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| Uploaded: | 2025-10-30 |
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Thanks to our good friends at Advisor.com for sponsoring this series! Schedule a FREE consultation call with Advisor today and never make another financial decision alone! Get $500 off your first year with them by signing up through TFD. Take this short quiz to get started: https://bit.ly/JGGepi2
Welcome to our brand new series, Just Getting Good, where Chelsea sits down with women over 50 to talk about life, love, money, aging, and everything in between.
For our second episode, we sat down with the wonderful Lindsay who spoke very candidly about motherhood, building a career as a working mom, finding your identity through all of life's season, beauty standards, and dating in your 50s. We loved speaking with Lindsay, and know you'll enjoy this episode!
Thank you so much to Lindsay for speaking so candidly with us! You can follow her accounts here: https://www.instagram.com/lindsayowenny/?hl=en
https://www.instagram.com/lindsayowenrealestate/
OTHER FINANCIAL PRODUCTS WE PERSONALLY ENDORSE:
For investing - Betterment https://bit.ly/JGGepisode02
Our favorite budgeting app - Monarch https://bit.ly/JGGepi4
We have new episodes dropping every Thursday! Come back for more!
Want to support TFD? One of the best ways is to join our membership program, The Society at TFD — join at the premium tier and get instant access to our latest member podcast, RomComOnomics! You can become a member here on YouTube or over on Patreon (we recommend Patreon for a better user experience!) — Join here: https://bit.ly/46jmyUE
EPISODE SUMMARY:
00:00 Intro
01:27 Ad Break
03:36 Interview begins
04:30 When life started feeling “good”: mid–late 40s after kids and identity shift
05:21 Years as stay-at-home mom; feeling invisible and deprioritized
05:45 Return to work, rising success, divorce, and rebuilding self
06:09 What a better relationship with self looks like—ongoing work
06:45 Mostly single the past five years; higher standards and comfort alone
07:11 Redefining goals beyond marriage; forgiving self and valuing inner success
08:21 Success as a whole life, not just work or relationship status
08:29 Divorce talk: fears, stigma, and being “poster girl” among friends
09:04 Advice to those considering divorce: try everything, own your part, therapy
10:18 Son’s candid remark as catalyst to leave and model healthier love
11:34 Modeling a happy single life as better parenting
12:13 Rebuilding career: why real estate at 44 and immigration constraints
13:33 Picking real estate for flexible path and income potential
15:22 Kids’ ages then; emotional load; daughter’s “time to work” moment
16:46 Why real estate can be a helping profession and deeply satisfying
18:00 Parallels: midwifery and real estate are both about transitions
19:26 A client story that “changed our lives”
20:11 Homebuying question: treating it as an emotional and financial decision
20:59 Case for homeownership: live in your investment, leverage, tax benefits
21:31 Time horizon matters; long hold vs. quick flip
23:45 Her 2019 purchase, rates context, and market quietness
24:20 Approaching empty nest: timing, appreciation, and retirement planning
25:05 Practical rule: you live in the payment, not the price
25:46 Having kids in mid-30s; late college; non-linear path
27:44 Parenting surprises: best of times, worst of times
28:55 Postpartum identity shock; loving baby while grieving former self
32:01 “Conspiracy of moms”: it’s wonderful and really hard
33:45 Did divorce enable identity? Reclaiming preferences and voice
35:29 Running, music, and deliberately rediscovering “what do I like?”
36:49 Intentional life design through stories, community, and curiosity
37:24 Dating at 52: the app treadmill and social attitudes
38:04 Dating pools: lifelong singles vs. divorcés; wishing for “ex-references”
39:26 Tactic: FaceTime screens save time and energy
40:03 Age-gap dynamics; many men avoid same-age women
41:02 How older-man/younger-woman differs from older-woman/younger-man
42:51 Power, challenge, and why some men prefer younger partners
45:37 Opening the aperture without settling; guarding her peace
47:40 Beauty and aging philosophy; has she had work done?
48:05 Past Botox/filler experiments; choosing natural lately
48:42 Modeling messages for her daughter; embracing emerging white hair
50:02 Teens’ vote: “don’t dye it”—encouragement to stay natural
51:19 Viral street interview; “sunray eyes” and reframing wrinkles
52:14 Temptation vs. values: facelift content and targeted ads
53:59 Culture’s message: “too old to love” and resisting it
54:59 Vision for aging: long white hair, laugh lines as life’s map
55:21 Rapid-fire begins
55:27 Aging insight: layered memories colliding across time
57:03 Money lesson: start now; compounding and property appreciation
57:30 Relationship lesson: partners need separate lives and interests
58:22 Advice to 30-something single, child-free, not “there” financially
59:33 Life is long; start retirement investing early but drop the deadlines
Welcome to our brand new series, Just Getting Good, where Chelsea sits down with women over 50 to talk about life, love, money, aging, and everything in between.
