Carl Sullivan

Carl Sullivan has been a Flywheel Publishing contributor since 2020, focusing mostly on personal finance, investing and technology. He started his journalism career covering mutual funds, banking and business regulation.

Besides his freelance writing, Carl is a long-time manager of editorial teams covering a variety of topics including news, business and politics. He’s currently the North America Managing Editor for Flipboard and worked previously for Microsoft News and Newsweek.

Carl loves exploring the world and lived in India for several years. Today, he resides in New York City’s Queens borough, where you can hear hundreds of different languages just by riding the subway.

Carl Sullivan | May 31, 2026 at 6:52 AM EDT

A $600,000 Annuity Pays $3,700 a Month for Life. What About Your Spouse?

A 65-year-old retiree walks into a meeting with $600,000 in an IRA and walks out with a pitch. Hand it…

Carl Sullivan | May 30, 2026 at 10:27 AM EDT

73-Year-Old Widow With $2.1M Discovers Husband’s IRA Beneficiary Election Triggered a $96K Tax Bill

Margaret is 73. Her husband died in March, and six months later, her CPA delivered some bad news. A single…

Carl Sullivan | May 29, 2026 at 5:32 PM EDT

62-Year-Old Retiree’s $2.4M Portfolio Could Drop to $1.1M by 80 in the Wrong Market

A 62-year-old single retiree just walked away from work with a $2.4 million portfolio split between 60% stocks and 40%…

Carl Sullivan | May 29, 2026 at 8:46 AM EDT

What $10K a Month Really Looks Like in Retirement at Age 67 With a $2.4M Portfolio

The $10,000 a month retirement sounds great. A 67-year-old couple with $2.4 million and Social Security already claimed assumes the…

Carl Sullivan | May 29, 2026 at 7:23 AM EDT

68-Year-Old Software Architect With $2.6M Discovers His Severance Triggered Huge Medicare Premium

The Medicare welcome packet arrived in the mail, and the premium quote inside did not match anything a 68-year-old retiree…

Carl Sullivan | May 28, 2026 at 5:23 PM EDT

58-Year-Old Just Inherited $1.2M IRA. One Wrong Move Could Cost Her $310K in Taxes

A 58-year-old marketing director earning $245,000 just inherited a $1.2 million traditional IRA from her father, who died in 2026…

Carl Sullivan | May 28, 2026 at 2:13 PM EDT

Tax Bomb: Employer Stock Inside $4.2M 401(k) Could Cost Dearly

A senior director at a public mega-cap company is wrapping up her career at age 61. Her 401(k) sits at…

Carl Sullivan | May 28, 2026 at 1:12 PM EDT

$750,000 Annuity Locks In $4,200 a Month for Life, but Gives Up $610,000 Inheritance

The pitch sounds clean. Hand an insurance company $750,000 and receive $4,200 a month for life, regardless of what the…

Carl Sullivan | May 28, 2026 at 7:29 AM EDT

Retirees Realize a $3M Nest Egg at 70 Only Means $70K in Real Annual Spending

A $3 million portfolio at age 70 sounds like the finish line. Then you actually do the math on what…

Carl Sullivan | May 27, 2026 at 5:15 PM EDT

Why Your $2M Portfolio Doesn’t Determine Your Retirement (This One Withdrawal Number Does)

Linda is 64, single with no dependents, and staring at a $2 million brokerage statement wondering if it is enough.…

Carl Sullivan | May 27, 2026 at 4:37 PM EDT

Why a 72-Year-Old With $2.2M Faces $7.4K in Annual Medicare Surcharges

A single 72-year-old retiree sitting on a $2.2 million traditional IRA looks, on paper, like a textbook success story. Then…

Carl Sullivan | May 27, 2026 at 8:19 AM EDT

The Retiree Who Did Everything Right and Still Got a Huge Tax Bill

Picture a 73-year-old widow who retired at 66, lives on Social Security plus modest portfolio withdrawals, and has watched her…

Carl Sullivan | May 27, 2026 at 6:53 AM EDT

A $1.2M Portfolio Lost $187,000 in Three Weeks. Could a Bond Sleeve Help?

A 67-year-old retiree opens her brokerage statement after three turbulent weeks and sees the balance has fallen from $1.2 million…

Carl Sullivan | May 26, 2026 at 5:52 PM EDT

Can You Retire at 63 With $1.6M? Expect to Cover a $57,000 Bridge Before Medicare Eligibility

You and your spouse are both 63. Combined retirement assets sit near $1.6 million. You want to stop working in…

Carl Sullivan | May 26, 2026 at 8:27 AM EDT

Can You Retire at 60 With $900,000? Don’t Forget Health Insurance Costs

You are 60, single, and have $900,000 saved. You want to stop working in 2026. The 401(k) math looks fine.…

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Carl Sullivan

A $600,000 Annuity Pays $3,700 a Month for Life. What About Your Spouse?

