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“I cannot emphasize enough how important it is to live beneath your means.” with Earl Rubinoff and Beau Henderson

I cannot emphasize enough how important it is to live beneath your means. I know a family who sold their business to a public company while the father was still in his fifties. He immediately retired and enjoyed a lavish lifestyle with a huge home, vacation properties, fancy cars, and exotic trips. Fast forward to […]

I cannot emphasize enough how important it is to live beneath your means. I know a family who sold their business to a public company while the father was still in his fifties. He immediately retired and enjoyed a lavish lifestyle with a huge home, vacation properties, fancy cars, and exotic trips. Fast forward to today and this father is now in his nineties living with his children because he outlived his money.


As a part of my series about the “5 Things Retirees Say They Wish They Were Told Before They Began Retirement” I had the pleasure of interviewing Earl Rubinoff, President and CEO of the Rubinoff Group in Deerfield, Illinois. Founded in 1984, The Rubinoff Group specializes in estate planning, wealth maximization, retirement planning, insurance planning, business continuation plans, employee benefits, and selected executive programs. Earl is a registered representative with Park Avenue Securities LLC, a broker-dealer, and indirect, wholly owned subsidiary of The Guardian Life Insurance Company of America. He is a frequent public speaker on financial services and insurance topics at national conferences, including Guardian’s Million Dollar Round Table.


Thank you so much for doing this with us! Our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?

Leading my own firm was always part of my DNA. My father passed the bar at 20 years old and immediately started his own law practice and only worked for himself throughout his life. When it came time to launch my career, working for a big corporation never appealed to me. I knew I wanted to do something meaningful that fed my entrepreneurial spirit, which led me to a career helping families prepare for a strong financial future.

Early on, I witnessed how quickly families who appeared affluent with fancy cars, vacation homes and country club memberships faced severe financial hardship when their fortunes turned and they were not properly prepared. Seeing their struggles had a real impact on how I approach financial planning with my clients. With many Americans living well into their nineties, the need to prepare for long-term financial wellness is critical so you don’t outlive your money.

Can you share the most interesting story that happened to you since you started your career?

One client situation that I think about often is a husband and father in his forties who was diagnosed with liver cancer. His term life insurance was just about to expire and he was devastated. Not only was he facing a life-threatening illness, but he believed he would be leaving his wife and children destitute with no financial safety net. I was able to exchange his term policy for a permanent whole life insurance policy that did not require a health exam. They were overjoyed, and I still remember the relief on their faces when I explained the continuation of coverage.

I am delighted to tell you that he is still alive, although he has faced many other serious medical issues since his initial cancer diagnosis. He is a dear friend as well as a client and we meet periodically to review his financial plan as well as enjoy some rounds of golf together. Knowing that I can help clients get the right protection to get them through life’s highs and lows and make a real difference in their lives is incredibly fulfilling.

Can you share a story with us about the most humorous mistake you made when you were first starting? What lesson or take-away did you learn from that?

Very early on in my practice, we mistakenly identified a male client as female in the policy paperwork for his new life insurance coverage. I had not yet met him in person and made an incorrect assumption based on his name. This impacted his initial rate quote, but was ultimately corrected. It taught me an invaluable lesson on the importance of triple checking your facts and not making assumptions.

None of us are able to achieve success without some help along the way. Is there a particular person who you are grateful towards who helped get you to where you are? Can you share a story about that?

Without a doubt, I am grateful that Herb Davis, who was with Guardian Life Insurance in Chicago, was an early mentor in my career. Herb had been in the industry several decades before I joined and was an exceptional example of what a good businessman and human being should be. He taught me the importance of maintaining positive relationships and expressing gratitude to those around you. A true gentleman and professional, it was from Herb that I learned the importance of becoming a knowledgeable expert in your industry, the significance of having a good reputation and standing by your word. Every work day, I attempt to replicate those traits.

What advice would you suggest to your colleagues in your industry to thrive and avoid burnout?

If you worry about how much money you will make with each transaction, you will never be successful. Put your attention into the relationship and don’t worry so much about the compensation. The vast majority of my new clients come from referrals from existing clients because I have invested in these relationships over time.

Make learning a priority throughout your career. If you stop learning, you become stagnant and stop growing. Throughout the year, I attend seminars and professional events to stay up to speed on developments in the industry. I also make time to read about ways to improve my skills such as how to be a better manager or use my time more efficiently to get more out of my day.

What advice would you give to other leaders about how to create a fantastic work culture?

Number one is to show appreciation to your colleagues at every level. In my office, we regularly offer free lunches and happy hour outings to acknowledge our team’s hard work. But what is more important is what you do on a daily basis to encourage a supportive work environment. Be clear with all your communications to avoid misunderstandings and manage expectations. I tell my colleagues that we are like a football team whose goal is getting to the Super Bowl. We all need to work together to accomplish that goal and we cannot get there without each member of the team giving 100 percent every day.

