Financial advice
at personal checkpoints

You manage your own money and finances, by choice.
Yet on occasion, you need personalized financial advice to stay on track.
Get the advice you need, when you need it, without strings attached.
Advice only, and only when needed:
No pitches to manage money
No financial product offers
No long-term commitments

What is a personal checkpoint?

You might be approaching an important financial decision, a change in life circumstances, a career transition, or you recognize the need for a concrete financial plan.  Here are some examples:
"An advisor wants to charge me 1% per year to manage my money. Can I do it myself?"
"I believe I have enough resources to shift to part-time work, but I need an outside opinion."
"One of my parents passed away. My surviving parent needs my help managing the investments.  How?"
"I save money consistently, mostly remaining in cash at the bank.  How should I invest the money?"
"I am thinking about a career change.  Do I have the financial capacity to make the change?"
"I bought a deferred annuity many years ago. Should I keep the policy, replace it, or cash it in?"
"A broker spread my money over two dozen funds. How do I make sense of this portfolio?"
"I have not adjusted my investment allocations in years. Should I rebalance the portfolio?"
"We'd like to start saving for our kids' college education. What strategies should we consider?"
"I'd like to donate a substantial sum to a specific charity.  What's the best way to do it?"
"I am thinking about buying a house. How much can I afford and how much should I borrow?"
"Do we need long-term care insurance? Or can we rely on savings (self insure)?"
"I am worried about the stock market crashing.  Should I be invested in stocks at all?"
"My hobby makes money, and I'd like to grow it into a for-profit business.  How do I go about it?"
"Our first child is on the way. How should we prepare our finances for our expanding family?"
"I'd like to take a sabbatical from work. How should I prepare my finances for it?"
"I'd like to retire early but I am concerned about health insurance. What are my options?"
"I just received an inheritance, including cash, IRAs, and property. What should I do?"
"My brother-in-law is pitching me permanent life insurance. What should I do?"
The Services and Fees

The two services provide advice only

"Advice only" means we do not manage investments or sell financial products.  
We are compensated by "fee only" which means we do not accept commissions or referral fees.

Summary Financial Review

For DIY accumulators seeking a one-time second opinion
Top-down assessment of financial goals, holdings, and flows
2-3 video sessions to establish context and to discuss high-priority topics
Write-up providing targeted knowledge and directional guidance
Follow-up email Q&A available for 1 month after delivery of write-up
Fixed fee based on an allotment of 7 hours at $300/hour
* $525 due up front, remainder on delivery
Book a Free Discovery Call

Full Financial Plan

For those seeking detailed guidance or a foundation for future advice  
Bottom-up examination of financial goals, holdings, and flows
Highly iterative and collaborative process of planning and analysis
Comprehensive plan document with strategic and tactical guidance
Follow-up email Q&A available for 3 months after delivery of plan
Hourly fee subject to a minimum of 10 hours
Future check-in meetings are available by the hour with no minimums
* 25% of estimated fee due up front, remainder on delivery
Book a Free Discovery Call
Who we serve

Collaborative DIYers seeking knowledge, advice, and efficiency

We serve clients across America
The Advice Categories

Our advice is holistic and integrated

We coordinate your plan across six categories

Plan saving and borrowing

We help estimate your future spending goals, and formulate realistic saving and borrowing strategies to fund those goals.

Calibrate investment strategies

We help align investment strategies with your financial goals, and recommend investing routines you can stick with, especially during turbulent markets.

Minimize lifetime taxes

We lay out actionable strategies squarely within the law that can lower your tax bill now AND over the long haul.

Manage risk exposures

We identify potential threats and opportunities that could emerge on your journey, and make sure you are prepared for whatever happens.

Design insurance solutions

We assess your insurance needs and collaborate with trusted insurance brokers to find the best fitting insurance products.  

Plan gifts and your estate

We help get the most of your gifts to charity, family, and friends during your lifetime, and we collaborate with trusted attorneys on your estate plan.
Our Approach

We keep it simple, disciplined, and efficient

Guiding mottos:  Keep it simple. Stay the course. Hold costs down.
Plan saving and borrowing
The foundation of your financial plan is based on spending projections and the strategies to fund the spending.  Forming this foundation can be daunting at first because of the many assumptions about spending needs, often in the distant future. We simplify matters by helping you clearly define and prioritize goals, project the timing and level of spending, and tailor a funding strategy that works for you.  

Most of us anticipate spending goals spread over decades such as college tuition, discretionary spending on "bucket list" activities, living expenses during a sabbatical, basic needs in full retirement, and potential health care or long-term care expenses.  We will help you form assumptions about future spending, specifically how much you’ll spend and when the spending will occur.  Based on these assumptions, we can help project the spending cash flows over the goal horizon.  

