It was a late Sunday afternoon in October. The weather was perfect — sunny, a hint of fall in the air with the leaves beginning to turn colors. We sat on our deck at our weekend home with friends. They were chilling. Our “chill” was rapidly dissipating. We were beginning to think about the workweek. Both of us had high-pressure jobs and we weren’t looking forward to Monday.
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Our friends, on the other hand, were already retired. “Why don’t you just retire?” they asked.
We don’t have enough money to retire, we responded.
Then they said something that set us on a new course. “You’ll never think you have enough money to retire.”
Three months later we retired in our mid-50s while living in the New York City area (sixth most expensive city to live in the world) and Singapore (tied with Paris as the second most expensive city in the world). Our retirement plan was to split our time between the two cities. While we are well off, neither of us worked on Wall Street (we weren’t making millions) and we didn’t come from wealthy families. We had planned to retire in our mid-60s, with Medicare (health insurance) and social security supplemented by our retirement savings.
Since we moved the timeline 10+ years earlier, the picture was different. No social security. No Medicare. Less savings. And too young to access our retirement income without penalties.
Questions And Worries
We had a million questions and worries. Can we afford it? Will we run out of money? What will we do with our time? How much do we have to cut our expenses? How do we get health insurance? Do we need to move somewhere less expensive? Do we have to sell our properties? How do we manage our investments? What if it doesn’t work — we spend too much money or are unhappy?
We’d been saving and planning for retirement for decades, but this was a quality-of-life decision, not purely a financial one.
Here are 14 things we learned along our journey.
1. Deciding What Is Most Important
Many people focus on the dollars and cents when deciding to retire. That is an important consideration. But not the only one. Quality of life matters. Creating the life that you want to live may mean balancing both.
2. Start Planning Early
We started planning more seriously in our early 40s. We were already saving as much as we could, but we wanted to save more. We maximized our income by finding new (higher paying) jobs and paying down mortgages. We also sold our apartment in our favorite neighborhood in the Village and moved to Jersey City (one subway stop from New York City). This move enabled us to invest the earnings from the apartment sale. We still miss living in the Village, but we were able to get an apartment twice as large for a third of the expense.
In our early 50s, we began discussing spending more time in Singapore. Reggie is a citizen and lived there until her late 20s. We have many family members and friends there. It is home for us as much as New York is home for us.
Reggie had purchased an apartment there many years ago to help support her parents. We now stay in the apartment when we are in Singapore and rent it out when we are not there. As a result, we are able to live in one of the local areas, which has the important benefit of being less expensive than the expat and tourist areas.
Many overseas retirement articles assume that you’ll be staying in the expat areas. It’s important to research the neighborhood possibilities as a way to decrease expenses. Plus, you’ll have the local experience.
3. Prioritizing Expenses
When we retired, we cut our expense budget by 50 percent. That probably sounds drastic, but while we were working, we lived on one salary and saved the other. It’s still been an adjustment to live on less when we were used to spending very freely. It caused some fights in the first year as we learned to adjust. The good news is that we no longer have dry cleaning and business attire expenses.
4. Reducing Debt
Being in debt while planning on retirement can add to your stress levels. We never had credit card debt. If you do, evaluate how much credit card balances, mortgage, and other loan payments you are carrying. Can you eliminate these, and if not, can you reduce them? Credit card payments and a high mortgage can make it very difficult to retire early.
If you rather not carry any debt even with a low-interest mortgage, then pay it off and sleep better at night.
5. Deciphering Healthcare
Healthcare is the biggest challenge for early retirees in the U.S., and one that we research extensively. We now live in Jersey City (as we said earlier, a short subway ride away from NYC). Our doctors are all in New York. The affordable healthcare plans available to us in New Jersey do not cover NYC doctors. For some folks, these plans will work. Do your research well ahead of time so you know that this option works for you.
We had another alternative in our back pocket. Adjunct Professors at New York University (NYU) are eligible for healthcare (for a fee) from the university. Sue started teaching classes at NYU 15 years ago. She loves teaching, but it was a difficult balancing act while she was working 60+ hours a week at her full-time job. We knew that it might come in handy if we did retire early, so we persevered. Sue now teaches a few classes a year when we are not traveling and loves her students.
