Run the numbers at the source.
Calculators and references published by the agencies that actually administer these programs, not our estimates of them.
Every retirement plan begins with understanding the relationship between two things: what reliably comes in and what actually goes out.
We begin by identifying predictable income streams—Social Security, pensions, and other dependable sources of income—and comparing them against the household’s expected expenditures. The difference between the two helps establish what the rest of the financial plan needs to accomplish.
That makes understanding your expenses critically important. In our experience, most people underestimate what they actually spend. Not intentionally—it’s simply difficult to account for the dozens of expenses, both large and small, that make up a family’s lifestyle over the course of a year.
That’s why the first resource on this page is a worksheet we developed ourselves. It’s designed to help establish what you spend today, what may change in retirement, and ultimately the amount your retirement plan may need to provide.
Below it, you’ll find calculators and resources published by the agencies that actually administer these programs—Social Security, Medicare, the IRS, and others—organized by the type of planning each supports. We point you to the agency’s own calculator instead of rebuilding it here, because the only benefit estimate worth acting on is the one from the organization that will be writing the check.
These tools can help tell you what a number is … they won’t tell you what to do about it.
That depends on the rest of the plan: the other accounts, the tax bracket, the spouse, the date—and how all of those pieces work together.
That’s where planning begins.
From Other Side Asset Management
Household Monthly Budget Worksheet
What you spend today isn’t necessarily what you’ll spend in retirement.
This worksheet is designed to help identify both. Two tabs—Current and Future—allow you to compare what leaves the household today with what you expect to spend later, helping establish the income your retirement plan may ultimately need to provide.
It’s the same framework we use in our planning process, and it’s yours to use whether or not we ever speak.
- Household
- Utilities
- Automotive
- Debt repayment
- Personal care
- Family expenses
- Entertainment and leisure
- Giving
Retirement Planning
Where does the paycheck come from once the paycheck stops?
- Social Security Retirement Estimator ↗Social Security AdministrationBenefit estimates at every claiming age, run against your own earnings record.
- Full Retirement Age calculator ↗Social Security AdministrationThe birth-year table that sets your full retirement age, and the permanent reduction for claiming early.
- Earnings test calculator ↗Social Security AdministrationWhat working while claiming before full retirement age withholds, and when it comes back.
- Medicare Plan Finder ↗Centers for Medicare & Medicaid ServicesCompare Part D and Advantage plans against the prescriptions you actually take.
- Medicare costs and late-enrollment penalties ↗Centers for Medicare & Medicaid ServicesCurrent premiums, deductibles, and what missing an enrollment window costs for life.
- Required minimum distribution worksheets ↗Internal Revenue ServiceThe IRS life expectancy tables and worksheets behind each year's required withdrawal.
- Long-term care cost planning ↗U.S. Administration for Community LivingFederal reference on how much extended care people need, for how long, and who pays for it.
Investment Management
How should the money be invested, and in which account?
- Tax Withholding Estimator ↗Internal Revenue ServiceCheck withholding against a year with unusual income: a conversion, a sale, a first year of distributions.
- Investment adviser and broker background check ↗U.S. Securities and Exchange CommissionLook up any adviser's registration, disclosures and Form ADV, including ours.
- Compound interest calculator ↗SEC Office of Investor EducationWhat a fee or a rate difference costs over a full holding period, without a product attached.
Tax, Estate & Legacy Planning
Who receives what you built, on what terms, and after how much tax?
- Estate tax overview and filing thresholds ↗Internal Revenue ServiceWhich estates have to file, and the exemption the threshold is measured against.
- Planning for diminished capacity ↗Consumer Financial Protection BureauFederal guides for anyone acting as an agent, trustee, or representative payee for a family member.
Charitable Planning
How do you give what you intended to give, at the lowest cost to the plan?
- Tax Exempt Organization Search ↗Internal Revenue ServiceConfirm a charity is eligible to receive deductible contributions before you give.
- Publication 526, Charitable Contributions ↗Internal Revenue ServiceDeduction limits, substantiation rules, and what different asset types are worth as a gift.
Business Succession
What happens to the business, and to the family, when you step away?
- Retirement plan options for small businesses ↗Internal Revenue ServiceCompare SEP, SIMPLE, solo 401(k) and defined benefit plans against what the business can fund.
- Closing or selling your business ↗U.S. Small Business AdministrationThe federal checklist for a transition: valuation, sale structure, and the filings that follow.
The budget worksheet above is published by Other Side Asset Management as a general organizing aid. It performs arithmetic on figures you enter and does not produce a recommendation, a projection, or a financial plan. Everything else on this page is published and maintained by third parties, in most cases federal agencies. Other Side Asset Management does not control, verify, or endorse their content, and is not connected with or acting on behalf of the U.S. government, the Social Security Administration, the Centers for Medicare & Medicaid Services, or the federal Medicare program. Program rules, premiums, thresholds and benefit amounts are set by those agencies and change, in most cases annually. Output from any calculator is an estimate based on the assumptions you enter, is not a projection of your result, and is not investment, legal, or tax advice.
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