The Road Less Travelled: Bold Moves for Career Advancement

Estimated reading time: 8 Min
Many dream of steering professional roles in new directions. The thought of taking that first step can be daunting. However, career advancement depends on it!
Have you ever found yourself staring out of the office window, wondering what route your career could take, yet feeling anchored to the spot by uncertainty?
I’m sure you realise you’re not alone.
Welcome to the road less travelled in the realm of career advancement—it’s a path where bold moves and courage are your best companions.
Deep down, the new path might well require a change of mindset.
Here we focus on practical steps you can take, which can also have a profound effect on your mindset.
In this post, we’ll reveal an approach to making unconventional choices that can lead to fulfilling and unexpected career achievements.
It should be an exciting journey that reshapes your professional outlook.
Figuring Out Your Career Advancement Direction
Imagine you’re at the helm of a ship, the vast ocean of career possibilities stretching out before you.
How do you decide which direction to sail?
This is where your career compass comes into play.
Obviously, I guess it’s a metaphorical compass that guides you through inward-looking self-awareness towards your true career aspirations.
To create your career compass, ask yourself:
What are my core values?
What am I truly passionate about?
What does success look like to me?
Take your time to answer these three questions.
The answers are like guiding stars, helping you navigate through murky societal expectations and peer pressure.
Realise that a ship without a destination is left to the mercy of the seas—knowing your end goal is the first step in plotting a course that’s uniquely yours.
This is about laying the foundation for living your life deliberately.
Think back to a time when you risked something unknown, perhaps the first time you tried to ride a bike and wobbled uncontrollably or strummed the strings of a guitar, creating harmony (or more likely, disharmony) from silence.
Just as these experiences signalled new possibilities, understanding your career compass can point out paths you never considered before, highlighting the way for bold, potentially career-defining decisions.
The Art of Risk-Taking
Why do we cling to the safety of the harbour when adventure awaits us beyond the horizon?

The answer often lies in our aversion to risk.
An aversion is a natural outcome of our brain’s reluctance to support change unless we persist!
The art of risk-taking is a fundamental skill in the world of career growth.
The skill of assessing risks is about differentiating between a blindfolded jump off a cliff and a metaphorical leap of faith into the unknown.
To master this art, we must first overcome our fear of failure, viewing it instead as a stepping stone to success.
The thing is that a fear of failure stops us from assessing risk at the first hurdle.
Consider the tales of intrepid explorers who, despite facing storms and uncertainties, discovered new lands and treasures.
In the career context, this could translate to accepting a job in a new field, relocating for a unique opportunity, or even starting your own venture.
Reflect on a time you took a calculated risk—maybe it was presenting an unconventional idea in a meeting, perhaps similar to proposing a radical new theme for a community festival.
The outcome, whether it was a resounding success or a learning experience, added a rich layer to your character, teaching you lessons only the road less travelled could have offered.
Networking Unconventionally
Networking is a term that conjures images of awkward small talk at industry events.
But what if we redefined networking as searching for and connecting with like-minded souls, sharing passions and ideas in settings that spark fun and creativity?
This positive approach can lead to genuine relationships and unexpected career opportunities.
Think outside the work environment—network in environments where you’re most passionate.
For example, during the 1990s, for me, it was the vibrant community proposal of a water sports festival, where conversations flowed as freely as the wine!
Each interaction was more than just an exchange of business cards; it was an opportunity to share dreams, experiences, and ideas.
Consider your own hobbies and interests.
Perhaps it’s time to join a tennis club, not just for the love of the game but as a way to meet potential mentors, partners, or clients.
Or maybe volunteer for a project outside your job scope, exposing you to new people and perspectives.
Networking in these settings isn’t just enjoyable—it’s more likely to lead to meaningful connections that can steer your career in exciting new directions.
Acquiring New Skills and Knowledge
The world of work is constantly evolving, and with it, the toolkit you need for success.
This is where your commitment to lifelong learning becomes your secret weapon.
But let’s sidestep the conventional classroom setting.
Learning in this context means exploring more unconventional avenues of skill acquisition.
Think of the internet as a vast library, overflowing with knowledge on every imaginable subject.
Online courses, webinars, and tutorials offer a treasure trove of expertise, all at your fingertips.
You could explore this digital treasure trove to learn coding, digital marketing, or even the nuances of graphic design—or any other skills that could open new doors in your career.
However, don’t stop there!
Unique experiences forge unique individuals.
Volunteer for projects that push you out of your comfort zone.
Perhaps join a start-up, if only for a short while, to grasp the essence of entrepreneurship.
Such experiences are like adding vibrant, diverse brush strokes to your professional CV, making you stand out in the crowded job market.
My own journey from the structured world of IBM to the dynamic world of a solopreneur taught me more about business management and resilience than any course could.
So, challenge yourself.
What new skill can you learn this year, and how can it highlight a surprising path in your career?
Creating Opportunities Instead of Waiting for Them
In the tapestry of your career, you are the artist, not merely a spectator.
This means not waiting for opportunities to come knocking, but creating them yourself.
This proactive approach is the foundation for a dynamic, evolving career and living life deliberately.
You could begin by identifying gaps in your industry or workplace that align with your passions and skills.

