The $1 Million Business Owner Wealth Checkup

1. Could you personally maintain your current lifestyle for 10 years if your business income suddenly disappeared?

Your business may be highly profitable. That doesn't necessarily mean your personal wealth is independent of it.

2. Do you know exactly how much money you need personally to never have to work again?

Not a guess. A specific number based on your lifestyle, taxes, inflation, family obligations and desired retirement.

3. If someone offered to buy your business tomorrow, do you know approximately how much you would actually keep after taxes, transaction costs and other obligations?

A $10 million sale price does not mean $10 million of personal wealth.

4. Is your personal investment portfolio designed separately from your business?

Your business is already a concentrated investment in one company. Your personal portfolio should not accidentally create another version of the same risk.

5. Do you know whether you're paying more in taxes than necessary?

High-income business owners often have planning opportunities involving business structure, retirement plans, charitable giving, investments, timing of income and other strategies.

The question isn't simply: “How do I pay less tax?” It's: “What decisions should I make now because of the tax consequences five or ten years from now?”

6. If you sold your business, do you already know what you would do with the proceeds?

A business sale can transform your financial life. It can also create a completely different financial problem: what do I do with $5M, $10M or $20M of investable wealth?

7. Do you have enough personal liquidity that you wouldn't be forced to sell your business at the wrong time?

One of the most dangerous situations for a business owner is needing the business to produce cash precisely when the business is struggling.

8. Is your family financially protected if something happens to you?

This includes more than life insurance. It can involve ownership, estate planning, business succession, liquidity, beneficiaries and the ability of your family to access the wealth you've created.

9. Could your business continue without you?

If you're the rainmaker, decision-maker, salesperson and relationship holder, your business may be worth significantly less without you. That can become a personal wealth problem.

10. Do you have a written plan for turning business income into personal wealth?

Making $1 million a year is income. Keeping, investing and transferring that money effectively is wealth planning.

11. Are you intentionally deciding how much money stays in the business versus how much becomes personal wealth?

Many owners continually reinvest because they're good at growing businesses. But eventually the question changes from “How do I grow the business?” to “How do I make sure the business doesn't have to keep growing for me to be financially secure?”

12. Do you know your personal net worth excluding the value of your business?

If your business is worth $10 million and your personal investments are worth $500,000, you may be wealthy on paper — but still highly dependent on one asset.

13. Have you modeled what happens if your business is worth 50% less than you expect when you eventually sell?

A good financial plan shouldn't only work in the best-case scenario.

14. Do you know what financial decisions you should make before you sell your business rather than after?

Some planning opportunities disappear once a transaction is already underway. The best time to think about the financial consequences of a sale is usually before you have a buyer at the table.

15. If you stopped working tomorrow, would you know exactly what your next financial move should be?

If the answer is no, that's not necessarily a problem. But it is a signal that your financial plan may be less developed than your business plan.