The Smartest Move You’re Not Making: Ask for Help Sooner

Heather Monahan

Five years ago, I connected with Heather Monahan on LinkedIn. This month, we’re finally partnering.

I’m excited to announce Heather’s joined Stride as one of our Founding Sponsors. Her expertise and experience providing razor-sharp content on confidence, overcoming adversity, and leadership will help Stride and our wonderful members scale and transform.

A Wake-Up Call From Someone Who Saw the Bigger Picture

After my family sold our business, I started building Stride — a new community for family business leaders. I assumed it would be like my last business selling toilet paper and paper towels: transactional, measurable, straightforward.

It’s not. It’s personal. It’s about people, not products. Heather called me out — kindly but directly.

“Jason, you’re building a movement. These family business owners don’t need another network. They need real connection.”

That landed hard. And it was true.

What’s wild is that she’s been in my network this whole time. I liked her posts. I watched her rise. But I never asked for help. Why?

Success Doesn’t Automatically Transfer

This was my mistake — and maybe it’s yours too. I assumed past success meant future success in a different field. But every new venture requires fresh perspective, humility, and help.

The smartest thing I did was reach out to someone who’s already built what I’m trying to build. Heather helped me zoom out, see the bigger picture, and aim higher.

So, Who’s in Your Network That You’ve Been Ignoring?

You probably already know someone who could help you level up.
Tag them. Thank them. Or just reach out.

Don’t wait five years. Ask sooner.

You’ll be glad you did.