What My US Trip Taught Me About Homelessness, Succession Planning, and Retiring Overseas

Since the late 90s, I have been to different parts of the US for work almost every year and I recently just returned from a near 2-week business trip to San Francisco, Dallas and Austin with several thoughts on money, business and life.

On the Homeless Situation in the US

When I was walking along the streets in these three cities, I witnessed homeless people everywhere and the stench of urine was on almost every street. These poor souls were begging for money, bathing themselves near water fountains and in public toilets. In one instance, when I was in the toilet at a public library, it was full of homeless people using it. They even placed a security guard permanently there to make sure they don’t use the basins to wash themselves. I witnessed one of them being hauled out for trying to do so. It was a really sad sight to see and the worst I have seen since my travelling days in the US.

According to a December 2023 report by the U.S. Department of Housing and Urban Development (HUD), 653,104 Americans experienced homelessness, tallied on a single night in January last year. That figure was the highest since the HUD began reporting on the issue to Congress in 2007.

This has also caused the frequent shoplifting incidents in the cities. In one of the malls I visited, I saw queue stand barriers in front of the shops with security guards screening shoppers before allowing them into the shops. I witnessed them turning away homeless people trying to enter supermarkets. In a Lululemon shop, I overheard staff discussing items being stolen off the shelves the day before and saw with my own eyes a security guard giving chase to a shoplifter who stole a bag from Lululemon. Inexpensive items such as shampoos were locked behind glass cabinets to prevent them from being stolen.

Scholars, healthcare workers, and homeless advocates in the US agree that two major contributing factors to the current situation are poverty and a lack of affordable housing. While we are grateful that Singapore is far from the situation in the US, we should never be complacent. With housing becoming more expensive, there are genuine concerns among young people (my children included) that they may not be able to afford a HDB flat one day. Even if they can buy one, they worry that it does not leave them with much disposable income to save for the future and live a reasonable life today.

If you are contemplating buying a house, buy one that you can afford to pay off as soon as possible so that you can always have a permanent abode. Contrary to many of my peers in finance, I do not believe in debt. While I understand the power of leverage, I believe more in the peace of mind that comes from being debt-free. As a guide, your total monthly debt repayment (which includes all loans including the mortgage) should not be more than 40%-45% of your gross income.

Not having a job is also one of the contributing factors to the homeless situation in the US and is also a common concern among young adults in Singapore. My daughter graduated from university in December 2023 and has not been able to find a suitable job. Of course, she might be able to find one if she accepts ANY job, but I don’t think that will make her happy. That is why she decided to intern for a global advertising agency where she can learn and apply what she has studied although at some point, she would need to get a full-time position so that she can earn enough to support herself.

To those of you still looking for that preferred job, don’t be jobless for too long. Do anything that will get you closer to what you ultimately desire to do and for the rest of us, always stay relevant regardless of how senior we are. This way, we will never fear losing our jobs and not being able to find the next one. Having a shelter over our heads and a job that gives us income does not only meet our basic needs but gives us dignity and purpose.

On the Lack of Succession Planning Among Wealth Advisory Firms in the US

Over the years, I had the opportunity to visit many successful wealth advisory firms in the US. One thing that stood out for me in all my visits is that many of these firms, while successful, do not have succession plans in place. Having a succession plan means:

  1. Having an identified second generation
  2. Having a development plan for the successors
  3. Investing in the firm for future generations

In this recent trip, one of the firms I visited had a five-man team managing US$1.3 billion of client assets and the founder is already 56 years old. They have a net profit of between 65% to 70% of their revenue. While it sounded impressive to some, to me, it tells me that they are not investing for the future. They are just maximising their wealth for the now and for themselves.

When there is no succession plan, the firm will close down when the founders retire. It will also be difficult to sell their firm with no successors to run the firm and most importantly, the clients will not be taken care of. In the work that we do for our business owner clients, we observe the same situation in Singapore. Many business owners do not have a succession plan in place. So, if you are a business owner reading this, for your own sake, for the sake of your staff and clients, have a succession plan.

On Retiring in a Foreign Land

There was a time when I thought about retiring in another country where there is more space, more nature and with a better climate. With each passing year and my most recent trip to the US, I found it harder and harder to live elsewhere.

When I am overseas, I find myself not coping very well with the weather, the food, the culture and most importantly, the loneliness of not being with “my people”. I have shared that one of the definitions of a good life is “living in the place you belong, with the people you love, doing the right work, on purpose”.

My family and friends are in Singapore. My heart is in and with Singapore. I find that the work I do and want to do in the future is in Singapore. It would be hard for me to be somewhere else. At least this is how I think now. It may change in the future but for now I hope to age with my friends and witness their demise and for them to witness mine.

You may feel differently from me but before you decide where you are going to retire, ask yourself: where is the place you belong, where there are people you love and who love you, and what are you going to do that will impact the most people.

The writer, Christopher Tan, is Chief Executive Officer of Providend Ltd, Southeast Asia’s first fee-only comprehensive wealth advisory firm and author of the book “Money Wisdom: Simple Truths for Financial Wellness“. He is also a Certified Ikigai Tribe Coach.

The edited version of this article was published in The Business Times on 19 August 2024.

For more related resources, check out:
1. Beyond Finances: Are You Really Prepared for Retirement?
2. My Condo Downgrade to HDB Was Tough, but It Was Worth It
3. Retirement – It’s About the Kind of Life You Want to Lead


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