Your Money, Your Wealth

When to HOLD OFF on Doing Roth Conversions

Retirement Savings: When to Take Your Foot Off the Gas - 528

Taxable Income, Dividends, Roth & SMA: What's Missing in Your Early Retirement? - 527

Roth IRA is "The Greatest Account Ever" Per Ed Slott. But Why?

Risks Threaten Retirement. Rewire Your Plans

Will the Tax Cuts and Jobs Act Be Extended?

3 Key Predictors of Retirement Happiness

Choosing Your Retirement Income Style and Top 5 Ways to Manage Market Volatility

What’s the Future of Social Security Under the New Administration?

Haven't Yet Saved a Million. Can We Still Retire Early?

What's a Safe Withdrawal Rate in Retirement? (So You Won't Run Out of Money)

Should You Switch Retirement Contributions to Roth?

0% Capital Gains Tax vs. Roth Conversion vs.... a Cruise? - 517

Mutual Funds vs. ETFs, Bonds to Bourbon

Financial Planning for Marriage, Separation, and Singlehood

Deferred Comp, Roth Strategies, Asset Protection (and Gold) - 514

I Work in a Toxic Office. Can I Retire Early?

Choosing the Right Investments for You

Grow Your Wealth Tax-Free & Retire Sooner: YMYW Best of 2024 - 511

Defusing a Future Tax Bomb With Roth Conversions - 510

When to Claim Social Security and the Truth About Annuities

Bonds and Annuities, Social Security and Retirement Spending - 508

9 Answers to Boost Tax-Free Roth Retirement Income - 507

How to Plan for 35 Years of Retirement Spending With Smart Roth Conversions - 506

How to Retire ASAP - and Where to Save to Get There - 505

Rules for Inheritances and Making Roth Contributions for Others - 504

When to Pay Off Your Home, Retire, and Do Roth Conversions - 503

Spitballing Early Retirement for the One Percenters - 502

How to Reduce the Widow’s Tax Penalty - 501

Top Funniest Moments From the Your Money, Your Wealth Podcast, Vol. 2 - Ep. 500

How to Get Into Real Estate Investing, Spitballing Retirement - 499

Spend RMDs, or Reduce Distributions and Taxes With Roth Conversions? - 498

Tax-Savvy In-Plan Roth Conversions and Inherited IRA Withdrawals - 497

Age Plus 20 Rule for Retirement Contributions - 496

3 Strategies to Pay Roth Conversion Taxes - 495

How to Get Into the Stock Market: Dollar Cost Average or Go All In? - 494

How Much Money Do You Need to Retire ASAP? - 493

Exchange Funds Explained, Roth Conversion Timing - 492

Alternative Investments, Annuities, and Real Estate Syndications - 491

Can You Retire? Here’s How to Calculate How Much You Need - 490

Good Tax Planning Can Save You HOW Much?! Find Out From IRA Guru Ed Slott, CPA - 489

Market Timing Retirement Withdrawals and Roth Conversions - 488

Should Siblings Take Out Life Insurance on Parents Before Inheriting $10M? - 487

How to Pay Less Tax and Invest for Retirement - 486

Retirement Planning With a Large Age Difference: A Case Study | YMYW Extra - 6

Spitballing Retirement From Apple to a Tax-Friendly State | YMYW Extra - 5

Spousal Social Security, Retirement Expenses and Roth Conversions | YMYW Extra - 4

