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Guide
The Personal CFO Playbook
How successful families coordinate retirement, taxes, investments and estate planning into one clear roadmap.
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Most families don’t struggle because they lack financial resources. They struggle because their financial decisions are often made in separate silos.
Investments are managed by one advisor. Taxes are handled by another. Estate documents sit in a drawer. Insurance policies are reviewed only when they come up for renewal. Meanwhile, life keeps moving forward.
The Personal CFO approach brings these moving pieces together into a coordinated strategy, helping ensure every financial decision supports the broader goals of the family.
Step 1: Start With the Destination
Before discussing investments or tax strategies, define what success looks like.
Key questions include:
- What does an ideal retirement look like?
- When would work become optional?
- How much income will be needed to support your lifestyle?
- What financial goals do you have for children, grandchildren, or charitable giving?
- What legacy do you hope to leave behind?
Without a clear destination, it becomes difficult to make confident decisions along the way.
Step 2: Build a Retirement Roadmap
Retirement planning is more than determining whether you have enough assets.
It is understanding:
- When retirement becomes financially possible
- How income will be generated during retirement
- How market volatility may impact withdrawal plans
- When Social Security benefits should be claimed
- How healthcare and Medicare costs fit into the plan
- How spending may evolve throughout retirement
The goal is to replace uncertainty with a comprehensive strategy built around real-world decisions.
Step 3: Coordinate a Tax-Efficient Strategy
For many successful families, taxes become one of the largest ongoing expenses.
A coordinated tax strategy may include:
- Managing tax brackets proactively
- Roth conversion analysis
- Retirement account withdrawal sequencing
- Tax-efficient investment placement
- Charitable giving strategies
- Capital gains planning
- Coordination with CPAs and tax professionals
The objective isn’t simply minimizing taxes this year. It’s reducing taxes over a lifetime.
Step 4: Align Investments With Your Goals
Successful investing begins with planning, not performance chasing.
Questions we help families answer:
- Is the portfolio aligned with retirement goals?
- Are we taking the right amount of risk?
- Do investment decisions support tax objectives?
- Is there unnecessary complexity in the portfolio?
- How should investments adapt as life circumstances change?
Investments should serve the plan, not become the plan.
Step 5: Protect Against the Risks You Can't Predict
Every financial plan should account for the unexpected.
Areas to review include:
- Life insurance needs
- Disability protection
- Long-term care considerations
- Property and liability coverage
- Umbrella insurance
- Business risk exposure
- Family emergency planning
Risk management helps preserve decades of financial progress when life doesn’t go according to plan.
Step 6: Ensure Estate Plans Reflect Current Intentions
Estate planning is often one of the most important and least reviewed areas of a family’s financial life.
Considerations include:
- Wills and trusts
- Beneficiary designations
- Powers of attorney
- Healthcare directives
- Wealth transfer strategies
- Family governance and legacy planning
- Coordination between legal, tax, and investment strategies
A well-designed estate plan helps ensure your wealth is transferred according to your wishes and with minimal disruption to the people you care about most.
Step 7: Coordinate Your Team of Advisors
Successful families often work with multiple professionals.
The challenge isn’t finding advisors. It’s ensuring they are working from the same blueprint.
Your Personal CFO helps coordinate:
- Accountants
- Estate attorneys
- Insurance professionals
- Investment managers
- Business advisors
- Lending and banking relationships
The result is fewer gaps, fewer conflicts, and better decision-making.
Step 8: Revisit the Plan as Life Changes
Financial planning is not a one-time event.
Plans should evolve as life evolves:
- Career changes
- Retirement transitions
- Business sales
- Inheritances
- Births and marriages
- Market volatility
- Tax law changes
- Health events
The most successful families are not those who create the perfect plan. They are those who continually adapt the plan to changing circumstances.
The Personal CFO Difference
Most financial advice focuses on a single product, account, or transaction.
A Personal CFO focuses on the bigger picture.
By coordinating retirement planning, tax strategy, investments, insurance, and estate planning into one integrated roadmap, families gain clarity, confidence, and a trusted partner to help navigate important financial decisions for years and decades to come.
Because financial success isn’t about managing individual accounts. It’s about ensuring every financial decision works together to support the life you’re trying to build.
