Wanted Help

A tale of dogs, daughters, and people who apparently prefer failure over free advice.

I am lucky—ridiculously lucky—to have four women in my life who I love dearly, who each own a part of my heart, and who I can trust with it.

Three of them—my wife Traci, and my daughters Emily and Jensen—are wise beyond their years. They’ve spent decades making me marginally less of a curmudgeon and far more of a decent partner, father, and human.

The fourth?

Wisdom isn’t her specialty. She gets by on her looks alone.

(The first three wouldn’t mind me including the fourth in this column—they all know and love her.)

It’s Peasley.

Our dog.

She’s adorable, joyful, and funny. But dumb as dirt.

Traci has been out of town for the past week, leaving me as Peas’ emotional support stand-in. It’s the same story as always: for the first day or so, a hunger strike, upset that her favorite person in the world has left her alone with this stooge. Then, when starvation finally overpowers loyalty, Peasley, of course, eats. That dumb…she’s not. But a few times I had to spoon-feed her the first few pity bites, at which point she caught on and realized there’s an entire bowl of food sitting in front of her nose.

I’m trying to help the poor dog, but I fear she’s trained me to feed her. Guess I’m the dumb one. When she’s finished eating, she returns to her real mission: staring at the front door and praying for Traci to save her from me.

The whole thing begs the question:

Why doesn’t Peasley just ask for help?

Like stare at the empty bowl? Wag her freakin’ tail while I prepare her meal? Something.

I don’t know, but this conundrum has sent me on a wild tangent about the nature of help itself:

Why don’t people ask for help either?

Years ago, some friends and I got into the co-working business and opened HatchToday in San Francisco, years before the WeWork debacle.* Most of our tenants were startups that had an employee base that you could count on one hand.

My co-founders?

One owned a successful lobbying firm.

One had started and sold three other successful ventures.

One was a successful entrepreneur whose last name is very familiar, not only in California politics, but also nationally.

And then there was me—who’d spent 28 years bootstrapping Men’s Wearhouse from a dream to $2 billion in sales.

One would think that the four of us had a great deal of guidance to offer any new business venture. And while I can’t speak for my partners, I can tell you how many requests for advice I’ve had over the years.

Ready?

The number is 1. As in uno.

And even that request was a poorly couched effort to ask for seed money. Short of putting a “Wanted Help” sign on my head, I don’t know what I could have done differently. Considering that almost all the startups ultimately failed, one would think that a little free advice would have been something they’d crave before they cratered.

Back then, I asked myself why this was so. The best answer I could come up with is that these companies looked at me and thought, “Men’s Wearhouse is not where I shop, so what does that guy know?”

Now I look at it differently. The reason is more subtle and more pernicious:

I believe it was ageism.

Yeah, that sounds harsh, but it’s this bug in my gut that’s feeling this. And if the only place I’ve seen this was at the co-working space, then I’d call it a one-off, but I’ve seen it in other organizations, other rooms, other generations:

People just don’t ask for help. Not when they need it. Not when it matters. And definitely not from someone older.

I’m self-aware enough to think that maybe the real reason is something that I put out there. Maybe I have some closet arrogance that not even I can see. Maybe I smell bad.

Which brings me back to Peasley.

She’s convinced she has to starve in silence when she could just…tell me. She assumes help is unavailable simply because it’s not her preferred provider.

Sound familiar? But I’m willing to put my theory to the test.

So, here’s my experiment:

Do you have a project, company, or idea that you need help with?

I’m not looking to pad my CV, nor am I interested in making a few bucks. My personal ethos at this point in my life is to pay it forward by helping when and where I can. Just for the sake of doing it.

Who knows? Maybe Peasley has a few friends, but their paws are too clunky for their iPhones. Your paws are not.

You know where to reach me: curmudgsubstack@gmail.com

Looking forward to helping—finally.

*The universe has a way of evening things out. Men’s Wearhouse caused its share of small men’s retail stores out of business by being the giant that it is. WeWork knocked HatchToday out of business by being the giant that it was.

TL;DR: While dog-sitting Peasley, I realized she’d rather starve than ask for help. Turns out, many people are the same—especially when it comes to seeking advice from someone older. Consider this my open call: need help? Ask.