7 Habits of Highly Successful Retirees: Your Complete Guide to Financial Freedom

​Just got off the phone with a client who officially retired last week. When I asked how it felt to be a free man, his excitement was palpable!

​Just got off the phone with a client who officially retired last week. When I asked how it felt to be a free man, his excitement was palpable. He couldn't even find the words to describe the sense of relief and enjoyment he's experiencing in just his first few weeks of retirement.

Stories like this are why we do what we do at Jazz Wealth.

After managing over half a billion dollars in assets and creating hundreds of retirement plans, we've identified seven critical habits that separate successful retirees from those who struggle. These aren't theoretical concepts—they're proven strategies we've used to help real people achieve their retirement dreams.

Habit 1: Know Your Number (And No, It's Not What You Think)
​This is probably the most important habit, and frankly, one of the most frustrating things we encounter as advisors.

When we say "know your number," most people immediately think about their target nest egg—"I want to retire with $2 million" or whatever that magic number might be. But that's not the number we're talking about.

The number that truly matters is your monthly expenses.

Why? Because your expenses drive everything else. They determine how much you need to save, how your portfolio should be structured, and whether your retirement plan will actually work.

How to Calculate Your Real Number
If you're someone who keeps a detailed budget or runs Excel spreadsheets tracking every dollar, great! You're already ahead of the game.

But for most people, that's not realistic. Here's a simple method that works:

1. Exclude massive one-time expenses - If you bought a truck or boat last year, that's probably not a recurring expense
2. Gather all your statements - Credit cards, bank statements, everything
3. Add up your total annual spending
4. Divide by 12 - This gives you your monthly baseline

This rough calculation is enough to get started with proper retirement planning. Without knowing this number, you're essentially flying blind into your retirement years.

Habit 2: Have a Healthcare Strategy (Before It Becomes a Crisis)
Healthcare has changed drastically over the past five to ten years, and it continues to evolve in ways that can devastate an unprepared retirement plan.

Right now, we're seeing major changes with the Affordable Care Act. Tax subsidies that many retirees relied on are going away. As of this writing, legislation has passed in the House and is heading to the Senate, so these subsidies might return—but we can't count on it.

The Real Cost of Healthcare Uncertainty
We're currently working with clients who were paying $15,000 to $20,000 annually for healthcare. Without those tax credits, they're now facing $30,000 to $40,000 in annual healthcare costs. That's a devastating blow to any retirement budget.

Strategic Healthcare Planning by Age
If you're 63.5 years old: Consider taking COBRA from your employer, which typically provides 18 months of coverage. This bridge gets you to 65, when Medicare kicks in.
If you're 65 or older: You'll transition to Medicare, but you still need to understand your options for supplemental coverage.
If you're under 63.5: You need to develop a comprehensive plan for those gap years until Medicare eligibility. This is where consulting with a healthcare specialist becomes critical.

Healthcare is one of the biggest stressors we see for people stepping into retirement. Don't let it catch you off guard.

Habit 3: Optimize Your Pre-Tax vs. Post-Tax Balance
We hear from so many people who want to convert every single dollar to Roth accounts. While we love Roth conversions, they don't always make sense for everyone.

Introducing the Dough Score
At Jazz Wealth, we've built a unique tool called the Dough Score that helps clients understand their optimal pre-tax to post-tax ratio.

The Dough Score shows a pre-tax score that indicates how well you're splitting your retirement dollars. When it's green, you're doing a great job. When it's not, adjustments are needed.

A Real Client Example
One of our clients has an ideal pre-tax versus post-tax split of 64/36. Currently, they're at 42/58, meaning they're actually saving more toward post-tax accounts than necessary.

Why does this matter?

This particular client will retire in a lower tax bracket than they're in now. For them, it doesn't make sense to do aggressive Roth conversions and put so much into post-tax dollars. Instead, they can save on taxes today, and when they withdraw funds in retirement, they'll pay taxes at that lower rate.

The key takeaway: Tax strategy isn't one-size-fits-all. Your optimal approach depends on your specific situation, projected income, and tax bracket both now and in retirement.

Habit 4: Master Your Withdrawal Strategy (This One's Worth $717,000)
When it comes to withdrawal strategies, the order in which you tap different account types can make or break your retirement success.

The Traditional Approach
We often see this withdrawal sequence recommended:

1. Taxable brokerage accounts first
2. Tax-deferred accounts (traditional IRAs, 401(k)s) second
3. Tax-free accounts (Roth IRAs) last

But Is It Always Right?
Let me share a real client example that illustrates why personalized planning matters.

We ran projections comparing two withdrawal strategies for one of our clients:
Strategy A: Taxable → Tax-Deferred → Tax-Free
​Strategy B: Tax-Deferred → Taxable → Tax-Free

Many clients tell us, "I'm going to take all my IRA dollars first. It'll solve for Required Minimum Distributions (RMDs) down the road." That sounds logical, right?

