Introduction
Most of us wait to feel brave before we begin, for the fear to leave, for the confidence to arrive, for the moment when the thing feels safe enough to try. Kerry Damiano built a life on the opposite order. She took the step first, and the confidence came after, every single time.
She has visited 146 countries and all 50 states, most of it alone, and she got there one small beginning at a time, with her fears left at home.
Why This Conversation Matters
This conversation matters because it turns the usual advice upside down. The usual advice says to believe in yourself first, then act. Kerry Damiano says the acting is what builds the belief, and she learned it by doing it over and over until the evidence was impossible to ignore.
She started traveling as a child, riding along while her mother drove the family all over the Northwest. They traveled together for about ten years, until she decided she could do it by herself. That decision, made with no guarantee, is the whole story in miniature. She did not wait until she felt ready. She stepped out, figured it out, and discovered that confidence follows the step, never the other way around.
You Do Not Have to Feel Brave First
Most people, she says, think you have to have confidence before you have courage. She has it the other way around. You have the courage to try, and once you try, that is where the confidence comes in.
I can do it, that it’s okay. I can do it on my own, and not to be fearful of that. I talk to women a lot about that, to not be fearful, and just do it. So take those steps, do it. Step out in faith, step out of your comfort zone. You’ll never know if you can do it until you do it.
She is describing a sequence, not a feeling. The step comes first. The feeling comes after. She talks about it as faith, and the comparison is exact: you get faith first, you step out, and then you get more faith. Confidence works the same way. You earn it by moving.
Her own history proves the sequence. She spent ten years traveling with her mother, building experience under her belt, and then she went alone. She ran two companies in two states, then started her own business in 2000, which gave her flexibility even when the money was tighter. She did not launch Ms. World Traveler until three years ago, in her early sixties, after a lifetime of travel. None of it happened because she finally felt brave enough. It happened because she kept stepping.
Baby Steps Are Still Steps
When someone asks her what to do if they have never traveled alone, Kerry Damiano does not tell them to book a month in Sydney. She tells them to spend one night in a hotel by themselves, then a weekend away. Do not go to Russia for two weeks first. That is not a baby step.
The advice sounds small, and that is the point. A baby step is still a step, and the confidence it produces is real. She lived it: each solo trip made the next one easier, until places that once seemed impossible, Namibia, Botswana, Zimbabwe, Zambia, Lesotho, became the normal next trip.
Travel has gotten easier around her, and she is honest about that. When she started in the eighties, very few people spoke English outside the English-speaking world, and there was no Google to find your way. Now there is Google Translate and a far more connected world. The tools changed. The rule did not.
Trust the Timing You Cannot See
Kerry Damiano talks about faith the way she talks about travel, as something lived, not performed. She trusts that there is a reason when things do not go as planned, and that the reason may not reveal itself for days, months, or even years.
On a trip to Cambodia, Laos, Malaysia, and Vietnam, a snowstorm over Seoul kept her plane circling for seven extra hours. She landed in the middle of the night with no hotel and no taxi, spent the night on the airport floor in tropical clothes, and was stuck for three days. She lost nearly all of her Cambodia time. But she arrived the night before her guide picked her up, and the trip still happened. Her read: God’s timing is perfect, and maybe she was not supposed to be where she had planned to be.
It is easy to say after the fact and hard to live on an airport floor with no coat. Her answer is plain: getting mad at the weather does not change the weather, and getting mad at the people rebooking your flight does not change the flight. You exhale, you run the strategies like a coach, and you keep going.
I recognize myself in the other side of that conversation, the part about gratitude. She came home from rural Africa appreciating a nice bathroom, a light switch, an air-conditioned grocery store. Her line stays with me: there are people out there that wish they had the life that you have. It is okay to want more, and it is still important to remember what you already have. The two truths sit side by side, and neither one cancels the other.
Growing Older, Growing Bolder
Kerry Damiano is 64, and she is blunt about what aging has given her: she is more comfortable in her own skin, cares less about what other people think, and is done pretending to be something she is not. She still uses paper tickets as a backup. She takes month-long trips now, Paris, Rome, Barcelona, New York, and Sydney is next, in March, living like a local instead of running around for three days trying to see everything.
Her bucket list still has entries. Bali is the one she is almost embarrassed she has not reached yet. Vietnam surprised her most, returning twenty-five years after a 1996 visit to find it bustling, a completely different place. The list never empties, and that is the point.
The same boldness runs through the rest of her story. She has worked in pageantry for over forty years, and she still dresses up, sequins to the grocery store, no sneakers in the house. She never married and has no children, and she is content with that. Joy, she says, is a little of both a choice and a discipline: you choose to see the beauty even in the chaos, and you practice that choice when life throws you lemons.
Lessons for Living Audaciously
Take the step before you feel ready. Confidence follows the step, never the other way around. Waiting to feel brave is how the step never happens.
Start with a baby step. One night in a hotel alone. One weekend away. A small beginning you can actually complete is worth more than a grand plan you never start.
Plan carefully, then trust the timing. Research the trip, pick the hotel, hire the guide where it matters. Then, when the plan breaks, exhale and run the next strategy instead of fighting what you cannot change.
Let the evidence compound. Each time you do the hard thing, the next hard thing gets easier. Confidence is a record of kept promises to yourself.
Choose joy on purpose. Joy is a choice and a discipline at the same time. Practice seeing the beauty, especially in the chaos, until it becomes the way you move through the world.
Conclusion and Call to Action
Kerry Damiano did not become Ms. World Traveler by waiting until she felt like Ms. World Traveler. She became her by taking the next small step, again and again, for forty years, until the steps added up to 146 countries and a life that looks like fearlessness from the outside. From the inside, it was never fearlessness. It was courage first, confidence second, repeated until the order became a habit.
The question she leaves is a practical one. What is the small step you have been waiting to feel ready for? You do not have to cross the world to take it. A night in a hotel. A weekend away. A conversation you have been putting off. Take the step, and let the confidence catch up.
Hear the full conversation on The Audacious Living Podcast.
