Disrupting the Career Paradigm: Strategic Sprints & Entrepreneurship

Does it pay to be your own boss?

I have worked in the government, in senior corporation positions and for myself, and I can unequivocally say that working for myself has trumped working for others, bar none!

What is it about working for yourself that makes it better than employment? After all, when employed, we don’t have to worry about the next paycheck, and if we maintained a reasonably frugal lifestyle, we could live a very comfortable life.

At least that’s what everyone thinks.

The Risks are Higher when you are Employed

As it turns out, working for others is highly risky!

There is no job security anymore. You may be indispensable on Monday and surplus to requirements on Tuesday! When that happens, the company drops you like a stone, oftentimes without warning. Employment has become transactional; they don’t owe you a living, and you don’t owe them loyalty. You trade your time and expertise for money, offering that exclusively to them. But the cost of that exclusivity is very high.

An 8.30am start time means that you have to wake up at 6am and a 5.45pm end time sees you returning home at 7.30pm.  You are paid for eight hours’ work, but you give away thirteen. You normally return home too exhausted to have any other life.

There was an article on Singapore media that highlighted the plight of a software engineer who, despite all his efforts of upgrading his skills to contribute to his employer, was laid off over a 15-minute phone call. He now has difficulty finding a job. Two problems were highlighted in this article; one, that even after investing in upgrading his skills to contribute to the company, he was suddenly let go; two, that trying to get back into the job market despite having certifications was extremely difficult.

So while you may not be mentally stressed by having to scrounge for your next paycheck, you are worked to the point of exhaustion; and this has untold impact on your physical and mental wellbeing. And while you sense that you may be "exploited" by your employer, you cannot leave because of the "security" that your monthly paycheck provides. Yet, when you are finally physically or mentally spent, or simply "too expensive", you will be discarded; often at the very moment you can least afford to be without a job. This is what some call the “Corporate Stockholm Syndrome”.

This is probably the riskiest aspect of working for someone.

You are being made use of because companies know they can get away with it.

To mitigate these risks, you can either treat your employment like “strategic sprints,” or you could work for yourself. Let’s explore the first option first, which we shall term the “Two-year Up-cycling Career Model”.

The Two-Year Up-cycling Career Model

"Two-Year Up-Cycling" involves committing to a role for a defined period (typically two years), then moving on to a higher-level position elsewhere. This is not job-hopping, it is strategic career compounding; it is about getting the jump on the company to leave on your terms, rather than to be booted out when it is convenient for them. Done well, it can bring our career to very promising levels in the fastest run-up times. To achieve this, we need to:

1. Remain plugged into the larger job ecosystem.

In the past, when we worked for a company over an unspecified period, we would give them our loyalty, cutting ourselves out of the broader job market. This isolates us from the ecosystem, and we wouldn’t know what was happening both skills-wise and career-wise. And when we get axed, we would be totally lost because so much had changed. However, with a two-year tenure, we must stay connected throughout the marketplace; continuously assessing how the environment was evolving and continuously staying abreast of it. We would therefore have to participate in industry events, seminars and workshops, both to learn, and to maintain ties, because the best jobs are seldom advertised but obtained by word of mouth. So, if nobody knew you, you would be out of the running even before you started.

2. Market our value relentlessly

As an extension to the point above, we need to advertise our achievements on platforms like LinkedIn or publish on Substack. Continuously publish original ideas to showcase your expertise. Document your accomplishments without exposing trade secrets, quantifying them in dollars, percentages or tangible outcomes. Fight to be in cutting-edge projects at work, volunteering your time because you would be gaining invaluable expertise on the “tuition” that your company is paying. Make sure that you have accomplished something worthwhile in your current job that would make your resumé stand out. By updating them on LinkedIn, you are constantly advertising your skills and expertise progression to your industry connections. This will enable you to secure your next, higher-level, job with some time to spare before your current tenure runs out.

3. Keep producing and documenting 

Develop new skills and capabilities and apply them in your current employment. Be valuable to them. Document all that you had contributed, testing new hypotheses and applying new techniques so that they improved their topline or bottom-line. The thing is, while you help your company get better, you also add valuable knowledge and skills to your own repertoire. So you get better too. You would probably not be paid more for your increased contribution because most companies are myopic, believing that your monthly salary was reward enough. However, another employer can easily see that value and pay you for your current worth and more. That is why moving on every two years accelerates your career faster than waiting for a promotion that may never come. Of course, the higher up you go, you might probably put in a little more time over the target; hence 3 to 4 years before subsequently advancing to your next role.

However, there is still a downside to this model. You can employ this strategy for, at most, 20 years. In many countries, the minute you cross 45 years old, ageism and competition from younger (and cheaper) competitors kick in. Yet, while retirement age is increasing, and your value is dropping, you are caught in a conundrum; do you downsize your role and ask for a lower salary, or do you simply quietly quit in your current job, waiting for the axe to fall? Regardless, your career decline kicks in while your financial obligations are the highest!

Is this the BEST way to build your career?

Working for Yourself

Let us now consider the other option - to work for yourself.  Does it pay off? In an article published by The Conversion entitled, “Being your own boss doesn’t always payoff: What 30 years of data reveal”, authors Xiaoying Wang and Seok-Woo Kwon, university professors in Canada, studied data across 30 years from the US and Canada of four types of entrepreneurs and concluded that “solo freelancers earn no more than salaried workers and report lower well-being.” But far from being anti-entrepreneurship, the authors found that those who had incorporated their business (as opposed to freelancers who were more gig-related) were more likely to expand and earn more along the way. And “among people who built incorporated businesses, lifelong entrepreneurs earned the most, early starters reported the strongest life satisfaction and those who started in midlife struck the best balance between the two.” Ultimately, what this longitudinal study showed was that if you started out in a structured manner into entrepreneurship, you would be better off than if you worked for someone else.

