The Fear of Trying and Failing in a Digital World

My body count of “failed startups” now stands at 2. In a couple of weeks, I will officially deregister a business for a second time. The first one was about 10 years ago. My wife and I created a cool independent music label in 2004 and we were early pioneers of e-commerce. We had used the internet to market and sell music CDs to fans globally. By 2008, internet technology improved dramatically and helped fuel music downloads, via both legal channels (iTunes) and illegal ones (IRC, Soulseek, Napster, etc.). It meant our customers started reducing purchase of music CDs and thus the disruptor was disrupted.
This time my business partner and I will cease our online marketplace for Muslim travellers as an official registered business. We had used our considerable experience in digital and media technology companies to imagine, fund and build the platform to my specifications. While the platform functioned as desired, made noise at launch and served Muslim travellers as designed, it is an industry that I have very little knowledge about. I failed to properly understand the needs of SME travel business owners and hence we didn’t make much progress on getting them onboard.
While moving on is always hard to swallow, I am extremely proud of these episodes because we tried, “failed” and, more importantly, we learned tremendously and grew up from these experiences. There was no process to follow but we made them along as we tried to make a difference to other people’s lives.
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True robot tales
Let me share these recent non-fiction true-to-life experiences.
Fear of Trying & Failing 1: Top 2 Singapore university
I had delivered a LEGO Serious Play team building experience for a group of the university’s employees, not at Kent Ridge but at a nice hotel location. Upon completion, I emailed a PDF invoice for services rendered to the Finance department. That got rejected because they needed a hard copy on paper. I suspected they aren’t quite sure how to use a printer, so okay, hard copy it was.

A Finance employee then asked if I was able to receive a GIRO payment, which is practically a bank-to-bank transfer. I said “Yes, let’s use GIRO for convenience.” The old school alternative is, otherwise, a cheque in the mail.
Unfortunately, the Finance employee remained unconvinced and wanted a confirmation. Okay. I called DBS to “double confirm” that there’s no special arrangement required for businesses to use GIRO. I advised the Finance employee to try and execute the GIRO transaction since DBS okayed it. In any case, I mentioned to the employee that there is also FAST transfer which works for business to business too. Just. Try. It.
A week later, I received a paper GIRO form in my mailbox. #slaps_forehead_hard
Since cash flow wasn’t a concern, I chose to ignore and binned the form to see what happens next.
A few weeks later, upon prompting my university client that I have not received payment, a cheque arrived in my mailbox in all its papery glory.
Someone had a massive fear of clicking the button.
Fear of Trying & Failing 2: Potential marketing technology buyer
In the early days of Elisan Partners, I was still working on a viable business model. One of the options that I took up was to be a reseller of HubSpot, a marketing and customer software platform that I really like and admire as a company. At that time, I was also training professionals on digital marketing. I received a sales lead from one of my learners who happened to be an employee of this potential SME buyer.
I duly went to meet the SME buyer with my learner who had made great recommendations for my services and for HubSpot itself. This SME buyer is in the business of selling accounting softwares to other companies including Xero, the popular cloud-based accounting platform.
I presented the benefits of inbound marketing, the end-to-end customer technology and my implementation and coaching services to two company directors and a marketing manager. The marketing manager was keen to learn and operate HubSpot and improve how the company does customer marketing.
While discussion generally went well, one of the directors seriously asked how much it would cost for me to operate their HubSpot platform, create online marketing campaigns and practically own their marketing operations.
I was shocked.
I replied: “Erm, just like Xero is software for accountants, HubSpot is software for marketers. Why would you want to outsource your marketing ideas and operations to me? This is a great learning opportunity for your marketing manager to try and learn a new way of doing marketing as well as hands-on a best-in-class marketing automation technology.”
The reply: “The marketing manager has no time to learn this and needs to focus on other things.”
Great. I walked away from the potential deal. While I did wonder what those “other things” were, I can’t help anyone who are not keen on trying to improve themselves or their people. Marketing is literally getting as close as possible to customers. This can’t be outsourced.
I was also flabbergasted that a company in the business of helping other companies to “digitally transform” is trying to outsource its own “digital transformation”. I sincerely hoped that, bless his heart, the marketing manager has seek other learning opportunities by now.
Outsource and die

I was present at a marketing tech conference where I heard this comment from a top (3) Singapore government minister. He said that Singapore doesn’t have much left to offer to China and the door is closing, if it hasn’t already. The Chinese have surpassed us (and everyone else) in terms of technological and infrastructure knowledge and skills. How did this happen?
If there’s one reason for me to support Donald Trump, it is his desire to bring back manufacturing industries to the USA. Years of outsourcing work to China translated to years of trying, failing and valuable industrial knowledge gleefully gained by the Chinese workforce. While Americans and rest of the world have been deprived of these learnings (the consequence of corporates chasing profit margins through outsourcing), China has been using these precious knowledge to produce cutting-edge technologies and products for the world’s consumption. Today, Chinese brands, such as Huawei and Lenovo (ex-IBM), are ubiquitous and powers product made by American companies (who are merely brand owners). Case in fact: the American GE Appliances brand is owned by Haier, a giant Chinese company.
The message I have for business managers, owners and even marketers who depend a lot on agencies: stop trying to outsource everything. Do the work, try something new and learn to fail. It is beneficial for you and your people in the long run.
Fear of Trying & Failing 3: Digital marketing and Agile learners
This bugs and pains me all the time. As a digital marketing trainer and now an Agile trainer-coach, there is always an expectation from a large segment of my learners that I will provide either a “template” or “a model” on how to get started.
I’m sorry to disappoint. There is no template, no best practices and certainly no model to follow.
The digital world moves too fast for such thinking. Happened many times to me where a Facebook or Google software feature I had demoed in a previous class disappeared in the next class. And, in general, digital marketing syllabus is usually outdated within 3 months or, at best, 6 months (apart from evergreens such as inbound marketing or AdWords).
There’s no paint by numbers approach for the digital world. You have to try it. Experiment. See what works for your organisation. If it doesn’t, learn from mistakes, make adjustments, iterate and try to find your success spot. Repeat approach at all times because there is no “end-of-project date” for “digital transformation”. It is a digital evolution together with your customers on a daily basis.
Why? Because disruption is now a daily occurrence. Without trying and failing, you simply won’t be able to figure out its rhythm and dance a classy tango with it.
The state of today’s workforce

