First the Life, Then the Money
Lifestyle-First Retirement Planning

First the Life, Then the Money

Most retirement planning starts with a nest egg and works backward. We’re going to flip that and start with the life you actually want. This short retirement income questionnaire takes just a few minutes, answer the questions and I’ll personally take a look and get back to you.

Related: what people leave out when they talk to a planner

What Are 20 Questions to Ask Yourself to Know If You’re Ready to Retire?

There’s no official list. These are the 20 we’d ask, life first, then money, then the dates that don’t move.

The life

  1. What does a great ordinary Tuesday look like for me?
  2. What are my non-negotiables: the trips, the time with grandkids, the experiences I won’t give up?
  3. What will those cost each year, on top of everyday bills?
  4. What will fill the hours work used to fill?
  5. Have my spouse and I each said out loud what we want?
  6. Where do we want to live, and for how long?

The money

  1. What are our essential monthly bills, including health care?
  2. How much will Social Security pay me at 62, at full retirement age and at 70? Your my Social Security account shows estimates at different ages.1
  3. Do I know my full retirement age? It’s 67 for anyone born in 1960 or later.2
  4. Do I have a pension, and does it have a survivor option?
  5. How much of my essentials and non-negotiables is covered by income that lasts as long as I do?
  6. If the market dropped hard the year I retire, would my plan still work?
  7. How much do I keep on hand for emergencies?
  8. Who is this money for: me, or my heirs?
  9. What happens to our income and taxes if one of us dies first?

The dates

  1. If I retire before 65, how will I pay for health insurance? Losing job-based coverage opens a special enrollment period on the Marketplace.3
  2. Do I know my Medicare window? It runs 7 months, starting 3 months before the month you turn 65.4
  3. When do my required minimum distributions start? At 73 or 75, depending on birth year.5
  4. Have I planned for a long life? Social Security puts average life expectancy at 65 at about 18 more years for men and about 21 for women.6 Private-sector numbers run longer: J.P. Morgan gives a 65-year-old couple of non-smokers in excellent health a 74% chance that one of them is still here at 90.7 We tend to plan with the longer numbers.
  5. How would we pay for long-term care if one of us needed it? See How Much Does Long-Term Care Cost Per Month?

The questionnaire above walks you through questions 2, 3, 7 and 11, and we take it from there.

Sources

  1. The Social Security Administration’s my Social Security page lets you estimate benefits at different ages.
  2. The Social Security Administration’s retirement age chart shows full retirement age by year of birth.
  3. HealthCare.gov’s page for retirees explains that losing health coverage qualifies you for a Special Enrollment Period.
  4. Medicare.gov explains the 7-month Initial Enrollment Period around your 65th birthday.
  5. The Treasury and IRS final required minimum distribution regulations set the starting age at 73 or 75 depending on birth year.
  6. Social Security’s Period Life Table for 2023, as used in the 2026 Trustees Report.
  7. J.P. Morgan Asset Management, Guide to Retirement 2026, the Life Expectancy Probabilities page.
Kurt H. Jackson, Retirement Lifestyle Architect
About Kurt H. Jackson

Experience: Since founding KJ Financial in 2010, Kurt H. Jackson has worked with retirees and pre-retirees across Missouri, Nebraska, Kansas, Iowa, and Florida who discovered that the retirement plan they had built around a fixed withdrawal rule was far more fragile than they realized. He has worked directly with clients coming out of the 2008 crash, and with clients who retired into the 2020 COVID drop and the inflation spike of 2021 to 2023, and he has seen firsthand what sequence of returns risk does to a withdrawal-only strategy versus a Lifestyle-First plan with a guaranteed income floor. Before founding KJ Financial, he spent 20 years as a Certified Mortgage Planner working with more than 1,000 clients on major financial commitments, giving him deep insight into how financial decisions compound over time.

Expertise: Kurt is a Retirement Lifestyle Architect and the creator of the Lifestyle-First Retirement Income Planning framework. He builds guaranteed lifetime income, which he calls Protected Lifetime Income (PLI), under both his clients’ essentials and their non-negotiables, the adventures, the experiences and the memories with those they care about. With that income floor in place, the rest of their money no longer has to pay the bills, which means it doesn’t have to be sold in a down market. He is Life and Health Insurance Licensed in MO, NE, KS, IA, and FL. His practice focuses exclusively on insurance-based, tax-optimized retirement income strategies. He does not manage investments or sell securities.

Authoritativeness: Kurt founded KJ Financial and operates MaxMyRetirementIncome.com as a dedicated educational resource for retirees. His work is grounded in peer-reviewed and independently published research, cited directly on each page. He applies that research to the practical income planning decisions retirees face every day in the states he serves.

Trustworthiness: KJ Financial is a compliance-first firm. All figures and research citations on this page are sourced from publicly available, independently published studies and are linked directly in the content. Kurt is paid by commission from the insurance company that issues the policy. Kurt H. Jackson is not a securities broker, registered investment advisor, or CPA. Guarantees rely on the claims-paying ability of the issuing insurance company.

Contact KJ Financial:
1014 E. 5th St., Maryville, MO 64468
Direct: 816.582.5532
Email: kurt@kjfinancialonline.com
Website: www.MaxMyRetirementIncome.com
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