As I get ready for my fourth Zoom discussion for the NextGen Playbook on June 11, I’ve been reflecting on something that’s consistently hard: inviting close friends and family to support my work. Oddly enough, I find it easier to send invites to strangers or distant acquaintances than to the people I’m closest to.

Each time I prepare to reach out to friends, especially those I’ve invited before, I find myself thinking: I hope I’m not bothering them. Even though I’d love for them to be there, I hesitate—worried I’m asking too much or risking the relationship.

Why We Overthink Reaching Out to Friends

With friends, there’s a deeper emotional investment. I catch myself creating stories in my head when someone doesn’t reply—assuming I annoyed them or crossed a line. The truth is, I’ve been approaching these invites as if I’m asking for a favor rather than offering something meaningful.

You’re Not Asking—You’re Offering

My events offer career advice and real conversations about generational differences at work. That’s not a favor—it’s a valuable opportunity. When I shift my mindset from asking to inviting, the fear starts to fade.

This mindset applies to any new business or project. Your friends aren’t just passive observers—they know your story. They often want to support you; they just need the opportunity.

Flip the Script: Serve, Don’t Sell

Reframing your business or passion project as serving others instead of selling to them can take the pressure off. People invest in people. And when you show up authentically, it gives others permission to do the same.

Your work might inspire someone else to share what they’re passionate about—because you took the first step.

Stay Connected Between the Asks

One thing that helps? Check in outside of invitations. Send a message on their birthday, celebrate their wins, or just say hello. It reminds both of you that your relationship isn’t transactional.

My Strategy: Feel the Fear and Do It Anyway

When someone comes to mind and I hesitate, I use a 24-hour rule: I reach out within a day before I overthink myself into inaction. It keeps me moving and reminds me not to let fear make the decision.

Take the First Step

If you’re working on something new and feeling nervous to share it, I get it. But I also encourage you to go for it. Whether we’re close friends or complete strangers, I want to hear what you’re working on—and I bet others would too.

Your community is ready to show up. Just give them the chance.