By Meredith Calloway, Chief Growth Officer
Over the course of my career, I’ve watched advisors leave this business despite having the talent and the clients needed to succeed. What wore them down was that long stretch in the middle where discomfort starts to feel like evidence you chose wrong. I understand the instinct, since frustration can feel so much like failure while you’re inside it.
I once heard a Duke professor tell a room of high school students that the dominant feeling between where you are and where you want to be is frustration, and that the most successful people are the ones who can tolerate it longest. If you never learn to sit with that feeling, you never reach the part that makes the effort worthwhile. That advice holds as true for a business owner as it does for a teenager.
Rachael O'Brien, founder of How Far Adventures, learned that lesson earlier and harder than most. She had built a career as a television reporter and a sports broadcaster when her 13-year marriage ended, leaving her a single mom to a three-year-old and a one-year-old. Because she wanted to be home when the bus came and when the boys were sick, she turned to travel, which had always been how she recalibrated. She did it entirely on her own, securing her own credentials and selling Disney and the Caribbean to the moms around her. Eventually she was earmarked by Disney and booking six trips a month between early mornings, late nights and long hours on hold. She found GTN in February of 2020 when she attended our Book More Travel Workshop in Charlotte, NC, but within weeks of that event, the pandemic shut the industry down.
Rachael has a phrase for what carried her through all the ups and downs: We can do hard things. For example, she took her boys to Costa Rica for nearly two months during the school year to give them the world as a classroom. The trip delivered accidents, lice, a broken toe and an illness that laid her flat. This all happened during wave season, which meant she was checking into five-star hotels just to get reliable internet for her client work. After facing all those challenges with her boys, she came home knowing that they could do hard things, and they could do them together.
Another “hard thing” Rachael faced on her journey was accepting help. She described herself as an island in those early years, raised on the belief that nobody was coming and she had to pull herself up alone. For her, joining a host agency felt like she was letting go of an identity that had carried her through her worst season. But Rachael did the work to overcome this mindset block, and found that every time she intentionally leaned in, a door opened. That is a big part of why we’ve built GTN around community rather than competition, because a rising tide lifts all boats. I’ve seen how much faster advisors grow once they stop treating support as a weakness.
That Costa Rica trip is a good example of those two hard things working together. Before anything was booked, Rachael said it out loud in one of our meetings, telling us she was taking her boys out of school and going. Saying it in front of people who believed in her made it easier to trust that she could do it, and it also turned the idea into a real plan to which she was held accountable.
Rachael set out to show her boys a world bigger than their comfort zone, and she learned the same lesson about her business along the way. However far you hope to take your own business, the road will more than likely run through stretches you’d rather skip. But every time you face those stretches head-on and get to the other side, it reminds you that you can do hard things.
If you love hearing stories like Rachael's, tune into The Travel Business Unpacked podcast! Each episode dives deep into the real stories, practical strategies, and transformational moments that turn travel dreams into thriving careers. Listen and subscribe on Spotify and Apple Podcasts, and check out Rachael's full episode here.