How I did it: This has been on my mind since childhood, when shyness made it out of the question. However, teachers standing next to me in church or music class told me for years that they liked my voice, so I knew I could sing, and felt the talent was wasted on someone so shy. Yet I loved singing with a group or when absolutely sure I was alone. By college I learned to do karyoke with large groups and strong drinks. By grad school, I used karyoke to help overcome shyness as part of my education towards becoming a teacher. The rave reviews given to me by boozehounds encouraged me and gave me confidence, but I still was afraid of singing solos in church, in the daylight, sober, in front of respected older relatives. Yet I was determined to try someday, because my grandparents faithfully attended our church and would have been overjoyed to hear me sing (if the boozehounds were any judge of vocal perfmance, anyway).
I was by no means ready to do this, however, when my beloved grandmother got sick and died. All 19 of her grandkids were recruited to take part in her funeral mass service as readers, pallbearers, gift carriers etc. or singers. Singing felt like the right choice for me, and I'd have two cousins to sing with...of course, both of them were experienced and trained. I enlisted a close friend of mine wth 3 years of voice training to prime me on the rudiments and critique my awkward, hesitant Panis Angelicus rendition during a long car ride. Although she told me there wasn't much we could cover in one day, I found her advice very helpful and met my cousins prepared to take the choir loft. There was a song in which we each had to take one verse solo, and a few with harmonies. It was such a nerve-wracking morning, but my uncle, who is also one of our church's regular vocalists, said to us, "You can't get it wrong. Remember you're singing for the love of your grandma and the glory of God, and you can't get it wrong. However well or badly you sing, everyone there loves you either way, so you can't get it wrong."
Resources: Angelica, uncle Fran, the late Sister Hildegard who taught me to play piano, Ted, Nora and Annie, Good Old Days Saturday Night Karyoke in Bloomsburg, Mary Therese the wonderful organist, and Mary Therese the supremely incredible grandmother from whom I received both the gift of my voice, the opportunity to meaningfully employ it, and the courage to sing with my whole heart.