Should You Sell Your House? Watch This Before You Decide

Don’t Sell Just to Time the Market

Don’t sell your home until you’ve listened to this advice. One of the top five regrets I have in life is selling the properties I once owned. I’ve moved 11 times in 21 years, and every time I sold instead of holding, I regretted it.

If you’re considering selling, you’re likely talking to other Realtors, watching YouTube videos, or trying to time the market. You might be thinking: “Look at all the money I’ve made—I should sell, rent for a while, and then jump back in.”

Some Realtors may even encourage it, since we’ve seen massive appreciation recently. But is this really a good decision long-term? From experience, I can say it hasn’t worked out for me—and I don’t want you to make the same mistake.

When It Might Make Sense to Sell

There are legitimate reasons to sell a property:

• Inheriting a home after the death of a loved one

• Divorce and splitting assets

• Job loss or being unable to afford your current home

• Relocation where managing a rental isn’t feasible

In these cases, selling makes sense. But if your motivation is simply to “cash out,” buy bigger, or avoid a potential crash—you may want to reconsider.

Lessons From 2008–2009

Back in the crash, my husband and I owned multiple properties. When both of our industries (M&A and real estate) were hit hard, we liquidated everything to pay down debt. While it gave us short-term relief, it was the biggest financial mistake we’ve ever made.

If we had simply held those properties for 10 years, our financial position today would be completely different. The key lesson: don’t make real estate decisions based on fear, uncertainty, or doubt.

The High Cost of Selling

Selling a home isn’t as “clean” as it sounds. There are:

• Closing costs

• Moving costs

• Hassle and inconvenience costs

• Capital gains taxes (after exemptions of $500K for joint filers or $250K for single filers)

• 
  

When you add it all up, the money you “walk away with” may be far less than you expect.

A Smarter Alternative: Tap Into Equity

Instead of selling, consider an equity line of credit or a second mortgage. The money you pull out of your home is not taxable. You could:

• Use it for a down payment on a new property

• Rent out your current home to create cash flow

• Start building generational wealth

Yes, rates on equity lines are high, but many homeowners still have historically low rates on their primary residence. Rents are strong right now, which could offset costs and make this strategy work long-term.

The Reality of Today’s Market (October 2023)

• Mortgage rates are above 8%

• Housing inventory is constrained

• Buyer demand is low

At open houses, traffic is sparse, and buyers are making offers far below list price. Yet, just like in early 2023, the market can change quickly. You can’t time it perfectly—so don’t try.

If You Must Sell

If selling is the right choice for you, make sure you:

1. Stage your home beautifully (a checklist is linked below).

2. Hire the right Realtor. The wrong representation can cost you thousands, while the right one is worth their weight in gold.

Buyers are savvy and won’t even schedule a showing if your listing looks unprofessional.

Avoid Drastic Moves

Moving to a much larger or much smaller home often leads to regret. Bigger homes mean higher property taxes, more furniture, and more maintenance. Downsizing too much can feel restrictive. Most people end up back in the middle ground.

Final Takeaways

• Don’t sell out of fear.

• Real estate is typically an appreciating asset—holding long-term creates wealth.

• Live below your means and always have reserves for unexpected downturns.

• If you can, rent out your current home instead of selling.

The cheapest car is the one you already own—and in many cases, the cheapest house is also the one you’re living in.