The speaker shares a deeply personal journey through three divorces, reflecting on the complexities of love, compatibility, and timing in relationships. He candidly reveals that despite public scrutiny and personal pain, each divorce taught him invaluable lessons that transformed his understanding of love from youthful fantasy to mature realism. His first marriage was built on intellectual attraction and untested assumptions, which crumbled under the weight of grief and incompatible coping mechanisms. The second marriage fell into the rebound trap, where he chose a partner as a reaction to previous pain, leading to repeated patterns and eventual separation. The third relationship, with a fellow high achiever, introduced new challenges of balancing intense careers, public life scrutiny, and parenting, ending in an emotional separation rather than marriage. Through these experiences, he distinguishes love from compatibility, emphasizing that love alone is insufficient for a sustainable partnership. Compatibility encompasses shared values, aligned life philosophies, and similar approaches to stress and conflict. He stresses the importance of timing and emotional availability, warns against trying to change partners, and reframes divorce as an act of courage and love rather than failure. Ultimately, he advocates for honesty, self-awareness, and conscious choice in relationships, encouraging people to prioritize compatibility and mutual growth over mere attraction or societal expectations.
Before we start, I want to know where you’re listening from. Drop your country in the comments below. Maybe you’re going through a separation right now, or you’re in a relationship that feels like it’s falling apart, or you’re single and wondering if you’ll ever figure this whole love thing out. Maybe you’re divorced and people look at you like you failed. It’s something fundamental. This conversation is for you. I’m going to tell you something most successful
people never admit. I’ve been divorced three times. three times in the public eye, where every failure becomes a headline, where every personal struggle becomes entertainment for strangers. And you know what? Each divorce taught me something about love that I couldn’t have learned any other way. Each ending became a beginning. Each failure became a foundation for understanding what real love actually looks like. This isn’t going to be comfortable. I’m going to tell you things about relationships that
most people spend their entire lives avoiding. But by the end of this conversation, you’re going to understand why divorce isn’t always failure. Sometimes it’s clarity. Sometimes it’s courage. Sometimes it’s the most loving thing you can do. So, let’s talk about love loss and what it really means to choose someone for the right reasons. The first marriage, building on fantasy, Justine and I met in college. Um, I was this awkward kid from South Africa trying to figure out how to fit into
Canadian university life. She was brilliant, a writer, confident in ways I wasn’t. I was attracted to her mind before anything else. But here’s the thing nobody tells you about young love. You don’t fall in love with a person. You fall in love with a projection. You see someone and your brain fills in all the gaps with fantasy. You think you know who they are, but really you know who you want them to be. Um, Justine and I were together for 8 years before we got married. 8 years. You’d think that
would be enough time to really know someone, to understand if you’re compatible, to work through the major issues. But compatibility isn’t about how well you get along when life is easy. It’s about how you handle stress together, how you grieve together, how you grow together. And we never really tested those things until it was too late. When we got married in 2000, I thought love meant having someone who understood your ambitions, who supported your dreams, who could match your intellectual energy. I thought if we
could talk for hours about books and ideas in the future, we could handle anything life threw at us. I was wrong. The first real test came with loss. We lost our son Nevada to Sids when he was just 10 weeks old. And instead of bringing us together, it revealed how fundamentally different we were in processing pain. Justine needed to talk about her grief, to process it with others, to feel it fully and openly. I needed to channel mine into action, into building something that would prevent other families from experiencing what we
had. Neither approach was wrong, but they were incompatible. While she was trying to heal through connection, I was trying to heal through creation. While she needed presence, I was giving productivity. While she wanted to process the past, I was racing toward the future. We had five more children together through IVF. But the fundamental disconnect remained. We were two people who loved each other, but couldn’t figure out how to grieve together, how to support each other’s different ways of processing trauma. The
divorce in 2008 was devastating, but it was also honest. We had built our marriage on the fantasy that love conquers all. That if you care about someone enough, you can bridge any gap. But some gaps aren’t meant to be bridged. Some differences aren’t meant to be overcome. The lesson from my first divorce, love isn’t enough. Compatibility matters. Shared values matter. Similar approaches to life’s challenges matter. You can love someone deeply and still not be able to build a life with them.
