Question 1

Why work with a financial advisor instead of doing it yourself?

Accepted Answer

It’s possible to manage your own investments. But retirement planning is about much more than picking funds or watching the markets.

Once you stop earning a paycheck, you only get one shot to make the most of what you've saved. A good advisor helps you:

Avoid unnecessary taxes (now and in the future)
Create a steady, tax-efficient income stream
Plan for unexpected events like a spouse passing, market downturns, or rising health care costs
Make smart decisions around Social Security, Roth conversions, IRMAA, and more

Most of our clients aren’t completely hands-off. They want a collaborative approach—someone to guide the process, keep them informed, and help them avoid mistakes that are hard to undo.
Whether you're a delegator or a hands-on planner, our job is to match the right strategy to your preferences—without pushing a one-size-fits-all solution.

Question 2

Are you a fiduciary financial advisor?

Accepted Answer

Yes. A fiduciary has the highest ethical obligation to put the client's interests ahead of their compensation and any other considerations. LifePoint Planning is a fiduciary.

Question 3

What kind of clients do you typically work with?

Accepted Answer

Most of our clients are smart, financially successful individuals or couples who are approaching retirement—or already retired—and want to make sure they’re doing everything they can to be tax-efficient and intentional with what they’ve built.

Typical traits of a LifePoint Planning client:

Age 50–75 and focused on transitioning from saving to spending
$1 million or more in investable assets
Wants to reduce taxes and create a reliable retirement income plan
Values professional advice, but still wants to understand the "why" behind key decisions
Often already working with an advisor, but looking for more depth—especially around tax strategy and retirement income

They don’t want a generalist. They want a true partner to help them make smart, lifelong decisions with their money.

Question 4

Who is NOT a good fit for your firm?

Accepted Answer

We’re not the right advisor for everyone—and that’s a good thing.

You may not be a good fit if:

You prefer to day trade or believe in timing the market
You’re not comfortable using email for key communication and follow-ups
You strongly prefer in-person meetings (we work virtually with clients across the U.S.)
You’re not interested in planning around taxes, income strategy, or long-term outcomes

Our clients tend to value strategy, clarity, and long-term planning over short-term speculation. If that’s not your style, that’s okay—we’re probably not the best match.

Question 5

What questions should I ask when interviewing a financial advisor?

Accepted Answer

Choosing the right advisor is a big decision. Here are some key questions that can help you separate generalists from true retirement planners:

What will I pay—in real dollars—not just percentages?
 A 1% fee on a $2 million portfolio is $20,000 per year. Make sure you understand both the percentage and the actual dollar cost.
What do I get for that fee?
 Are you only getting investment management? Or does it include tax planning, retirement income strategy, estate planning, and proactive advice?
Do you ask for my tax return every year? Why?
 Real planners use your tax return to look for opportunities—like Roth conversions, avoiding IRMAA, and charitable planning.
What’s your process for ongoing planning?
 Do they meet regularly with clients? Do they adjust your plan as laws or life changes? You want to understand their follow-up and accountability structure.
Are you a generalist or a specialist?
 Retirement planning comes with its own challenges—taxes, Social Security, withdrawal strategy, Medicare, and more. Make sure they have experience in this specific area.

Asking these questions can save you money, reduce your risk, and help you find a planner who fits your needs and style. Learn more about how to help you determine the type of "style" you have here.

Question 6

What should I ask myself before hiring a financial advisor?

Accepted Answer

Before choosing an advisor, it helps to get clear on what you want. Ask yourself:

What do I value most in an advisor?
 Do you want someone to handle everything so you can focus on life? Or do you prefer to collaborate and stay involved in decisions?
How do I want to pay for advice?
 Some advisors charge a percentage of assets. Others (like us) charge a flat annual fee. Which model feels fair and transparent to you?
What level of fees am I comfortable with?
 Would you be okay paying $20,000 per year for 1% of your portfolio? Would a flat-fee structure save you money while providing the same or better service?
How often do I want to meet with my advisor?
 Do you want regular check-ins, or just a few key meetings each year? Your preferences should match your advisor’s service model.
What type of client am I?
 Are you a delegator who wants things off your plate? A collaborator who wants input? A validator who wants to check their own thinking? Or a DIYer looking for backup?

Understanding your own style helps you find the right advisor—not just any advisor.

Question 7

Can a financial advisor help reduce my taxes in retirement?

Accepted Answer

Yes — the right financial advisor can absolutely help reduce your taxes in retirement.

In fact, smart tax planning is one of the most overlooked parts of retirement strategy. Many people focus only on investment returns, but managing when and how you withdraw money can save you thousands—or even tens of thousands—over time.