With a projection of your future spending goals, we can help formulate a funding strategy. Funding your projected spending can be achieved in countless ways, whether from current income, borrowing, savings, insurance, or often a mix.  We can advise on securing the cheapest borrowing and aligning loan terms with your situation, for example, borrowing to purchase real estate or to fund an education.   We can help formulate savings strategies by evaluating savings patterns that align with your projected income.  We can point out savings vehicles with tax incentives and low-cost investment options.  In cases where the spending is contingent on an event like a need for long-term care, we might consider an insurance solution, itself a form of savings.

This process often requires more than one pass. That is, we might evaluate multiple spending projections based on various assumptions and consider a range of funding strategies.  It is time well spent, as it becomes the foundation of your financial plan.
Calibrate investment strategies
Our approach to investments can be summarized by the following tenets.

The first key investment decision pertains to the allocation of your portfolio over major classes such as cash, bonds, stocks, and real estate. We will recommend an allocation based on the time horizon for your spending goals along with any personal preferences.  Please note, we avoid "risk tolerance" surveys because we believe you can adjust investing behavior to match your need to take risk, discussed further below.  We will evaluate cash, bond funds and bond ladders to meet spending goals within the next ten years, and expand consideration to stocks and real estate for goals beyond ten years.  We generally favor a global stock allocation for greatest diversification.  We will consider other "factors" like style and size, as long as you are comfortable with the additional complexity and are willing to stay the course over the investing horizon.

Second, with a target asset allocation in place, we generally recommend investing in diversified, low-cost mutual funds or ETF's that passively replicate market indexes (best) or otherwise exhibit adequate diversification, low turnover, and low costs.  We do not favor actively-managed funds or individual stock selection due to the well-documented evidence showing that the overwhelming majority of managers cannot beat market indexes over the long-run after operating expenses and tax drag.  

Third, we will collaborate to find an investment strategy that you can stick with in normal and turbulent markets. We believe your investing behavior, especially in turbulent markets, will likely be the primary factor in determining your investing outcomes. We generally recommend formalizing an investment policy to encourage a regular discipline for re-balancing (or holding) and to promote rule-based actions that blunt the negative effects of emotions brought on by volatile financial markets.

Finally, to be clear, we absolutely do not believe in market timing in any way, shape, or form. Effective market timing for just one market cycle requires correctly "calling" the market twice in succession: once to leave or enter the market, and again to re-enter or leave the market, respectively, which we believe has a very low probability of success and can impose a high cost when unsuccessful.   
Minimize lifetime taxes
Income taxes warrant special attention! Taxes are a large lifetime expense, possibly the largest. Not only is the tax code complex at any given time, but the federal tax code changes as the U.S. Congress enacts new tax laws, and your state tax laws can change as well. Furthermore, taxes are pervasive, consequential in most financial transactions in the current year and potentially far into the future. For those reasons, we prioritize helping you minimize your tax expense by taking a lifetime planning view.

First, we raise awareness of adjustments, deductions, and credits that could apply to your situation, starting with unambiguous opportunities, that is, opportunities without any assumptions of future income levels or future tax rates. These opportunities are the lowest hanging fruit, though easy to overlook.  

Second, considering a lifetime view, we can evaluate opportunities to defer income recognition using vehicles such as IRA's, company 401(k), 403(b), and 457.  And, crucially, with any income deferrals, we will make sure you have a strategy for future income recognition to avoid unwelcome tax surprises down the road.

Third, we can evaluate strategies to minimize the drag of taxes on your investment returns.  Guided by your holistic asset allocation, we can support decisions for locating your investments among taxable, tax deferred, and tax-free accounts.  In addition, we can evaluate strategies for opportunistically realizing gains or losses, commonly referred to as harvesting gains or losses; though we will highlight the potential benefits, we will offer counsel on execution risks and whether the benefit is worth the hassle.

Finally, if you are considering starting a business or already own a business, we can evaluate business plans, establish sound bookkeeping processes, and minimize your tax burden.
Manage risk exposures
A holistic risk management discipline plays a central role in your financial plan, not simply to eliminate all risk exposures but rather to identify opportunities to reduce risk or to retain and manage risk when appropriate. Your risk management appetite will guide the rest of your financial plan including investments, insurance and estate planning.

First, we help identify all forms of risk to your financial strength, including insurable risks like accident, morbidity, mortality, and longevity; investment risks like credit and market risks; information security risks; and plan continuity risks.  

Second, after creating an inventory of risk exposures, we can assess both potential losses under adverse scenarios and opportunities under extreme yet favorable scenarios.  We generally prefer to form and evaluate “what if” scenarios rather than interpreting probabilistic results from Monte Carlo simulation models.   After a career in risk management including direct experience with stochastic analysis, we are skeptical of Monte Carlo simulation models, especially when projecting over multi-decade horizons.

