I’ve had a pretty eclectic career since I started working long ago as a Mathematics teacher in the distant mists of the past. Did I want to be one? No. I succumbed to pressure from my father, who insisted that a government job would give me security. I caved in and accepted it. But as I often tell my workshop participants, boredom can be a powerful motivator for change. I eventually broke out of that box, moving into real estate, recruitment, journalism, and corporate training—proving to myself that living a multi-hyphenate life was not just possible, but deeply fulfilling.
Key Takeaways
- The Multi-Hyphenate Mindset: A multi-hyphenate professional leverages a portfolio of diverse skills and identities (such as Trainer-Coach-Writer) rather than confining themselves to a single, traditional corporate job title.
- Portfolio Career as an Economic Shock Absorber: Relying on a single skill set creates professional volatility. Cultivating additional “hyphens” builds a personal hedge against industry shifts, providing career agility during economic disruption.
- Cross-Disciplinary Skill Synergies: Diverse career strands are not distractions; they reinforce one another. Expertise in one arena (e.g. journalism or data analysis) feeds into and elevates primary leadership competencies such as coaching and strategic decision-making.
- Passion vs. Paycheque Balance: A hyphen does not always require immediate commercialisation. Pursuing non-monetised passions builds neural plasticity, prevents executive burnout, and expands creative perspective.
- Elevating Baseline Professional Confidence: Successfully stepping into new, unfamiliar disciplines expands an individual’s comfort zone, boosting overall confidence and problem-solving capability in their primary executive role.
- The Multi-Hyphenate Audit: Executives and teams can audit their weekly routines to dedicate time toward sidelining non-traditional skills or interests, treating them as long-term investments in personal authority and organisational agility.
A few years ago, I wrote an article for The Star titled “The Joy of the Hyphen”, reflecting on this very journey. Hearing of my frequent career changes over the decades, an old uncle of mine once affectionately called me a “rolling stone”.
But in today’s rapidly evolving world, being a rolling stone isn’t a liability—it is a superpower. Today, the world has a much sexier name for it: being a multi-hyphenate.
The Metaphor of the Multi-Hyphenate Life
In the corporate world, we are taught to specialise. We are told to pick one box, stay in it, and climb a single vertical ladder. But true security doesn’t come from a single title; it comes from the depth of your personal portfolio.
Think of your mind as an investment fund. If a financial advisor told you to put 100% of your life savings into a single, volatile stock, you would walk out of the room. Yet, we do exactly that with our careers when we rely on just one skill set.
The global disruptions of recent years have shown us the danger of putting all our eggs into one basket. The people who thrived were those who knew how to pivot. When you look at my title today, it reads Trainer-Coach-Writer-Artist-Innovator-Storyteller. Each hyphen isn’t a distraction; it is a pillar that reinforces the others.
Why Every Hyphen Strengthens Your Core
When I look back at my journey from teacher-journalist-trainer-coach-writer-artist, I realise that none of those experiences were wasted. They all feed into one another. My background in mathematics helps me analyse organisational data; my years in journalism allow me to ask incisive questions as a coach.
When you allow yourself to add hyphens to your name, you unlock three powerful organisational benefits:
- The Ultimate Back-Up Plan: A hyphen gives you a built-in economic shock absorber. Whether you choose to monetise a side skill immediately or keep it in reserve, it ensures you are never at the mercy of a single industry shift.
- The Passion vs. Paycheque Balance: A hyphen doesn’t always have to be a commercial side hustle. It can simply be a passion that feeds your soul and prevents professional burnout. That is exactly how my journey as a painter began—by challenging an old schoolteacher’s limiting belief that I “couldn’t do art to save my life”.
- Elevated Professional Confidence: Stepping into entirely new arenas expands your comfort zone. When you prove to yourself that you can master an entirely different discipline, your baseline confidence in your primary career skyrockets.
“Your hyphens don’t even have to be a side hustle. My journey as an artist started purely as an interest. Today, it’s a small business with a purpose, where a portion of the proceeds goes directly to a cause close to my heart. It didn’t dilute my corporate work; it enriched my soul and vastly raised my confidence.”
— Sheila Singam
Shifting Your Mindset: How to Add Your First Hyphen
Growth always begins in the mind. If you are feeling trapped in a single professional identity, it is time to break out of the box.
The Multi-Hyphenate Audit
Look at your current daily routine. What is one skill, hobby, or deep interest you have sidelined because it “doesn’t match your job description”? Dedicate just two hours a week to developing it. Do it not because you need an immediate payout but because you are investing in the architecture of your own authority.
Who knows? Tomorrow you might add hyphens like pastry chef, podcaster, or poet to your name. As long as it takes you to a place of personal fulfilment, let them call you a rolling stone. Gather your moss, build your portfolio, and expand your human equation.
What hyphens are you ready to add to your name today?
Walking the Talk: My Kaleidoscope of Art The multi-hyphenate life isn’t just a theory I teach; it is how I live. After shattering the limiting belief that I couldn’t do art, I turned my passion into a purpose-driven project. I invite you to see where this “rolling stone” has gathered her moss. You can follow my artistic journey, view my latest pieces, and see how I balance the canvas with the corporate world over at my Kaleidoscopic Art Facebook Page.
Frequently Asked Questions
What does it mean to be a multi-hyphenate professional?
A multi-hyphenate professional is an individual who leverages a portfolio of diverse skills and identities—such as Trainer-Coach-Writer—rather than restricting themselves to a single, traditional job title.
How does a multi-hyphenate career protect against economic volatility?
By cultivating multiple skill sets, you avoid putting all your professional eggs into one basket. If one industry faces a downturn, your additional hyphens serve as immediate backup plans or alternative avenues for income generation.
Can a hyphen be a hobby, or must it be monetised?
A hyphen does not have to lead to a pay cheque. It can simply be a structured passion project or creative outlet that builds neural plasticity, prevents burnout, and enriches your overall perspective.
Media & References
- Original Publication: This insight article is expanded from the national lifestyle feature, “The Joy of the Hyphen”, originally penned by Sheila Singam and published in The Star Newspapers.
