Financial Planning
Fee-Only Financial Planning Built Around Your Life
Most people have never had a real financial plan. What they’ve had is a sales pitch. A document handed over by an insurance agent or a commissioned broker that ended with a product purchase, not a path forward.
At Oak Street Advisors, our plans typically run 40 to 75 pages and cover every corner of your financial life: investment strategy, tax planning, employer benefits, insurance, Social Security claiming, estate considerations, and more. As a fee-only fiduciary firm, we are legally and ethically required to act in your interest. We are never paid commissions. We never sell products.
What Is a Fee-Only Financial Planner?
A fee-only financial planner is paid by you and only you. No commissions from mutual funds, annuities, insurance policies, or any other product.
That distinction matters more than most people realize. When an advisor earns money from the products they recommend, they have a financial reason to steer you toward some options and away from others. Fee-only advisors don’t have that incentive.
Fee-only advisors are also typically fiduciaries, which means they are legally required to act in your best interest at all times, not just when it’s convenient.
Oak Street Advisors is a fee-only, fiduciary Registered Investment Advisor (RIA). Every plan we build and every recommendation we make is based on one thing only: your best interests, not ours.
What a Comprehensive Financial Plan Covers
Retirement Income Planning
How much can you spend? When can you retire? Which accounts do you draw from first to keep your tax bill low and your money lasting longer?
Tax Planning and Lifetime Tax Minimization
We model your current and future tax brackets and look for places to do Roth conversions, harvest losses, maximize QBI deductions, and time income strategically.
Investment Strategy
Risk-appropriate asset allocation, tax-smart asset location, and coordination with your existing employer retirement plans.
Social Security Optimization
Most people claim Social Security at the wrong time and leave real money on the table. We model the numbers for your specific household and tell you exactly when to file.
Insurance Review
We review your life, disability, and liability coverage for gaps and inefficiencies. Because we earn nothing from insurance sales, our take is fully objective.
Estate Planning Coordination
We work with your estate attorney to ensure your financial plan aligns with your legacy goals, beneficiary designations, and wealth transfer preferences.
Employer Benefits Optimization
We help you optimize your HSAs, FSAs, group insurance, deferred compensation, and after-tax 401(k) options. Most people are not getting everything their employer is offering. We find what's being missed.
How We Have Helped Clients
Retirement, Healthcare, and Tax Planning for a Couple Nearing Retirement
One spouse worked for a large corporation and planned to retire first. The other owned a business and wasn't ready to stop yet. The problem: once she retired, he would lose access to her employer's health insurance and would need coverage until Medicare kicked in.
We built a coordinated plan that covered asset allocation, Roth conversion timing, and optimization of the business owner's QBI deduction. We also got him enrolled in a private marketplace health plan with an HSA that was tax-deductible and further reduced his taxable income. The healthcare gap to Medicare was resolved without them overpaying.
Reducing a Lifetime Tax Bill for a Retired Couple with Large IRA Assets
This couple had rental income, a pension, and Social Security coming in. They also had a large rollover IRA and knew that Required Minimum Distributions were going to force them into higher and higher tax brackets in the years ahead.
We mapped out a lifetime tax and cash flow plan across all income sources and modeled what RMDs and IRMAA surcharges would look like without any action. The Roth conversion strategy we put in place is projected to save hundreds of thousands of dollars in taxes over their lifetime. It also reduces the tax-impact of the SECURE Act on their heirs and creates a pool of tax-free income they can draw from going forward.
Small Business and Retirement Tax Planning for a Self-Employed Professional
A real estate professional in the top federal tax bracket came in wanting to reduce her taxable income without cutting back on retirement contributions.
We built a plan around a Solo 401(k) with profit-sharing and after-tax components, a Mega Backdoor Roth IRA strategy, and a high-deductible health plan with an HSA. The result: over $100,000 of income deferred annually that would otherwise have been taxed at the highest marginal rate. We also set up a safe-harbor 401(k) for her husband's business and layered in additional tax reduction strategies across the household.
Savings Allocation for a High-Earning Couple with No Clear Strategy
An architect and his wife, who had recently started a fast-growing business, were piling up cash in low-yield accounts while their tax bill kept climbing. They had the income to save aggressively but no clear plan for where to put it.
We coordinated his employer benefits (Mega Backdoor Roth, FSA, group insurance, HSA) with her options as a business owner (Solo 401(k) with profit-sharing, Backdoor Roth IRA, S-Corp restructuring to cut payroll taxes) to tax-efficiently optimize every dollar of savings.
Retirement Tax Planning for a Physician with Over $1 Million in Tax-Deferred Accounts
She had more than $1,000,000 in a traditional IRA, a substantial 401(k), and $700,000 in taxable accounts. The concern was straightforward: those tax-deferred accounts would generate a large tax bill one way or another, and she wanted to control when and how that happened.
We designed a multi-year Roth conversion strategy that moved $530,000 from her tax-deferred accounts into a Roth IRA at a 12% federal rate. She hadn't paid that low a rate in decades. Without a coordinated plan, she would have paid 10 percentage points more on those same dollars.
Insurance Review: Finding a Better Policy as Fiduciaries
A client came in for a holistic financial plan with a 10-year timeline to retirement. During the planning process, we identified that his variable universal life policy had high internal costs and poor investment choices.
We recommended a 1035 exchange into a product with an 84% lower annual premium and better options. We also aligned the investments inside the policy with his overall asset allocation strategy. Because we earn nothing from recommending any insurance products, only an asset management fee for managing the underlying investments, the recommendation was based solely on what worked best for him.
Disclaimer: The examples above are illustrative case studies based on actual client engagements. Details have been changed to protect client privacy. They are provided to show the type of work we do and are not representative of any particular client’s experience. Individual results depend on each client’s specific circumstances, and similar results are not guaranteed. Dollar figures reflect specific facts and assumptions and, where described as projections, are estimates that are not guaranteed.
Financial Planning Frequently Asked Questions
Start the Conversation
In more than 20 years of doing this work, we have yet to meet a prospective client whose financial picture couldn’t be improved in some way. Usually it’s taxes. Sometimes it’s the investment structure. Occasionally, it’s something the client never thought to ask about. The only way to find out is to sit down and go through it.
Call us at (843) 946-9868 or use the link below to schedule a no-cost intro call. No obligation.