While I have read a lot about the growth of local Singaporean entrepreneurs taking their chances these days, the other reality is that, by and large, Singaporeans are entrapped in a very severe risk-averse Asian environment, especially those in corporate and governmental organisations. The fear of trying and failing are practically ingrained in the way we do things at work. Trying something new is almost taboo.
Is this a result of our Singaporean educational system? Very likely although I am very glad change is happening (my first child entered Primary 1 this year). More pressing is the fact that our overly cautious attitude means we are becoming increasingly less competitive and desirable as a workforce in the digital era. I know this first-hand from my corporate days at global technology companies based in Singapore. My expatriate colleagues, both Asians and Westerners, always had the desire to “let’s do something differently” and rock the boat a little when necessary. More importantly, they had a desire to actually make a difference for the organisations they work for and, ultimately, for Customers.
In comparison, some local Singaporean colleagues and job candidates I interviewed were more inclined to take orders, be slaves to process and policies and remained tentative or immovable to any new initiatives or change. Depressingly unimaginative, upsettingly unproductive.
In many cases I encountered, Singaporeans view working hard without question and maintaining status quo as a ‘good thing’.
Unfortunately, it’s not. It’s what we call in Singapore military lingo “hentak kaki” or “marching on the spot“. Doing a lot of work but going nowhere.
What should workers and bosses avoid in today’s digital world
It’s time to ignore your MBA-trained colleagues *cough cough*. You have to consider new and Agile ways of working and thinking. To do this, start by reconsidering this type of thinking which is outdated in today’s digital environment:
“Best Practices”
If everyone follows a “best practice”, wouldn’t it mean everyone is doing the same thing as everyone else? How does this make you stand out among the competition? You are not differentiated by doing something that may work for someone else with no guarantee it may work for you.
The only “best practice” you should follow religiously is to listen to your customers. They will tell you what you’re doing right and what is wrong. Not your competitors. Your customers will help you find the right practice or approach that will deliver value for their needs (not yours).
Also, wouldn’t doing “best practices” make you predictable and boring? While we all want to be the next Grab or Netflix, we keep fantasising the next big shiny piece of tech, such as AI, blockchain or programmatic advertising, that we can buy. Reality check: Hundreds of your competitors can afford to buy these things too and more.
You can figure out the winners here.
“Return on Investment”
ROI. I get this a lot when I speak to business managers and owners. There’s always a need to translate an investment, be it in marketing or technology, into 5x or infinity-x monetary gains or performance improvement. It’s a generic preoccupation. First in mind.
ROI is an innovation killer. It creates a culture of being afraid to take risks and making mistakes. 3M Post-It was a mistake. Penicillin, inkjet printers, potato chips and the microwave oven were all mistakes that came out from experimentation and a willingness to take risks.
This is where leadership matters. Giving trust and room for people to make mistakes and learn from them is a greater teacher than any training course they can attend. Yet, we are always preoccupied with how efficient our capital is in making more us money at the expense of creating value for our customers.
Here’s the mindset shift moment: Focus first on how much differentiated value your experiments and mistakes can create for the Customer. That will always eventually end happily in the money sense.
“When I worked for X, I did Y and it worked very well…”
In today’s rapid digital environment, every Customer problem requires a customised solution. If you’re not willing to invest in customisation, then the digital world has also opened doors to many of your more nimble and agile competitors to take away your customers.
It’s a problem then when we continue to hire people based on what they did in their last jobs. They bring what they know in their last environment and try to fit it in the new environment. They recycle ideas that may have worked in the past (“best practices”) but fail to find new ways of doing things for their new set of customers. And when old ideas don’t work, they will blame it on everything else but the stale ideas that they brought to the table.
This is legacy thinking. All of my knowledge in digital technology and online media did not save my Muslim travel startup from irrelevance. I failed to bring in my potential customers of today into a conversation that will help solve their problems of the day. Instead, I tried selling them on an idea of the future that they are hesitant to participate in. You can’t drag people into the future (another issue with most “digital transformation” projects). They have to come willingly.
Final word
Let trying and failing be a part of your work culture. Give people room to fail so that they can learn from their mistakes and become better and stronger. It helps our workforce to meet the needs of the digital world and improve our ability to compete as an economy. I shall leave you with a quote from Meredith Grey’s Anatomy:
“Knowing is better than wondering. Waking is better than sleeping, and even the biggest failure, even the worst, beats the hell out of never trying.”
To more trying and failing!