When Did You Stop Dreaming?

If dreaming feels risky or irresponsible, you’re not alone. But the dreams aren’t the problem.

When I asked couples in my Wealth Together class how they felt about dreaming of their future, some of the responses hit hard:

💬 “Dreams feel risky.”

💬 “Dreams are irresponsible.”

Ouch… But I get it. I imagine some of you have felt that way too—or maybe still do.

Here’s why they said it:

These couples had taken steps toward their dreams. But the steps weren’t grounded in the right strategies, or they weren’t aligned with each other. And it didn’t work out. The consequences of those choices left them feeling vulnerable and discouraged. So now, dreaming feels dangerous.

It’s no wonder they don’t want to go there again.

They also talked about guilt (about having made mistakes), and shame around where they are now. For some, dreaming again feels like a luxury they no longer “deserve.” As if wanting more is selfish. As if they’ve lost the right to hope.

That’s a heavy place to be. And it's hard to move forward when you’re carrying that kind of weight.

Why it hurts to dream again.

If you're struggling to imagine a hopeful future, you’re probably up against some serious emotional roadblocks. Things like:

• Shame over past mistakes

• Fear of repeating those mistakes

• Guilt, telling you, “We don’t deserve that anymore”

• Overwhelm, because you’re not even sure how to fix what’s in front of you. So why dream past it?

If that’s where you’re at, I want you to know that you’re not alone. I see this all the time, and I understand.

At some point, you started blaming the dreams themselves. You might be thinking, “If dreaming is what got us into this mess, why would we open ourselves up to that again?”

But the dreams aren’t the problem. They never were.

Most likely, the issue was the steps you took to get there—maybe rushed, maybe not thought through completely, maybe not done together. That’s where things went wrong.

So, please let go of the shame 💜 Mistakes happen. Especially when you're doing something new, or doing it under stress, or doing it alone. Learning from those moments is part of what makes us stronger and wiser moving forward.

Know this: Dreaming again is not naive. It’s necessary.

If any of this sounds like you… 

If you’ve been holding back from dreaming because it feels too painful or too “irresponsible,” know that you’re not alone. You’re human. And you’ve likely just been trying to protect yourself from more disappointment.

But you still need your dreams.

Next week, I’ll share why—and how dreaming again, especially with your partner, might be the most powerful step you can take right now.