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4 Things All Successful Retirees Do, #287

Retire With Ryan

Release Date: 01/06/2026

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More Episodes

In this episode, I’m helping you kick off 2026 by reflecting on financial habits that pave the way for a successful retirement. As we set our goals for the year ahead, I share the four key traits I’ve observed in successful retirees, drawn from years of experience working with people from all walks of life. You’ll hear practical advice on how to work hard and invest consistently, the importance of living within your means, and ways to avoid common investment pitfalls that can derail your progress.

Whether you’re just starting your retirement planning or fine-tuning your financial strategy, this episode is full of actionable tips to help you improve your financial life in 2026. If you’re ready to take charge of your future and put a solid plan in place, this episode is a must-listen.

You will want to hear this episode if you are interested in...

  • 00:00 Retirement success traits revealed.
  • 05:29 Budgeting for financial growth.
  • 07:49 Invest simply and consistently.
  • 10:36 Improve and grow net worth.
  • 13:38 Keep an eye on your net worth.

Four Habits of Highly Successful Retirees

There’s no magic bullet to achieving a comfortable retirement. Many successful retirees weren’t born into wealth; in fact, about 80% of millionaires started with little and built their nest eggs from scratch. The through-line is diligence and perseverance.

A powerful habit among this group is paying themselves first. Rather than saving what’s left at the end of the month, successful retirees set aside a portion of their income before budgeting for other expenses. Many automate investments into employer-sponsored retirement accounts or other savings vehicles. This intentionality ensures that the priority remains on building wealth, not just sustaining a lifestyle.

Budgeting plays an essential role here. I recommend reviewing your annual spending, categorizing transactions, and identifying excesses. Small changes can help you free up cash for investments and debt reduction. If you struggle with credit card overspending, consider switching to cash or debit cards, which make it easier to visualize your available funds and stay disciplined.

There’s also a growing temptation to “keep up with the Joneses,” especially when social media showcases other people’s amazing vacations! Appearances can be deceiving, you never know whether your neighbours are deeply in debt despite flashy photos. The key is to focus on your own financial journey, not someone else’s highlight reel.

Keep Your Investments Simple

Despite the barrage of complex investment themes and “get rich quick” schemes circulating online, the most effective investors stick to the basics. Avoid speculative strategies like day trading, option contracts, and penny stocks for the bulk of your portfolio. These approaches can lead to significant losses, or even financial ruin.

Successful retirees typically lean on a diversified, straightforward mix of investments: blue-chip stocks, index funds, bonds, and some real estate. A simple, repeatable investment plan not only reduces stress but also reduces the chance of costly errors. If an investment sounds complicated or “too good to be true,” it likely isn’t the right tool for you.

Track Your Net Worth, Every Year

A great habit to get into is consistently tracking your net worth. For example, every year, I  take inventory and value all of my assets, subtract any liabilities, and calculate my own net worth. This exercise isn’t just about patting myself on the back, it’s an important annual check-in on financial progress which helps me course-correct if I’m getting off track.

If you discover stagnant or shrinking net worth, it’s a signal to look at spending, debt, or investment choices. For those carrying high-interest debt (over 6–7%), prioritizing repayment can yield safer and higher “returns” than most investments. Even in retirement, monitoring net worth is vital. Spending down savings is natural, but keeping an eye on the pace ensures your money lasts as long as you need it to.

Take Action Today

Successful retirees don’t wait for luck or windfalls, they put in the work, invest with discipline, stay clear of fads, and track their progress. Start by reviewing your own budget and net worth, and set realistic, meaningful goals for the year ahead. Your future self will thank you.

Resources Mentioned

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