HeyJaredWes - The Catch-Up Investor
Welcome to Wes – The Catch-Up Investor. Practical retirement planning for Americans aged 55 to 65 — pensions, Social Security, Roth conversions, and retirement taxes explained without the jargon.
- Indexed videos, last 90 days
- 89
- Latest publication
- Sep 29, 2026
- Audience
- ~8.5K subscribers
- Earliest in this view
- Jul 3, 2026
Latest videos
The Retirement Rules Changed on Gen X Mid-Game — What's Different in 2026 (opens the original)
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(247) Will Social Security be there for Gen X, and what changed for retirement in 2026? The 2026 Trustees Report says full benefits last until 2034, then about 83% if Congress does nothing, and the retirement fund alone runs short in late 2032. Wes walks through the rules that moved mid-career for Gen X: the 1983 fix behind full retirement age 67, the $11,250 super catch-up for ages 60 to 63, the new Roth catch-up rule for earners over $150,000, RMDs at 75, the WEP and GPO repeal, the return of
Don't Fully Retire at 60 — Why Part-Time Work Is Worth $600,000 (opens the original)
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(246) Should you fully retire at 60, or is part-time work in retirement worth far more than it looks? See how a part-time paycheck can replace about $600,000 of savings, let your Social Security benefit keep growing, and protect your 401(k) and IRA from a bad market in the first years. Wes walks through a side-by-side example of working part time from 60 to 65 versus retiring at 60 and claiming Social Security at 62, then covers the three traps to avoid: the Social Security earnings test, self-e
Can't Work Until 62? SSDI Can Pay 43% More Than Early Social Security (opens the original)
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(245) SSDI vs early Social Security: if your health won't let you work until 62, Social Security Disability Insurance can pay roughly 43% more than claiming retirement at 62, because it pays your full, unreduced benefit. Wes breaks down the 5-month waiting period, the 20-of-40-quarters work credit rule, the 2026 substantial gainful activity limit of $1,690 a month, and the Medicare gap of up to 29 months. You'll see how SSA's grid rules make age 50, 55 and 60 work in your favor, what the 5-year
Laid Off at 58? The First 90 Days That Decide Your Retirement (opens the original)
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(244) Laid off at 58? The first 90 days after a layoff can decide your whole retirement. Wes walks through the 21-day (or 45-day) severance review window older workers get by law, how December vs January severance timing changes your tax bill and the ACA subsidy cliff at 400% of the poverty level, and when COBRA beats a Marketplace plan. You'll see why rolling your 401(k) into an IRA on autopilot can cost you the Rule of 55, how unemployment and HSA money can bridge you so fear doesn't push you
What Do You Actually Live On Between 62 and 70? (opens the original)
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(243) Delaying Social Security from 62 to 70 means your savings must pay the bills for eight years. Wes puts a real price on that bridge: on a $3,000 full benefit, $288,000 of income to replace and $201,600 in skipped checks. He shows what the 8% delayed credits buy, why sequence of returns risk matters most during the bridge years, and why spending pre-tax IRA money first can shrink RMDs at 73 or 75 and lower taxes later. You'll also get his personal 25% guardrail for spotting when a portfolio
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Measured Sep 19, 2026
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