Do You Feel Lucky?
- Nov 30
- 3 min read

In the 1971 movie classic, Dirty Harry, Clint Eastwood has a criminal cornered and utters one of the most iconic lines in movie history…
“I know what you’re thinking: 'Did he fire six shots or only five?' Well, to tell you the truth, in all this excitement, I’ve kinda lost track myself. But being this is a .44 Magnum, the most powerful handgun in the world, and would blow your head clean off, you’ve got to ask yourself one question: 'Do I feel lucky?' Well, do you, punk?”
Recently, this quote came to mind when the market hit an all-time high. It has been an amazing run, and for many people, the only run they have ever known. On the other hand, those who experienced the devastation caused by the 2008 – 2009 crash may not remember the anguish associated with losing almost 40% of their life savings.
So, ask yourself, “Do I feel lucky?” Have you given serious thought as to what would
happen if…?
I’m not suggesting Armageddon is near, but an honest conversation about the potential risk to your nest-egg is absolutely in order. When you do, “put pants on it.” By that I mean don’t think in percentages (Like a 40% loss). People don’t spend percentages, they spend dollars.

For example, how would you feel if you woke up tomorrow and your $1 million nest egg was worth only $600,000? Should you consider pulling some of it off the table and putting a floor under it so you are protected on the downside but can still participate in a portion of any gains? Financial advisors tools to do just that.
Those who suffered the losses of 2008-2009 took almost 10 years to recover from the loss. Do you have that much time? If you are in the “Retirement Red Zone”, five years before through five years after retirement, a major loss could be devastating. Talk with your advisor and be sure you are comfortable with the potential risk in your portfolio.
By the way, Harry had one more shot left.
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Tom Kestler has been involved in the financial planning field for over 45 years. He is a graduate of Millersville State University and the College for Financial Planning in Denver, Colorado (for which he has acted as an adjunct instructor) and carries the Certified Financial Planner (CFP) designation.
He has also been awarded the Chartered Life Underwriter (CLU), Chartered Financial Consultant (ChFC) and Chartered Mutual Fund Counselor (CMFC) designations from the American College in Bryn Mawr, PA. He was the founder of Kestler Financial Group, Inc., a firm which specialized in the marketing of financial products and services to over 5,000 independent representatives throughout the United States. Kestler Financial Group was acquired by Highland Capital in 2018.
Mr. Kestler carries Life, Health and Variable Products licenses in several states and provides consulting services to insurance companies on product design and development. He also acts as an expert witness in securities and insurance litigation cases.
Prior to his retirement, Tom served as VP Advanced Sales at Highland Capital, and also CEO of Branch Development Partners, an Office of Supervisory Jurisdiction (OSJ) for Securities America, Inc. (now Osaic), an independent securities broker/dealer.
Tom will be teaching an upcoming Financial Wellness Course— the first class is scheduled for Monday, December 8th. Sign up today!
In the meantime, if you have a question for Tom, please post it in the Comments box below and he'll answer it for you.