A qualified advisor can help you:

Plan Roth conversions at the right time
Avoid Medicare IRMAA surcharges
Withdraw from the right accounts in the right order
Time Social Security benefits for tax efficiency
Use charitable strategies (like donor-advised funds or QCDs) to lower taxable income
Minimize taxes on inherited assets

Most retirees don’t realize they have control over their tax bill in retirement—but you do. And the earlier you plan, the more options you’ll have.

At LifePoint Planning, tax strategy is a core part of every client relationship. We review your tax return every year and build your retirement income plan around reducing taxes—not just now, but over your lifetime.

Question 8

What’s the difference between a financial advisor and a retirement specialist?

Accepted Answer

A financial advisor is a broad term that can mean anything from someone who sells insurance or investment products to someone who builds full financial plans. Not all financial advisors focus on retirement—and many don’t offer tax planning at all.

A retirement specialist, on the other hand, focuses specifically on helping people transition from working to retirement. That includes:

Creating a retirement income plan
Timing Social Security and pension decisions
Minimizing taxes on withdrawals
Planning for Medicare and health care costs
Managing investment risk during retirement

Retirement comes with a unique set of financial challenges. A retirement specialist understands the strategies needed to turn your savings into a reliable, tax-efficient income stream—without running out of money or triggering avoidable taxes and penalties.

At LifePoint Planning, we specialize in retirement planning. That means we go beyond investment management to help you solve the real problems that come with living off your portfolio.

Question 9

How big is your firm? How many clients do you work with?

Accepted Answer

We’re a boutique firm with a focused client base. Our team includes three experienced advisors, and we serve around 125 client households across more than 25 states.

This size allows us to:
Keep relationships personal
Offer deep, ongoing planning
Be highly responsive and proactive

You’ll never be just a number. We know our clients, their families, and their goals—and that’s exactly how we like it.

Please click/tap here to learn more about the firm.

Question 10

How do I know my money is safe? What is a custodian?

Accepted Answer

Your money is never held by us. It stays with a trusted third-party custodian—typically Charles Schwab, Altruist, or Betterment—who safeguards your assets.

Here’s how your money is protected:
Third-party custody: We use independent custodians who hold your accounts and process all transactions. We can manage your portfolio, but we can't move your money without your permission.
Monthly statements: You receive direct statements from the custodian (not from us), so you can verify everything independently.
Registered Investment Adviser (RIA): As an RIA, we’re regulated, audited, and legally bound to act in your best interest. We don’t hold your money or earn commissions from product sales.

This structure—independent custodian + fiduciary advisor—is the gold standard for transparency and protection. It’s designed to prevent fraud and ensure your assets are always in your control.

Here is Investopedia's explanation of what a custodian is.

Question 11

How experienced is your team, and what credentials do you have?

Accepted Answer

Our advisory team combines deep experience with specialized knowledge in retirement, tax, and investment planning.

Doug Oosterhart, CFP® – In the industry since 2013, Doug is a CERTIFIED FINANCIAL PLANNER™ professional who specializes in retirement and investment planning. He focuses on building long-term, tax-efficient strategies for clients transitioning into or living in retirement.
Ted Perry – Also in the industry since 2013, Ted specializes in financial, tax, and retirement planning. He’s known for simplifying complex topics and designing income and tax strategies that help retirees make smart, efficient decisions.
Aaron Harris, CFP®, CLTC – Aaron is a seasoned financial advisor with over 20 years of experience in financial planning, investment strategies, and strategic leadership. Specializing in retirement planning, asset management, and insurance solutions, Aaron helps clients build secure financial futures through tailored investment portfolios and risk management. Aaron is a CERTIFIED FINANCIAL PLANNER™.

We work together to ensure every client gets a personalized, well-rounded plan backed by both strategy and execution.

Question 12

Is a flat-fee financial advisor better than a percentage-based one?

Accepted Answer

It depends on your situation, but for many people—especially those with $1 million or more in investable assets—a flat-fee advisor can offer better value.

Most percentage-based advisors charge around 1% of your portfolio per year. That means if you have $2 million, you’re paying $20,000 every year—often for the same or even less service than you’d get from a flat-fee advisor.

Flat-fee advisors charge a fixed dollar amount, regardless of your portfolio size. This structure often results in:

Significant savings as your assets grow
Aligned incentives (your advisor doesn’t earn more just because your balance increases)
Transparent pricing so you always know what you're paying

It’s not just about the fee structure, though. What matters most is what you get in return—investment planning, tax strategy, retirement income planning, and more.

At LifePoint Planning, our flat annual fee includes all of that. We’re not just portfolio managers—we’re retirement planners, tax strategists, and fiduciaries focused on helping you keep more of what you’ve earned.

Question 13

What are your fees, and how do they compare to percentage-based advisors?

Accepted Answer

We charge a flat annual fee of $10,800 (billed monthly or quarterly) for clients with up to $4 million in investable assets.

