Regret or Reset? What Past Powerball Winners Would Do Differently

Discover the surprising challenges Powerball winners face and learn how to avoid common regrets with smart, practical advice straight from real winner stories.

You Won Powerball! Now What?

Imagine you’ve just won $300 million. It’s the kind of dream that keeps millions of people buying Powerball tickets every week. But while the fantasy usually ends at “cash the check and live like a rockstar,” the reality is a lot more complicated.

When you look at real Powerball winner stories, you’ll find plenty of cautionary tales. For many past winners, that life-changing moment came with a side of stress, isolation, regret, and more than a few bad financial decisions. So let’s take a look at what Powerball winners regret most and how you can avoid those same mistakes in case you find yourself holding the winning Powerball ticket one day.

The Biggest Regrets from Powerball Winners

Over the years, many Powerball winners have been open about the things they wish they had done differently. Their stories reveal patterns and plenty of lessons for the rest of us.

1. Going Public Too Soon: One of the top regrets? Not protecting their privacy. Sharing the news too quickly can lead to everything from unsolicited requests to scam artists knocking at your door. Some winners say the attention changed their lives overnight, and not for the better.
2. Lack of Financial Literacy: Several Powerball winners admitted they weren’t ready for the responsibility of sudden wealth. Without basic financial knowledge, it’s easy to fall into spending traps, mismanage investments, or trust the wrong people.
3. Not Building a Team: Winners who didn’t hire a financial advisor, tax professional, and lawyer early on often regretted it. Having a smart team in your corner from day one helps you stay grounded, avoid common tax issues, and make a real plan for your future.
4. Saying “Yes” Too Often: Helping friends and family feels good until it doesn’t. Past winners say they wish they had set firmer boundaries sooner. Giving away too much too quickly often caused friction, financial stress, and even broken relationships.

Avoiding the Spending Spree Spiral

The temptation to spend big is very real. After all, you’ve just become a multimillionaire. But some winners say this is where regret creeps in fastest.

• Sudden Wealth Syndrome is real. It’s a term used to describe the stress, anxiety, and confusion that can come with overnight financial change. Many winners feel overwhelmed and unsure of who to trust.
• A surprising number go broke. Studies show that a significant percentage of large prize winners end up bankrupt within five years.
• Smart spending starts with a plan. Pay off your looming debt, build an emergency fund, and invest for the long term. You can enjoy your money, but start with structure.

Protect Yourself from Bad Advice

Not every smiling advisor has your best interests at heart. That’s another hard lesson learned by past Powerball winners.

• Vet your team carefully. Check credentials and licenses. Make sure your financial advisor is a fiduciary, meaning they’re legally required to act in your best interest.
• Understand how they get paid. Whether it’s a flat fee or commissions, be sure you know how your advisor earns their income.
• Stay engaged. Don’t just hand off your money and walk away. Ask questions, get regular updates, and review your statements.

The Isolation Factor

Several past Powerball winners (of all jackpot sizes) have shared that the emotional impact of winning was harder than expected. Friends treated them differently. Some felt lonely or even depressed. That’s why it's important to take care of your mental health, too.

• Talk to a therapist. Processing a sudden life shift takes time and support.
• Find purpose. Whether it’s through volunteer work, starting a foundation, or mentoring others, giving back can help restore balance.
• Stay grounded. Keep a circle of people who knew you before the win and will support you through the change.

Learn from Those Who’ve Been There

Winning Powerball should feel like the best thing that ever happened to you, and it can be. But it takes smart decisions, steady guidance, and a little patience to turn that jackpot into long-term joy.

The best part? You don’t have to learn the hard way. Past Powerball winners have already shared what they’d do differently. Now you can win smarter.