From Corporate to Lifestyle Entrepreneur: Navigating My Unforeseen Path
From Corporate to Lifestyle Entrepreneur: Navigating My Unforeseen Path
Dare to Escape: Chapter 3
✏️ DARE TO ESCAPE: Break Free from the Rat Race and Create Your Ideal Life
This is CHAPTER 03 of my book project. Read past chapters: 1 | 2.
From Corporate to Lifestyle Entrepreneur: Navigating My Unforeseen Path
“And the day came when the risk to remain tight in a bud was more painful
than the risk it took to blossom.”
— Anais Nin
The Day My World Turned Upside Down
In the cold embrace of 2009's Canadian winter, I found myself staring into the abyss of uncertainty. Thanks to the Global Financial Crisis, the project manager role I had clung to, my safety net, vanished in the blink of an eye.
Toronto's sprawling cityscape suddenly seemed a maze with no exits, my savings a ticking clock winding down. Panic wasn't just knocking. It had kicked down the door.
A Dance of Chance
2008, a year before I left Sydney for Toronto, I had taken up salsa dancing lessons.
My friend was supposed to come with me to the first class, but he didn't show up. I seriously felt like I had two left feet and almost quit after the first lesson. But I’m glad that I stuck with it.
When I landed in Toronto, I joined a salsa school. It was a great way to make friends in a new city.
Eventually, I joined an intermediate salsa and bachata dance crew. I also started teaching volunteer classes at Toronto’s Trinity-St Paul United Church once a week.
So when I lost my job, my fantastic housemate Maria encouraged me to teach classes in our living room. I created the "Toronto beginner dance lovers" group on Meetup.com, and within two weeks, I had 200 hundred new members!
A few weeks later, six people attended my first “Salsa for Newbies” class, which was held in our living room, and I made $45.
As my passion for teaching salsa grew, a couple of my students invited me to teach at their corporate offices across the city.
It was a humbling experience to see my love for dance inspire others and lead to new opportunities.
My career as an entrepreneur had begun without me even realising it.
Volunteering: My Unlikely Teacher
Whilst salsa dancing was fun and making a little cash on the side was nice, on the professional front, I was learning how to use Facebook and Twitter for marketing and business.
I went to a workshop hosted by a non-profit called Young Social Entrepreneurs of Canada, and I was so inspired by what they were doing that I emailed them right after the event, offering to volunteer for them. Impressed by my unique mix of corporate leadership experience, Neuro-Linguistic Programming (NLP) training, and passion for social media, I ended up on their event programming and marketing team.
This experience included successfully planning, promoting and delivering YSEC’s inaugural 100-person weekend conference re:Vision 2010. Filling up a conference venue with 100 participants in less than five months is no easy feat, but we managed to pull it off. This showed me what was possible with the proper marketing and PR strategy and an excellent team to execute it.
Kaboom Hub: A Spark in the Dark
Then, after returning to Sydney in 2010, came the spark — Poy TB, a fellow dreamer met amidst the whirlwind of a business seminar, "Escape your day job."
We birthed Kaboom Hub, a Facebook ads and social media training business.
Our business failed after two years of hustling, but that experience taught me two fundamental lessons.
First, mastering your cash flow is key to keeping your business afloat while ensuring you're compensated for your hard work.
Also, picking the right business partner matters — a lot. It's vital to regularly touch base on personal ambitions and shared visions of success. This alignment, or the lack of it, can significantly influence the journey and outcome of your business venture.
Thankfully, Poy and I remain friends today, but breaking up and shutting down the business was difficult to do.
Rising from the Failures
Undeterred by past failures and following a month-long soul-searching adventure to the USA and Canada, I found my footing again as a full-time Marketing Lead at Hub Australia, a national coworking space, in 2014.
Marketing campaigns became my canvas, each event, partnership and piece of content a brush stroke that painted a broader picture of my capabilities.
It wasn't long before the seeds of a new venture sprouted from the ashes — my own content agency (or “productised service”) in July 2016. Specialising in the written word, I navigated the growth from a solo freelance endeavour to an agency team adventure, learning the intricate dance of leadership and business systemisation along the way.
2022: A Reflection in the Mirror of Time
Seven years of toil, growth, a global pandemic, and a second brush with burnout forced me again into the chair of reflection.
