from the machine keeping her alive at the hospital, something mom would not have wanted.

The doctor had explained that the procedure had two steps:

• Step 1, administer a drug that would prevent her body from panicking when the machine no longer supported it;

• Step 2, remove the machine.

When they came into the room, it felt chaotic. We were on the phone with the sister who was in transit; the situation seemed unreal; unless you’re in the medical profession, it never seems clear what the heck is going on.

It wasn’t until they removed the machine and my mother sat up, desperately gasping, and crushed my hand in hers, that I realized the hospital hadn’t performed step 1.

In her final moment, I had dropped the ball.

But, I told my friend, I didn’t feel like a failure. I didn’t feel like I had failed her.

I made the best decision based on the information that I had.

That’s all you can ask of yourself.

Um, well, kindness is important, too…

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If you’re a GenX woman and want to be part of my passion project, give me a holler.