Uploaded August 2026 | Updated September 2026, 2 weeks ago
Preorder Wes Moss’ new book “The Retire Sooner Method” here: retiresoonermethod.com
Check out the Retire Sooner Podcast with Wes Moss: wesmoss.com/podcast
Retirement happiness isn’t just about how much money you’ve saved—so what actually matters most? Brian, Bo, and retirement researcher Wes Moss put it to the test with a Retirement Happiness Draft, taking turns building their ideal retirement from 12 choices like $100K of income, eight hours of sleep, close friends, travel, hobbies, a paid-off home, and multiple income streams. Who builds the happiest retirement? Along the way, they unpack new research on happy retirees, retirement planning, financial independence, health, relationships, and purpose after work—and reveal what the data says really separates a fulfilling retirement from an unhappy one.
Timestamps
00:00:00 What Actually Makes a Happy Retirement?
00:02:49 Wes Moss' Research on the Happiest Retirees
00:07:28 Drafting the Perfect Retirement
00:13:35 The Surprising Retirement Superpower
00:15:28 Who Built the Happiest Retirement?
00:21:02 Why Financial Freedom Changes Happiness
00:24:27 Which Accounts Should You Withdraw From First?
00:30:19 HSA vs. Better Health Insurance When Having a Baby
00:35:14 How Pensions and Social Security Change Retirement
00:43:20 How Fast Should You Rebuild an Emergency Fund?
00:46:26 When Should You Invest More Conservatively?
00:56:00 3 Keys to Successfully Transitioning Into Retirement
01:03:40 Stress-Testing Your Retirement Plan
🔗 The Money Guy Guide to Retirement → moneyguy.com/resource/the-money-guy-guide-to-retirement
🔗 Retirement – Money Guy’s Ultimate Guide → moneyguy.com/guide/retirement
🔗 How Much Should You Save? → moneyguy.com/resource/how-much-to-save
🔗 Know Your Number Course → moneyguy.com/products/know-your-number
🔗 When Should I Claim Social Security? → moneyguy.com/resource/when-should-i-claim-social-security
🎓 Brian Preston (CFP®, CPA) and Bo Hanson (CFA®, CFP®) share professional insights to help you own your financial future.
Jump start your journey with our FREE financial resources: moneyguy.com/resources
Subscribe on YouTube for early access and go beyond the podcast: youtube.com/c/MoneyGuyShow?sub_confirmation=1
Connect with us on social media for more content: moneyguy.com/link-in-bio
Take the relationship to the next level and become a client: moneyguy.com/become-a-client
#WealthBuilding #PersonalFinance2026 #RetirementPlanning #FinancialFreedom
Preorder Wes Moss’ new book “The Retire Sooner Method” here: retiresoonermethod.com
Check out the Retire Sooner Podcast with Wes Moss: wesmoss.com/podcast
Retirement happiness isn’t just about how much money you’ve saved—so what actually matters most? Brian, Bo, and retirement researcher Wes Moss put it to the test with a Retirement Happiness Draft, taking turns building their ideal retirement from 12 choices like $100K of income, eight hours of sleep, close friends, travel, hobbies, a paid-off home, and multiple income streams. Who builds the happiest retirement? Along the way, they unpack new research on happy retirees, retirement planning, financial independence, health, relationships, and purpose after work—and reveal what the data says really separates a fulfilling retirement from an unhappy one.
Timestamps
00:00:00 What Actually Makes a Happy Retirement?
00:02:49 Wes Moss' Research on the Happiest Retirees
00:07:28 Drafting the Perfect Retirement
00:13:35 The Surprising Retirement Superpower
00:15:28 Who Built the Happiest Retirement?
00:21:02 Why Financial Freedom Changes Happiness
00:24:27 Which Accounts Should You Withdraw From First?
00:30:19 HSA vs. Better Health Insurance When Having a Baby
00:35:14 How Pensions and Social Security Change Retirement
00:43:20 How Fast Should You Rebuild an Emergency Fund?
00:46:26 When Should You Invest More Conservatively?
00:56:00 3 Keys to Successfully Transitioning Into Retirement
01:03:40 Stress-Testing Your Retirement Plan
🔗 The Money Guy Guide to Retirement → moneyguy.com/resource/the-money-guy-guide-to-retirement
🔗 Retirement – Money Guy’s Ultimate Guide → moneyguy.com/guide/retirement
🔗 How Much Should You Save? → moneyguy.com/resource/how-much-to-save
🔗 Know Your Number Course → moneyguy.com/products/know-your-number
🔗 When Should I Claim Social Security? → moneyguy.com/resource/when-should-i-claim-social-security
🎓 Brian Preston (CFP®, CPA) and Bo Hanson (CFA®, CFP®) share professional insights to help you own your financial future.
Jump start your journey with our FREE financial resources: moneyguy.com/resources
Subscribe on YouTube for early access and go beyond the podcast: youtube.com/c/MoneyGuyShow?sub_confirmation=1
Connect with us on social media for more content: moneyguy.com/link-in-bio
Take the relationship to the next level and become a client: moneyguy.com/become-a-client
#WealthBuilding #PersonalFinance2026 #RetirementPlanning #FinancialFreedom
