Retirement planning
"Will my money last?" — and the four other questions retirement planning is actually for.
Most personal-finance apps tell you what you spent last Tuesday. Very few try to answer the questions that actually keep people up at night: Can I retire at 62? Should I be doing Roth conversions this year? Is it really worth waiting until 70 for Social Security? If I retire before 65, how do I afford health insurance until Medicare kicks in?
Those are the questions you'd hire a financial planner to answer. GlidePath is the app built around them — and every projection comes with the formula, the assumptions, and a plain-English "here’s why," so the answer isn’t a black box you have to trust on faith.
The questions, one at a time.
Each one comes with a quick "what this really means," so the technical name isn’t a wall.
Will my money last?
No spreadsheet can give you one honest answer — the future’s too uncertain. Markets crash, recover, then crash differently. So instead of one number, we project your plan through 1,000 different possible futures (the technique is called Monte Carlo simulation), including the worst sequences-of-returns that have actually happened to real retirees. The result is a fan chart that shows where your portfolio might land in the typical case AND in the worst-decile tail. That worst-tail is the part nobody else shows you, and it’s the part that matters.
Claim Social Security at 62, 67, or 70?
The basic tradeoff: claim early, get less per month for life. Wait, get more — but for fewer years. We run the lifetime real-dollar totals side by side, including spousal and survivor math when you’re claiming as a couple. There isn’t one right answer; there’s the right answer for your earnings history, lifespan expectation, and what other income you have.
When should I do Roth conversions?
“Tax Valley” is shorthand for a simple idea: the years between when you stop working (income drops) and when Social Security + Required Minimum Distributions start (income comes back up) are usually your lowest-tax years for life. Doing a Roth conversion in those low-tax years is dramatically cheaper than waiting until your 70s when RMDs force you to pull money out anyway. We find your specific Tax Valley years, show how much bracket headroom you have, and estimate the lifetime tax savings.
If I retire early, can I afford health insurance until Medicare?
Medicare doesn’t start until 65. If you retire at 60, you have a five-year “ACA bridge” — buying coverage on the marketplace and paying real money for it. We estimate the cost (the silver-plan benchmark, net of the premium tax credit you’d qualify for at your projected retirement income) so the gap isn’t a $50,000 surprise that wrecks an otherwise solid plan.
Is my net worth heading the right way?
Multi-year history with month-over-month deltas, top movers per account, and the running answer to “are we still on track?” The Net Worth view doesn’t just show today’s number — it shows the trajectory, and tells you when the trajectory has changed direction.
…and we show our work, on every number.
Every projection comes with the assumptions feeding it, the formula, and the caveats — written in plain English. Hover any (?) icon for the methodology, or toggle “Explain Mode” in the top bar to keep them all open while you browse. The numbers should defend themselves; you shouldn’t have to take them on faith.
See it in action.
Two views from the live app, rendering a fictional 42-year-old household planning to retire at 65 — Pat and Jordan Acme.
Liquid + retirement + real estate, less loans & cards. Updates as you snapshot balances.
Watch the trajectory tilt up as retirement compounds and the mortgage balance falls.
1,000 simulations of market returns. The fan shows where you might land at every age — the median trajectory plus the 10–90% range around it.
Most outcomes cluster around the median, but you'll see the worst-case tail too — the part nobody else shows you.
Your finances are connected. So is the app.
Most personal-finance tools treat your credit cards, your 401(k), and your retirement plan as separate dashboards. They're not. A decision in one area ripples through every other. GlidePath models the ripples so you can see what each choice actually costs (or earns) you.
Mid-career: a $5,000 card paid off 6 months early Mike, 42 · married · two kids · $180K in 401(k)
Mike has a 0% APR card with a $5,000 balance and 6 months left in the promo. He's planning to make minimum payments. The app's Balance Transfer page asks: what if you accelerated this?
- Card balance: $5,000 → $0 (6 months sooner)
- Freed-up monthly cash flow redirected to 401(k): $833/month × 6 = $5,000
- Tax savings this year at his 22% marginal bracket: +$1,100
- Future value of that $5,000 at 7%/yr for 23 years to retirement: ~$24,000
- Retirement Monte Carlo success probability: +1–2 percentage points
The decision lives on Balance Transfers. The impact lives on Net Worth and Retirement. All three pages share the same underlying ledger and assumptions — change one input, watch the others respond.
Early career: an extra $200/month into a Roth IRA Sarah, 27 · just paid off student loans · $30K in 401(k)
Sarah just got a raise and is debating whether to bump her Roth contribution by $200/month. It feels small. The math says otherwise.
- Annual contribution increase: +$2,400
- Time horizon to age 65: 38 years
- At 7%/yr average return, future value of those contributions: ~$479,000
- Total she actually contributed: $91,200 (the rest is compounding)
- Retirement Monte Carlo: shifts from "comfortable" to "well-prepared"
A "tiny" decision on Cash Flow becomes a six-figure outcome on Net Worth and Retirement. GlidePath shows the magnitude up front so you can give yourself credit (or push yourself harder).
Pre-retirement: delaying Social Security and timing Roth conversions Linda, 61 · single · $850K in 401(k) · retiring at 63
Linda is two years from retirement. The standard advice ("claim SS at 67, retire when you're ready") leaves money on the table. GlidePath lets her see the difference between three connected decisions at once.
- Claim SS at 70 instead of 67: monthly benefit +24% (delayed retirement credits)
- Years 1–7 of retirement: convert $40K/yr from 401(k) to Roth in the low-bracket "Tax Valley"
- Lifetime tax bill: ~$25,000 lower vs. waiting to convert until RMDs force it at 73
- ACA bridge cost (years 1–4, before Medicare at 65): ~$56K total — already factored into the Monte Carlo
- Estate at age 85: roughly +$120K compared to the "do nothing fancy" baseline
Five connected decisions — SS timing, Tax Valley, Roth conversion windows, ACA bridge, and withdrawal strategy — all visible side-by-side on the Retirement page. Change one assumption and the other four respond in real time.
The unifying idea: your dashboard isn't five views of five things — it's one view of one financial life, expressed five different ways.
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