Article
Should You Do a Roth Conversion?
A practical framework for thinking about Roth conversions in the years leading up to and through retirement.
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Roth conversions are one of the most talked-about retirement planning strategies, but they’re often misunderstood. The real question isn’t whether Roth conversions are “good” or “bad.” The question is whether paying taxes today may improve your financial situation tomorrow.
For some families, Roth conversions can create significant long-term benefits. For others, the added tax bill may outweigh the advantages. The key is evaluating the decision within the context of your overall financial plan.
Start with the Bigger Picture
Before discussing conversion amounts or tax brackets, it’s important to understand your goals:
- Are you trying to reduce future taxes?
- Are you concerned about large Required Minimum Distributions (RMDs)?
- Do you want greater flexibility when creating retirement income?
- Are you looking to leave assets to children or beneficiaries?
- Do you expect your future tax rates to be higher or lower than they are today?
A Roth conversion should support a broader objective, not become the objective itself.
Situations Where Roth Conversions Often Make Sense
Many retirees and pre-retirees consider Roth conversions during periods when:
- Income is temporarily lower than normal
- They have retired but have not yet started Social Security
- RMDs have not yet begun
- Market declines create opportunities to convert assets at lower valuations
- Future tax rates may be higher than current rates
- They want to create a source of tax-free retirement income
These years are often referred to as “tax planning windows” because they may offer opportunities to proactively manage future tax liabilities.
Questions to Consider
When evaluating a Roth conversion, consider:
- What tax bracket am I in today?
- What tax bracket am I likely to be in later?
- How much can I convert without moving into an unfavorable tax bracket?
- Do I have cash available to pay the taxes generated by the conversion?
- How will the conversion affect Medicare premiums or Social Security taxation?
- How does this fit into my long-term retirement income plan?
The answers are rarely black and white, which is why conversion decisions often benefit from careful modeling and analysis.
Common Mistakes to Avoid
- Converting too much in a single year and creating an unnecessary tax burden
- Ignoring the impact on Medicare premiums
- Focusing only on current-year taxes instead of lifetime taxes
- Failing to coordinate conversions with investment and withdrawal strategies
- Assuming Roth conversions are beneficial for everyone
Our Approach
We view Roth conversions as one tool within a larger planning framework. Rather than asking, “Should I do a Roth conversion?” we ask:
“Will a Roth conversion improve your overall financial plan?”
That means evaluating retirement income, tax projections, investment strategy, estate planning objectives, and future spending needs together before making a recommendation.
A Roth conversion is ultimately a tax-planning decision. The goal is not simply to pay less tax this year, but to create greater flexibility, potentially reduce lifetime taxes, and improve the efficiency of your retirement income strategy.
For the right family, a Roth conversion can be a powerful planning tool. The key is understanding when, how much, and whether it fits the bigger picture of the life you’re trying to build.
Media
Tom on WGN — Markets & Retirement
Tom Koleski, CFP®, joins WGN to share perspective on markets, taxes and retirement income planning.
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Tom Koleski, CFP®, Founder and CEO of Cedar Capital Advisors, brings more than 20 years of experience helping families navigate life’s most important financial decisions. As a CERTIFIED FINANCIAL PLANNER™ professional and Fee-Only Fiduciary, Tom is committed to providing objective advice that is always aligned with his clients’ best interests.
Throughout his career, Tom has worked closely with successful professionals, business owners, and retirees to help them build, preserve, and transition wealth with confidence. He believes financial planning should go beyond investments, serving as a framework for making informed decisions across every aspect of a family’s financial life.
Tom founded Cedar Capital Advisors with a vision of creating the trusted advisory relationship he wished his own family had access to: independent, transparent, and focused on long-term outcomes rather than product recommendations. He is known for simplifying complex financial issues and helping clients make confident decisions with clarity and purpose.
Tom has been featured on WGN as a trusted voice on financial planning. He lives in the Glen Ellyn with his family and enjoys spending time with family and friends, supporting local organizations, and helping clients build financial confidence for generations to come.
- Certified Financial Planner™
- Independent RIA
- Fee-Only Fiduciary
- WGN Featured Advisor
Checklist
When Can I Retire?
