Retirement Planning Tips: What Thousands of Retirees Taught Me (No One Tells You This)
- Kimmy Wan
- 3 days ago
- 7 min read
Written by Kimmy Wan
After 28 years of sitting across the table from people with different incomes, different backgrounds, and different personalities, I’ve learned something simple: Everyone lives differently. But the fundamentals? They’re surprisingly the same. Some people want to travel the world. Some don’t want to leave their neighborhood. Some keep working. Some stop completely. Some say they’re retired but somehow busier than before. Different lifestyles. Same truth underneath.
Retirement isn’t about stopping work.
It’s about finally having control over your time.
Retirement Planning Tips: The First Blind Spot
People think retirement will fix their lives. It doesn’t.
If you don’t know what you enjoy before retirement, you won’t magically figure it out after. If your identity is only tied to work, retirement can feel empty, even with money. That’s not a financial problem. That’s a lifestyle problem.
And no portfolio can fix that.
Let me give you a real example.
Back in the 90s, I worked on a commodity trading desk, fast-paced, high-pressure, constant decision- making. One of the senior bosses I worked with was extremely successful. He made a lot of money over the years. But he was rarely home. He didn’t really spend time with his kids. To his credit, he provided everything: the best private schools, private tutors, luxurious vacations, and top private colleges. But life doesn’t work like an asset statement. Later, he went through a bitter divorce. Over time, he lost his relationship with his kids.
After he retired, he didn’t slow down. He turned to politics. He had always been ambitious, sharp, driven, and if I’m being honest, a bit cutthroat and emotionally distant, and everyone who worked for him was a bit scared of him. What he missed wasn’t the money. I don’t believe anyone aims to make lots of money to become a politician.
What he missed was power, identity, structure, purpose, and the competition. He couldn’t figure out what life looked like without it. That’s the part people don’t often think about.
Retirement doesn’t remove who you are. It reveals it.
People say, “I’ll finally relax in retirement.”
Maybe. Maybe not.
A lot of people carry their habits with them. If you were always anxious, always busy, always chasing the next thing, retirement doesn’t automatically change that.
And here’s another part most people don’t talk about. For years, most people put everyone else first: kids, parents, spouse, and work. That makes sense during certain stages of life. But if you continue that pattern into retirement, you never actually get your own life.
Now here’s the balance:
I’m not saying don’t help your kids. I’m saying don’t sacrifice your own stability for it. Many retirees who struggle later didn’t overspend on themselves. They oversupported others.
Help your kids if it brings you joy. Pause if it brings pressure.
Let’s Talk About Money—Honestly
Yes, money matters. You need enough. And here’s where I’ll push back on the “money doesn’t matter” narrative. It does.
Studies show roughly 40% of retirees worry about outliving their savings at some point. So no! This is not about ignoring money. It’s about getting to a point where money supports your life, not controls it, because I’ve also seen the other extreme: people who are financially fine, but mentally stressed. One pattern I often see, especially with very smart people, is the need to outsmart the market.
It’s not unusual, as a financial advisor, to have friends or clients who want daily “hot tips.”
One of them is actually a very good friend of mine, a brilliant PhD engineer from Peking University. She loves numbers. Over time, that interest turned into a daily obsession in retirement. When she makes money, she’s happy. When she sells because of uncertainty, she immediately wants to get back in, to make money back quickly. Every time we talk, I tell her, "You don’t need to look at your account every day. This is long-term money. You also don’t need to take that risk, given that you are comfortable with your retirement income." But the conversation always circles back: “So, based on your experience… should I not have sold? What if I buy back when the S&P hits 6000 or 7000?” I asked her once, “Where did 6000 come from?” She said, “I have software.” I told her gently, “But it hasn’t worked.” Over the years, she’s made a lot, lost a lot, and stressed a lot.
At some point, we have to call it what it is: That’s not investing. That’s gambling.
Watching your money every day doesn’t improve returns. It increases anxiety.
If your plan is solid, your job is not to babysit your portfolio. Your job is to live.
The Ability to Do Nothing
Here’s something people underestimate: The ability to enjoy an ordinary day. No schedule. No urgency. Some retirees struggle with this. They feel like they need to be productive all the time. But the happiest ones?
They get comfortable doing nothing and realizing nothing is wrong.
The $8 Coffee Problem
Let me make this personal because this is where retirement becomes real. I grew up with very humble beginnings. Money was always tight. Resources were always scarce. For years, I worked hard to move forward, through school, into college, and eventually into corporate America, trying to find my place in the financial world as a minority woman with a Chinese accent.
Nothing came easy.
So I learned early:
Save money. Invest money. Count the money. Repeat. For the first 20 years of my career, I never bought coffee for myself on the way to work. Not once. Today, I can walk into any coffee shop and buy whatever I want without even looking at the price. But that old mindset doesn’t just disappear. Even now, spending $8 on a coffee can still make me feel guilty.
And one day I caught myself thinking:
I manage money for so many people. Why does it feel like my money is still managing me?
That’s when it clicked.
The problem isn’t the $8.
It’s the relationship with money.
And this is exactly where it ties into retirement. Because retirement is not just about having enough money. It’s about being able to use it. So the rule became simple:
If you can afford it in retirement, enjoy it without guilt. Live for today and tomorrow.
If you can’t, skip it without feeling like you’re missing something essential. Because the truth is:
Nobody is watching whether you buy coffee or make it at home. No one is keeping score. Only you are.
And that feeling, that balance, is where real retirement peace comes from.
The Missing Piece: Community
This is where data is often missing, but the pattern is very real.
Loneliness is one of the biggest risks in retirement.
I’ve seen many retirees feel isolated and even depressed, especially after losing a spouse. Let me share one experience that stayed with me. I once had a French couple as clients. They were kind, thoughtful people. After retirement, they decided to move back to France. I remember feeling a little sad when they told me, not because it was a bad decision, but because I knew I wouldn’t get to see them as often.
But they followed their heart and moved. Within six months, one of them passed away due to a sudden terminal illness. It was heartbreaking.
And yet, at the same time, I felt something else: Gratitude.
Because the one who stayed was surrounded by family, by friends and by a community she grew up with. She wasn’t alone. And in that moment, it became very clear:
The happiest retirees don’t just have money.
They have people.
They choose where they live carefully. They build a support system. They stay connected.
Because in the end, money can support your lifestyle.
But only people can support your life.
My Version of Retirement (And What It Taught Me)
People ask me what my retirement looks like. Honestly, it’s not that dramatic.
I picture myself like a simple version of Warren Buffett. I’ll probably still wake up in my 80s, wearing sweats, going into my office, not because I have to, but because I’m happy to be curious.
What’s cheap? What’s happening in the world? Why or why not?
That doesn’t feel like work. That’s just who I am.
I won’t be drinking Coke like Buffett. I prefer green tea or coffee.
I’m not a big traveler. I’m more of a home person. Give me a familiar place, a few people I enjoy, maybe a mahjong table, and I’m good. And that’s the point.
After 28 years, here’s my honest conclusion:
Retirement is not about having the most money. It’s not about copying someone else’s lifestyle. It’s not even about stopping work. It’s about alignment.
Your money, your time, your habits, your environment, all working in the same direction. Because most people already know what they want. They just don’t give themselves permission to live it.
So, maybe the real question isn’t: “Do I have enough to retire?”
It’s: “Do I know how I actually want to live—once I finally can?”
Disclosure
This material is provided for informational and educational purposes only and does not constitute investment, tax, or legal advice. The views expressed herein are those of the author as of the date of publication and are subject to change without notice.
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