Ok thank you for all that. Now let’s move to the main focus of our interview. Retirement is a dramatic ‘life course transition’ that can impact nearly every aspect of one’s life. Obviously everyone’s experience is different. But in your experience, what are the 5 most common things that people wish someone told them before they retired?

For men, it is particularly important to make more friends and keep up personal relationships. Many men neglect this aspect of their lives to their detriment. They need to establish a social life with other men that can continue throughout retirement.

You cannot discount good health, so it is imperative to stay healthy and get regular checkups. You must be able to travel and remain active.

Don’t let your paycheck stop. Set up an investment plan that pays you a monthly income along with Social Security. We have all grown accustomed to receiving a steady stream of income throughout our working life and this should not stop in retirement.

I tell my clients about the Permission Slip theory. If you have permanent life insurance, then it gives you permission to spend your money and enjoy it while you are alive since you know your life insurance will be there to leave something to your loved ones.

It is important to start thinking about your tax plan strategy early. At age 70½, you are forced to take taxable distributions from your Non-Roth qualified retirement accounts. Your portfolio should be balanced to offset this taxable income.

Let’s zoom in on this a bit. If you had to advise your loved ones about the 3 most important financial issues to keep in mind before they retire, what would you say? Can you give an example or share a story?

I cannot emphasize enough how important it is to live beneath your means. I know a family who sold their business to a public company while the father was still in his fifties. He immediately retired and enjoyed a lavish lifestyle with a huge home, vacation properties, fancy cars, and exotic trips. Fast forward to today and this father is now in his nineties living with his children because he outlived his money.

Related to this is to work as long as you can. Keep a steady flow of income coming in as long as you are mentally and physically able to.

Finally, take advantage of all forced savings systems available. Maximize your 401(k) and similar investments. Have the funds taken directly from your paycheck so this money never hits your pocket. It is amazing how this forced nest egg will grow over time with little to no impact on your current lifestyle. You’ll be glad you were disciplined in this area once you retire.

If you had to advise your loved ones about the 3 most important health issues to keep in mind before they retire, what would you say? Can you give an example or share a story?

Maintain regular checkups to catch any potential problems early.

Remain active physically.

Take care of your mental health. Reduce stress through yoga, meditation, exercise and massages. Mental care is just as important as physical care and can greatly reduce your quality of life if neglected.

If you had to advise your loved ones about the 3 most important things to consider before choosing a place to live after they retire, what would you say? Can you give an example or share a story?

Carefully consider the cost of living when selecting a place to live after retirement. This includes housing as well as food, gas, services and taxes.

Consider a college town for your post-retirement life. They typically have a lot of activities and cultural events to enjoy. You might even take classes at the local college to keep your mind sharp, meet new people and learn new skills.

Consider safety a top priority for your new town. Seek places that have low crime rates.

You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. 🙂

Americans are consumed by instant gratification. We revere those with the most expensive house, the fancy car, and the most fashionable clothes. We are a society that spends money we don’t have on things we don’t need. My movement would be to provide more financial education starting at a young age to improve the financial literacy of all Americans. This could go a long way toward reducing the crushing debt facing many people.

I recently conducted a seminar for millennials on the importance of having disability insurance. This came about from a discussion with my three millennial daughters who were confused about all the different workplace benefit options offered. When you think about it, you’re most valuable asset is your ability to earn a living. If illness or injury prevented you from doing that for an extended period of time, what would you do? The reality is that one in four 20 year olds will experience a disability for three months or more before they retire. That’s a sobering statistic but can easily be avoided with proper financial planning looking at the long term versus demanding immediate gratification.

Is there a particular book that made a significant impact on you? Can you share a story?

I recently read Grit by Angela Duckworth and it really stayed with me. She is a psychologist who makes a compelling case on what it takes to be successful. It is not about who is the smartest, richest or most talented, etc. The real key to success in business and life is persistence and hard work. There are no short cuts. Each day, I aim to incorporate these lessons into my personal and professional life. As I look back on my 35+ year career, I have focused on consistency, similar to a Tiger Woods or Coach Pete Carroll of the Seattle Seahawks, who are featured in the book.

Can you please give us your favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life?

I tell my daughters constantly that “thrift is a badge of honor.” Living beyond your means is a nationwide epidemic. If you don’t want to outlive your money, you need to start saving more than you’re spending now.

What is the best way our readers can follow you on social media?

The best way to reach me is through my website: http://www.earlrubinoff.com/contact-us/ or on LinkedIn at https://www.linkedin.com/in/earlrubinoff/

Thank you for these fantastic insights. We wish you only continued success in your great work!

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