Making mistakes comes with entering new territory, but you can always learn from them, even if it’s embarrassing in the moment.
Hindsight is 20/20 – it’s about what you learn from faux pas that can push you to go further. So what if you messed up? Sometimes, how you pick yourself up matters more. If you can find humour in the situation, even better. Starting a business from scratch comes with lots of learnings, so we spoke to entrepreneurs about embarrassing moments that popped up along the way and what they gained from them.
Entrepreneurs share their embarrassing moments
1. Using laughter to lighten a slip-up
During an investor pitch, I stumbled over certain industry jargon, causing a momentary lapse in my speech. I quickly recovered with a light-hearted laugh, attributing it to my nerves. This genuine reaction created a human connection, shifting the atmosphere positively. After the shared laughter, I found myself more at ease and able to articulate my passion for my business more effectively. This incident reinforced the lesson that authenticity prevails over perfection and showed the power of shared laughter in building connections.
– Michelle Chan, 50s, founder of Miseico
2. Anything to save $$
When I first started my handbag business, House of Sheens, I remember saving every cent. The business was starting out, and we were hosting our first large event. We needed a tall branch that plant people could write their hopes on. I didn’t want to spend on a tree that I couldn’t use again. So with my children and helper, I drove around Alexandra Road looking for fallen branches, tied them to my car roof and drove the huge bundle around town. I got crazy looks from drivers and felt totally embarrassed. But I was thrilled I did it without spending a cent!
– Shireena Shroff Manchharam, founder and creator of Getting to Happy
3. Finance 101
For me, it started with not having a deep understanding of my company’s financial health. As a result, we accumulated one business loan after another during the good times. Only when the Covid-19 pandemic started and our revenue slumped did the full impact of our financial mismanagement hit us. Even with government support, we had to let our team go, give up our art studio space and start from scratch. This incident taught me the importance of financial prudence in business and the need for every founder to have a solid understanding of every aspect of their business.
– Senthilkumar Subramanian, 31, founder of SEO With Senthil
4. Imperfect action is better than inaction
When I sold my first deal with my current business, I had no brand, no logo, no business account… and I was meant to send the contract the next day! I had learnt from my three previous failed businesses that I needed to get clients before doing all the shiny things in my business (mistakes I had repeatedly made in my previous ventures).
So, I hustled to do all the administrative work and find a name overnight. I landed on an imperfect name, Focustra (still laughing at this name). For a perfectionist like me, it was not easy! Since then, I’ve been all about embracing the mantra that imperfect action is better than inaction.
I ended up disclosing to the client the next day when we met for her to sign this huge partnership contract that the name would change soon as I had to create all the business structure overnight. She loved the authenticity and that’s how Essential Shift was born.
– Laetitia Andrac, 39, founder and CEO of Essential Shift Consulting
5. The delivery dilemma
Early on in my business, I used to personally deliver local items to save money. Once, while discreetly dropping a parcel, the customer emerged from her home, catching me in the act. We shared an awkward exchange. She recognised me, though we’d never formally met. Surprisingly, she revealed her connection as my ex-boyfriend’s current partner, adding an unexpected twist. Despite the discomfort, I expressed gratitude for her support. From that day, I relied on my courier service instead. I also learnt the golden rule of entrepreneurship: expect the unexpected.
– Tess Nguyen, CEO of Midnight Mischief
6. What’s in a name?
Picture this: at a bustling networking gig with 50 faces to remember, I was a handshake dynamo. But then came the cringe-worthy slip-up. I called a promising client by the wrong name, and he saved it as his little secret until the party’s end.
My cheeks turned tomato red; I seriously considered digging a hole for a swift escape. Ever since that blush-inducing moment, I’ve employed a quirky survival tactic. After around eight handshakes, I’ll ninja my way to the restroom, sneakily jotting down people’s clothing colours and distinctive traits on their name cards. A lesson learned in the most awkward of ways!
– Dr Jolene Ng, 33, director of O2genes
Got your own embarrassing moment as an entrepreneur to share? Want authentic connections with fellow business owners? Check out Launchpad, a networking platform that offers support and community for entrepreneurs.
