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I recently worked on a retirement plan with a married couple in their early 50s. They initially viewed their retirement spending as a flat number that would last for decades. When I asked them to step back and reflect on how spending could change over time, the picture became clearer.
They mapped out higher spending during early retirement — often called the “go-go” years — when they plan to travel more adventurously and visit family.
We scaled their spending down for the later years, when activities and travel will become infrequent, but allocated funds for caregiving and other health needs.
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That simple shift in perspective gave them confidence they hadn’t felt before, because they realized their plan finally reflected practical spending.
This couple’s experience mirrors findings from Boldin’s recent survey of more than 1,000 Americans who manage their own retirement plans. One message came through clearly: Reflection builds confidence. And that confidence translates into better financial decisions and outcomes.
The power of regular check-ins
Among the survey respondents, the majority of whom have between $1 million and $5 million in assets, financial planning isn’t a once-a-year exercise. It’s an ongoing practice:
- 27% check their financial plan once a week or more
- 21% review it two to three times monthly
- 25% assess their situation monthly
- Only 6% review annually, twice a year or when something comes up
This regular engagement pays dividends. An overwhelming 92% of respondents agreed that frequent reflection on their big-picture financial goals significantly increases their confidence.
Furthermore, 90% said that knowing where they stand financially gives them the confidence to make better decisions for the future.
Strategic vs tactical: A critical distinction
As 2026 unfolds, financially successful individuals approach planning differently than others might expect. Rather than focusing primarily on tactical moves — such as fine-tuning investment allocations by a few percentage points or optimizing taxes around a single tax year — they take a strategic view.
The survey found that 87% of respondents approach financial planning as a long-term strategic exercise, with only 12% saying their planning is primarily tactical. When respondents were asked which activities they complete during their planning sessions, the strategic activities far outweighed tactical ones:
Strategic activities:
- Reviewing spending and income patterns (62%)
- Assessing overall financial performance (60%)
- Examining savings goals and progress (44%)
- Setting or reviewing financial goals (43%)
- Evaluating asset allocation (37%)
Tactical activities:
- Planning health care coverage (50%)
- Adjusting investment allocations (45%)
- Optimizing tax liability or tax-loss harvesting (40%)
- Completing Roth conversions (39%)
- Making charitable contributions (24%)
What keeps retirement planners up at night
The survey revealed that two priorities tie as the top concerns for people in or nearing retirement: Taxes and investments, each cited by 68% of respondents. But the full picture shows a complex web of interconnected worries:
- Taxes and year-end planning: 68%
- Investment performance or portfolio mix: 68%
- Inflation or cost of living: 44%
- Planning for upcoming goals: 43%
- Managing expenses or cash flow: 42%
- The political environment: 31%
- Savings progress: 27%
- Economy or job market: 27%
- Interest rates: 16%
This blend of concerns reinforces that effective planning isn’t about optimizing any single variable in isolation. It’s about understanding how different pieces fit together and making adjustments that support long-term goals.
The real motivation: Confidence, not just returns
The survey’s most striking finding is that when asked why they dedicate time to financial planning, respondents overwhelmingly cited confidence-building over wealth-building.
Nearly eight out of ten (79%) said they plan to feel more confident in their financial decisions or increase confidence in their plan.
By contrast, less than half (43%) said they do so to build more wealth over time, and only 50% cited reducing tax burden as a primary motivation.
Here’s the complete breakdown of motivations:
- 66% to feel more confident in financial decisions
- 64% to feel more financially secure
- 61% to increase confidence in their plan
- 50% to reduce tax burden
- 48% to gain more clarity on where they stand
- 45% to feel like they’re doing the right things financially
- 44% to stay on track toward goals
- 43% to reduce financial anxiety
- 43% to build wealth over time
This data tells a powerful story: People aren’t planning simply to chase returns. They’re planning to feel clear-headed, informed with a clearer understanding of their full financial picture and capable of moving forward with their lives.
Five factors to consider going forward
Based on the survey findings, here are five critical steps that confident retirement planners take — and you can, too:
1. Monitor spending patterns and lifestyle reality. Review whether your actual spending aligns with your expectations. Are there changes driven by factors within your control (lifestyle choices) or outside of your control (inflation, health care costs)?
More than 60% of successful planners regularly examine their spending and income patterns.
2. Align investments with risk tolerance. Does your current asset allocation still support your goals? Are you invested more aggressively or more conservatively than the level of risk you’re willing to accept? With 68% of planners citing investments as a top concern, regular portfolio review is essential.
3. Optimize tax positioning. Consider whether you need to adjust withholdings, explore strategies like Roth conversions, or optimize your tax liability. Taxes ranked as the number one concern alongside investments for retirement planners.
4. Plan for health care and insurance coverage. Half of survey respondents prioritize planning their health care coverage. This includes reviewing Medicare options, supplemental insurance and long-term care considerations as your needs evolve.
5. Reflect on life changes and goals. Has anything changed that should shape your decisions moving forward? The 43% who regularly review and set financial goals recognize that life circumstances shift, and plans need to adapt accordingly.
Questions to guide your reflection
Whether you’re reviewing your plan quarterly, monthly or more frequently, these questions can help focus your thinking:
Looking back:
- Was my spending in line with what I expected?
- What caused any significant deviations, and were they within my control or due to external factors?
- How did my investments perform relative to my expectations and risk tolerance?
Looking forward:
- Does my current asset allocation still support my goals?
- Do I need to adjust my tax strategy or consider moves like Roth conversions?
- Have my health care needs or coverage options changed?
- What goals do I want to accomplish this year, and what adjustments do I need to make?
The confidence connection
What ties all these findings together is a clear pattern: Reflection leads to understanding, understanding builds confidence, and confidence enables better financial decisions.
Financial planning doesn’t require you to spend hours agonizing over details you cannot control. It requires dedicated time to understand what has changed and what matters most going forward.
People who do this regularly, whether monthly, quarterly or at natural transition points throughout the year, tend to feel more prepared because they have a clear sense of what they want to accomplish and what they need to adjust to get there.
That’s the real value of regular planning. It helps people nearing or in retirement move through the year feeling grounded, informed and ready for what comes next — not because they’ve eliminated uncertainty, but because they’ve made uncertainty manageable.
