How Well Do You Manage Wealth? Take the Millionaire Decision Quiz

"Jim" considers himself a savvy investor. He saved just over a million dollars before turning 50, but recognizing that he may have some financial blind spots he scheduled a meeting with a fiduciary financial planning firm. At the first meeting, the advisor asked him, "How do you pick stocks?" Jim provided various answers. He pays attention to the news, listens to conversations around him, watches CNBC, and analyst recommendations. But when the advisor followed up with "When do you sell?" Jim found himself at a loss for words.

We live in a culture dominated by influencers, whether it's on social media, through television advertisements, on Amazon devices, or even from well-meaning friends. It seems like everyone has an opinion on how you should spend your money. Whether recommending stocks, the latest gadgets, a larger home, or designer clothing, the chorus of voices loudly urges us to buy, buy, buy! We rarely hear the calm voice advising us to sell, except when it's driven by fear or panic (or when your realtor is trying to get you to list your home).

So, how can we make the best financial decisions? If you are a Midwest Millionaire and want to understand how you make financial decisions, take this nine-question quiz to see if you are on track and identify areas where you might need some help. Drawing from experiences of wealthy individuals, each question presents a real-world scenario from estate planning dilemmas to managing family dynamics around money. These questions will test your ability to apply sound financial principles when the stakes are highest.

The Millionaire Decision Quiz

As a millionaire, your financial decisions carry greater complexity and consequence than those of typical investors. This quiz evaluates your understanding of the framework for making smart financial decisions, specifically tailored to the unique challenges you may face as a high-net-worth individual.

Instructions: Select the best answer for each question. At the end, you will find the scores and accompanying interpretations. This assessment will help you understand your capacity and knowledge of managing financial choices as a millionaire.

Question 1: Identifying True Needs
Your after-tax bonus at the end of the year was $50,000, and now you want to allocate those resources. You have three options:

Fix up your primary residence which has some foundation issues and the HVAC system is at the end of its useful life.
Use that money as a down payment on a vacation home in Florida.
Increase your emergency fund from $50k to $100k, per the advice of your financial advisor.

What of these options represents your highest priority "need"?

A) The vacation home for family enjoyment and potential appreciation
B) The primary residence renovations for safety and structural integrity
C) Increase the emergency fund
D) Split the money equally among all three options

Question 2: Taking Care of Responsibilities
Congratuations! You just sold your business for $10 million after 20 years of hard work. Your estate planning attorney recommends updating your will and trust, you have $3 million in various debts, and you have two kids in high school with little to no college saving. What should be your first financial responsibility?

A) Invest the entire amount in growth stocks for maximum returns.
B) Pay off all debts and update estate planning documents.
C) Set aside funds for children's education and lifestyle maintenance.
D) Purchase additional life insurance policies.

Question 3: Prioritizing Desires Among Multiple Options
With $20 million in liquid assets beyond your needs and responsibilities, you've decided this year you want to spend some money. You read about the most expensive hobbies in the world and now consider the following purchase options: a $12 million private jet (and pilot training to go with it), an $8 million art collection, a $10 million yacht docked in Puerto Rico, a $15 million investment in a friend's startup, and a $10 million charitable foundation. How should you prioritize these desires?

A) Choose the most expensive option for maximum impact.
B) Rank them by long-term value, legacy impact, and personal fulfillment.
C) Avoid all options and keep the money in cash.
D) Invest in whichever option your wealthy friends recommend.

Question 4: Choosing Financial Influencers Wisely
You have $5 million in cash, and want to put those lazy dollars to work, but you're receiving conflicting advice. Your influencers include a celebrity financial guru who suggests options trading, your golf buddy who made money in crypto, a fee-only fiduciary advisor with 20 years experience who will invest mostly in ETFs and Mutual Funds, and a hedge fund manager seeking investors for a private equity fund. Given these varying perspectives, whose opinion should should carry the most weight in your decision?

A) The celebrity guru because of their media presence and promise of high returns in options.
B) The fee-only fiduciary advisor with relevant credentials.
C) Your golf buddy, since he has recent success.
D) The hedge fund manager because they manage large sums of money.

Question 5: Choosing Influencers - Family and Social Pressure
At your nephew's wedding, your brother-in-law offers you an opportunity to invest in an "exclusive" real estate development that promises 25% annual returns. He mentions several family members and wealthy acquaintances who have already committed millions. What's your best approach to evaluating this pressure?

A) Invest immediately since other family members and known acquaintances are involved.
B) Analyze the opportunity independently and consider the motivations behind the pressure.
C) Invest a small amount to maintain social relationships.
D) Ask a family member to decide for you.

Question 6: Managing Fear
During a market correction, your $10 million portfolio drops to $8.5 million. You're experiencing intense fear about losing your wealth and considering moving everything into government bonds yielding 3%. Which of the following sounds like the most appropriate financial decision?

A) Move everything to bonds immediately to prevent further losses.
B) Review your long-term wealth management strategy.
C) Sell half your holdings and wait for market recovery.
D) Increase risk by buying more stocks at lower prices.

Question 7: Managing Greed
A private equity opportunity promises to triple your $2.5 million investment in 18 months, backed by "guaranteed" contracts. You're tempted to liquidate your diversified portfolio to maximize this opportunity. How should you manage this greed-driven impulse?

A) Invest the full amount since the returns are guaranteed.
B) Recognize this as excessive risk-taking and maintain portfolio diversification.
C) Borrow against your assets to invest even more.
D) Invest half your portfolio as a compromise.

