Earlier this year, I enjoyed a great meal with a colleague who was seeking guidance on how to incorporate his practice and on how to find time with his busy career to begin investing in real estate.

High-earning incorporated professionals like us have “good problems” (as I call them).

We are frequently bombarded with investment opportunities and the often time-sensitive process of weeding out the lucrative offers can trigger anxiety in the most knowledgeable investors.

Seasoned investors often rely on a series of questions to help them mitigate the risk-aversion and feelings of anxiety that often go hand-in-hand when making important investment decisions.

Tips for managing investment anxiety:

The trick is to ask yourself a series of questions.

• Begin with quantitative questions. What is the expected return? What is the risk? How can I execute this in the most tax-efficient manner?
• Then dig a little deeper. Can I afford it right now? Do I trust these people? How does my spouse/partner feel about this?
• And finally, let me share my personal favourite set of questions when dealing with big stakes. I like to call these the “Sleep Test” Does it add to my happiness and peace of mind? Does this investment bring me closer to my dreams? Will I sleep better?

Ideally, wealth will give you a sense of security, but achieving wealth can often heighten your insecurities.

The next time that you’re faced with an investment opportunity, do the math and the research required to develop a solid investment strategy.

To ease your mind, reflect on the questions that I shared with you. And to get closer to your dreams, go to sleep.