Happily Ever After in Retirement? | YMYW Extra - 3

Spitballing Retirement During the Expensive Kid Years - 485

Roth Conversions vs. Required Minimum Distributions - 484

Asset Location & Roth Conversion Retirement Spitball | YMYW Extra - 1

Slopes Vs. Suits: How Couples Bridge the Retirement Gap - 483

FDIC vs. SIPC, Annuities, SSDI & Early Retirement Strategies - 482

Which Account Should Fund Living Expenses in Retirement? - 481

401(k) vs. Roth: Where to Save for Retirement - 480

Tax Loss Harvesting, Tax Gain Harvesting, Financial Advisor Value - 479

How to Manage Taxes When You Win the Lottery - 478

What’s the Break-Even Point on Roth Conversions? - 477

Which Mortgage for Early Retirement? What is Private Credit? - 476

Is Your Retirement Withdrawal Rate Too High? - 475

How to Take the Uncertainty of Taxes Off the Table - 474

Does Your Financial Advisor Just Want to Collect Fees? - 473

Will Roth Conversions Put You On Track to Retire Early? - 472

How Much Should You Convert to Roth IRA? - 471

Spitballing Retirement for Fat Wallets - 470

401(k) Ins & Outs, Roth Conversion Benefits, and Divorce Finances - 469

How Much to Save in Tax-Free, Tax-Deferred, and Taxable Accounts? - 468

What Does Retirement Look Like for You? - 467

Roth Conversions to Pay Less Tax on Retirement Withdrawals - 466

Personal Finance 101: How to Teach Teens About Money - 465

Tax Strategies, Backdoor Roth, Buy vs. Rent - 464

Retirement Investing, Roth Conversion Pros & Cons: YMYW Best of 2023 - 463

Can You Retire Early at Age 50 or 60? - 462

Roth & Retirement Spitball, Insurance, and the Origins of YMYW - 461

How to Invest: Bonds, CDs, and Roth Conversions - 460

Advisor Touts 8% Returns, But Says I Can Only Withdraw 4%?! - 459

Retirement Spending and Timing Your Mortgage Payoff - 458

How to Cut Your Taxes Before Year-End - 457

How to Bridge the Gap to Retirement Income: Pension Spitball - 456

Can High Earners Fund a Roth IRA Without Paying More Tax? - 455

Is Our Retirement Savings Enough to Ever Retire? - 454

No Retirement Advice or Recommendations, Just Spitballing - 453

Why Would a Tax Advisor Discourage 529 Plan College Savings? - 452

Mega Backdoor Roth Conversion 5-Year Rule and Bond Investing - 451

Retirement Withdrawals: What's a Safe Distribution Rate? - 450

What To Do With Your Employer-Sponsored Retirement Plan? - 449

Low Mortgage Interest Rate vs. Future Gains: Is Trading Up Worth It? - 448

Can You Shorten Your Working Years? - 447

DIY Early Retirement Planning - 446

Market Timing, Pension, & Roth Conversion Retirement Spitball - 445

What Are the Rules for Taking Money From a Roth IRA? - 444

Spitballing Retirement and Social Security for Worst Case Scenarios - 443

RSU, Mutual Funds, Bonds, and Annuities - 442

Early Retirement Withdrawals & Capital Gains Tax Explained - 441

Are Roth Conversions Really As Good as They Sound? - 440

$7M Tax-Free or $10M Retirement? Backdoor Roth or Lower Fees? - 439

When Will You Be Able to Retire? - 438

Two Unspoken Assumptions About Collecting Social Security - 437

Invest or Pay Off the Mortgage? - 436

How to Maximize Your Inheritance: IRA Options and RMDs - 435

Ready to Retire? 5 Retirement Spitball Analyses - 434

Bonus Depreciation, Retirement Income, and Portfolio Diversification with Real Estate - 433

Tax Jailbreak Early Retirement Strategy: Sense or Nonsense? - 432

How to Calculate Your Retirement Needs in Future Dollars - 431

How to Consider Your Pension Options for Retirement - 430

HSA to Roth, RMD Investing, and Social Security Strategies - 429

What to Do With Inheritance Money? - 428

Trust Issues, Death & Taxes: Estate Plan Spitball - 427

Spitballing Retirement Real Estate and Tax Strategies - 426

Annuity? CD? Money Market? Where to Invest for Safety - 425

Investments vs. Retirement Withdrawal Strategy, FDIC Insurance - 424

What to Do When There’s Too Much Money in Your Traditional IRA - 423

How to Reduce Taxes and Get Better Investing Returns? Asset Location - 422

Roth Conversions & Retirement Spitball Analysis - 421

Mutual Funds vs. ETFs, SECURE 2.0 & Capital Gains Strategies - 420

How to Start Planning for Retirement - 419

“Will I Ever Be Able to Retire?” - 418

What to Do When You Get a Huge Pay Increase - 417

Set-and-Forget Investing, Real Estate vs. Bonds, Pension, Social Security and Medicare - 416