This fee covers comprehensive financial planning, tax strategy, investment management, retirement income planning, and more.

Unlike advisors who charge a percentage of your portfolio, our flat-fee model means:

You always know exactly what you're paying
Your fee doesn’t automatically increase as your account grows
There’s no conflict of interest tied to how much you invest

Here’s how our flat fee compares to a 1% AUM model:

$1,000,000 portfolio = $10,800 (flat fee) vs. $10,000 (1%)
$2,000,000 = $10,800 vs. $20,000
$3,000,000 = $10,800 vs. $30,000
$4,000,000 = $10,800 vs. $40,000

Most clients save thousands per year while getting deeper planning and ongoing strategic advice.

For clients with greater than $4 million in assets, we generally charge a flat fee derived from a 0.25% multiplier. For example, a client with $10,000,000 usually pays a $25,000 flat fee unless their situation is overly complex.

Question 14

What do you specialize in, and what services do you provide?

Accepted Answer

We specialize in helping people transition into and through retirement with a focus on reducing taxes, creating reliable income, and managing investments intentionally.

Our core areas of expertise include:

Retirement planning – turning your savings into a long-term income strategy
Tax planning – strategies like Roth conversions, managing Medicare IRMAA, and optimizing withdrawal order
Income planning – designing when and how to take income from different accounts
Investment planning – building portfolios that align with your retirement timeline and risk comfort

We also help with Social Security timing, estate planning coordination, charitable giving strategies, and other complex financial decisions that come with retirement.

Our approach is fully integrated—everything works together to support your goals and minimize costly mistakes.

Click/tap here to see the specifics.

Question 15

How often will we meet, and how do you communicate with clients?

Accepted Answer

We believe good communication is the foundation of a great planning relationship. Here’s what you can expect:

Two in-depth planning meetings per year (spring and fall, 60–90 minutes each)
Open-door scheduling — clients can book additional meetings anytime using our online calendar
Ongoing communication via email for action items, planning updates, and questions
Monthly email updates written by Doug, sharing timely insights on your portfolio, the market, and relevant planning topics

Meetings are held virtually (Zoom or Google Meet), which allows us to work with clients across the country. Some clients meet with us multiple times per year, others prefer less frequent check-ins—we tailor it to your preferences.

Question 16

What’s your investment philosophy?

Accepted Answer

We believe your investments should match your goals, your timeline, and your comfort with risk—not just your age or a generic risk score.

That’s why we use a “bucket” or timeline-based approach to portfolio construction. Instead of focusing on asset classes, we organize your money based on when you’ll need it:

Stability (1–2 years): cash and cash-like investments for short-term needs
Income (2–5 years): CDs, bonds, and other fixed-income options
Protected Growth (5–7 years): strategies that provide growth with downside protection
Growth (7+ years): equities for long-term goals
Home-run (10+ years): optional, speculative sleeve for small, higher-risk opportunities

Each dollar has a job and a purpose. This helps:

Reduce emotional decision-making during market volatility
Improve long-term returns by keeping you invested
Give you clarity about why your portfolio is built the way it is

We also use hedging strategies and buffered investments where appropriate to reduce downside risk—especially for clients entering or already in retirement.

Question 17

What complex financial issues can you help with?

Accepted Answer

We specialize in solving the complex problems that arise in retirement—especially the ones most generalist advisors overlook.

Some of the advanced strategies we help clients with include:

Reducing taxes over time through Roth conversions, bracket management, and IRMAA planning
Creating a tax-efficient income plan by coordinating withdrawals across IRAs, Roths, brokerage accounts, and pensions
Lowering risk while staying invested, using tools like buffered ETFs, hedging, and capture ratio analysis
Timing Social Security benefits for optimal tax and income impact
Using charitable giving to reduce taxes, including donor-advised funds and qualified charitable distributions (QCDs)
Reviewing and optimizing insurance policies for long-term care, life, and income protection in retirement

Most advisors focus on growing wealth. We focus on making the most of it when it matters most—in retirement.

Question 18

Is the first meeting free?

Accepted Answer

Yes. The first meeting is completely free—and it’s not a sales pitch.

It’s a working session where we answer your questions, help you identify planning opportunities, and give you a feel for how we think and work. We’ll talk through your goals, review your current strategy, and discuss whether we’re a good long-term fit.

Even if we don’t end up working together right away, you’ll walk away with insights you can use.

Question 19

Where are you located? Do you work with clients outside your area?

Accepted Answer

We have an office in Schaumburg, Illinois and Bloomfield Hills, Michigan.

Doug lives in Illinois and Ted & Aaron live in Michigan.

Question 20

I'd like to learn more. What is the next step?

Accepted Answer

Click here to schedule a meeting.

Frequently Asked Questions