My wife and I moved to Danang, Vietnam. I took four months off doing client work and started swimming daily, zipping around town in our rented scooter, enjoying (way too much) Vietnamese coffee, journaling and writing again - this time, for me.
Here’s what I wrote in October 2022:
Somewhere between the start of the pandemic in 2020 and the start of 2022, I went through a rollercoaster of emotions, which led to reassessing my priorities and what I wanted out of life.
I won’t get into all the details here, but suffice it to say that I went through periods of languishing, burnout, and soul-searching. After grinding for six years, it was time to take a break and rediscover the things that brought me joy.
My wife and I also decided in early June that after being stuck in the same apartment and routine in Sydney for the past two years, it was time for us to move to greener pastures (and lower our cost of living at the same time). Danang, Vietnam, would be our new home.
In less than two weeks, we put our stuff in storage, returned our apartment keys, said bye to friends and family, and booked a one-way ticket out of Sydney.
Looking into the mirror, I saw glaring gaps in what I had been doing — poor communication & leadership, an unsustainable business model, disruption caused by a global pandemic (thanks COVID-19!), undervaluing my skills and experience (as well as others on my team), and an industry that was ripe for disruption by AI.
It was time for yet another pivot and re-invention.
2023: The Pivot to Fractional CMO
Over seven years running my content agency, I collaborated with diverse businesses, including eCommerce accounting firm Bean Ninjas, The Growth Hub, SYSTEMology, James Schramko (formerly SuperFast Business), The Change Starter, and other service-based businesses.
I observed the business owners consistently encountering challenges such as:
🌪️ Marketing overwhelm
🧭 Lack of strategic direction
🎲 Inconsistent results
📈 Scaling issues
⏳ Limited resources
💸 Concerns with overblown marketing spend.
Then the COVID-19 pandemic hit, and that only amplified existing hurdles for small businesses:
Severe reductions in marketing budgets and teams 💰
Urgent need for strategic marketing 🎯
Businesses generating around $500K+ annually lacked in-house expertise and faced unreliable agencies 🏢
Full-time Chief Marketing Officers (CMOs) were a significant expense many couldn't afford 💼
Next, The Tech Evolution Challenge
Another issue arose as generative AI and tools like ChatGPT began to reshape content production.
Many businesses struggled to leverage these powerful tools effectively, adding another layer of complexity to their marketing efforts.
The Fractional Solution 💡
The rise of "fractional Chief Executive Officers" (CXOs), including fractional Chief Marketing Officers (CMOs), presented an opportunity in this complex landscape.
I pivoted my career to offering Fractional CMO services, providing part-time strategic marketing leadership and guidance on leveraging AI in content production.
I tested the service with three paying clients in 2023, and it had different levels of success. I also made a few mistakes along the way (which I’ll cover in a future newsletter).
My one-person (plus part-time VA) business is now consistently making $10K+ per month in revenue, working with two amazing fractional CMO clients.
We’re also supporting a few other clients with productised podcast outreach and done-for-you case study services (which I’m not actively promoting).
While I’m not currently hanging out at the beach (like I was last year when I was in Danang), I’ve come a long way from long days in the corporate cubicle.
7 Life and Career/Business Lessons from My Unconventional Journey
Looking back on my past jobs, business ventures, wins, failures, and life experiences, I realise each chapter is a part of my story. Those experiences taught me way more about myself than any fancy achievement or status symbol ever could.
Now let’s take a look at some of the most important lessons from my road less travelled, shall we?
Embrace Uncertainty for Growth
Uncertainty isn't just a roadblock; it's a springboard into exciting new chapters. When life feels upended, that's your cue to uncover the opportunities waiting in the wings.
Persist Through Challenges for Rewards
Even when the going gets tough, the grit to keep going can unveil benefits you never anticipated. From mastering new hobbies to overcoming challenges, perseverance is your secret weapon.
Transform Passion into Opportunities
Your passions aren't just pastimes; they're pathways to unexpected doors. Sharing your interests can lead to opportunities that might reshape your career.
Leverage Volunteering for Growth
Volunteering isn't just about giving back—it's a goldmine for personal and professional development. It broadens your network and adds a rich layer of experience to your resume.
Extract Lessons from Failures
Failures are far from final—they're invaluable lessons in disguise. Each misstep offers insights, from honing your business acumen to building resilience.
