3 Jobs, 3x CPF: Overemployment as a Path to Retirement? How to juggle it [W&S 73 ft Stanley Kan]

The Whirlwind Life of an Overemployed Marketing Maverick

In the latest episode of the popular personal finance podcast “Wise and Shine”, hosts Reggie and Dawn welcomed an unconventional guest – Stanley, a marketing professional who is proudly overemployed with not one, not two, but three full-time jobs across various marketing agencies.


Stanley introduces himself as an employee of three marketing agencies, each with a distinct focus and role. He works at an Integrated Marketing Agency called Seconds Media, a Social Media Marketing Agency named Alto Global, and a specialized Influencer UGC Marketing Agency called Social Jet. His overemployment journey began during his early days when he balanced full-time work with his studies, demonstrating a remarkable level of commitment and ambition.

The OverEmployment Phenomenon Explained

As Reggie put it, “You’ve heard of unemployment and underemployment, but have you ever heard of overemployment?” For the uninitiated, overemployment refers to the practice of working multiple full-time jobs concurrently, often without the knowledge or blessing of one’s employers.

Stanley shares that his extensive experience in the marketing industry, spanning over 12 years, paved the way for his overemployment. Stanley’s journey into this uncharted territory began rather conventionally. “I started [working] since I was 16 and a half, with a weekend job that became a full-time job. After that, I went back to school and decided to take a full-time job while having a full-time study,” he explained.

The Slippery Slope of Opportunity

Stanley’s first overemployment opportunity came about organically. As the Partnership Director at Seconds Media, an integrated marketing agency, he was approached by an influencer marketing agency, Xten. They sought his expertise as an advisor, valuing his seven years of experience in the industry.

“The founder was saying that maybe you could value-add because you offer quite a lot of opinions and thoughts,” Stanley recounted. With his employer’s approval, as long as there were no conflicts of interest, Stanley embarked on a side gig. This was the start of a slippery slope that would eventually lead to his overemployed status.

Balancing Commitments: One might wonder how Stanley manages to balance multiple roles without compromising his performance. At the beginning of his overemployment journey, the time commitment for his additional role as an advisor was relatively manageable, requiring a few hours per day. However, as time went on, the intensity increased. Stanley strategically planned his schedule, dedicating specific days to each role, allowing him to effectively manage his time.

The Power of Synergy

Stanley emphasizes that his overemployment arrangement was carefully structured to avoid conflicts of interest. Stanley’s role at Xten complemented his responsibilities at Seconds Media, creating a symbiotic relationship between the two roles. “When Xten needed integrated marketing support, they could get Seconds Media to support. So it’s always a win-win,” he explained. This win-win situation not only resulted in referrals and business opportunities but also strengthened his position as a valuable asset to both organizations.

This synergy extended to his third concurrent role at Alto Global, a sister agency of Seconds Media. The founders approached Stanley to solve team-related developmental issues, capitalizing on his ability to juggle multiple portfolios effectively.

Strategies for Sustainable Overemployment

So, how does Stanley maintain this whirlwind schedule across three full-time roles? Here are some of his key strategies:

  1. Remote Work: The rise of remote and hybrid work models post-COVID has been a game-changer for Stanley’s overemployment lifestyle. “It was full remote technically, or like hybrid – which to me is equivalent to full remote because I could [work from anywhere].”
  2. Strategic Time-Blocking: Stanley meticulously schedules his days, allocating specific time blocks for meetings and tasks related to each role. “For example, 2 to 4 PM, I’m having a meeting with SocialJet’s clients or programs. Then from 4 to 6 PM, I’ll be meeting with Seconds’ stakeholders.”
  3. Night Owl Strategizing: The real work happens after hours for Stanley. “Around 11 PM to around noon, that’s when I think of the strategy for the next week, month, and quarter,” he revealed.
  4. Maximizing Weekends: While weekdays are a constant juggling act, Stanley aims to reserve weekends for personal time and passion projects. “Weekends are a downtime for me. Any freelance work I take on is more for improving my own personal craft.”

The Financial Rewards of Overemployment

While some might assume that Stanley’s overemployment would result in reduced pay, he clarifies that his salary was not exceptionally high to begin with. Although he didn’t receive significant pay cuts, he did not experience substantial salary increments either. Stanley saw this as a trade-off, recognizing that his unique arrangement offered other valuable benefits beyond financial compensation.

For Stanley, the financial incentives of overemployment are substantial. “On average, it’s like a low five-digit [salary] cumulatively,” he shared. However, he emphasised the importance of each role providing CPF contributions and long-term commitment for it to qualify as full-time employment in his view.

The Taxing Reality of Overemployment

Stanley’s journey showcases the possibilities and challenges of being overemployed. His story challenges conventional career paths and highlights the potential for personal and professional growth in non-traditional roles.

With multiple income sources, Stanley’s tax filing process is understandably complex. “Last year, I had all four companies [I worked for] on my tax returns,” he admitted. This intricate financial situation is one of the many challenges that come with an overemployed lifestyle.

A Cautionary Tale

While Stanley’s overemployment story is undoubtedly impressive, it also serves as a cautionary tale about the potential pitfalls of taking on too much. As Dawn, the co-host, aptly expressed, “Stanley, this is too much. Please control yourself.”

The relentless pace, with little downtime and an ever-increasing workload, raises concerns about burnout and work-life balance. Stanley’s experience, though extraordinary, highlights the importance of setting healthy boundaries and prioritizing self-care, even for the most ambitious professionals.

As the conversation came to a close, one thing was clear: Stanley’s overemployed lifestyle is a true testament to his exceptional work ethic, time management skills, and passion for the marketing industry. Whether his unconventional career path is something to be admired or cautioned against remains a matter of perspective.

You can check their full interview on Wise & Shine, Episode 73 on Spotify, YouTube, Google podcast, Apple podcast for a candid conversation as we dive into Stanley’s experience as an overemployed professional and the alternative career paths and the changing nature of work. His ability to balance multiple roles while delivering value to each organization is a testament to his dedication and adaptability. The conversation with Stanley serves as a reminder that success can be achieved through unconventional approaches, and that exploring new avenues can lead to unexpected opportunities.

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