As I approach turning 50, I will reflect on some of the challenges I have been struggling with. I'd like to start with the most complicated area of my life, so I'll discuss the earned income component of my life.
My earned income component has been the least successful area in my life. That also sucks up most of my life energy because I've always felt that it's an essential area of struggle. After all, it answers this question:
Post-FIRE, what are the possible career moves to enjoy a good income and quality of life?
Sadly, I don't have a better answer than anyone else after a decade, but I'm here to show everyone my working.
a) My training business
I'll forever be grateful to Dr Wealth because I found an alternative to the back-breaking legal career I initially planned after my JD. The first three years as a trainer brought me 2x my salary in my previous job and paid off my school fees in 6 months, confirming that this is a viable career. It also allowed me to develop skills I could not acquire in my earlier career. A seven-digit revenue for ERM, followed by an appearance on Money Mind, can't hurt my resume.
Like all businesses, that golden era appears to be over as interest rates begin to go up, but I enjoy the work of investment training a lot. It has even made me a much better investor now. Once I started coding my investment advisors and using AI to generate analyst reports, I could tolerate the work even as a sideline that generated a small allowance.
Nevertheless, my training business will be in an existential crisis in 2025. I will either need to make adjustments and change the price point of the courses, or the business may need more time to justify the time I spend on it.
b) My role as an adjunct lecturer in a tertiary institution
To preserve my training job and to earn a more stable income, I spent the year taking on an adjunct lecturer role in a tertiary institution teaching adults Corporate Law and Legal Technology. The value of doing this is exposing myself to life with a more conventional role with the skillsets I developed at Dr Wealth.
The initial plan was to introduce a more stable income to my fluctuating revenues without giving up my business. I would also need a "barbell" strategy in my earned income strategy: a volatile and high-earning job and a stale one that even pays a bit of CPF.
But this job has its own set of challenges. Contract renewals are done in drips and drabs, so you cannot project your income with certainty a semester moving forward. I was initially unhappy that I was only retained for one subject next semester, but as more contracts arrived, I was too happy to complain about being overbooked.
Payment platforms can be improved, and you often wait an additional month to be paid.
Nevertheless, after a year of struggle, during which unhappy and sometimes entitled adult students often yelled at me, I can now sell more weekly lecture hours.
The system is not designed as a leading source of income, but it's okay if you have a day job and plenty of passive income.
Is a portfolio career easy compared to a conventional one?
There have been moments this year when I wanted to quit everything and start looking for a conventional job ( likely in AI ) because there were moments when I was just doing administrative unpaid work just to keep this portfolio career machine running.
The numbers need to look better as well. I'm averaging $4k+ when my basic family expenses are close to $6k a month, so some digging into my dividend income was necessary in 2024. But this is easily the worst year of the decade, and I've already rebounded from 2023.
But from another perspective, this is a massive win because many post-FIRE folks complain about needing a real career identity, which we are primarily conditioned to do in Singapore. When people ask me what I do, I tell them I teach investing classes over the weekends, but I'm also a law lecturer at a local institution. Afternoon swims, fooling around with my kids, and meeting folks for coffee when they have a work break doesn't hurt.
If I sound very theoretical right now, I'd like the more savvy readers to recall Coarse's theorem about the firm in Economics. Firms are hierarchical structures that prefer to contract work that can be well-defined to someone else who can do the job better.
My Dr Wealth work is something society contracts out to me to perform. I'm subject to the same business forces and cyclicality as every other entrepreneur. My work with a public institution puts me in a complicated bureaucracy, where a bulk of my work is administrative in nature, just to get the system working.
There may be no way out if you want a portfolio career.
You must have a passive income flow, actually a large one, to avoid going crazy.
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