For our second episode, we sat down with the wonderful Lindsay who spoke very candidly about motherhood, building a career as a working mom, finding your identity through all of life's season, beauty standards, and dating in your 50s. We loved speaking with Lindsay, and know you'll enjoy this episode!
Thank you so much to Lindsay for speaking so candidly with us! You can follow her accounts here: https://www.instagram.com/lindsayowenny/?hl=en
https://www.instagram.com/lindsayowenrealestate/
OTHER FINANCIAL PRODUCTS WE PERSONALLY ENDORSE:
For investing - Betterment https://bit.ly/JGGepisode02
Our favorite budgeting app - Monarch https://bit.ly/JGGepi4
We have new episodes dropping every Thursday! Come back for more!
Want to support TFD? One of the best ways is to join our membership program, The Society at TFD — join at the premium tier and get instant access to our latest member podcast, RomComOnomics! You can become a member here on YouTube or over on Patreon (we recommend Patreon for a better user experience!) — Join here: https://bit.ly/46jmyUE
EPISODE SUMMARY:
00:00 Intro
01:27 Ad Break
03:36 Interview begins
04:30 When life started feeling “good”: mid–late 40s after kids and identity shift
05:21 Years as stay-at-home mom; feeling invisible and deprioritized
05:45 Return to work, rising success, divorce, and rebuilding self
06:09 What a better relationship with self looks like—ongoing work
06:45 Mostly single the past five years; higher standards and comfort alone
07:11 Redefining goals beyond marriage; forgiving self and valuing inner success
08:21 Success as a whole life, not just work or relationship status
08:29 Divorce talk: fears, stigma, and being “poster girl” among friends
09:04 Advice to those considering divorce: try everything, own your part, therapy
10:18 Son’s candid remark as catalyst to leave and model healthier love
11:34 Modeling a happy single life as better parenting
12:13 Rebuilding career: why real estate at 44 and immigration constraints
13:33 Picking real estate for flexible path and income potential
15:22 Kids’ ages then; emotional load; daughter’s “time to work” moment
16:46 Why real estate can be a helping profession and deeply satisfying
18:00 Parallels: midwifery and real estate are both about transitions
19:26 A client story that “changed our lives”
20:11 Homebuying question: treating it as an emotional and financial decision
20:59 Case for homeownership: live in your investment, leverage, tax benefits
21:31 Time horizon matters; long hold vs. quick flip
23:45 Her 2019 purchase, rates context, and market quietness
24:20 Approaching empty nest: timing, appreciation, and retirement planning
25:05 Practical rule: you live in the payment, not the price
25:46 Having kids in mid-30s; late college; non-linear path
27:44 Parenting surprises: best of times, worst of times
28:55 Postpartum identity shock; loving baby while grieving former self
32:01 “Conspiracy of moms”: it’s wonderful and really hard
33:45 Did divorce enable identity? Reclaiming preferences and voice
35:29 Running, music, and deliberately rediscovering “what do I like?”
36:49 Intentional life design through stories, community, and curiosity
37:24 Dating at 52: the app treadmill and social attitudes
38:04 Dating pools: lifelong singles vs. divorcés; wishing for “ex-references”
39:26 Tactic: FaceTime screens save time and energy
40:03 Age-gap dynamics; many men avoid same-age women
41:02 How older-man/younger-woman differs from older-woman/younger-man
42:51 Power, challenge, and why some men prefer younger partners
45:37 Opening the aperture without settling; guarding her peace
47:40 Beauty and aging philosophy; has she had work done?
48:05 Past Botox/filler experiments; choosing natural lately
48:42 Modeling messages for her daughter; embracing emerging white hair
50:02 Teens’ vote: “don’t dye it”—encouragement to stay natural
51:19 Viral street interview; “sunray eyes” and reframing wrinkles
52:14 Temptation vs. values: facelift content and targeted ads
53:59 Culture’s message: “too old to love” and resisting it
54:59 Vision for aging: long white hair, laugh lines as life’s map
55:21 Rapid-fire begins
55:27 Aging insight: layered memories colliding across time
57:03 Money lesson: start now; compounding and property appreciation
57:30 Relationship lesson: partners need separate lives and interests
58:22 Advice to 30-something single, child-free, not “there” financially
59:33 Life is long; start retirement investing early but drop the deadlines
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