The Diary of a CEOJames Sexton: Marriage fails 70 percent of the time
Divorce attorney audits 22 years of cases on sex, money, and prenups: 70 percent of marriages quietly fail, yet 86 percent of divorcees remarry.
CHAPTERS
- 0:00 – 14:00
The Odds of Divorce and Why We Still Marry
Sexton introduces himself as a high‑conflict divorce lawyer and lays out bleak statistics on marital failure contrasted with a high rate of remarriage. He questions what problem marriage is supposed to solve and why society treats it as an unquestioned default rather than a risky choice.
- •Roughly 56% of marriages end in divorce; adding miserable but intact marriages pushes ‘failure’ toward 70–75%.
- •Despite this, about 86% of divorced people remarry within five years, showing how compelling the marriage ideal is.
- •Marriage is treated as assumed: people congratulate engagements but suspect issues if couples say they won’t marry.
- •Sexton compares marriage to going skydiving with a 70% failure rate and argues we should ask, “Why do this?”
- 14:00 – 28:30
Gold Diggers, Love as an Economy, and Delusion
The conversation explores relationships with large age and wealth gaps, challenging simplistic ‘gold digger’ narratives. Sexton frames love as an economy of exchanged value and warns against delusion—like billionaires believing their partners are indifferent to money.
- •He avoids the term ‘gold digger’, arguing partners often bring different but valid forms of value (money, beauty, energy, respite).
- •An honest transactional component doesn’t inherently make a relationship predatory if both know what they’re trading.
- •The real problem is self‑delusion: wealthy, undesirable men convinced that their money plays little role in the attraction.
- •He shares a case of a billionaire marrying a woman 30 years younger after four months, insisting “this time it’s different.”
- 28:30 – 48:00
What Prenups Really Do and How the Law Sees Marriage
Sexton defines marriage as a legal status distinct from the social or spiritual ceremony and explains how prenuptial agreements let couples override default state rules. He details typical prenup structures, enforceability standards, and why ignorance of legal rights is so dangerous.
- •Marriage has three layers: religious/spiritual, social/relational, and a specific legal status—with Sexton dealing in the latter.
- •Most people never read or understand the legal rights and obligations marriage confers, yet it’s one of their most consequential contracts.
- •Prenups let couples, not legislators, decide rules for property, support, and debt allocation—especially important because laws change.
- •A simple ‘yours, mine, ours’ model can structure assets and debts but requires ongoing communication about where money goes.
- •Unconscionability is the bar for voiding a prenup; contracts can be shockingly lopsided in outcome yet still enforceable.
- 48:00 – 1:01:00
Extreme Prenups and Fidelity Clauses
The discussion turns to the most shocking prenups Sexton has seen, including one tying alimony to a woman’s weight. He then explains ‘fidelity clauses’ and why trying to punish cheating contractually is both legally messy and practically ineffective.
- •A notorious prenup reduced alimony by $10,000 per month for every 10 pounds the wife gained; a court found it “disgusting” but enforceable.
- •Sexton analyzes such clauses like an engineer: if representing her, he’d maximize the baseline weigh‑in to protect her payout.
- •Fidelity clauses define cheating and attach a financial penalty, but he calls them a “terrible idea.”
- •Distinctions between one‑off drunken sex, ongoing affairs, and emotional affairs make a one‑size cheating definition unrealistic.
- •He argues infidelity already carries immense emotional and logistical costs; an extra financial fine is unlikely to deter it.
- 1:01:00 – 1:21:00
The Generational Shift Toward Prenups and Performative Relationships
Sexton notes a sharp rise in prenups among younger couples and contrasts this pragmatic trend with a culture obsessed with performing happiness online. He describes seeing ‘perfect’ Instagram couples fighting brutal divorces behind the scenes.
- •Prenup usage among people in their 20s and early 30s is, in his experience, roughly five times higher than 10–25 years ago.
- •Younger generations seem more willing to treat relationships pragmatically, at least around finances.
- •Social media encourages ‘hashtag blessed’ facades even while relationships rot internally.
- •He worries about people judging their adequate relationships against fabricated online ‘relationship goals’.
- •The same couples publicly denying rumors of trouble soon announce ‘amicable’ splits, exposing the performance.
- 1:21:00 – 1:34:00
Sex, Comparison, and the Death Spiral of Resentment
The conversation zeroes in on sex: how much is ‘enough’, how it functions as the glue of romantic relationships, and how sexual decline often signals deeper problems. Sexton describes common blame spirals where sex, kindness, and respect all erode together.
- •Sex distinguishes a spouse from a roommate; without it, marriage is essentially a co‑living arrangement.
- •Most people compare their sex lives either to their early ‘honeymoon’ phase or to imagined norms, not to real couples.
- •He hears chains like: ‘I cheated because she stopped sleeping with me’ / ‘I stopped because he wasn’t kind’ / ‘I’m not kind because she criticizes me.’
- •He urges couples to treat sexual changes as early warning signs and talk before the spiral becomes terminal.
- •His core prescription: pay attention to what you and your partner are feeling, then actually say it.
