The Princess Gloves Principle

The Princess Gloves Principle

And the Monty Hall Moment That Proves It

Date Night

Once a month, I take my three-year-old granddaughter Emery out for dinner. Just the two of us. We call it our Grampa and Emery date night.

She picks the restaurant. Last night she chose Olive Garden, because, and I am quoting directly here, "it's a good family restaurant." The girl knows what she wants.

She also knows how to dress for the occasion. We're talking a full outfit: dress, sparkly shoes, handmade jewelry (necklace and bracelet she crafted herself). She is not playing around.

And she carries a purse. Not a toy one. A real purse. An adult purse. Because apparently at nearly four years old, that is the appropriate accessory, and she is absolutely correct.

Now, I never know what's going to be in the purse. That's part of the charm. The contents change every time, based entirely on what caught her attention that day as she was getting ready. It's always some combination of a household trinket, a small toy, something she grabbed off a shelf on the way out the door, and whatever else seemed important to her in that moment.

She curates it fresh every time. No repeating herself. No formula. Just: what matters today?

On this particular evening, she ordered her usual, mac and cheese, a side of grapes, and a strawberry smoothie. Your typical Italian cuisine, at least when you're three.

"I Have Gloves."

The smoothie arrived. She took a couple of sips, set it down, and looked at her hands with genuine concern.

"It's making my hands very cold."

I said, jokingly, "Too bad we didn't bring gloves."

She paused. Her face lit up. And then, with the confidence of someone who has never once doubted herself:

"I have gloves!"

She reached for the purse.

Out came a matchbox car. A toy baby bottle from one of her dolls. A little stuffed animal. A small 2x3 picture frame. A card game.

And then: gloves.

Not winter gloves. We live in Florida. These were pink satin, elbow-length gloves, the kind that come with a Disney princess costume. The kind that have absolutely no practical application in any situation a reasonable adult could predict.

She pulled them on with great focus and considerable effort. Picked up her smoothie. Took a long sip.

"All better," she announced. Loudly. The people at the next table were watching the whole thing unfold, and I genuinely thought they were going to applaud.

She didn't pack gloves for a cold smoothie. She packed them because they were fabulous. And that's exactly the point.

I should mention, because it proves this is a pattern and not a fluke, there was another evening when she reached into that same purse and pulled out a copy of Allen Ginsberg's Reality Sandwiches. Beat poetry. Belonging to my son, who is a fan. She'd spotted it on her way out the door and it looked interesting. Into the purse it went. The look on my face when that came out, I imagine, was something.

This is what I've come to call a Monty Hall Moment.

If you watched Let's Make a Deal growing up, you remember the bit: Monty Hall would stop somewhere in the audience and offer cash, sometimes serious cash, to the first person who could produce a bizarre, specific item. A hard-boiled egg. A left-handed glove. A photo of a man with a beard. Something nobody could have reasonably prepared for.

And invariably, someone had it.

Not because they knew what Monty was going to ask. But because they had packed broadly, curiously, and without a specific plan. And when the moment arrived, they were ready.

The Princess Gloves Principle: Building for Optionality

Most business owners and entrepreneurs understand contingency planning. You anticipate the likely problems, you prepare the likely solutions. That's smart. That's necessary.

But contingency planning only works for problems you can see coming.

What Emery demonstrated is something different. She didn't pack gloves because she foresaw a cold smoothie emergency. She packed them because she valued them. Because they were interesting to her. Because on that particular day, they made the cut.

That is what I call building for optionality, assembling a toolkit that is wider than your current problems require, because you simply cannot know in advance which resource will matter when something unexpected lands in your lap.

For entrepreneurs, this translates directly. The skills from a past career that seem unrelated to your current business. The relationship you built in an industry you've since left. The perspective you carry from a decade doing something completely different. The "weird stuff" you've accumulated that doesn't fit neatly on a resume.

That's your purse. And you have been packing it for decades.

The encore entrepreneur doesn't just have more experience. They have a broader, stranger, more interesting toolkit than anyone else in the room.

The Wrecking Crew understood this intuitively. If you're not familiar, the Wrecking Crew was a rotating group of elite Los Angeles session musicians, Carol Kaye, Hal Blaine, Tommy Tedesco, and others, who played on an almost impossible number of iconic recordings through the 1960s and into the 70s. The Beach Boys. Sinatra. The Monkees. Elvis. Sonny and Cher. The list goes on so long it becomes almost comedic.

