Four Habits of Successful Retirees (and How to Apply Them in 2026)
As we kick off a new year, it’s natural to reflect on where we’ve been and think about where we’re headed. For many people, that includes taking a hard look at their financial life and asking an important question:
Am I truly prepared for retirement?
After working with hundreds of individuals and families who are approaching or already in retirement, I’ve noticed something interesting. Despite coming from different backgrounds, careers, and income levels, the people who are most successful in retirement tend to share the same core habits.
Success, in this case, doesn’t mean extravagance—it means having enough. Enough saved, enough planned, and enough confidence to enjoy retirement without constant financial stress.
Below are four habits I consistently see among successful retirees, along with practical ways you can begin implementing them in 2026.
1. They Worked Hard—and Stayed Consistent
This may sound obvious, but it’s also universal.
Most people who are financially prepared for retirement worked hard for decades—often 30, 35, or even 40 years. They didn’t assume anything was owed to them, and they didn’t expect success to come quickly.
In fact, studies consistently show that roughly 80% of today’s millionaires were not born wealthy. They built their wealth over time through consistent effort, career growth, and disciplined financial decisions.
Some owned businesses, but many simply worked for an employer, earned promotions, increased their income gradually, and stayed committed to long-term goals. What often goes unseen is the effort beneath the surface—much like an iceberg, where only a small portion is visible above the water.
Takeaway:
There’s no shortcut. Long-term effort and consistency are foundational to financial success.
Click here to listen to this week’s episode on: The 7 Best Investment Options To Preserve Your Money in 2026
2. They Pay Themselves First and Live Within Their Means
One of the most important habits successful retirees share is that they invest a portion of their income every month—no matter what.
They follow the principle of paying themselves first by:
Automatically contributing to their 401(k)
Automating savings and investment contributions
Building their lifestyle around what’s left—not the other way around
Instead of increasing spending as income grows, many increase savings. This discipline prevents overspending, limits debt, and allows assets to compound over time.
If Overspending Is an Issue
If you’re unsure where your money is going, start by downloading your past year of transactions from:
Bank accounts
Credit cards
Investment accounts
Categorize your spending and look for patterns. Often, small changes—like cutting back on dining out or subscriptions—can free up meaningful dollars for saving and investing.
You may also find it helpful to:
Create a written budget
Use a budgeting app
Track spending monthly
Credit cards, in particular, can make overspending easy because the impact isn’t felt until the bill arrives. Some people find success using debit cards or even cash for discretionary spending to stay more aware of their limits.
Takeaway:
Build your lifestyle around saving first—not spending first.
3. They Keep Their Investments Simple
Another key trait of successful retirees is that they avoid complexity and speculation.
They don’t chase:
Get-rich-quick schemes
Day trading strategies
Options trading
Penny stocks or highly speculative investments
Instead, most successful investors focus on:
Broad, diversified stock index funds
Bonds or bond funds
Cash reserves
Real estate (either directly or through REITs)
This simple, diversified approach has proven effective over long periods of time. If an investment sounds too good to be true—or is too complicated to understand—it usually is.
While it’s fine to allocate a small portion of your portfolio to higher-risk ideas if you choose, the majority of your assets should be invested in high-quality, diversified holdings designed for long-term growth.
Takeaway:
You don’t need an exotic strategy to build wealth—simplicity often wins.
4. They Track Their Net Worth
Every successful retiree I know tracks their net worth.
Net worth is calculated as:
Assets – Liabilities = Net Worth
While you’re working, your net worth should generally increase as you:
Save and invest more
Pay down debt
Grow your assets over time
If your net worth isn’t growing, it may signal:
Overspending
Too much high-interest debt
Insufficient savings
Poor investment decisions
High-interest debt, especially above 6–7%, should be a top priority. It’s difficult for investments to consistently outpace that kind of interest over time.
How to Track Your Net Worth
At least once a year:
Gather investment statements
Estimate real estate values (using tools like Zillow or Redfin)
List outstanding debts and loans
Calculate your total assets and liabilities
Many people use Excel because it’s flexible and easy to update year after year. Over time, tracking your net worth becomes incredibly motivating as you see the power of compounding take hold.
Even in retirement, net worth tracking remains useful. While it’s normal for net worth to decline as you spend your savings, monitoring the pace of that decline helps ensure your money lasts.
Takeaway:
What gets measured gets managed.
Your 2026 Financial Homework
If you want to improve your financial life this year, start here:
Review last year’s spending and identify areas to improve
Create or refine a budget and track it consistently
Commit to paying yourself first
Track your net worth annually
Focus on simple, long-term investing
Want Help Creating Your Retirement Plan?
If you don’t yet have a clear retirement plan, now is the time to build one.
As a special New Year offer, my Retirement Readiness on Demand online course is available for $99 (normally $297) through the end of January.
The course includes over 7 hours of content covering:
Retirement income planning
Taxes
Insurance
Medicare
Social Security
Estate planning and more
To enroll:
Visit retirewithryan.com
Click Courses
Select Retirement Readiness on Demand
Use promo code RETIRE99
Here’s to a successful and financially confident 2026.
If you have questions or want personalized guidance, feel free to reach out—and I look forward to continuing the conversation next week.
Written by Ryan Morrissey
Founder & Principal Advisor of Morrissey Wealth Management
Host of the Retire with Ryan Podcast