- 1:34:00 – 2:03:00
Preventative Maintenance, Conflict Habits, and Small Acts of Romance
Sexton explains ‘preventative maintenance’: deliberate, recurring efforts to maintain connection before crisis hits. He gives practical tools, from pre‑agreeing on how to argue, to leaving short love notes, to his “hit send now” framework for hard conversations.
- •The worst time to learn how your partner fights is in the middle of a fight; agree in advance on conflict rules (time‑outs vs solve‑now, etc.).
- •Tiny daily gestures—like a 10‑second handwritten note about why you appreciate your partner—have outsized impact over time.
- •He advocates his ‘hit send now’ email technique: mark the subject as such, share a hard truth calmly, and give your partner time to process.
- •Uncomfortable conversations traded now are investments in long‑term intimacy, much like exercise discomfort leads to health.
- •Culture normalizes mocking partners (‘ball and chain’, ‘happy wife, happy life’), which he sees as corrosive and unworthy to aspire to.
- 2:03:00 – 2:34:00
Sexlessness, Cheating, and Why Affairs Are Almost Never the Whole Story
Sexton shares how often sexlessness and infidelity show up in divorces, while cautioning against simplistic narratives where one affair ‘causes’ the divorce. He distinguishes men’s and women’s typical sexual complaints and recounts extreme double‑life cases.
- •Men more frequently complain of low or nonexistent sex; women more often want better quality and emotional connection.
- •He’s seen marriages go six years without sex; he questions both the partner refusing and the one tolerating it.
- •Affairs are common and often symptoms of deeper, long‑standing dissatisfaction rather than the initial cause of divorce.
- •He’s handled cases where a person ran two full families in parallel, each unaware of the other.
- •He stresses that everyone narrates themselves as the hero, so self‑reported stories about cheating are heavily biased.
- 2:34:00 – 3:08:00
Violence, Despair, and the Emotional Cost of Divorce Work
The tone darkens as Sexton recounts rare but extreme violence, including a client whose spouse tried to kill her, and multiple suicides connected to divorce. He reflects on the moral weight of being a ‘weapon’ in high‑conflict cases and how clients’ resilience often moves him to tears.
- •He’s seen only one attempted spousal murder in 25 years: a husband who stabbed and ran over his wife four times; she survived, he received life in prison.
- •Suicides on the opposing side have happened several times; he’s acutely aware his effective advocacy can help push desperate people over the edge.
- •He views himself as a weapon: protective in good hands, devastating in bad ones.
- •Cases that move him most often involve small but profound victories, like reuniting a man with his dog.
- •He cries more from witnessing beauty and resilience than from horror—clients’ strength and love frequently overwhelm him.
- 3:08:00 – 3:56:00
Dogs, Death, and Choosing to Love What You Will Lose
Using stories about his aging dog Kaba, his late mother, and a Buddhist mindfulness exercise, Sexton dives into impermanence and grief. He argues that remembering everything is temporary should radically change how we treat loved ones right now.
- •We’re always losing everything: every day your child is a new person; every relationship is marching toward separation by death or breakup.
- •Thich Nhat Hanh’s exercise: hug someone, imagine they’re dead and this is your last embrace, then realize they’re alive and still in your arms.
- •Putting down pets is the final act of love and responsibility; the pain of loss is inseparable from the joy they gave.
- •He admits it’s ‘insane to love anything’ given the inevitable heartbreak, but insists that the richness of love makes the pain worth it.
- •His dog Kaba, adopted after another dog’s death, “saved” him by proving his capacity to love again; he knows losing Kaba will devastate him yet would still choose the relationship.
- 3:56:00 – 4:32:00
Soulmates, Chapters, and Rethinking Relationship Success
Sexton critiques the soulmate myth as fertile ground for divorce and proposes seeing relationships as chapters in a long life, not permanent all‑or‑nothing bonds. He touches on gay marriage, open relationships, and tradition as ‘peer pressure from dead people.’
- •The soulmate concept fuels divorce: if ‘the one’ feels imperfect, people assume they chose wrong and look for a new soulmate.
- •He suggests judging relationships by growth and learning, not duration; a relationship can ‘succeed’ even if it ends in divorce.
- •Non‑heterosexual couples historically created their own rules due to exclusion; with marriage equality, they’re inheriting the same flawed institution.
- •He’s seen many open or ethically non‑monogamous arrangements collapse—but admits his sample is biased to failures.
- •Memorable line: “Tradition is peer pressure exerted by dead people” – questioning whether old rules fit contemporary realities.
- 4:32:00
Should We Get Married? Marriage vs. Love
In closing, Sexton separates the legal institution of marriage from the human experience of love. He describes his ideal of a public commitment and ongoing mutual accountability, while insisting that none of this requires government involvement, and answers a final question about his first experience of true love.
- •He’s pro‑love, cautious about marriage: marriage is a legal construct that can support or hinder love, but they are not synonymous.
- •A beautiful wedding vow, ring, and public accountability can be powerful symbols—but you can have that without a marriage license.
- •He describes how friends can support monogamy by actively discouraging cheating rather than enabling it.
- •His earliest sense of true love came from his father silently giving up pizza slices for him as a child—love as preferring another’s fulfillment to your own.
- •He reiterates that love’s impermanence is the very reason to act on it now: to hug more, appreciate more, and speak love while we can.
