How to Convince Family Your Crazy Creative Pursuit is Worthwhile

When you start as a freelance creator it’s hard to convince loved ones you’re not crazy. Here’s a story that motivates me.

There’s this scary thing that happens once we take the road less traveled — as we zig instead of zag. Maybe the box wasn’t meant for us. Perhaps we’re so far outside it we need binoculars to see it.

No matter where you are along your creative freelance continuum, it’s hard to convince loved ones we’re not insane.

Those closest to us want to protect us from harm. They may not understand our drive. They may not have the drive we have. They watch us stay up all night, covered in legal pads and markers. They get worried quick.

The hardest part about convincing loved ones of our dreams is the lack of a product.

When we start we’ve got nothing. I write books. The books are in my head until they’re not. My family can watch me typing all day and night, but until the book is on the shelf (and earning money) it can be really hard to help sell that dream to others.

Sure, they’re supportive. Our loved ones want us to succeed. They don’t mean to be negative. It’s easy to get motivated by someone who doesn’t believe in you. Those people are negative all the time. For an entrepreneur, naysayers help stoke the fire of success.

But I’m not talking about negative naysayers. This is about the people who really care about us, but don’t understand our work. How do we show them we’re onto something worth doing?

Well, I’ve got a story for you. It may not seem like it, but there’s a point at the end. I think about this story a lot. There are many stories like this in your niche too.

Read on.

The Gary Halbert Story

If you want to know anything about direct marketing, no matter your industry, you’ve got to spend a lot of time studying the master of mail — Gary Halbert.

Although Gary died a few years ago his accomplishments are legendary. There was no internet until the end of his life. Gary did everything he did through the physical mail. One. Letter. At. A. Time.

This is the story of the most successful direct mail campaign ever (and how Gary finally convinced his father he wasn’t wasting his time):

[paraphrased] Gary developed a direct mail campaign for a family coat-of-arms he could sell through the mail. He literally went through the phone book and picked blocks of people with unique last names, sent them a personal-sounding letter (forever a copywriting case study called the ‘Coat of Arms letter’) and people sent him five dollars to get their family coat of arms in return.

This wasn’t his first letter campaign — far from it. Gary was an amazing copywriter at this point, but the coat of arms promotion was Gary’s tipping point and now one of the most-famous letters in history (and this was the 1970s!)

Sounds a little weird, right?

Well, Gary’s father thought it was weird too. Here, his son was sending a one-page letter to random people in the phone book (Gary sent this letter 600 million times over 30 years. One first class stamp at a time).

Gary’s dad thought Gary was crazy. He was worried about his son and asked him when he’d start pursuing a career. Like all caring parents, we want those we love to do well and not suffer.

At first, I’m sure it looked like Gary suffered a lot. He staked his life-savings on this mailing. And poppa Halbert was relentless about making sure his son should quit screwing around with stamps and paper. It was time to get a REAL job.

At one point Gary’s house didn’t have running water or electricity, because they had been shut-off. But he never quit his pursuit of a direct mail business.

Instead of fighting him, Gary told his father to meet him at the bank one morning.

As they walked in the bank Gary took his father upstairs. He father balked and asked why they were going up to the employee area on the third floor of this lavish bank. Gary kept walking and opened the door to a room filled with 30–40 employees opening envelops.

“What’s this?” his father asked, confused and uncomfortable.

“These people are hired to help deposit all the money from my direct mail letter,” said Gary.

At his peak, Gary made $300,000 per day (in today’s dollars) from his coat of arms letter. These people had to open up to 20 thousand letters per day! He had trouble getting the money in the bank fast enough.

Eventually, this entire floor of the bank wasn’t enough and they had to open an entire building just to process Gary’s orders. They named it the Gary Halbert Bank.

And all this was done by first class mail, before computers.

Gary’s father never questioned his son’s pursuit again.

Sometimes we’ve got to eat dirt and keep grinding until we don’t

If we believe in our work strong enough, we’ve got to keep creating. Even when the phone bill is in limbo, or all our loved ones think we’re crazy.

This isn’t blind following of some crazy idea that won’t work.

You took calculated risk. You proved your business model on a small scale and now you work your ass off to scale it bigger.

Whether you write books, code apps, shoot videos, paint, speak, or dance — if your work is worth doing you’ve got to fight the urge to settle and conform.

If you’re just getting started, resist the urge to share your idea right away. Wait until you’ve got something that works on a small scale. I don’t mean be deceptive, but be careful who you allow inside your inner-circle before you release your dreams to the world.

Creative pursuits are so fragile at first.

It take just a comment or two from a well-meaning friend before we start to question our path. The herd wants to bring us back into the fray. Most of us listen to these internal and external voices — giving up on our true calling.

We’ve got to keep working.

Our a-ha moment will come.

We test small. We test bigger. We multiply, reinvest, and go bigger. There will be a day when we’ve got something to unveil. We may not get $300k per day, but our time will come.

We can’t convince naysayers until we’ve already made it, with middle fingers held high. But sometimes our loved ones want just a tiny sample our idea works.

Most people want hard proof our hair-brained idea will work before they’ll buy into it. If we’re careful enough with whom we share our idea, it will give us enough time to keep working.

It’s important to let loved ones in our passions, but these early ideas are incredibly fragile. I believe it’s best to wait until you can show the smallest success before you share too much.

We may find out our idea doesn’t work. There’s nothing worse than a string of I-told-you-so moments. Those around us will support us, but we’ve got to show proof, fast. The more proof the more support.

We need you to keep working.

We want what you’ve got to offer, but we won’t see it until you finish it.

We’re waiting for you.