SECURE 2.0, FIRE, Tax Arbitrage & Roth Retirement Spitball - 415

Medicare IRMAA, Roth Pro-Rata, & Real Estate Strategies - 414

Spitballing Diversified Portfolios for Retirement - 413

SECURE Act 2.0 & Retirement Rich, Cash Poor - 412

Bear Market Survival & the 5W1H of Roth Conversions: YMYW Best of 2022 - 411

Retirement Planning, Investing, and Tax Reduction Made Fun: YMYW Trailer

Diversification Vs. Fees: What’s More Important for Retirement Investing? - 410

Who to Trust? Second Opinion Retirement Spitball - 409

Where to Save for Early Retirement? - 408

Fixed Indexed Annuities, RMDs, and Early Social Security - 407

How to Forecast Your Expenses in Retirement - 406

Life Insurance, Muni Bonds, and Dividend Stocks in Retirement - 405

Roth IRA 5-Year Rules: How to Withdraw Money With No Taxes or Penalties - 404

Inflation Investing, Asset Location, and Real Estate Retirement Spitball - 403

Will Your Retirement Savings Last Until You're 90 Years Old? - 402

Should Young People Save for Retirement? - 401

Anything Stupid or Overlooked in Your Retirement Plan Spitball? - 400

Survivor Social Security and Lowering Taxes in Retirement - 399

How to Manage Financial Market Stress? With the Help of a Caddie - 398

Spitballing Retirement Planning in Your 40's & 50's - 397

Backdoor Roth, Investing, and Taxes - 396

Spitballing Early Retirement by the Ocean with Husband and Boyfriend - 395

How to Deal With Taxes When Income Goes Through the Roof - 394

Is Now the Time for a Roth Conversion, or Wait Until Retirement? - 393

How to Spitball Retirement Taxes and the 4% Rule - 392

Spitballing Retirement Planning in Your 30s - 391

Working After Retirement and Wealth Gifting Strategies - 390

Save for a Home or Save for Retirement? - 389

Pay Tax on This Move Now to Potentially Have More to Spend Later - 388

A Model Retirement Plan Spitball Analysis - 387

Should We Hold Off on Retiring Until the Markets Recover? - 386

Bonds and Series I Bonds, High Inflation, and High Interest Rates - 385

Can We Retire Soon? Retirement Spitball Analysis - 384

Where to Find Retirement Income When the Stock Market Freaks Out - 383

Where Should You Save for Retirement? Where Does Real Estate Fit? - 382

Don’t Retire Until You Can Answer These Five Practical Questions - 381

How to Ditch a Bad SIMPLE IRA? What's a Prohibited Transaction? - 380

6 Money Strategies for Down Markets Depending on Your Goals - 379

Is My BF BSing Me on RMDs? Required Minimum Distributions Explained - 378

Roth IRA, 457, TSP, and Retire Early Spitball - 377

Self-Employed Retirement, Fixed Index Annuities, and Investment Property - 376

Roth Conversion Retirement Spitball Analysis - 375

Annuities, Social Security, and Real Estate Taxes - 374

Can We Retire Early? Investing and Retirement “Rothification” - 373

Retirement Spitball: Social Security, Pension, and Self-Employed - 372

When Must You Pay Roth Conversion Taxes? - 371

Taxes and Real Estate Investing Explained - 370

Should You Claim Social Security Early? - 369

Why Is It So Difficult to Time the Market? - 368

Dollar-Cost Averaging, Small Cap, and Stable Value Funds - 367

Roth Conversions vs. Roth Contributions - 366

Real Estate Investing: What Are Cash-on-Cash and Cap Rate? - 365

Covered Call Investing Strategies Explained, RMDs, and Social Security Taxation - 364

Stock Acquisition, HSA, AMT, TSP, RSU, and Trust as Retirement Beneficiary - 363

Early Retirement, Roth Conversion Tax: YMYW Best of 2021 - 362

Financially Able But Afraid to Retire - 361

Should You Invest in the Stock Market or Buy Real Estate? - 360

Social Security Benefits for Spouses, Ex-Spouses, and Survivors - 359

Roth Conversions, the Rule of 55, and Retirement Withdrawal Regrets - 358

Does the 5 Year Rule Apply to Each Roth Conversion? - 357

Spitballing Retirement and the Build Back Better Tax Proposal - 356

Saving and Investing for Retirement with Company Stock, Bonds, and VTSAX? - 355

Retirement Pension Lump Sum or Monthly Annuity Payment? - 354

Retirement Spitballing, Social Security, and Hiring & Ghosting Financial Advisors - 353