Question 8: Checking Impulses - Lifestyle Inflation
Last year was particularly profitable for your company. You've decided to splurge a bit because you've earned it! It's time to upgrade your lifestyle, so you upgrade your home to a $2 million house on 5 acres and completely renovate the interior, hire a groundskeeper, and housekeeper, plus purchase a boat for your vacation property, and the fancy sports car you've been eyeing since you were 18 years old. These purchases consume almost all of your liquid assets. How should you check this impulse?

A) Make all purchases immediately while you have the cash.
B) Implement a waiting period and evaluate against long-term wealth goals.
C) Finance the purchases to preserve cash.
D) Make the purchases but reduce other expenses.

Question 9: Estate Planning and Generational Responsibility
Your estate planning attorney presents three strategies for transferring $30 million to your children:

Immediate gifting with tax implications,
A complex trust structure,
Waiting until death.

Your children are pressuring for immediate access. What's your most responsible approach?

A) Give them immediate access to avoid family conflict.
B) Evaluate each option against long-term family wealth preservation and tax efficiency.
C) Split the difference and give them partial access now.
D) Ignore professional advice and follow your instincts.

Answer Key and Scoring
Correct Answers:

B - Primary residence renovations (structural and replacement needs). Neglecting these essential repairs can lead to more severe damage, higher costs, and potential safety hazards down the line. While increasing your emergency fund and investing in a vacation home are important financial goals, they come after securing your primary residence.
B - Pay debts and update estate planning (responsibilities first). Clearing your $3 million in debts immediately reduces financial risk and interest expenses, freeing you from obligations that could otherwise erode your wealth over time. Proper estate planning safeguards your assets, clarifies your wishes, and helps avoid potential legal complications or family disputes down the line. While investing for growth, funding education are important, these come after you have addressed your immediate financial responsibilities. You may or may not need life insurance at this point.
B - Rank by long-term value and legacy impact (systematic prioritization). This approach ensures that your financial decisions align with your broader goals, rather than being driven by impulse, peer pressure, or the temptation of extravagance.
B - Fee-only fiduciary advisor (qualified, unbiased guidance). A fee-only financial advisor is legally and ethically obligated to act in your best interest, providing advice grounded in experience, transparency, and objectivity.
B - Independent analysis of motivations (wise influencer evaluation). Family and social connections can create a sense of urgency or obligation, but investing without thorough due diligence exposes you to unnecessary risk, especially when promised returns seem unusually high.
B - Review long-term strategy and maintain diversification (managing fear). No investment is without risk, and anyone who says so is trying to sell you something. Speculative investments should be evaluated by a trusted professional, someone who can provide a clear unbiased opinion.
B - Recognize excessive risk-taking (managing greed). Diversification is a fundamental principle of sound wealth management as it helps spreads risk across different asset classes and reduces the impact of any single investment’s poor performance. By maintaining a balanced portfolio, you safeguard your capital against market fluctuations and speculative ventures, ensuring long-term growth and financial security.
B - Implement waiting period and evaluate goals (checking impulses) Set a dollar amount that you must wait a period of time before spending. For example, some people decide to wait 24-hours for any purchase over $100. Perhaps your threshold is $1,000, or wait three months to spend over $1 million.
B - Evaluate against wealth preservation and tax efficiency. If your children are pressuring you for access, then do they truly value the relationship with you, or do they have issues with their own greed that may need to be checked? By keeping a revocable trust in place, you have the option to change the beneficiary and give it all away to charity if your children do not value you as their parent. (responsible planning)

Your Score Interpretation:
9 Correct: (All B answers) Outstanding! You demonstrate sophisticated understanding of wealth management principles. Your decision-making framework is well-developed and you're positioned to preserve and grow generational wealth effectively. Continue working with qualified professionals to refine your strategies.

7-8 Correct: Strong foundation with room for improvement. You grasp most wealth management concepts but may benefit from strengthening your emotional discipline and systematic approach to complex decisions. Consider talking with your financial advisor about the areas where you could use some more clarity.

5-6 Correct: Your wealth management decisions may be influenced too heavily by emotions or external pressures. Work closely with a fee-only financial advisor to develop a more structured decision-making process.

Below 5 Correct: You have a significant opportunity for improvement. Your current approach may put your wealth at risk. Consider engaging a team of qualified professionals including a fee-only financial planner, estate planning attorney, and accountant to develop a more systematic approach to financial decisions.

Next Steps
The journey to lasting financial prosperity is guided by proven principles that successful millionaires consistently apply. Whether you have $10,000 saved or $10 million, these strategies can help you build, grow, and maintain your wealth. Planning for success includes spending less than you earn while working, automating your investing strategy (or hiring a fiduciary to manage your wealth), and focusing on long-term goals instead of short-term emotions. If you are a Midwest Millionaire in need of assistance to reach your goals and stay on track, reach out to the fiduciary advisors at Hurlow Wealth Management today by calling 812-333-4226 or CLICK HERE to schedule an appointment.

Services offered through Hurlow Wealth Management Group, Inc., a Registered Investment Adviser. Hurlow Wealth Management Group, Inc. does not provide tax, legal or accounting advice. Advisory services are only offered to clients or prospective clients where Hurlow Wealth Management Group, Inc. and its representatives are properly licensed or exempt from licensure. Past performance is no guarantee of future returns. Investing involves risk and possible loss of principal capital. No advice may be rendered by Hurlow Wealth Management Group, Inc. unless a client service agreement is in place.