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Lessons in Resilience: The Road from Bartending to the Boardroom

Career paths are rarely perfectly linear, and mine definitely wasn’t. From flipping burgers to leading international companies, I've embraced the twists and turns, learning invaluable lessons along the way.

Looking back, it’s clear that cultivating a spirit of entrepreneurship and intrapreneurship, coupled with a willingness to take risks, has been the key to building resilience and achieving success.

This is a summary of the journey so far, along with a few pieces of advice I would have shared with my younger self if I had the chance.

Behind the Bar

As a teenager, I couldn’t sit still. My early jobs – from selling vinyl LPs at Woolworths to serving drinks as a barman – instilled in me a strong work ethic and the ability to adapt to different environments.

These experiences, while seemingly unrelated to my later career, were as crucial in developing essential skills like direct selling, communication, customer service, and problem-solving as any education I’d receive later in life.

My Dad once told me to stop waiting for life to come to me, and that struck a chord. The premature loss of my mother (30 years ago this month) was also a harsh reminder that life is too short for passivity.

The Corporate Years and the Entrepreneurial Itch

After university, I navigated the corporate world in London, gaining valuable marketing experience at renowned firms like Baker Tilly and PWC. But the entrepreneurial itch never left me.

In my 30s, I took the leap, relocating to Bristol and diving headfirst into the world of online startups. Balancing my role as Marketing Director, followed by 6 years with running my own travel start up, taught me the art of juggling priorities, managing risk, and the sheer determination needed to succeed as an entrepreneur.

Embracing Change and Intrapreneurship

My journey then took me into the hyper-growing world of digital media, consulting for giants like the BBC Worldwide in Bristol and Qype in Hamburg, Germany. This period reinforced the importance of staying curious and constantly adapting to new technologies and trends. It also ignited my passion for intrapreneurship – driving innovation and growth within established organisations.

Taking the Leap… Again

Relocating to Germany with my family was a significant risk, but it broadened my horizons and, crucially, deepened my understanding of different cultures. This international experience proved invaluable when I took on the role of CEO at Webgains, leading the affiliate network through a period of rapid growth in reach and profitability.

Continuing the Journey

Today, as CEO of Game Lounge, based in Malta but with a global remit, I continue to draw on my diverse experiences and entrepreneurial spirit. Building resilience has been a continuous process, fueled by a willingness to embrace challenges, learning from setbacks, and trusting my instincts.

What I’d tell a Teenage Richard

Embrace Diverse Experiences: Don’t shy away from experimentation. Every experience, no matter how small, contributes to your skillset and resilience in one meaningful way or another, even if you don’t realise it at the time.

Cultivate an Entrepreneurial Mindset: Whether you’re running your own business or working within a company, think like an entrepreneur. Be proactive, innovative, and always look for opportunities to grow.

Take Calculated Risks: Growth is impossible unless you step out of your comfort zone. Don’t be afraid to take risks, but make sure they are calculated and aligned with your goals and values. This might mean crossing into new verticals or even countries.

Trust Yourself: Believe in your abilities and instincts. Don’t let self-doubt hold you back.

Never Stop Learning: The world is constantly changing. Stay curious, embrace new challenges, and never stop learning.

My journey has been a testament to the power of resilience, entrepreneurship, and intrapreneurship. It has also been almost completely non-linear by anyone’s standards. By embracing these principles, you too can navigate the rollercoaster ride of life and achieve your own definition of success.

Link to Linkedin insight article by Richard Dennys.