Third, after a thorough assessment of risk exposures, we can recommend techniques to manage risk, that is, by reducing or altogether eliminating certain risks, and retaining or even increasing certain risks when the risk/reward balance is favorable.  For retained risks, we can help formulate plans for loss mitigation and recovery under adverse events.  We encourage formalizing risk policies which can guide behavior and otherwise blunt the effects of emotions during extreme scenarios.  

Because our clients are hands-on with their money and finances, we encourage special consideration of continuity plans for managing your finances in the event of incapacity or premature death.
Design insurance solutions
We will consider insurance products to reduce or altogether eliminate insurable risks according to your risk management decisions.  We believe in limiting the use of insurance products to mitigate catastrophic losses due to accident, theft, disease, disability, incapacity, premature death, or personal liability. Except in limited estate planning circumstances, we generally do not recommend insurance products as investment vehicles to fund savings goals or to manage market risks, primarily due to complexity, illiquidity, and hidden fees.

For health insurance, we can help you assess plans offered by your employer or plans from the Marketplace.  If you own a business with a partner or with employees, we will work with trusted brokers to identify options for group insurance plans.  

For property and liability insurance such as home, auto and business insurance, we will help you determine the proper amount of coverage and level of loss sharing such as deductibles. We encourage you to re-evaluate product offerings with your insurance agent every 2-3 years.

For long-dated insurance needs like life insurance, disability income insurance, or long-term care insurance, we work directly with brokers to locate the simplest and affordable insurance products offered by highly rated insurance companies.  In addition to selecting products, we help formulate the proper size and duration of the insurance products for your needs.  

We generally do not recommend annuities because of complexity, high fees and expenses, and the lack of inflation indexation.  

If you own any life insurance or annuity policies, we will evaluate the appropriateness of the policies for your long-term needs, and advise on strategies for managing, replacing, or lapsing the policy.
Plan gifts and your estate
Planning gifts and your estate are critical yet often overlooked components of a financial plan.  The topics may be difficult to discuss and may require difficult decisions. We can help you navigate these issues within the context of your overall financial plan, always in collaboration with an attorney licensed in your state and specializes in estate planning and administration.  

First, we can help you get the most from your charitable giving or giving to family and friends while you are alive and well.  We can help optimize your gifting strategy with techniques that minimize income taxes and gift taxes.  We can help coordinate your gifting strategy with your estate plan so that gift taxes and estate taxes are minimized at the federal and state level, if applicable.

Second, through a referral or direct collaboration with an attorney, we can guide you towards establishing the legal documents that can speak for you, or appoint someone to speak for you, on matters of health or matters of property if you become incapacitated.   That is, we will encourage you to establish health care directives such as a Power of Attorney (POA) for health care and a living will, and a Power of Attorney for property to handle your finances if you are unable to do so.    

Third, through a referral or in direction collaboration with an attorney, we can help you establish the legal documents such as a will and a living trust(s) so that your assets are transferred upon your death according to your wishes and in an orderly and cost-efficient manner, for example, avoiding the costly and time-consuming probate process.  Though your documents should be prepared and executed by a licensed attorney who specializes in estate planning an administration, we can help coordinate the process and ensure the estate plan is aligned with the rest of your financial plan.

Have more questions?

The Process

Our process is collaborative

We take time to confirm a fit, and then collaborate closely to develop your plan.

Discover (No Cost)

Tell your story and ask any questions on a 30-minute call.

Evaluate a Fit (Still No Cost)

Specify your financial profile: goals, assets, and cash flows. Let's meet for 1-2 hours to discuss your profile and to size a potential engagement.   

Launch and Plan

Agreement is signed, meetings are scheduled, and we start collaborating to develop your plan.  

Write-up and Deliver

You receive a document with our summary analysis and advice. We discuss the recommendations and offer implementation guidance.

Follow-up and Wrap

Email Q&A on write-up details for 1 month after delivery of Summary Financial Review, or 3 months for Full Financial Plan.

For those completing a Full Financial Plan, feel free to schedule future video meetings, as needed.

