Should I Liquidate My Singapore Stock Portfolio to Scale My Side Business?

Balancing Portfolio Gains, Job Dissatisfaction, and Scaling a Side Business

Portfolio Performance So Far

My Singapore stock portfolio has been reaching new all-time highs week after week. My strategy has always been straightforward: buy a small number of fundamentally strong stocks and hold them long term.

Recently, the gains have become meaningful. My REIT holdings are up nearly 30%, while my non-REIT stocks have increased by close to 80%. Overall, my portfolio is up about 40%. This wasn’t the result of exceptional timing or aggressive trading, but steady accumulation over time.

Growing Unease About the Market

What has prompted me to consider selling is not FOMO, but concern. Given the current global economic conditions and geopolitical uncertainties, it feels like something may be brewing beneath the surface. This could simply be noise, but it has made me question whether continuing to build a dividend-focused portfolio is still the right move for me at this stage.

The Side Business and Capital Needs

Alongside my full-time job, I am running a side business, with the long-term goal of eventually transitioning into entrepreneurship full time. To scale this business meaningfully, capital is important. Liquidating part, or even all, of my stock portfolio would give me more flexibility and runway.

At the same time, my full-time job provides stable income, and my investments, especially dividends, offer a sense of financial and psychological security.

Risk, Responsibility, and Personal Fulfilment

I am fully aware that a business can fail, and as someone with a small family, that risk cannot be ignored. However, I also have no real attachment to my current job. I derive little satisfaction from it and continue mainly for the income. Mentally, I feel disengaged and unfulfilled, even though I still meet expectations.

The Crossroads

This leaves me at a crossroads.

Should I continue holding my Singapore stocks for stability and passive income, or should I sell, partially or fully, to redeploy the capital into scaling my side business, with the aim of eventually leaving a job I no longer want?


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