Recognise Luck and Chance as Allies
Never underestimate the power of being in the right place at the right time. Openness to serendipity can pave the way for breakthroughs you never saw coming.
Cultivate Supportive Relationships
The company you keep can significantly shape your journey. Supportive relationships offer more than just encouragement; they provide practical advice, assistance, and opportunities that might otherwise remain undiscovered.
And so, Your Dance Begins...
As you step into the rhythm of your own journey, remember the lessons carved from the trials and triumphs of those who've danced before you.
Be bold in seeking wisdom from those who've navigated the path you aspire to tread.
Don't hesitate to extend your knowledge and support to those looking up to you, enriching your journey and theirs.
Embrace the falls as opportunities for growth, and always be ready to rise, armed with newfound insights and a community that supports you.
Your path in the passion economy is uniquely yours to forge, but the courage to move forward, the wisdom to learn, and the generosity to share will illuminate your way.
Start today by identifying one step you can take towards your dream: reaching out for mentorship, joining a new networking group, or simply dedicating time to hone your craft.
The dance of discovery, growth, and fulfilment awaits you.
Take Action:
Reflect on a recent challenge or period of uncertainty. Identify one actionable step you can take today to turn this situation into an opportunity for growth or learning. Share your action plan or insights below!
Next week:
Chapter 4: Cultivating an Entrepreneurial Mindset
The mindset vs. skillset debate
Predictable world vs. stochastic world
The role of randomness and luck in success
Overcoming fear, embracing risk and uncertainty
Free subscribers can view these essays for 48 hours post-publication.
Paid subscribers can join the community discussion (add comments/feedback directly at the bottom of each update and ask questions), enjoy full archive access, and additional benefits.
Your Feedback Matters
I value your input and would love to hear your thoughts. Together, we can make this book a reality.
Where to from here:
Reply or comment - to provide feedback, thoughts or comments on this chapter.
Upgrade - join the community, comment on posts via Substack, ask questions, access the entire archive of all past and future newsletters, and more.
Share - forward this to anyone you know who will enjoy reading it and benefit from future chapters.
👍 3 THINGS THAT CAUGHT MY ATTENTION
1/ Attend: Learn Angel Investing (and out a Real Deal through its paces)!
Did you know that you can start your angel investor journey with as little as $5,000?
Dive into the world of angel investing with guidance from an esteemed Berkeley professor and author, alongside two seasoned angel investors who have all placed their bets on Heatseeker AI.
Reserve your spot now and take the first step towards becoming a savvy angel investor.
Full transparency: I’m currently the head of marketing for Heatseeker.ai.
By the way, if you or somebody you know has a community or newsletter supporting Australian startups and scaleups - let me know! I’d love some help spreading the word about this event and I am open to win-win co-marketing collaborations.
2/ Read: Legal Issues for Fractionals & Startups - What to look out for in your Customer Agreements & Why
Written by Brian Heller, a fractional, virtual, on-demand general counsel with 20+ years of legal and biz dev experience doing deals and drafting and negotiating tech contracts.
This blog post covers:
• Better payment and collection terms & practices.
• What to put in your customer agreements.
• What to look out for when customers insist on using their own contract.
• Indemnity and limits on liability explained for non-lawyers.
3/ Listen: Jo Stanley - Creating Radio for Women, by Women
In this episode of the Birchal podcast, top radio host Jo Stanley, the visionary behind Broad Radio, shares her insights and passion for women's voices in the radio industry.
With only 27% of voices on the radio being women, Jo saw that there was a chance to make radio targeted towards Australia's 5 million-strong female-over-35 audience.
Jo’s not just talking about it, she’s currently looking for equity shareholders to help take her business to the next level.
I’m sharing this because I’m a huge supporter of female-founded businesses, and what Jo is doing is inspiring.
🔧 TOOL OF THE WEEK
Heatseeker.ai
Imagine if you could test and learn your best growth strategies in just two weeks.
What if you could answer critical growth questions about market, audience, and product features by testing your products and messaging with AI-powered market experiments?
Well, now you can with an Australian-born AI startup - Heatseeker.
We’ve now opened up a waitlist for Australian and US-based startups and scaleups interested in a demo and to be part of our next round of testers.
PS. – Did you get value from this newsletter? If yes, then please:
Forward it to someone else who might find it useful too.