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Doug Oosterhart, CFP®

60+ Ways LifePoint Planning Helped Clients in 2024 (Outside of Just Investment Portfolios)

For many years, one of the primary ways financial advisors added value to their clients' lives was by picking mutual fund managers, stocks, or simply putting their clients into a model portfolio (the classic "overcharge and underdeliver" business models).


Clients often begin to question what other areas an advisor might provide value for them.


At LifePoint Planning, we pride ourselves on offering tailored solutions to navigate the complexities of financial planning. In addition to answering the classic questions like, "Do I have enough money to retire?" or "How should I be invested during retirement?", we started compiling a list of different ways we've helped clients so far in 2024 that go beyond our standard service offering found here.


Below is a running list of 60+ ways we've helped clients so far this year, categorized into key areas of planning:


Investment Planning

  1. TIPs ladder construction and implementation for income in retirement

  2. Account consolidation to simplify household financials

  3. Optimizing large cash positions held in investment accounts (Roth IRA in some cases) at a previous advisor

  4. Recommendation to not purchase an annuity due to client’s income, risk, and legacy preferences

  5. Recommendation to purchase an annuity for a client with a “safety first” income preference

  6. Reverse mortgage planning for a client with a large home equity value

  7. “Rescuing” a client from a portfolio with 280+ positions at a previous advisor

  8. Reallocated bonds into other accounts than Roth IRAs (aka Asset Location)

  9. Implemented a 401(k) roll-in to isolate after-tax basis in a Traditional IRA for Roth conversion (tax efficiency strategy)

  10. Employer stock sale to fund home building (tax planning and investment planning)

  11. Navigating the payoff of a large margin loan opened by the client's previous advisor


Tax Planning

  1. Reviewing annual tax return

  2. Navigating and creating a plan for realizing large capital gains over multiple tax years

  3. Unwinding an annuity that turned capital gains taxes into ordinary income taxes

  4. Starting Roth conversions

  5. Stopping Roth conversions

  6. Capital gains tax budgeting for highly appreciated stock

  7. Income planning when retiring before 59.5

  8. Tax bracket management for income purposes when withdrawing from taxable accounts

  9. Tax-gain harvest for clients without high taxable income

  10. Tax planning for the sale of family business

  11. Navigating large capital gains and “trimming the winners” (triggering additional taxes) due to single stock concentration

  12. Set up and funded mega backdoor Roth 401(k)

  13. Donor-advised fund planning

  14. Navigating net unrealized appreciation (NUA) decisions for company stock held in 401(k)

  15. Navigating a non-qualified annuity inheritance and strategies to offset taxes on gains

  16. Roth IRA recharacterization back to Traditional IRA due to current year’s high income relative to other years (tax savings strategy)

  17. ACA vs COBRA for tax planning and health insurance planning

  18. Dependent care FSA strategy for tax savings on daycare costs

  19. Strategies for gifting between spouses for quicker step-up in basis


Estate Planning

  1. Planning for a special needs beneficiary

  2. Trusted contact communication rules for a widowed client with no other beneficiaries

  3. Funding of trusts/re-titling of assets

  4. Successor trustee vetting process with client and corporate trustee

  5. Gifting to beneficiaries while alive vs. after death

  6. Analysis of second-to-die life insurance strategy

  7. Planning for inheritances after the death of a parent

  8. Estate planning goals for a client with 80% of their assets tied up in annuities purchased before we met them

  9. Confirmed, changed, and added the correct beneficiary titling


Retirement Planning

  1. Pension decisions: lump sum vs. annuity option

  2. Coordinating income with tax-sensitive items (e.g. Medicare Premiums/IRMAA)

  3. Helping lifelong savers give themselves the "permission" to spend in retirement

  4. Social Security claiming strategy planning

  5. Navigating tradeoffs of semi-retiring and earning less vs. staying at a job the client dislikes for the next few years

  6. Going back to work after a sabbatical

  7. Career change/job change after 25+ years with one company

  8. Navigating a 2-year sabbatical from work

  9. Analysis of purchasing water rights and additional land


Cash Flow/Income Planning

  1. Paystub analysis (current or final paystub analysis for planning decisions)

  2. Logistics of purchasing a home using assets vs. financing

  3. RV purchase decisions

  4. Hip replacement surgery funding

  5. Best account to withdraw from for home remodel

  6. Major purchase decisions when only accounts were pre-tax assets

  7. Benefits elections at new company and/or open enrollment

  8. Securities-backed line of credit opening and logistics

  9. Wedding funding for a client's child

  10. Navigating the purchase/sale of a business over multiple of years

  11. Emergency fund advice for clients who prefer large cash balances

  12. Planning for windfalls from injury settlement


Insurance Planning

  1. Health insurance decisions (with employer, before Medicare, and enrolling in Medicare)

  2. Facilitating the payout of life insurance death benefits

  3. Analysis and recommendations for liability insurance and umbrella insurance

  4. Analysis of perpetual homeowners insurance only available in Maryland

  5. Long-term care insurance/plan funding

  6. Disability insurance claim negotiation with insurance carrier

  7. Purchase and/or surrender decisions for permanent life insurance


Other Specialized Planning

  1. Psychological and money advice for a recent divorcée


This list demonstrates the breadth and depth of services we offer to address a wide range of financial needs. LifePoint Planning's expertise ensures that every unique financial situation is handled with care and precision, allowing our clients to make informed, confident decisions about their futures.

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