Don’t Sell Your Home Until You Read This – My Biggest Real Estate Regret

One of the top five things I regret in my life is selling the properties I was holding. I sold four homes during the crash of 2008 and I’ve regretted it. If you’re thinking about selling, I urge you to pause and consider the long-term impact before deciding.

The Real Estate Trap: Timing the Market

If you’re considering selling, you’re likely talking to real estate agents, watching YouTube videos, and trying to time the market. Maybe you're thinking: ?? "Look at all this money I’ve made! Maybe I should sell now." ?? "I’ll rent for a little while and jump back in later." ?? "The market might crash – better to sell before it’s too late."

If you’re talking to other agents, they might encourage this thinking. After all, we’ve seen incredible appreciation over the past few years. But is selling really a good decision for the long haul?

From my own experience, I can tell you that selling properties I could have held onto was a financial misstep. And I want to make sure you don’t make the same mistake.

When Selling Makes Sense

Of course, there are legitimate reasons to sell:

?? Inherited Property: You and your family decide to sell an inherited home and split the proceeds.

?? Divorce: Assets need to be divided.

?? Relocation: Managing a rental property in another state isn’t practical.

?? Financial Hardship: If you can’t afford the mortgage or lost your job, selling might be necessary.

If you’re in one of these situations, selling makes sense. But if your reason for selling is simply to cash out, upgrade, or out of fear of a market downturn, you need to rethink your strategy.

Why Trying to Time the Market is a Bad Idea

I hear this all the time:

?? “We’re at the top of the market. I think I should sell before prices drop.”

I get it. The fear of another crash is real. But let me share my own experience.

In 2007, my best friend and real estate partner died suddenly and we owned multiple properties. When the market crashed, my business took a hit, and we had good tenants who were paying rent. But in a panic, I sold everything. Looking back, it was the worst financial decision I ever made.

Had I just held onto those properties for 10 years, my financial position would be dramatically different today. But as my father always said “We grow to soon old and too late smart.

This is my warning to you: Don’t sell out of fear, uncertainty, or doubt.

The Hidden Costs of Selling

Selling your home isn’t as simple as pocketing the difference between your purchase price and selling price. There are real costs involved:

?? Closing costs – realtor commissions, title fees, transfer taxes, etc.

?? Moving costs – Hiring movers, renting storage, time, and stress.

?? Capital gains tax – If you’ve owned your home for a while, you may owe taxes on the profit (beyond the exclusions see a tax professional for your situation).

?? Hassle costs – Showings, staging, repairs, and negotiations.

And what if you decide to rent? The rental market is expensive right now. Many sellers who planned to wait for a price drop are still waiting—losing thousands in rent payments while hoping for a better market.

A Smarter Alternative: Keep Your Home & Leverage It

Instead of selling, consider this:

? Take out a home equity line of credit (HELOC) or a second mortgage. The money you take out is not taxable and can be used to invest in another property.

? Rent out your current home to generate cash flow while moving into a new one.

? Build long-term wealth instead of cashing out short-term.

This is exactly what I’m doing now. After learning my lesson the hard way, I’m committed to holding onto real estate, even in tough times.

The Truth About “Upsizing” and “Downsizing”

Thinking about upgrading to a bigger home? Remember:

?? Bigger house = bigger bills (higher property taxes, more maintenance, and more furniture).

?? Downsizing sounds appealing, but many regret going too small and end up moving again.

?? Moving costs money! Staying put often makes the most financial sense.

Final Takeaway: Think Long-Term

Before selling, ask yourself:

?? Will this home be worth more in 10-20 years? (Hint: Yes.)

?? Am I selling because I’m scared? (Fear-based decisions rarely end well.)

?? Can I leverage this property instead of selling it?

If you must sell, make sure your home looks its best. I’ve seen too many sellers lose money because their agent didn’t market their home properly.

The right Broker makes all the difference.

And if you’re in northern Ohio and need guidance, I’d love to help.

?? Let’s connect. I’ve been through it all, and I want to make sure you don’t repeat my mistakes.

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