The $717,000 Difference
For this specific client, Strategy A (the traditional approach) provided $717,000 more in tax-adjusted ending dollars compared to Strategy B.

Yes, they would pay about $7,736 more in total taxes over their lifetime. But would you rather pay $7,736 more in taxes and have $717,000 more at the end of your plan? The answer seems obvious.

This example shows why cookie-cutter withdrawal strategies don't work. Your optimal approach depends on your unique tax situation, account balances, and legacy goals.

Habit 5: Implement the Two-Bucket Asset Allocation Strategy
We talk extensively about the Two-Bucket Powell Method at Jazz Wealth. It's a strategy we've refined to help clients navigate market volatility without derailing their retirement plans.

How It Works
Instead of a traditional 60/40 portfolio, you maintain two distinct buckets:

Conservative Bucket: 3-5 years of expenses (we typically lean toward five years)
Growth Bucket: The remainder, invested for long-term growth

Why This Beats Traditional Allocation
In a standard 60/40 portfolio, when the market drops, you can rebalance and shift allocations—but you're still forced to sell equities when markets are down. That locks in losses and can significantly damage long-term returns.

The Two-Bucket Advantage
When markets are positive: Withdraw from your growth bucket, capitalizing on gains
When markets decline: Switch to your conservative bucket, giving your growth investments 3-5 years to recover

This strategy proved invaluable during events like 2008, when markets took significant time to recover. Clients with conservative buckets could weather the storm without selling growth assets at a loss.

Once markets recover, you resume taking from growth and slowly replenish the conservative bucket.

The result: Significantly reduced stress and better long-term outcomes.

Habit 6: Plan for the Unexpected (Because It Will Happen)
I recently created a video about what happens if you lose a spouse in retirement. Nobody wants to face this reality, but statistically, one spouse will pass before the other.

When that happens unexpectedly, it can completely derail a financial plan.

Common Unexpected Events to Plan For
Loss of a spouse: Changes tax filing status, reduces Social Security income, and often increases per-person expenses
Natural disasters: We work with many clients in Florida who live in hurricane zones. Floods can devastate finances, especially if insurance coverage falls short
Major home repairs: Roofs, HVAC systems, and foundations don't last forever
Vehicle replacement: Cars break down or simply need replacing
Health emergencies: Even with insurance, out-of-pocket costs can be substantial

Building Resilience Into Your Plan
The goal isn't to predict every possible scenario—that's impossible. Instead, build enough flexibility and cushion into your plan to absorb shocks without completely derailing your retirement.
This might mean:

• Maintaining adequate insurance coverage
• Building larger emergency reserves
• Creating contingency plans for various scenarios
• Regular plan reviews and adjustments

Don't let the unexpected turn into the catastrophic.

Habit 7: Successfully Transition from Work Life to Retirement
Remember that excited client I mentioned at the beginning? Not everyone has that immediate sense of relief and joy.

The Retirement Identity Crisis
We recently worked with a client who refused to use the word "retirement." Instead, they called it an "extended leave," leaving the door open to return to work because they were struggling with the transition.

This is more common than you might think.

After spending 30+ years getting up at the same time, going to the office, and following a structured routine, that work becomes a fundamental part of your identity. When you leave, it's exciting—but it's also like losing a piece of yourself.

Strategies for a Successful Transition
Find new purpose through hobbies: Whether it's golfing weekly, woodworking, painting, or learning a new skill
Reconnect with relationships: Social media makes it easier than ever to reconnect with old friends from high school or earlier in life. Meet for coffee, catch up over the phone, or plan trips together
Pursue your passions: Many retirees tell us, "I worked all this time, but that really wasn't what I wanted to do. I just had to do it to pay the bills." Retirement is your chance to finally focus on what you want
Start a new venture: Photography businesses, acting classes, consulting work—whatever excites you
Volunteer: Animal shelters, community organizations, mentoring programs—giving back provides purpose and connection
Maintain structure: Even without a job, having a routine and commitments helps maintain mental health and life satisfaction

The transition from work to retirement is as much psychological as it is financial. Plan for both.

Your Next Steps Toward Retirement Success
These seven habits aren't just theoretical concepts—they're proven strategies that have helped hundreds of our clients achieve successful, fulfilling retirements.

But here's the truth: every retirement is unique. Your optimal strategy for healthcare, withdrawals, asset allocation, and everything else depends on your specific situation.

If you're approaching retirement or already retired and want to ensure you have all seven habits working in your favor, it's time to create a comprehensive plan tailored to your goals.

Ready to take control of your retirement? The clients who experience that incredible sense of relief and excitement all have one thing in common: they planned ahead with expert guidance.

Don't leave your retirement to chance. Start implementing these habits today, and build the retirement you've always dreamed of.

Schedule a call with our award winning fiduciary advisors at www.jazzwealth.com/chatwithjazz

This content is for educational purposes only and does not constitute personalized investment advice. Past performance is not indicative of future results. Before making any investment decision, consult with a qualified financial advisor who understands your complete financial situation.