Are you aware of a project that no one is willing to tackle?
A new market that has yet to be explored?
A new opportunity that others haven’t spotted yet?
These are your canvases, waiting for your brush.
I took inspiration for my own leap of faith when I chaired the organising committee for a water sports festival.
It was a blend of passion and madness, with only an idealistic vision and a relentless drive.
The success of this venture opened countless doors and taught me the power of initiative.
Therefore, think about what you can initiate in your current role or community.
By creating opportunities, you not only advance your own career but can also contribute to your industry, workplace, or community in a meaningful way.
Balancing Boldness with Wisdom
As we travel through the uncharted territories of our careers, it’s appropriate to balance our boldness with wisdom.
This doesn’t mean dampening our adventurous spirit, but rather navigating with a map and a compass.
Listen to your intuition, but also investigate and weigh the risks and benefits of potential decisions.
Seek advice from mentors who have walked their own paths, and learn from their experiences.
Realise that the goal is to make informed, strategic decisions that move you forward.
Consider the sailor, who must read the weather before setting sail.
In your career, this translates to understanding the market trends, the health of your company, and the dynamics of your team.
Like in sailing, preparation and timing can make all the difference between a joyful journey and a tempestuous trip.
Reflect on your own career to date.
Where do you need to be more adventurous and courageous, and where might you need to exercise more caution?
Finding this balance is an art in itself that will guide you safely to your desired destination.
It starts with thoughtful and honest self-assessment.
Summary
Setting off up the road less travelled in your career is a journey filled with risk, adventure, and learning.
By understanding your career compass, embracing risk, networking unconventionally, acquiring new skills, creating opportunities, and balancing boldness with wisdom, you prepare yourself for a journey towards success that is uniquely fulfilling.
Remember, the road less travelled is not just a path you find to walk on; it requires that you discover your own way of walking.
So, lace up your boots, set your sights on the horizon, and take that first step towards the career adventure of a lifetime.
Now, I’d love to hear from you!
Have you ever taken a bold step in your career that led you down an unexpected path?
Or is there a strategy from today’s post that you’re excited to try?
Share your stories and thoughts in the comments below.
Let’s inspire each other to embrace the roads less travelled in our careers.
😉
Richard
Reference Materials
These materials can provide further insights and strategies to help navigate your career path with clarity, innovation and courage.
Books
- “Daring Greatly” by Brené Brown – This book explores the power of vulnerability in transforming our lives, including our careers, encouraging readers to take bold and courageous steps.
- “What Color Is Your Parachute?” by Richard N. Bolles – A classic career guide that helps readers define their interests and skills, ideal for anyone looking to make a significant career change or find what truly drives them.
- “Drive: The Surprising Truth About What Motivates Us” by Daniel H. Pink – Pink examines what motivates us in our professional lives, which is useful for understanding and harnessing your passions for career advancement.
Online Resources
- LinkedIn Learning offers courses on a variety of topics, including risk-taking, leadership, and networking outside of conventional environments.
- Coursera provides access to courses from universities and colleges around the world, making it perfect for acquiring new skills and knowledge, as discussed in the networking and skill acquisition sections of your post.
Articles and Journals
- Harvard Business Review (HBR) is a valuable resource for in-depth articles on career development, risk management, and leadership.
- The Muse offers practical advice and personal experiences related to career changes and advancement strategies.
Podcasts
- “How I Built This” with Guy Raz shares stories from entrepreneurs who took significant risks to start and build their companies, which can provide inspiration and lessons on risk-taking and creating opportunities.
- “WorkLife” with Adam Grant focuses on improving work-life balance through innovative ideas and strategies, including unconventional networking and embracing bold career moves.
Workshops and Networking Events
- Meetup.com is a platform to find and attend local or virtual meetups that align with your personal and professional interests, making it ideal for networking in non-traditional settings.