Question: does it get easier to ask for help?

I've always been the "I can handle it" guy. Don't ask questions, don't burden people, just push through. My therapist says this is a problem (shocking, I know) and that I need to practice asking for help. This week my neighbor offered to pick up my kids one day and I actually said yes instead of coming up with excuses. It felt so awkward and uncomfortable and weird. But also... he seemed happy to help? And I got 90 minutes to just sit in my car. Is it always gonna feel this uncomfortable or does that change?