Why is that?

Review the three things we need to maintain the Two-Year Up-Cycling Career Model, and you will notice the first one is networking, the next one is marketing and the last one product development. These three requirements are equally important in running a business well. Hence, regardless of whether you work for others or for yourself, you need to perform these tasks. And the article informs us that those who incorporated a rigorous system of networking, marketing and product development created more value for their customers, enjoying greater career longevity and, ultimately, building greater wealth.

So, instead of deploying those skills to build your career through employment and building other people’s businesses, you could deploy those same skills for your own business that has the potential for never-ending career opportunities!

Entrepreneurship requires education

And here is where we encounter another problem, one that is globally relevant but particularly acute in Singapore, where the government had, from independence, created an education system that favoured employment. For decades, the social compact had been “study hard, graduate with good certification, get a good job, work hard, and retire well.”  

That compact is no longer valid.

With many roles being made redundant through shifting business landscape, AI or worsening unit economics, governments are scrambling. There is a growing skills-mismatch. While employment is still growing in Singapore, the growth is not uniform and there are talent shortages in industries that Singaporeans shun, like nursing, construction or quantity surveying. The new mantra is “lifelong learning” – retrain, reskill and redeploy. Let’s not talk about aptitude, prior knowledge or career goals; just go where there is a skills gap, so that you can put food on the table. The problem with this thinking is that not everyone can stomach the sight of blood, so that rules out nursing. Others don’t have an aptitude for mathematics, so quantity surveying is out. Hence, while there are job availabilities, not everyone can reskill for them. Humans are not machines, which can be swapped out and plugged in elsewhere with nary a downtime. We are much more complex than that, and to strip one’s humanity away in favour of uniformed mobility between industries is a recipe for disaster.

Entrepreneurship can solve that.

Yet, if SkillsFuture is the strategy for workforce mobility, why is entrepreneurship education not a core component?

Sure, we have business studies, which include marketing, technology, human resources, principles of accounts etc.; but these are taught with the focus of employment. Even when they are packaged into an entrepreneurship course, they are conducted in a classroom over a theoretical framework. To date, there is no course in Singapore that teaches us how to identify our market, uncover a hidden need, assess our ability to meet that need, test our assumptions, make a prototype, fine-tune the production, identify our suppliers, scale up our supply chain, and protect our market – all in an action-learning basis.

The truth is, anyone can teach theory; but few can translate that to a successful development program. Yet, that is exactly what we need. An Entrepreneurial School; where lessons are taught not in classrooms, but in multi-disciplinary, business-focused, marketplace learning labs. Where exams are replaced by market validation. Where students graduate only after launching a real business and writing a 10,000-word dissertation on the lessons learned.

Of course, not everyone is suited for entrepreneurship. Some will always be employees. But if we do not allow them to test their entrepreneurial mindset at an early stage, where the cost of failure is low, we end up with people “trying their hand” at a very low barriers-to-entry-type business like F&B when they can least afford to fail. Take the case of the HDB-themed restaurant, Lou Shang, that was forced to close after three years after incurring $400,000 losses. The back story of Lou Shang reads like a “what-not-to-do-when-starting-a-business” manual. The problem here was brought about by assumptions made by the founder that run counter to how good business should be founded.

There is a proper way to found a business which helps us to “fail fast and fail cheap”. Because no one knows how an idea will be received in the market, we must uncover all the ways that the idea WILL NOT WORK, so that we can land on those that will! That process of finding your market, identifying the need to be solved, creating your prototype, testing it in the market, fine-tuning, getting customer feedback, sizing the market potential, working out how to scale the solution, working out finances, seeking funding, figuring out how to protect the market (before launch), and THEN kicking the business off is the proven process of building a sustainable business. This is the DNA for all types of business startups.  

As The Conversation article so clearly pointed out, “the image of the brilliant young founder who drops out of school to build the next big thing is mostly a myth.” Yet, many people are drawn to this romantic notion of entrepreneurship either with bravado and hubris (“Yes, I can make it”, a la Lou Shang Founder) or self-doubt (“No, I don’t have any good ideas”). Neither is correct. Building a business is a process that anyone can master, it just takes patience, proper guidance and the right mindset. Mindset is key for success because it is driven by your perceptions; and your perceptions drive behaviour; behaviour drives actions, and actions lead to outcomes. The right mindset results in the right actions and the wrong mindset results in the wrong actions. The good news is, mindset can be measured and developed to lead to the right outcomes.

So, if it requires us to fail many times before we can succeed, wouldn’t it make more sense to embrace the right mindset towards failure; of failing faster and more cheaply? And if so, then shouldn’t entrepreneurship feature more prominently in pre-employment training (PET) than in continuing education and training (CET)?

So, does it pay to be your own boss?

We end off where we first started. Does it pay? The answer is absolutely yes, but not in the way most envision. We tend to equate entrepreneurial success with money; but that is only part of the equation. Entrepreneurship also pays in:

• peace of mind, as you have greater control over your time and activities;

• purpose, as you get to do things that you love;

• autonomy, as you drive your own actions, not the actions that your boss wants you to take;

• control, since you are in the driver’s seat of your own destiny, and not a passenger driven dangerously by someone else;

• longevity, in that your career does not end at 45; and

• fulfillment, in that you get the opportunity to live a fuller and more rounded life.

And yes, every once in a while, you might hit upon a sleeper business that delivers the $100M home-run.

You can’t get that with employment.