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Retired college director launches travel coaching business

Lisa Osborne is encouraging more women to solo travel through her business, Dr Lisa Osborne — Global Pathways (Photograph supplied)

When Lisa Osborne retired from the Bermuda College after 29 years, she was determined to stay busy.

“I wasn’t going to be sitting around with my feet up watching Netflix,” said the former director of learning assistance.

Instead she launched coaching business Dr Lisa Osborne — Global Pathways to empower people through personal development and travel, particularly women.

“The challenge right now is the transition from the mindset of an employee to entrepreneur,” she said.

Initially, Dr Osborne saw herself working with female retirees like herself.

“This year and onwards, Bermuda is going to see a spike in the number of retired people in the population,” she said.

In 2016, nearly 17 per cent of Bermuda’s population was over 65. In the decade since, that figure has risen to almost 25 per cent, meaning that one in four people on the rock is a senior citizen.

Life coach Lisa Osborne at Praça do Comércio, or Commercial Square, in Lisbon, Portugal (Photograph supplied)

People in this age group are calling her, but she is also finding an unexpected demographic of clients — Gen Zs between 14 and 29.

“Some of them are venturing out on their own for the first time and need advice,” she said. “Others are just travelling to university for the first time and need direction. They may not have support systems in place.”

Dr Osborne is particularly interested in women and solo travel and runs her own YouTube Channel, @IslandGirlGoesGlobal.

“I discovered solo travel as a way to build my own self-confidence,” she said.

One of her most recent trips alone was to Paris, France.

“A lot of women tell me they want to travel alone, but they are nervous,” she said.

She is all for family trips or girls’ trips, but said sometimes your schedule is never going to align with everyone else’s.

When women say they want to go some place on their own, they often get negative feedback in the form of: “Are you sure?”

“The biggest problem is fear of the unknown,” Dr Osborne said. “You can ask other people’s opinion of a place, but take it with a grain of salt. Decide based on your own research.”

She said it comes down to doing what you need to do in a foreign country, such as covering your head with a scarf, to remain safe so you can relax and have a good time.

Right now, she is travelling but is taking calls from clients by Zoom.

“I am going to be back in Bermuda for a couple of in-person workshops for some organisations,” she said. “I am working out some logistics but plan to open my own office in Bermuda in a couple of months.”

The cost of the service is based on the client’s needs.

“An initial discovery consultation is $75 whether that is in regards to life coaching or consultancy work,” she said.

See more about her travels on Instagram @islandgirlgoesglobal

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Published February 20, 2026 at 7:48 am (Updated February 20, 2026 at 7:47 am)

Retired college director launches travel coaching business

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