How to Convince the People Closest to You That Your Crazy Idea Isn’t Just a Pipe Dream

The other night I received an instant message from one of my readers.

She told me that her parents’ attitude continually crushed her entrepreneurial spirit.

They didn’t take her seriously.
They weren’t interested in her progress.
They only seemed to notice the negativity of her endeavors.

Can you imagine how disheartening that must be?

I can.

Even though I’ve been fortunate enough to have an endlessly supportive family, I can still relate to the ostensible futility of trying to convince the people you love that your crazy idea is isn’t just a pipe dream.

AFTER ALL: I did live in my parents’ basement when I first started my company.

For two years, eight months and twenty-nine days.

But who’s counting?

THE POINT IS: When you convince the people closest to you that your endeavors are worth enduring, they’re usually happy to offer the crucial support you need.

Not that you need anybody’s permission to make a name for yourself.


Without buy-in from your loved ones, you’re only making it the journey harder.

If you’re stuck trying to define your dream for the people who matter most, consider these ideas to help you along the way:1. Manage the ratio between enthusiasm and empiricism. People need to see the passion in your face. Every day. I learned this from my grandfather, who constantly reminds our family that the worst bankruptcy is the soul that has lost its enthusiasm.

But that doesn’t give you license to be all energy and no evidence. You have to manage the ratio.

For example, let’s say you plan to spend twenty minutes at tomorrow’s family dinner gushing about your next big business idea. Cool. My suggestion is: Plan to spend at least seven minutes graphing out the specific actions you’re going to take to execute that idea.

That’s a three-to-one ratio. And it’s a preemptive measure to satisfy the inevitable skepticism that will arise.

Remember: People aren’t trying to pummel your dreams – they’re trying to protect you from failure. How will you build firm confidence in the efficacy of your efforts?

2. Money is the great mouth closer. I’ve never been a financially fueled entrepreneur. It’s just not that important to me. Making a name for myself, yes – making money for myself, not so much.

All I ever wanted to do was earn enough revenue to support my lifestyle, underwrite my addictions, sustain my enterprise and bankroll my capacity to contribute to the world. That’s it. Everything else is just an indulgence.

However, about two and a half years into my entrepreneurial endeavors, I noticed something: When I started making money, people stopped asking questions.

It was like I was instantly and unarguably legitimate in their eyes. Especially the people closest to me. And whether you’re driven by the dollar or not, the reality is: The quickest way to shut people up is to show people zeroes.

Often times, that’s the Queen of Spades. That’s what closes cynical people’s mouths. But don’t worry: It doesn’t make you greedy – it makes you genuine.

As long as the money card isn’t the only one you play, I say slap that baby down on the top of the pile and shoot the moon with every bullet you’ve got. How will you use profitability to prove your legitimacy?

3. Align individual dreams with mutual values. Enrolling your loved ones into your dream is a continual process of constitutional alignment. That’s the secret to bringing people on board:

Helping them understand that the thing you do is in direct connection with the person they are. Otherwise they’ll never cross that threshold.

My friends Kim and Jason Kotecki come to mind. Their company, Escaping Adulthood, educates people worldwide on how to add fun to and subtract stress from their lives.

But it didn’t start out that way. Originally, it was just Jason’s comic strip. Ten years later, their characters (both in person and in print) took on a life of their own.

Now, Kim and Jason deliver strategies to their audience via multiple channels: They write books. Deliver workshops. Create artwork. Conduct interviews. Produce videos. And build learning systems to cure people of Adultitis.

The cool part is, Jason and Kim personify a healthy alignment between their dreams and values. “Although we hold very different roles in our enterprise,” Kim told me, “both Jason and I share the core mission of wanting to serve children. That way, whether we work with parents, educators – or the kids themselves – we’re able to combine our vision with our values.”

Lesson learned: If you want to make something more meaningful to people, align individual plans with shared purposes.

As best-selling author Tom Winninger once told me, “The finish magnifies the quality of the wood. And when people see themselves in the reflection, they will buy your furniture.” Do your loved ones see their values reflected in your vision?