Dividends, Asset Classes, and Diversification: How to Invest for Retirement? - 352

Estate Planning, Social Security, and TSP to Roth Conversions - 351

Spitballing the Sequence of Retirement Savings - 350

How to Pay the Tax on a Roth Conversion - 349

Medicare, Social Security, and FIRE Early Retirement - 348

What's the Right Mix of Stocks and Bonds for Your Investment Portfolio? - 347

Buying and Selling Your House or Real Estate - 346

Working or Retiring Abroad and Early Retirement Spitball - 345

It Could Be Over for the Mega Backdoor Roth IRA - 344

HELOC, All-in-One Mortgages, and What to Do With Old Life Insurance Policies - 343

Roth 401(k), Conversions, RMDs, and Cap Gains - 342

Early Retirement Spitball Analysis - 341

Where to Locate Assets for Tax Efficiency Without Compromising Growth? - 340

Should We Do a Roth Conversion? - 339

What to Do When You Own Too Much of One Stock - 338

Is It Crazy to Be Happy Paying Tax on Massive Stock Market Gains? - 337

How to Spitball Your Most Tax-Efficient Retirement Withdrawal Strategy - 336

Which States Are the Most Tax-Friendly in Retirement? - 335

Are We On Track for Retirement? Financial Plan Spitball Analysis - 334

Are Financial Advisors Really Worth the Money? - 333

Roth Conversions, Medicare, and Required Minimum Distributions - 332

What is the Best Age to Retire, Financially Speaking? - 331

Has the Government Ever Reduced Social Security Benefits? - 330

How to Protect Investments Against a Stock Market Crash? - 329

Should People in High Tax Brackets Save in Roth Retirement Accounts? - 328

How to Avoid a Tax Time Bomb: Retirement Plan Spitball Analysis - 327

How to Get Tax-Free Growth on Investments for Life - 326

Capital Gains Tax Vs. Ordinary Income Tax Explained - 325

Which Asset Classes Are Good Investments to Hedge Against Inflation? - 324

Real Estate: Should We Sell Rental Property to Buy a Primary Residence? - 323

Pay Down the Mortgage or Buy Long Term Care Insurance? - 322

Inflation, Variable Annuities, Real Estate: How to Invest Against Risk - 321

Early Retirement: Can You Afford to Retire Now? - 320

Roth IRA Excess Contributions and the Pro-Rata Rule - 319

Firefighters' Retirement Plan Spitballing, Annuities, and RMDs - 318

Charitable Giving and Roth Conversion Retirement Tax Strategies - 317

Monthly Retirement Pension Vs. Lump Sum Payment: How to Choose -316

Are These Three Investment Products Too Good To Be True? - 315

Is the Backdoor Roth IRA a Good Strategy For You? - 314

Are You Financially Ready for Retirement? - 313

"Super Roth": Should You Overfund Supplemental Executive Retirement Plan Insurance? -312

Social Security, Medicare, HSA and Roth Conversions - 311

[SPECIAL] GameStop: Stocks Gone Wild! Should You Join the Day Trading Craze? - 310a