They weren't called in because they specialized. They were called in because they could play anything, for anyone, on any given Tuesday. They walked into sessions with no idea what was waiting for them. And it didn't matter. Their versatility was the toolkit. Their breadth was the value.

They showed up. They assessed. They reached in and pulled out exactly what the moment needed.

Sound familiar?

There's a reason research consistently shows that founders over 50 outperform their younger counterparts at a significant rate. It's not despite the varied, winding path that got them here. It's because of it. The Wrecking Crew didn't become indispensable by specializing early and staying narrow. They became indispensable by playing everything, everywhere, for decades, until their range of options made them the answer to almost any question a producer could ask.

In The Amplified Entrepreneur, I call this the Preparation Paradox. The irony at the heart of it is this: you can never know exactly what you're preparing for, which makes broad, deep, wide-ranging preparation more important, not less. All those years. All that experience. All the skills and relationships and perspectives you accumulated across a career that probably took more than a few unexpected turns. They weren't wasted time. They weren't detours. They were preparation for the moment you never could have consciously and deliberately prepared for.

Emery didn't know she was going to need those gloves. She just knew she valued them. That instinct, to carry what matters to you without demanding to know in advance how it will be useful, is the Preparation Paradox lived out in real time. By a three-year-old. With a purse full of satin gloves and Beat poetry.

You have been doing the equivalent of that your entire career. The question is whether you recognize what you're carrying.

Do It in Style

Here's the part that the standard business frameworks always skip.

Emery didn't just solve the cold-hands problem. She solved it with elbow length, pink satin princess gloves. And here is the thing that most people miss: that was the better solution.

The people at the next table weren't just impressed by her resourcefulness. They were charmed by how she deployed it. Nobody sitting in that Olive Garden with sensible, practical winter gloves could have created that moment. The unconventional asset didn't just fix the problem, it elevated the response in a way that the conventional answer never could have.

This matters in business more than we know.

When an unexpected challenge arrives and you solve it by reaching into that deep, strange, wonderfully varied toolkit you've built over a lifetime, you don't just have an answer. You have a distinctive answer. One that carries your fingerprints. One that reflects perspectives and experiences that nobody else in the room has.

That's not just problem-solving. That's your brand.

The encore entrepreneur has spent decades developing a perspective that simply cannot be replicated by someone who is just getting started. When you bring that full range to bear on an unexpected problem, the solution you produce isn't just adequate. It often turns out to be more creative, more nuanced, and frankly more impressive than whatever the conventional playbook would have produced.

Don't just solve the problem. Solve it in a way that's distinctly, memorably you.

Emery sipped her smoothie through those pink satin gloves with complete satisfaction and zero self-consciousness. She had solved her problem with exactly the right tool, and the fact that the tool also happened to be spectacular was, from her perspective, entirely consistent with how things ought to go.

She's not wrong.

So, What's in Your Purse?

Here's what I'd ask you to take from this, and it's really three things:

•        Build the purse broadly.  Don't edit your toolkit down to only what seems immediately relevant. Carry the weird stuff. The skills from your old industry. The relationships from a chapter of your career you thought you'd left behind. The knowledge you picked up doing something nobody expected. A copy of Reality Sandwiches. You don't know yet which gloves you'll need, so stop deciding which ones aren't worth carrying.

•        Trust your Monty Hall Moment.  When the unexpected problem arrives, and it will, reach in confidently. The answer is probably already in there. You’ve been packing this purse for a long time, and it is significantly more useful than you may have given it credit for.

•        Bring the satin gloves.  Don't just solve the problem. Solve it in a way that's distinctly, memorably, entirely you. Your accumulated experience doesn't just give you more options, it gives you better ones. Options with personality. Options that carry a perspective that nobody else in the room has. Use them.

When it was time to go, Emery carefully packed everything back into her purse. The card game. The stuffed animal. The picture frame. The matchbox car. The toy baby bottle.

And the gloves.

Because you never know.

Keep rocking.

Alan McKee is the founder of AmpMyBiz.com and author of The Amplified Entrepreneur: Building a Business That Rocks. He helps professionals 50+ leverage a lifetime of experience to build businesses that rock. He is also the founder of Netwurx Technology Group and Acurata Hospice Software Solutions.

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