73-Year-Old Widow With $2.1M Discovers Husband’s IRA Beneficiary Election Triggered a $96K Tax Bill

62-Year-Old Retiree’s $2.4M Portfolio Could Drop to $1.1M by 80 in the Wrong Market

What $10K a Month Really Looks Like in Retirement at Age 67 With a $2.4M Portfolio

68-Year-Old Software Architect With $2.6M Discovers His Severance Triggered Huge Medicare Premium

58-Year-Old Just Inherited $1.2M IRA. One Wrong Move Could Cost Her $310K in Taxes

Tax Bomb: Employer Stock Inside $4.2M 401(k) Could Cost Dearly

$750,000 Annuity Locks In $4,200 a Month for Life, but Gives Up $610,000 Inheritance

Retirees Realize a $3M Nest Egg at 70 Only Means $70K in Real Annual Spending

Why Your $2M Portfolio Doesn’t Determine Your Retirement (This One Withdrawal Number Does)

Why a 72-Year-Old With $2.2M Faces $7.4K in Annual Medicare Surcharges

The Retiree Who Did Everything Right and Still Got a Huge Tax Bill

A $1.2M Portfolio Lost $187,000 in Three Weeks. Could a Bond Sleeve Help?

Can You Retire at 63 With $1.6M? Expect to Cover a $57,000 Bridge Before Medicare Eligibility

Can You Retire at 60 With $900,000? Don’t Forget Health Insurance Costs

U.S. Military Expert Issues Grave Warning: ‘We Need More Munitions, and Deliveries Are Years Behind.’ What Stocks Can Benefit?

The 3 Best Dividend ETFs to Build Lasting Retirement Income in 2026

Got $1,500? 1 Core Portfolio Cornerstone With an Unshakable Economic Moat to Buy on the Dip

They Dream of Retiring On The Road. How Big a Portfolio Do They Need for RV Living?

The Average American Leaves $2,954 on the Table Every Year by Skipping the 401(k) Match

U.S. Military Expert Issues Grave Warning: ‘We Need More Munitions, and Deliveries Are Years Behind.’ What Stocks Can Benefit?

The 3 Best Dividend ETFs to Build Lasting Retirement Income in 2026

Carl Sullivan

A $600,000 Annuity Pays $3,700 a Month for Life. What About Your Spouse?

73-Year-Old Widow With $2.1M Discovers Husband’s IRA Beneficiary Election Triggered a $96K Tax Bill

62-Year-Old Retiree’s $2.4M Portfolio Could Drop to $1.1M by 80 in the Wrong Market

What $10K a Month Really Looks Like in Retirement at Age 67 With a $2.4M Portfolio

68-Year-Old Software Architect With $2.6M Discovers His Severance Triggered Huge Medicare Premium

58-Year-Old Just Inherited $1.2M IRA. One Wrong Move Could Cost Her $310K in Taxes

Tax Bomb: Employer Stock Inside $4.2M 401(k) Could Cost Dearly

$750,000 Annuity Locks In $4,200 a Month for Life, but Gives Up $610,000 Inheritance

Retirees Realize a $3M Nest Egg at 70 Only Means $70K in Real Annual Spending

Why Your $2M Portfolio Doesn’t Determine Your Retirement (This One Withdrawal Number Does)

Why a 72-Year-Old With $2.2M Faces $7.4K in Annual Medicare Surcharges

The Retiree Who Did Everything Right and Still Got a Huge Tax Bill

A $1.2M Portfolio Lost $187,000 in Three Weeks. Could a Bond Sleeve Help?

Can You Retire at 63 With $1.6M? Expect to Cover a $57,000 Bridge Before Medicare Eligibility

Can You Retire at 60 With $900,000? Don’t Forget Health Insurance Costs

U.S. Military Expert Issues Grave Warning: ‘We Need More Munitions, and Deliveries Are Years Behind.’ What Stocks Can Benefit?

The 3 Best Dividend ETFs to Build Lasting Retirement Income in 2026

Got $1,500? 1 Core Portfolio Cornerstone With an Unshakable Economic Moat to Buy on the Dip

Featured Reads

They Dream of Retiring On The Road. How Big a Portfolio Do They Need for RV Living?

The Average American Leaves $2,954 on the Table Every Year by Skipping the 401(k) Match