What's the Best Way to Take Retirement Distributions? - 310

Retirement Plan Spitball Analyses for Side Hustles, Clergy & Grandkids - 309

How to Do the Mega Backdoor Roth IRA - 308

How to Choose Your Pension Options and Retirement Withdrawal Strategy - 307

Social Security, Medicare and Real Estate - 306

What’s the Best Retirement Withdrawal Strategy? - 305

5 Last Minute Ways to Cut Your 2020 Taxes - 304

How to Use Tax Diversification in Your Retirement Portfolio - 303

Should You Pay Off the Mortgage? First Consider Your Tax Strategy - 302

Borrow Money to Pay Tax on a Roth IRA Conversion? - 301

Top Funniest Moments From the Your Money Your Wealth Podcast - 300

Rental Real Estate Property: How to Calculate Cap Rates and Depreciation - 299

Retirement Portfolio Strategies and Making Sense of Fees - 298

The Barn Door, Garage Door, Mega Backdoor Roth IRA Conversion - 297

YMYW Spitball Analysis 3: Tax Diversification and Asset Allocation - 296

All About the Backdoor Roth IRA Strategy - 295

Rebalancing Your Retirement Portfolio in Market Downturns - 294

Backdoor Roth Conversions and Investing for Kids - 293

Will Estate Tax Law Changes Affect Your Family Financial Plan? - 292

Roth Conversions, Annuities and Inherited IRAs - 291

Market Timing and Day Trading in a Roth IRA? - 290

Backdoor Roth IRA Conversions, Stimulus and Self-Employed Retirement -289

YMYW Spitball Analysis 2: Retirement and Social Security - 288

Roth Conversion Tax Planning Strategies and Annuities - 287

Dividend-Paying Stocks and Investing Strategies at All Ages - 286

New Stimulus Check & Coronavirus Relief Package On the Way? - 285

What Is Your Retirement Number? YMYW Spitball Retirement Analysis - 284

Tax Gain Harvesting, Active vs. Passive Investments… and Roth Conversions - 283

How to Do a Roth Conversion and Pay Taxes On It - 282

Will These Three Things Affect Your Social Security? - 281

Are These Retirement Investment Strategies On Track? - 280

Real Estate, Roth Conversions, and Social Security - 279

Can You Do a Coronavirus-Related Distribution to Roth Conversion? - 278

Roth IRA Conversion and Contribution Rules - 277

Pre-Tax or Roth Contributions for Retirement Savings? - 276

Social Security WEP, GPO & Roth IRA Conversion Strategies - 275

CARES Act: Distributions, RMDs & Dependents - 274

Real Estate, Roth Conversions & Annuities - 273

Asset Location: Where Should You Hold Retirement Investments? - 272

4 Financial Strategies from the Stimulus Package - 271

In Market Volatility, Beware of Annuity Pitches - 270

Revisiting Roth IRA Conversion Strategies - 269

CARES Act: What's in the Coronavirus Stimulus Package - 268

Analyzing 5 Investing Strategies for Volatile Markets - 267

Tax Brackets Explained: How Much Are You Really Paying in Taxes? - 266

Bear Market Investing Strategies and Revisiting the 5-Year Roth IRA Withdrawal Rules - 265

