Date posted: 27/04/2018 5 min read

Side hustle your way to success

Former Rugby World Cup winner and pilot Shannon Willoughby shares her tips for career transitioning success

In brief

  • Goal setting is important for career progression and success
  • Passion and a support network are essential contributory factors
  • Career changes and “side hustling” are becoming more common due to technology

Shannon Willoughby

Shannon Willoughby is the ultimate career story success, having kicked goals as a professional rugby player, qualified as a commercial pilot, and founded several ecommerce businesses.

New Zealander Willoughby is one talented lady who wears many hats. Partly, she says, as a necessity, given rugby was not, until recently, a high earning career. This former Black Ferns team player, who won the World Cup in 2006, has achieved success in multiple careers.

She’s a self-confessed “side hustler” and set up ecommerce businesses, initially, to fund other projects, such as her goal of becoming a pilot. Willoughby is currently in Vietnam automating her ecommerce store businesses, which include NZ Aromatherapy, to enable her to step back and focus on other ventures. Also in the pipeline is the development of an aviation-related app, and she runs a consulting and mentoring business for other female entrepreneurs.

“I love helping people to break down barriers and succeed. It’s important to share my knowledge; about what’s worked for me, how I’ve approached challenges, and the rewards of being brave enough to take a risk.”

Yet, she’s incredibly humble and takes her accolades in her stride, “I never think of myself as having had a career,”

So, what does it take to achieve phenomenal success in such diverse, and traditionally male-dominated industries?

Willoughby believes it’s important to focus on the positive. Despite experiencing a few derogatory comments from males regarding being a female in both rugby and aviation, there were a lot more men encouraging and believing in her to succeed rather than willing her to fail.

Goals and passion

The common thread between all her very different career choices is her incredible passion. Becoming a rugby pro or a pilot are not the kind of careers you just fall into, they take vision, inspiration, determination, dedication, and a  huge amount of talent and hard slog to make it.

The inspiration to become a professional rugby player came to Willoughby from seeing Black Ferns in 1998 while playing school girl rugby. “I thought wow, I want that.” It was the same with flying, after watching Top Gun she felt inspired to achieve that goal too. In each case she set about taking small steps towards these goals.

Goal setting, Willoughby says, is a really important factor to her successes. Also, sharing your goals with others helps, it holds you accountable and motivates you.

Shannon Willoughby

Overcoming hurdles

The biggest career challenge for Willoughby was regaining confidence after being hospitalised at 32 after suffering a stroke. She’d given a lot up, including retiring from rugby and putting her businesses on hold, to focus on piloting.

“Learning to believe in myself at that time was really difficult”, she said, and being told she’d never be able to fly again hit her hard. Yet against all odds, a year after her stroke, she was playing rugby again, and after 18 months she was given the all-clear to fly.

She credits her incredible support crew with teaching her to “never, ever give up.” At every step of your career stage, having a solid network; of family, friends and mentors has been most important encouragement and support for Willoughby.

“You underestimate how much other people want you to achieve your goals, and you don’t know how much someone can help you,” she says.

This was very clear to Willoughby when she was invited to The International Women’s Forum & Leadership Foundation in 2017. Attended by the world’s top female leaders, including honorary inductee Hillary Clinton, “every one of them wants us to succeed.”

Despite the amazing recovery from her stroke Willoughby says it marked a change in her career path, redirecting her to focus on the ecommerce businesses as a career. Whereas previously they had been a means to fund the piloting.

5 tips for career success and transition

  1. Be brave enough to follow your goals
  2. Don’t expect a career transition to be smooth, there’ll be bumps and hurdles
  3. Seek advice and form a solid support network
  4. Be open to change and believe anything can happen
  5. Be prepared to deal with anything life throws at you