Have you ever achieved a financial goal that looked perfect on paper but left you feeling empty? Maybe you bought the house in the "right" neighborhood, maxed out your retirement contributions, or even reached that net worth milestone you'd been chasing, yet something still felt off.

When we help clients with estate planning, we often suggest they think beyond just wills and trusts. Your loved ones might appreciate your life advice as much as your legal documents… This past Father's Day, I decided to take my own advice.

“I have spent my whole life scared.  Frightened of things that could happen, might happen, might not happen.  Fifty years I spent like that. Finding myself awake at three in the morning.  But you know what? Ever since my diagnosis, I sleep just fine. I came to realize it’s fear that’s the worst of it.  That’s the real enemy.”

If I asked you to explain to a 5th grader the basics of how people make money investing in real estate, you probably wouldn’t miss a beat: buy a house, collect rent, subtract your expenses and the rest is profit.  Have the average person try to explain how the stock market works however and the answer will likely be about as helpful as asking Kim Kardashian to give her interpretation of campaign finance reform.

George Carlin made a great observation: most people will admit to being bad at math, but no one wants to own up to being a bad driver.  The problem is most of us are much, MUCH worse at math than we even admit to, and it ends up working against us when it comes to investing. 

How many success stories do you know of that started off by someone taking the safe route? I’m not suggesting you don’t need to put together a solid roadmap for how you plan to reach your destination, but overplanning and fear can lead to analysis paralysis, where you may never leave the garage.