4. Forego approval and start firing. One school of thought is to execute without permission. To just go. To say, “Screw it! I’m moving to Nashville.” If this applies to your situation, consider three counter-intuitive suggestions made by friends of mine.

First, Jamie, the owner of a local fitness club. He suggests to make your dreams so big and so out there that no one can touch them but you. “If someone can reach your dream or take it away,” he told me, “then it wasn’t big enough in first place.”

Secondly, consider what my Facebook friend Alejandro advises: “Just keep insisting until they eventually get tired of trying to stop you.”

Finally, you might attempt what my colleague Gil recommends: “Don’t even try. You have only so much energy to expend. Don’t burn it trying to blow away the black clouds in your life.”

Naturally, these suggestions aren’t the most practical. Especially when you’ve got bills to pay and mouths to feed. And while not everyone has the luxury of maintaining such a drastic mindset, it’s still a valid point to make: Approval is overrated.

It all depends how on much permission you require. Who knows? Maybe convincing the people you love that your crazy idea isn’t a pipe dream IS the pipe dream it itself. And if that’s the case, screw ‘em. Are you asking, “Who’s going to let me?” or wondering, “Who’s going to stop me?”

5. Mount an evidence campaign. Few things are more existentially agonizing than the prospect of not mattering. And what sucks the most is that you’re rarely the first one to find out.

It’s only through research and feedback and Google Alerts that you’re able to uncover the evidence that validates the importance of what you do. My suggestion is: Don’t just accumulate it – articulate it. Especially to the people who love you the most.

For example, I recently received a wonderful piece of fan mail from an audience member. But it wasn’t addressed to me – it was for my parents. Naturally, I called my folks as soon as I got back to the hotel room and read them the letter:

“Dear Mr. and Mrs. Ginsberg: From one parent to another, congratulations. You did an exceptional job giving your son all the tools and love to equip him to become what he is today. Thank you.”

Lesson learned: Anytime you move the dial with what you do, memorialize your accomplishments. Your evidence will take them miles beyond reasonable doubt. How are you constantly reminding the people you love that what you’re doing matters?

6. Patience might be your only proof. “If I attempt to turn this crazy idea into a reality,” you think, “my family will disown me, my spouse will leave me and my children won’t want to be seen in public with me.”

First of all, don’t be ridiculous: Your children never wanted to be seen in public with you in the first place.

Secondly, your fear response is perfectly healthy and normal. Hey, it happens to the best of us – even me.

After wearing a nametag twenty-four seven for ten years, I’ve finally come to terms with the fact that I’m a social liability. God, can you imagine how insane that’s going to drive my future children? Poor kids.

But that’s part of the deal. Sometimes you have to allow patience to triumph on its own time. That’s what legendary author JK Rowling explained in her 2008 commencement speech to Harvard University:

“My parents thought that my overactive imagination was an amusing personal quirk that could never pay a mortgage or obtain a pension.”

A half billion books later – that’s billion with a “b” – she showed them. Harry Potter might have been fiction, but the irony wasn’t.

Lesson learned: Sometimes the only way to get through to people is to become ridiculously successful despite their efforts to dissuade your dream.

Just make sure you don’t become smug in the aftermath of your own achievements. Otherwise you’ll blow any chance you had of reaching the people who matter most. How patient are you willing to be?

ULTIMATELY: You can change the world with your crazy idea.

And I know it’s not easy soliciting the support of the people closest to you.

But success never comes unassisted.

Who do you need to bring into your dream to make it a reality?

For the list called, “21 Things I Learned While Spying on Myself,” send an email to me, and I’ll send you the list for free!

* * * *
Scott Ginsberg
That Guy with the Nametag
Author, Speaker, Entrepreneur, Mentor

Who’s quoting YOU?

Check out Scott’s Online Quotation Database for a bite-sized education on branding success!


Daily updates straight to your inbox.


Author. Speaker. Strategist. Songwriter. Filmmaker. Inventor. Gameshow Host. World Record Holder. I also wear a nametag 24-7. Even to bed.
Sign up for daily updates


Daily updates straight to your inbox.

Copyright ©2020 HELLO, my name is Blog!