I Asked a Stockbroker What a Good Retirement Plan Looks Like. She Stumped Me.
A rare conversation where someone asked me more questions than I did.
I enjoy speaking to ‘insiders’.
Professionals, experts, and those inside the machine.
They [obviously] have exposure to the mechanics of the money game. They know what works.
And.
They know what doesn’t work. That matters.
So, when I had the chance to engage them — I fired away.
The 49-Year-Old Stockbroker
Strictly speaking, Lilly is a remisier, not a regular stockbroker.
She services clients in her capacity and name. She was affiliated with a bank, and she was provided tools, contacts, and a prestigious Bloomberg terminal.
That is how we got acquainted. Lilly called me. I answered.
The rest is history.
I’ve executed several trades using her service. It happened when I was on the road and was on calls all day. Placing an urgent buy/sell trade on mobile was difficult.
I thought about her. So, I called. She did as I requested. No questions asked.
With time, I learned to trust her.
Lilly is not a traditional stockbroker. She is not interested in paddling financial products.
She is interested in,
- Getting access to the financial tools and analysis for free [smart],
- Understanding financial instruments to avoid [again, smart],
- Identifying asset(s) that do well over time [super smart].
She is always thinking and verifying what she knows. The question(s) she asked me is telling.
I ask her questions, too.
The ones closest to my heart.
Like this one.
“Lilly, what does the perfect retirement investment portfolio look like?”
She smiled.
Silently.
“What Do You Think?”
This is her default answer.
She would throw this response out like clockwork each time I asked her a thinking question. I used to be annoyed.
Used to.
Lilly wants me to think deeper [and harder] about money and investments. It is a brilliant way to understand the person in front of you.
With time, I learned.
“Equities? They do well over many years. Gold? They hold their value.”
She looked at me and smiled.
Silently, of course.
And she said something thought-provoking.
“Aldric, if you already have answers… why are you asking me this question?”
I was stumped.
Lilly is right.
Something is amiss. Fundamentally, logically, and emotionally.
I was thrown into the deep sea of endless reflection.
Fortunately for me, Lilly fished me out. She interrupted me… softly.
“The real reason you are asking this question despite having answers is because…”
She took a pause and stared at me.
“You don’t trust your answer. You feel insecure about these financial assets and your investment philosophy. That is it.”
Now we enter the universe of behavioral economics.
I’ve never evaluated money and investment decisions from the perspective of trust. And maybe Lilly is right. It could be the reason.
From this point onwards,
- I stopped asking superficial investment questions.
- I allowed Lilly to probe me further.
She was curious.
Lilly wanted to know,
- How I think,
- What money and investment means to me,
- How financial assets affect my retirement planning.
It was a brilliant 1-way conversation.
I [absolutely] loved it.
“If You Have to Worry About Your Retirement, It Means Your Retirement Is Risky.”
She killed me.
Really.
Lilly turned the entire conversation upside-down. I must give it to her. I never thought about retirement this way.
I wanted a strategy to reduce financial risk during retirement.
Her logic?
If I worry about retirement, then The Big R itself is risky, not those financial assets I hold. Wow~.
I had no response.
I wanted Lilly to continue.
“You must flash out what you are worried about. If your answer is money issues… you are not thinking at all. There are one million types of money woes.”
Maybe I am getting it.
I can be paranoid without an active monthly income. If so, no amount of dividends will calm me down. Unless, of course, my portfolio pays me $1,000,000 every quarter.
That is not going to happen.
Or.
I can be worried about a depletion of cash. This plagues me more than any investment gaining 100% in value.
I was broke before.
I used to have only $100 in my bank account. It scarred me. Never again.
I was lost in my jungle of thoughts.
Lilly let me be.
She was busy with her phone. Maybe Lilly was placing trades. She could be monitoring her portfolio. I heard nothing from her for a long while.
“I guess you have your answers?”
This time, I smiled.
“How Do You Plan for Your Retirement?”
I wanted practical insights.
So, I asked how she did it.
Lilly did not dodge me.
She shared without hesitation. Her candidness surprised me.
“Me? I think about my worries. Then, I work to close them. That’s my investment plan.”
Hmm, intriguing.
Lilly elaborated.
“I worry about mental decline. So, I learn more about market trading. It is a game I love, and it keeps me going. Making money from it helps. Having a desk and Bloomberg terminal at the bank keeps me engaged.”
“I worry about good companies not paying dividends. It happens. So, I look for ways to generate income when sh!t happens. I am learning to sell my professional knowledge via online courses.”
“I worry about medical cost inflation. Not inflation. Medical cost inflation. A 10% jump in medical treatments can render my insurance coverage useless. I buy more hospitalization coverage.”
Fascinating.
Of course, she said more. But-
I never thought about retirement investing this way.
And… why not? It is simple, personal, and highly intuitive. This is an approach many people can understand.
And act on for their future retirement.
We may not know what to invest. But we sure know what we are [really] worried about.
The Close
I spoke very little.
I was [mostly] quiet during our conversation. Lilly spoke very little, too. Her style is to probe.
Her questions revealed her 2-step investment approach to retirement.
- Uncover worries,
- Cover them.
And I must say this.
It is way more elegant than any financial products or approaches I have been pitched to.
And straightforward, too.
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