Frequently asked questions

Checkpoint Financial Planning, LLC offers advice only, and only when needed
I live outside of Illinois.  Can I be a client?
Yes, we serve clients across the country through phone, video meetings, and email.
Can we meet in person if I live in Chicagoland?
Yes, if you prefer, we can arrange to meet at a co-working space or at your office, but please note, I charge my hourly rate for commuting time.
After an initial plan, can we periodically check in with you?
Yes, after a Full Financial Plan is completed, you are welcome to schedule future check-in meetings as needed, by the hour (no minimums).
As a new client, can I schedule just one hour for a quick question?
We will focus on your specific needs, but in order to provide sound financial advice, we must establish context to a reasonable extent, which takes more than an hour. Please consider a Summary Financial Review, our shortest-duration and lowest-cost advice package.  
How does payment work?
Electronic funds transfer or credit card.  
Which service level is right for me?
If you are a DIY accumulator with well-defined goals and organized records, and you seek a one-time second opinion, then the Summary Financial Review is likely sufficient. Otherwise, a Full Financial Plan is appropriate. We will discuss on a free discovery call.
Do you provide tax advice? Do you prepare income tax returns?
We do provide tax advice, however we do not prepare tax returns.  We will recommend user-friendly tax preparation software or we can refer you to a tax preparation service.
Will you implement my financial plan?
We offer advice only, that is, we do not manage investments or otherwise implement plans.  However if desired, you can share your screen with us, and we will answer questions live as you take the steps to implement your plan.
How do I transfer my information securely?
We will send you online forms to complete, requiring SMS (text) authentication to access. We ask that you do not enter any social security numbers, account numbers, driver's license numbers, or any other personally identifiable information. We recommend uploading redacted documents.    
What if I don't get much value from this service?
This outcome is highly unlikely.  Our top priority is client satisfaction. We will evaluate a fit during our discovery call, and if we have any doubt about delivering value to your satisfaction, we will not hesitate to refer you to other advisors.

Have more questions?


Brian Rhoads, CFA, EA

Personal story
Location: Brian, a lifelong Illinois resident, grew up in rural Oregon, Illinois.  After earning an undergraduate degree in 1997 from a liberal arts college in Rock Island, Illinois, Brian settled in the northern suburbs of Chicago where he remains, at least until another Chicagoland winter gets the best of him.  

Family: As luck would have it, Brian met his future wife, Mary, while on a daily train commute. Many commutes later, Brian and Mary tied the knot and eventually settled in Highland Park, Illinois, where they have been raising their son and daughter, now in their late teens.

Free time: In addition to spending time with family at home and traveling around the world, Brian jogs the Green Bay Trail, cycles throughout Lake County, volunteers as a tax preparer, and continues searching for a reliable golf swing.  Brian remains a loyal fan of the Chicago professional sports teams, and still reminisces about the '85 Bears.
Brian started Checkpoint Financial Planning, LLC to bring personalized financial advice to more people across the country. Brian observed that many people intentionally manage their own money and finances, yet still need professional financial advice from time to time, but without strings attached.  That is, they do not want to pay an advisor an on-going fee to monitor their investments, face pressure to buy an annuity or life insurance, or commit to an on-going subscription service. Rather, these people just seek unbiased, independent financial advice when needed.

To be clear, Brian is not crusading against advisors who manage investments, insurance and annuity brokers, or advisors offering subscription services. Indeed, some people need such services or products, and in those cases, Brian will refer those people to advisors who would be a better fit.
A math enthusiast at heart, Brian steered his education towards the applications of mathematics in the fields of economics and finance.

: Brian earned his bachelor's degree, summa cum laude, from Augustana College with concentrations in mathematics, economics, and finance.

Graduate: Early in his professional career, Brian earned a master's degree in financial mathematics from the University of Chicago, which provided an advanced quantitative foundation for evaluating risk and return in the financial markets.  
Professional credentials
Brian earned professional credentials in investments (CFA®) and income taxation (EA):

Chartered Financial Analyst (CFA®): Brian was awarded a CFA charter by the CFA Institute after passing three examinations covering a wide range of investment topics, including ethical and professional standards, fixed-income analysis, alternative investments, derivative investments, portfolio management, and wealth planning. As a CFA Charterholder, Brian must abide by the CFA Institute Code of Ethics and Standards of Professional Conduct.

Enrolled Agent (EA):  Brian earned the Enrolled Agent credential, the highest credential awarded by the Internal Revenue Service (IRS), after passing a three-part exam covering individual and business income tax returns. As an Enrolled Agent, Brian has the ability to provide tax advice and represent taxpayers before the IRS, and must adhere to ethical standards and complete 72 hours of continuing education courses every three years.  
Professional experience
Brian's professional experience in the financial services industry spans over 27 years. Brian is immeasurably grateful for the relationships with his colleagues and clients over the years.

At Quantitative Risk Management (QRM) for 23 years, Brian provided consulting services to life insurance companies and commercial banks on a range of topics including asset/liability management (ALM), financial planning and analysis (FP&A), portfolio optimization, capital management, stress testing and contingency planning. While at QRM, Brian developed expertise in the tools and techniques for aligning investments with liabilities, measuring and managing financial risks, and developing dynamic investment strategies.  

At Allstate Insurance Company for 4 years, Brian priced personal auto insurance in the property & casualty company for 2 years, and then managed interest rate risk and liquidity risk for Allstate's life insurance subsidiaries for another 2 years.  In these roles, Brian gained valuable knowledge of the insurance industry and insurance products including life insurance, annuities, property insurance, and liability insurance products.