Family Finances

Conduct A Regret Minimization Exercise To Help You Move Forward

One of the main reasons why I wrote my WSJ bestseller, Buy This, Not That was to help readers feel less regret by making wiser choices. Regret is one of the worst feelings, especially if it is a type of regret that could have been prevented through knowledge. The easiest way to stop saying, “If […]

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Overcoming The Trough Of Sorrow: Defeating An Emptiness Inside

Here in the San Francisco tech startup scene, we have a term called “the trough of sorrow.” The trough of sorrow refers to the sadness that comes after a setback or a big win. After a setback, you’re tasked with finding product-market fit to survive given your company has a limited runway of cash. You

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Vacation Property Comparison: Single-Family Mansion Vs. Resort Condo

If you’re in the market for a vacation property you will likely have to decide between purchasing a single-family home or a condo. However, what if you have enough money to buy a single-family mansion for $10+ million versus a condo at a luxury resort for $500,000+? I used to think a single-family mansion for

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How To Get Life Insurance For Free: Make More Money

Have you ever wondered how you can get life insurance for free? I’m not talking about getting free life insurance from work. The life insurance amount usually isn’t enough. I’m talking about how to get free life insurance outside of work. My wife and I have life insurance because with have two young children, a

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The Unexpected Financial Benefits Of Having Children

One of the main reasons why people delay having children is its cost. Rising prices for daycare, preschool tuition, and shelter plus the opportunity cost of not working, partially explains why our population replacement rate is declining.  The cost of raising children worried me so much that I actually had a $1 million net worth

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The Age Children Begin Loving Their Fathers As Much As Their Mothers

Are you a stay-at-home father or father who spends a lot of time with his children? If so, you may be second-guessing your decision to spend so much time with them during their early years. Without some reciprocating love, you might be wondering whether your effort is worth it. You see, the more time and

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The Fear Of Spoiling Adult Children By Giving Them Money Is Overblown

One of the worries about entering the decumulation phase is that you might start spoiling your adult children. If you end up giving your adult children so much money, you might just take away their motivation to work! Being able to earn your own money and provide for your family creates one of the most

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If You Love Your Spouse, You’d Make Them Financially Independent

If you love your spouse, you’d make them financially independent. If you don’t truly love your spouse, then you’d make them depend on you for all their financial needs. Depending on someone for money is a terrible feeling. Imagine being a grown adult and returning home to live with your parents after four years of

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Dear Older Parents, Having Kids Late Might Be The Best Choice After All

I’ve mentioned one of my regrets was having kids late. I was too focused on my career. Then I became too focused on achieving financial independence to make room for little ones. Ideally, I would have liked to have had my first kid at age 34 instead of at age 39. However, a conversation with

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