A self-assessment to see whether you're ready to retire — and what conversations to have first.
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Retirement is one of the biggest financial and personal decisions you’ll ever make. While online calculators can provide rough estimates, there is no universal retirement age or savings target that applies to everyone.
Every family is different. Your ideal retirement date depends on your lifestyle goals, spending needs, health considerations, income sources, and the resources you’ve accumulated along the way.
As you begin thinking about retirement, here are some of the most important questions to consider:
Retirement Readiness Checklist
Have I defined what retirement actually looks like?
Retirement means different things to different people.
- Will you stop working completely or work part-time?
- Do you plan to travel extensively?
- Will you relocate?
- Are there major goals or expenses you hope to pursue?
The clearer the vision, the easier it becomes to determine the financial resources required to support it.
Do I know how much I spend today?
Many retirement plans fail not because of investment performance, but because spending expectations are unclear.
Consider:
- Current household spending
- Mortgage or debt obligations
- Travel and leisure expenses
- Supporting children or aging parents
- Healthcare costs
Understanding your spending provides the foundation for determining how much retirement income you’ll need.
Have I identified my retirement income sources?
Retirement income often comes from multiple places, including:
- Social Security
- Retirement accounts (401(k), IRA, Roth IRA)
- Pension benefits
- Taxable investment accounts
- Rental income
- Business interests
- Part-time employment
The key question is whether these sources can reliably support your desired lifestyle.
Do I understand how much I can safely withdraw?
One of the biggest retirement risks is withdrawing too much too soon.
Questions to consider:
- How much income can my portfolio generate?
- How will market downturns impact withdrawals?
- Do I have flexibility if expenses increase unexpectedly?
A retirement income strategy should be designed to support both current needs and long-term sustainability.
Do I have a plan for healthcare before and after Medicare?
Healthcare expenses are among the most overlooked retirement costs.
Consider:
- Coverage before Medicare eligibility
- Medicare enrollment decisions
- Prescription costs
- Long-term care considerations
- Potential healthcare inflation
A retirement date that works on paper may look very different once healthcare costs are included.
Have I evaluated my Social Security strategy?
The timing of Social Security benefits can significantly affect lifetime retirement income.
Questions may include:
- When should I claim benefits?
- Should my spouse claim earlier or later?
- How does Social Security fit into our broader income plan?
Choosing when to claim is often one of the most important retirement decisions you’ll make.
Do I understand the tax impact of retirement?
Retirement doesn’t eliminate taxes.
Important considerations include:
- Retirement account withdrawals
- Roth conversion opportunities
- Required Minimum Distributions (RMDs)
- Social Security taxation
- Capital gains planning
The most effective retirement plans often coordinate income and tax planning together.
Is my investment strategy aligned with retirement?
The portfolio that helped build wealth may not be the portfolio best suited for retirement.
Ask yourself:
- Am I taking too much risk?
- Am I taking too little risk?
- Is my portfolio designed to support income needs?
- How will I respond during periods of market volatility?
Retirement planning is often less about maximizing returns and more about managing risk.
Have I prepared for the unexpected?
Life rarely unfolds exactly as planned.
Consider whether you have addressed:
- Premature retirement
- Health issues
- Market declines
- Loss of a spouse
- Large unexpected expenses
- Family support needs
Strong retirement plans include flexibility.
Am I emotionally ready to retire?
Retirement isn’t just a financial transition. It’s a life transition.
Many future retirees ask:
- What will I do with my time?
- How will I maintain purpose and connection?
- What activities will bring fulfillment?
Sometimes the emotional side of retirement deserves as much attention as the financial side.
Am I emotionally ready to retire?
Retirement isn’t just a financial transition. It’s a life transition.
Many future retirees ask:
- What will I do with my time?
- How will I maintain purpose and connection?
- What activities will bring fulfillment?
Sometimes the emotional side of retirement deserves as much attention as the financial side.
Can I retire while maintaining the lifestyle, flexibility, and peace of mind I want?
The answer depends on far more than a retirement account balance. It requires understanding how spending, income, taxes, healthcare, investments, and life goals all work together.
The most confident retirees aren’t necessarily those with the largest portfolios. They’re the ones who have a clear plan for what comes next.