As for Singapore, healthcare is subsidized there and much less expensive than in the U.S. When in Singapore, we purchase travel insurance with medical coverage and evacuation/repatriation riders. We do a lot of regional travel from Singapore, so it is important for both us to have travel insurance.
6. Creating Passive Or Additional Income Streams
As we noted earlier, we wanted to invest the proceeds from selling our Manhattan apartment. Some of this was invested, but we also bought a small rental apartment in Jersey City. This provides passive income. During COVID, we decided to do some nonprofit and fundraising consulting since we could not travel and wanted to do some renovations. There are many other ways to earn income doing something you love while retired. We will continue to do that because it’s fun and rewarding. It’s so much easier to consult when you are not dependent on the income.
7. Deciding Who Should Manage Your Investments
Retiring early is a double whammy — you forgo 10+ years of savings while you are using your investments to live on.
We managed our own investments until recently, when we decided that we needed expert advice relative to withdrawals and planning. We shopped around for a financial planner that we trusted a few years before we retired.
We went to see our financial planner after the October conversation to ask him to run the numbers with an earlier retirement date. When we arrived back for the follow-up meeting, we informed him we’d already decided. This was before he presented his report. Luckily, the numbers supported our decision.
8. You Don’t Need To Move… Unless You Want To
Every day, we read about someone who has retired early and moved to someplace warmer or cheaper — Florida, Portugal, elsewhere. And that works for some people. We wanted to live in the NYC area and Singapore for our retirement (we got the warmer message but not the cheaper one).
If you go the moving route, make sure to research and plan for it. It can be disorienting to make that big of a change right off the bat.
9. Yes, You Can Break The Rules
Conventional wisdom is to not make big purchases or drastic decisions in the first year of retirement. That’s good advice.
We didn’t follow it.
Our dream lake house came up for sale a few months after we retired. We’d been waiting for a few years for the house, and we bought it immediately. It was a good decision, as it became our home base during COVID. We still have the Jersey City apartment for when we need to be in NYC, and the apartment in Singapore. At some point, we plan to sell one of the New Jersey properties.
10. Retiring Internationally As An LGBTQ Couple
Our plan is to spend 4–5 months in Singapore and 7–8 months in the U.S. We would spend even more time in SIngapore if we could.
In the U.S., we are married, and in Singapore we are not. Singapore does not recognized gay marriage. It also does not have a retirement visa. Tourists are generally only granted continuous stays in Singapore for 90 days. It is also difficult for green card holders to be out of the U.S. for more than 6 months. We have to juggle all of this in our planning.
At one point, we researched retiring in a third country that would put us both on equal standing but decided against this because New York and SIngapore are our homes. We will eventually have to choose between the two places, but we are putting that off until we are in our 70s.
11. You Can Only Prepare For So Much
You can only anticipate so much. Life throws curveballs — COVID, health issues, inflation. Preparing and planning, like practicing a sport, allow you the space to improvise and make new decisions when something unexpected happens.
12. Do It Socially
As we retired, our differing visions of budgeting and spending time came to light. We had some disagreements and some learning experiences in the first years. Allow some space for that process. For a couple or a family, communication is so important. Take time to talk through how it is going — not just the finances, but the living.
If you are retiring as a single person, find others to talk to about how your retirement is going. Join groups (virtual or in person). Find new activities. Don’t do it alone.
13. Remember, It Is About Quality Of Life
In terms of quality of life, retiring early has been a home run for us.
We have a leisurely breakfast and start our day at the pace that works for us. Then we exercise, go for a walk, or kayak on the lake. We now have new hobbies like pickleball, Mah Jongg (spelled mahjong in Singapore), gardening, and glass blowing. There are new friends to visit with and volunteer activities that we didn’t have time to do while working.
We are glad to have laid the groundwork much earlier in our lives, and grateful that we were able to adjust the plan to be able to retire in our mid-50s.
For more stories and words of advice like these, peruse our Inspire and retirement categories.
