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Doug Oosterhart, CFP®

Owner/Financial Advisor

 

LifePoint Planning, PLLC

1821 Walden Office Square, Suite 400

Schaumburg, IL 60173

 

Phone:  844-505-3618

 

Email: doug@lifepointplanning.com

Website: www.lifepointplanning.com

September/October 2026

Cash Out or Keep Assets?

Smiling senior couple working on budget at home with a laptop and smartphone, discussing finances.

Retirement is a time to kick back and enjoy life. Years of hard work have likely left you with a diverse array of assets, from appreciated stocks and real estate to luxury items like RVs and sports cars. Before selling assets to fund your bucket-list dreams, consider both the financial and emotional implications.


Tax Considerations
Taxes can take a hefty chunk out of profits from the sale of investments and appreciated property. Gains may not be as great as they appear. Consult your advisors before making any major decisions. They can help you navigate the nuances of tax implications for your assets.


Emotional Implications
Selling a classic sports car or a beloved vacation home can be emotionally difficult. Don't discount these feelings. Instead, consider other uses for your assets. Could you rent out a vacation home for passive income? Or create memories instead of liquidating prized possessions?


Long-term Impact
Think about the lifestyle changes you may need to make if you sell. Downsizing your home or liquidating your investments could lead to a significant shift in your daily life and future planning. It's one thing to have money in the bank. It's another to ensure your lifestyle aligns with your financial decisions. Take a moment to consider the long-term implications on your retirement journey.


It's not just about numbers—it's about enjoying the lifestyle you've earned. Weigh your options carefully.


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