How Much of Your Net Worth Should Be in Cash? - 264

7 Roth Conversion Strategies - 263

What's the Right Retirement Asset Allocation for You? - 262

Real Estate Investing: How to Find Bread & Butter Rental Properties - 261

When is the Tax Deadline for a Roth Conversion? - 260

"Collect Social Security at Age 70" is Common Advice. Why? - 259

International Funds, Safe Investments, 1031 Exchange: Email Round-Up - 258

Why Not Just Go All in On VTSAX, Vanguard’s Total Stock Market Index Fund? - 257

Your SECURE Act Retirement Questions Answered - 256

Breaking Down the Confusing 5-Year Roth Clock Rules - 255

Roth Conversions from a Thrift Savings Plan TSP? - 254

Rules for Your Retirement Savings and Distributions Are Changing - 253

Strategies for Social Security, Annuities, and Inherited Assets - 252

Should You Convert to Roth IRA All at Once or Over Time? - 251

Tanja Hester on the Flexibility of Financial Independence - 250

What’s the Break-Even on a Retirement Roth IRA Conversion? - 249

Is a Roth Conversion Affected By Social Security? - 248

How to Talk to Mom & Dad About Their Money - 247

Why This Life Insurance Is for the Most Part a Scam - 246

Is It Time to Fire Your Financial Advisor? - 245

5 Unique Social Security Questions Answered - 244

The Truth About Indexed Universal Life Insurance - 243

Investing the Money from a Real Estate Sale - 242

Answers to Your Top Roth Conversion Questions - 241

How to Choose Your Own Financial Independence Adventure - 240

How Should You Invest? As Always, It Depends - 239

Roth Conversions, Life Insurance & More: Email Round-Up - 238

Mad at the Roller Coaster? Then You Don't Understand the Ride - 237

How Much Can You Spend When You're On FIRE? - 236

Recession and the Inverted Yield Curve - 235

Tax Postcard, Stretch IRAs & Life Insurance for Education - 234

Using Alternative Investments to Boost Portfolio Returns? - 233

Time to Dial Down Risk and Do a Roth Conversion? - 232

Appreciate How Good the Economy is Now - 231

The Effect of the Media on Financial Markets - 230

Strategies for Social Security, Gifting, and Estimated Taxes - 229

Liz Ann Sonders: Investing in the Face of Recession - 228

This Retiree Helps Golfers Reach the Big Time - 227

Medicare Beginner’s Guide: What You Need to Know Now - 226

Real Estate Investing: Should You Buy Raw Land? - 225

New Retirement Legislation: Death to the Stretch IRA? - 224

Financial Independence Retire Early Hits the Big Screen - 223

How to Be Like the Millionaire Next Door - 222

How to Hedge Risk From the Brothel to the Surfboard - 221

Social Security, TSP Changes, & Maintaining Your Tax Bracket - 220

Standup Comedy: Gid Pool's Retirement Hustle - 219

3 Ways to Turn Your Financial Negatives Into Positives - 218

How to Use Rental Real Estate to Build Legacy Wealth - 217

Here's What to Do When You're a Victim of Debit Card Fraud - 216

Will Trump's Latest Proposals Reduce Student Loan Debt? - 215

The Real Keys to Being Rich and Truly Wealthy - 214

Social Security Changes in 2019 - 213

Problems With the Arguments Against Roth IRAs - 212

Retire Early Without Pinching Pennies - 211

“Hold It” Until You're Purple to be a Better Investor - 210

Are These Two Funds the Only Ones You Need for Life? - 209

Spousal Social Security Claiming Strategies You Need to Know - 208

This Myth is the #1 Barrier to Financial Freedom - 207

How to Avoid the Five Horsemen of the Retirement Apocalypse - 206

5 Key Attributes That Make Millionaires Successful - 205

Liz Ann Sonders: Recession Inevitable, the Question is When? - 204

Sex and Immigration: How Do They Affect Social Security? - 203

4 Simple Ways to Keep Your New Year’s Resolutions - 202

7 Benefits of the Federal Reserve Interest Rate Hikes - 201

How to Avoid the Top 8 Holiday Scams of 2018 - 200

How to Use Leverage to Reduce Risk and Increase Returns - 199

7 Tips and Financial Benefits for Military Families - 198

Mobile Home Parks: Is This Undiscovered Real Estate Investment Right For You? - 197

Living Beyond Your Means Now? You’ll Live Beneath Your Means In the Future - 196

Do These 9 Simple Things to Improve Your Retirement - 195

Apple, Spotify and RMDs Feeling Volatile Markets - 194

Why Market Corrections Are a Good Thing - 193

Jean Chatzky on the Big Shift to Women in Financial Power - 192

Tempted to Panic and Sell? Do These 3 Things Instead - 191

4 Roth Conversion Options for Tax-Free Portfolio Growth - 190

IRA Basics: What You Need to Know About Individual Retirement Accounts - 189

Risks and Rewards of Vacation Rentals and Real Estate Investing - 188

Trump Retirement Security Executive Order: Small Business Opportunities and Concerns - 187

Stop Spending Money the Wrong Way: 77 Days to Financial Happiness - 186

What You Need to Know About Social Security and Making Money - 185

How to Manage 8 Risks That Can Derail Your Retirement - 184

Your 2018 Taxes: 10 Ways to Prepare and Save - 183

Morgan Housel: How to Cure the Investing Disease of Fear and Greed - 182

Are More Trump Tax Cuts and Big 401(k) & IRA Changes On the Way? - 181

Why Do You Need To Understand Financial Markets? With Marc Levinson - 180

Can Risk Revolutionize How You Work? With Joel Comm - 179

Michael Batnick: The Best Investors and Their Worst Investing Mistakes - 178

50 Or Older? Don't Skip These 5 Key Retirement Questions - 177

Use This Quick Calculation to See If You're on Track for Retirement - 176