Starting a business can be rewarding and deeply fulfilling, but it also requires discipline and a willingness to step outside your comfort zone.
Lisa Osborne spent nearly 30 years at Bermuda College before deciding to take on a new role as an entrepreneur.
Through her business, Dr Lisa Osborne – Global Pathways, she offers classes in English as a second language, academic coaching, life and career transition support, as well as guidance for women interested in solo travel.
“Basically, I’m doing what I’ve always wanted to do, but on my own time, and being able to fully dive into what I believe is part of the reason why I’m here, my mission here on the earth,” she said.
For anyone thinking about starting a business, Dr Osborne warned that entrepreneurship can be very demanding.
“You’ve got to work on your mindset,” she said. “It’s a shift. And I didn’t realise just how much of a shift it was going to be.”
One of the biggest adjustments is learning how to manage your own time and remain disciplined without the structure of a traditional workplace.
“When you have a job, everything’s spelled out. They want you to do this. They want you to arrive at this time. You can leave at certain times, they tell you when you can take your break,” she said.
“When you’re an entrepreneur, you decide, you choose. But having that power to make those decisions – you’ve got to have your time management sorted.”
To stay organised, Dr Osborne plans her schedule carefully and uses digital productivity tools to keep herself on track.
“Every Monday, I sit down and I map out what I am doing for the week,” she said. “If you expect your business to survive, you’ve got to be disciplined.”
She encouraged aspiring entrepreneurs to seek guidance rather than assuming they should already know how to handle every aspect of running a business.
“I submitted my registration for payroll taxes — I had to get advice on that. I went straight to the Tax Commissioner’s office, I had a meeting with a representative at the Bermuda Economic Development Corporation and that helped me tremendously,” she said.
“You have to put the pride aside and you have to reach out and ask questions.”
She believes mindset and confidence are just as important as business planning, particularly during the early stages when uncertainty and self-doubt can easily take hold.
“You’re going to encounter naysayers,” she said. “Even within yourself you’re going to experience times when you’re feeling a little doubtful. ‘Do I really have what it takes? Is this really going to work?’”
Her advice is to protect new ideas while they are still developing and focus on building skills and confidence quietly behind the scenes.
“At the very initial stage, when it’s a seed, don’t tell everybody what you’re doing,” she said. “Keep it to yourself and grow it. Grow yourself.”
Part of that growth, she said, involves continuing to learn and invest in yourself. Alongside her doctorate in education, Dr Osborne completed additional certifications in teaching English as a second language and life coaching to expand the services she could offer through her business.
“Go out and get the training that you need,” she said.
Despite the challenges that come with entrepreneurship, Dr Osborne said the experience has also been deeply rewarding because it allows her to fully focus on work that aligns with her purpose.
“These are things that I was doing for somebody else,” she said. “Now I get to do it for myself. I get to take the ownership.”
