Party-Pooper Questions To Build Your Wealth

I was on the ground floor of the UMASS Amherst library, shelves of dust-covered tomes looming over me. I flipped open a book as big as a bread loaf. As I sifted through the pages, a woman stared at the text with the crumb-size letters. “Looks like fascinating stuff.”

Quick! Think of a clever reply!

“Yeah,” I said, coming up blank. A decade would pass before my social graces improved by more than a hair.

The book was called the SRDS — a giant directory of mailing lists available for rent, for everything from people interested in exercise equipment, homeowners, travelers, and aficionados of pornography. *

I’d have bet a large sum that nobody else had touched the SRDS book for at least a couple of years and nobody would touch it again until the library received an updated replacement. So why was I rummaging through it?

I’d recently discovered the newsletters of a marketing guru named Gary Halbert. In one issue, he gave a lesson that I wouldn’t fully appreciate for several more years, writing that many people dream of starting their own direct mail business, but few are willing to do something as simple as research potential customers’ mailing lists, found in the SRDS.

A day or two after reading that, I marched almost a mile from my dorm to the campus’s towering, red-brick library to get my hands on an SRDS book.

While I didn’t assemble a direct mail campaign to any pet owners or smut enthusiasts, I pushed myself beyond mere dreaming and did some nitty-gritty research.

Fifteen years later, I’ve realized a deeper lesson. I’ve started a few businesses and failed at most, enjoyed windfall profits, gone bankrupt, crawled back from being declared financially dead, and have now achieved many of my wealth-building dreams. I’m editing this article sitting on my patio, in between coffee sips and glances at the hang gliders as they swoop like falling leaves along the foothills of the Rocky Mountains. It may not be the stuff of Instagram superstars, but it’s my version of heaven. What I’ve learned about business can save you time — and heartbreak.

I succeeded only when I was willing to withstand the miseries that arrived after the excitement to create something new had withered away.

Paging through that SRDS book was a small example of such misery. Later, I pushed myself to write advertisements and marketing campaigns, testing them with my own cash when credit card companies were a step away from sending a couple of burly guys to whack my head and demand I pay up.

Before working with the SRDS tome, I’d sat on Barnes & Noble’s plush couches and breezed through books on getting rich in real estate — even buying a few of them. But I never bothered to look up any listings or appraise or remodel a house. No enduring misery, just comfortable excitement — so the closest I came to making money in real estate was buying a house for my fiancé and me.

If you want to get wealthy, forget about setting goals or dreaming of the lifestyle you want — at least for the moment.

Instead, imagine the misery you’ll need to withstand. Ask yourself if you’re willing to put up with that.

Here are some sample party-pooper questions to get you going:

For real estate: “Am I willing to do home repairs or work with contractors? Keep up-to-date on laws and regulations? And put up with tenants who might skip paying rent or defecate on my walls?”

I’m serious about that last part. I’ve heard weird stories.

Even though I’ve never been a landlord, I got a taste of real estate’s headache-inducing grind when I bought our home. My wife had it worse. Answering the contractor’s questions… and then correcting them when they did something wrong anyway, became her unpaid part-time job. Oh, and they stole from us.

I’m not saying to avoid real estate. I’m suggesting you start with questions to clarify your willingness.

Here are some questions for starting a business:

“Am I willing to put up with employees who will need constant babysitting and might steal from me or sue my company?”

“Am I willing to meet total strangers and get them interested in my product?”

“Am I willing to risk losing my startup capital?”

“Am I willing to work far more than the standard 9-to-5?”

For becoming a writer:

“Am I willing to write hundreds or thousands of words every single day for the rest of my life?”

“Am I willing to start every day feeling mentally constipated until I excrete those words?”

As one copywriter in my industry said as he left a party early in a hotel bar, “You know, this copywriting gig would be great if it weren’t for all this f***ing writing I have to do.”

If you want to write for a living, there’s a strong chance you’re going to spend the next few decades shuffling around in a daze while you think about an article or chapter idea. You’ll ponder how to phrase a title as you bump into objects, remain lost in thought as you stumble to the bathroom and, if you’re lucky, just before you unzip, your gaze will come into focus and you’ll realize you’ve wandered into your backyard. It’s worse if your home is in an apartment building. Welcome to the writer’s life.

For going back to school:

“Am I willing to study for years and then spend years after I graduate building my experience in a high-competition field and risk it becoming obsolete?”

Having fun yet?

If you answered, “No!” to most of the above questions, then you’re welcome. I saved you from fruitless fantasies of riches. You can now reclaim the time and effort you were going to waste on a dream that would implode under the weight of your half-finished projects — and direct those resources toward a project that will blossom from your devotion. These questions won’t steal your dreams, but clarify them, while saving you from self-doubt, confusion, shame, and wasted brainpower.

All these questions start with, “Am I willing…” because they seek to clarify what you bring to the table and how prepared you are to bring it when times get tough.

You’ll probably answer, “No” to most of these questions. That’s good. You’re on a mission to find the party-pooper question to which you can say, “Yes.” When you do, instead of finding the right answer to building wealth, you just found the right question.

*Any time you receive so-called “junk mail,” you can thank a directory like the SRDS, where your name, address, demographic, and psychographic information are available to any business that wants to assemble a mailing list. If you’re aghast at such an invasion of privacy and barely consensual marketing, throw away your smartphone, a data-collecting device that makes old school direct mail data-gathering seem like rubbing two sticks together.

***

After dropping out of college, Nate Rifkin had dedicated himself to self-help and pursuing his entrepreneurial dreams. Yet he failed to achieve any of his goals. Worse, he spiraled into debt, drank every morning, felt lonely, lost, and hated himself.

A few years later – after a brutal bankruptcy and a stint spinning signs on a street corner – Nate Rifkin had quadrupled his income, married the woman of his dreams, and found happiness and contentment. He's about to publish a book on how he did it. Read the first chapter here.