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Five-Year Retirement Discovery
Five Years to Freedom
Connie’s Retirement Discovery Plan
This is not a test, a lecture, or a list of everything you should have done twenty years ago.
This is a discovery path designed to answer one much more useful question:
What would it actually take for work to become optional within about five years?
A month ago, we started exploring whether retirement in roughly five years was realistic.
Since then, something important has become clear: the answer cannot come from a generic retirement calculator.
The real plan has to account for your actual retirement savings, pension, Social Security,
permanent rent, student debt, old tax debt, other monthly obligations, healthcare, spending and the kind
of life you actually want.
The questions below are designed to collect exactly that information.
Exact numbers are best. Estimates are fine. And “I don’t know” is a useful answer,
because it tells us what we need to research next.
Privacy first
Do not enter Social Security numbers, bank account numbers, credit-card numbers, passwords,
tax-login credentials or account numbers. We only need planning information such as balances,
monthly payments, income, interest rates and goals.
Step 1
Destination
What do you want retirement to look like?
Step 2
Resources
What have you already built?
Step 3
Income
Pension and Social Security.
Step 4
Obstacles
Student loans, tax debt and other debt.
Step 5
Cost of Freedom
Rent and retirement spending.
Step 6
Firepower
What can the next five years accomplish?
Step 7
Security
What would make retirement feel safe?
Step 1
Where are you trying to go?
Before we calculate anything, we need to know what kind of life the money is supposed to support.
1. What age would you ideally like to stop working full-time?
2. If money were not the deciding factor, what year would you choose?
3. Which description sounds most like the retirement you want?
☐ Stop working completely
☐ Occasional work
☐ Part-time work
☐ Seasonal work
☐ Easier career
☐ More travel
☐ More time at home
☐ I am not sure yet
4. Would you work one or two additional years if it dramatically improved your retirement security?
☐ Yes ☐ No ☐ Maybe
5. What are three things you want more time for after full-time work ends?
Step 2
What have you already built?
Retirement is not starting from zero. We need to inventory what already exists.
6. Current Hendrick Health 403(b) balance
7. Current employee contribution percentage
8. Employer match or employer contribution, if known
9. Other retirement or investment accounts and approximate balances
10. Checking and savings balance
11. Emergency fund balance
Step 3
What retirement income is already waiting for you?
Fire-department pension
12. Estimated pension amount per month
13. Pension eligibility age or date
14. Does the pension have a cost-of-living adjustment?
☐ Yes ☐ No ☐ I don't know
15. Does the pension include retiree medical coverage?
☐ Yes ☐ No ☐ Possibly ☐ I need to verify
Social Security
16. Estimated benefit at age 62
17. Estimated benefit at full retirement age
18. Estimated benefit at age 70
Step 4
What needs to be cleared away?
Debt is not a moral issue. It is a cash-flow issue. Every payment that survives into retirement increases the amount of retirement income you need.
Student debt
19. Total student-loan balance
20. Current monthly payment
21. Interest rate or rates
22. Loan type
☐ Federal ☐ Private ☐ Both ☐ Unsure
23. Current repayment plan
24. Any known forgiveness, public-service, discharge or employer-assistance eligibility?
Past tax debt
25. Approximate total tax debt
26. Who is it owed to?
☐ IRS ☐ State ☐ Both ☐ Other
27. Current monthly tax-debt payment
28. Are you on a formal payment agreement?
☐ Yes ☐ No ☐ Unsure
29. Are penalties or interest still being added?
☐ Yes ☐ No ☐ Unsure
30. What does the most recent tax notice say?
Other debt
31. Credit-card balances and minimum monthly payments
32. Car-loan balance, monthly payment and expected payoff date
33. Personal loans or other debts
34. Any accounts currently in collections?
Step 5
What will retirement actually cost?
Because home ownership is not part of the plan, rent never disappears from the retirement budget.
We need the retirement plan to work while continuing to pay for housing.
35. Current monthly rent
36. Average monthly utilities and other housing-related costs
37. Do you expect to stay in the same area after retirement?
☐ Yes ☐ No ☐ Maybe
38. Would you consider a lower-cost rental if it significantly improved the retirement plan?
☐ Yes ☐ No ☐ Maybe
39. Approximate total monthly spending today
40. Estimated monthly spending after retirement
Step 6
How much five-year firepower do you have?
This is where the plan starts becoming powerful. The remaining high-income working years can be used intentionally to build assets and reduce obligations at the same time.
41. Approximate annual income today
42. After bills and debt payments, how much money is normally left each month?
43. How much could realistically be redirected each month toward retirement savings, student debt or tax debt?
44. Would you follow a five-year priority plan if it still left room to enjoy your life?
☐ Yes ☐ No ☐ I would want flexibility
Step 7
What does safe retirement feel like to you?
Retirement is mathematical, but it is also emotional. The plan has to solve the problems that actually matter to you.
45. How comfortable are you with normal stock-market ups and downs?
☐ I strongly prefer stability
☐ I can tolerate normal market fluctuations
☐ I am comfortable with moderate investment risk
☐ Large swings make me uncomfortable
☐ I honestly do not know
46. Which of these matters most before retiring?
☐ Tax debt gone
☐ Student debt gone
☐ No consumer debt
☐ Stronger retirement balance
☐ Secure healthcare
☐ Larger emergency fund
☐ Ability to work part-time if needed
☐ Something else
47. What is your biggest financial fear about retirement?
48. What is your biggest non-financial fear about retirement?
49. Complete this sentence:
“Five years from now, I would feel successful if…”
50. Complete this sentence:
“Before I stop working full-time, I absolutely want to have accomplished…”
The next step
Turn the answers into the real five-year roadmap
Once these answers come back, we stop guessing.
We can build a year-by-year plan showing:
403(b) growth
Pension income
Social Security timing
Student-loan strategy
Tax-debt payoff
Emergency reserves
Permanent rent costs
Monthly retirement income
Retire earlier vs. later
What the finished roadmap may look like
Year 1 — Establish the baseline
Confirm every number, stabilize debt and establish the exact retirement target.
Year 2 — Attack expensive obligations
Redirect available cash toward the debt and savings priorities with the biggest effect.
Year 3 — Midpoint review
Recalculate retirement income, debt remaining, account growth and healthcare options.
Year 4 — Position for the transition
Finalize Social Security timing, pension decisions, emergency reserves and retirement spending.
Year 5 — Make work optional
Decide whether the numbers support retirement, part-time work or one final year of accumulation.
Connie’s homework
Answer the 50 questions above.
Use exact numbers where possible. Estimates are okay.
If you do not know an answer, simply write “I don’t know.”
Then send the answers back to Jason.
The next deliverable will be Connie’s Five-Year Retirement Roadmap.
The goal is not perfection.
The win is reaching the point where the numbers say:
You have choices now.
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