39-year-old millionaire says why he ‘regrets’ paying off his 2 mortgages: ‘I felt trapped’

Three years ago, I paid off two mortgages: our primary residence and a three-bedroom house that my wife and I rented for $1,500 a month.

I felt I was on the right financial track. I was officially debt-free and also ran a successful music blog and business coaching service — both of which brought in a combined annual income of $1 million. Before that, my family and I lived on food stamps.

But now, at 39, I regret paying off my two mortgages. Just a year after paying off the mortgage, my wife and I enrolled our daughters in a school an hour away from our home in Tampa, Florida.

Getting closer would be ideal, but most of our money was already tied up in real estate. Our options were limited and I felt trapped.

But the experience taught me several important lessons:

1. Have your own philosophy about money.

I didn’t grow up learning much about money, but I knew I had to get my finances in order after I got married at 22. So, I turned to self-help books and experts for guidance.

Having watched family and friends struggle with debt my entire life, I was drawn to the camp of money advice advocates for zero debt, even mortgages.

But different people have different situations. Eliminating my bad debt but maintaining a lot of liquidity would have given me the most financial flexibility.

After months of fighting the banks, I was able to refinance a house and buy a new one closer to my daughters school. But this time, I followed my own money philosophy.

I only put 50% into my new home after selling my old one and invested the remaining 50% of the value of the new home into an index fund.

2. It’s okay to get emotional about money.

Money can be a source of stress and hardship, and it’s okay in some situations to let your emotions play a role in your decisions.

I assumed that having a paid off house would reduce my stress. As it turned out, a paid off house with little access to money ruined my sleep. I had to develop a more practical approach to my mortgage debt.

My investment of 50% of my house’s value in an index fund wasn’t just an attempt to build wealth. It was mainly to give me peace of mind that I could access my money in the event of an emergency or major life change.

If you’re about to make a big financial decision, do a “sleep test.” In any given financial situation, ask yourself, “Which choice will help me sleep better at night?”

3. Your money goals should be constantly evolving.

Leave a Reply

Your email address will not be published. Required fields are marked *