The second marriage, the rebound trap. 6 weeks after my divorce from Justine was finalized, I met Tula Riley. 6 weeks. Looking back, that should have been a red flag the size of Texas. Tula was everything. Justine wasn’t where Justine was serious and intellectual. Tula was playful and artistic. where Justine was American and grounded, Tula was British and whimsical. Where my first marriage had been heavy with shared trauma, this felt light and effortless. I thought I had learned from my mistakes. I thought I was choosing
differently this time. But I wasn’t choosing at all. I was reacting. I was running from the pain of my first divorce straight into the arms of someone who represented everything that relationship wasn’t. That’s the rebound trap. You don’t choose your next partner based on who they are. You choose them based on who they’re not. You’re so focused on avoiding the problems of your last relationship that you don’t pay attention to what new problems you’re creating. Tula and I got married in
- The wedding was beautiful. The honeymoon was perfect. And for a few months, I thought I had figured it out. This was what love was supposed to feel like. Easy, joyful, uncomplicated. But easy isn’t sustainable when you’re building companies that require 80our weeks. Joyful becomes difficult when you’re dealing with the stress of near bankruptcy. Uncomplicated turns complicated when two people have fundamentally different relationships with ambition and work. Tula wanted a husband who was present, who prioritized
a relationship, who could separate work life from personal life. She wanted romantic dinners and weekend getaways and the kind of attention that that makes you feel like the center of someone’s universe. I wanted a partner who understood that the work I was doing wasn’t just a job, it was a mission. I wanted someone who could handle the intensity, the unpredictability, the fact that sometimes saving humanity has to come before date night. Again, neither of us was wrong, but we were wrong for each other. The first divorce
from Talot happened in 2012. But here’s where it gets embarrassing. We got remarried in 2013. Because when you’re not dealing with the root issues, when you’re not addressing the fundamental incompatibilities, you convince yourself that maybe you just needed a break. Maybe time apart will fix everything. It doesn’t. The same problems that broke you up the first time are still there, except now they’re worse because you’ve added the stress of having already failed once. You’re
trying to prove that your love is strong enough to overcome anything, but you’re just repeating the same patterns with more desperation. We divorced again in 2016, final this time. The lesson from my second marriage and remarage, don’t choose someone because they’re different from your ex. Choose them because they’re right for your actual life, not the life you wish you had. And never ever try to fix a broken relationship by recreating it. The third marriage, the success trap. By 2018, I had learned a
lot about what didn’t work in relationships. I was older, more self-aware, more successful. Tesla was thriving. SpaceX was launching rockets regularly. And I felt like I had my professional life figured out. I thought success would make love easier. I thought financial security would eliminate the stress that had contributed to my previous relationship failures. I thought being clear about my priorities and my mission would help me find someone who truly understood what they were signing up for. Enter Grimes,
Clara Boucher, an artist, a creative genius, someone who understood the pressure of public life and the demands of creative work. someone who had her own career, her own identity, her own relationship with intensity and perfectionism. On paper, it looked perfect. Two successful people who understood each other’s worlds, who could support each other’s ambitions while maintaining their own independence. But here’s what I learned. Success doesn’t eliminate relationship challenges. It just changes them. When
you’re both high achievers, both used to being in control, both accustomed to having your vision went out, how do you build something together? Um, how do you compromise without feeling like you’re diminishing yourself when you’re both in the public eye? When every argument might end up in tabloids? When every moment of happiness gets scrutinized by strangers? How do you maintain intimacy? How do you be real with each other when the whole world is watching? when you’re both busy changing the world in your own
fields herb music my companies what how do you create space for a relationship how do you prioritize each other when you’re both fighting for time that doesn’t exist and then we had our son xa0 and everything became more complex suddenly it wasn’t just about whether we could make a relationship work it was about whether we could be good co-parents while potentially being incompatible compatible partners. Claire and I never got married, but we went through the emotional equivalent of a
divorce. The end of our romantic relationship in 2021 was different from my previous breakups because we both approached it with more maturity, more honesty about what we needed and what we couldn’t give each other. The lesson from my third relationship, compatibility isn’t just about understanding each other’s work or sharing similar success levels. It’s about having compatible visions for how you want to structure your daily life, how you want to handle conflict, how you want to balance individual ambition with
shared goals. What these divorces taught me about love. After three major relationship endings, I’ve learned things about love that I never could have understood from a successful first marriage. Things that most people spend their whole lives avoiding because they’re too painful to face. Lesson one, love and compatibility are different things. Um, you can love someone’s mind, their spirit, their ambition, their creativity, and still not be able to live with them. Love is about appreciating who someone is.
Compatibility is about whether who you are and who they are can function together in the real world. Most people think love should be enough. It’s not. You also need shared values, compatible life rhythms, similar approaches to conflict resolution, and aligned visions for what a relationship should look like. Lesson two, timing matters more than people want to admit. I married Justine when we were both figuring out who we were as adults. I rushed into marriage with Tallula when I was rebounding from loss. I tried to build
something with Clare when we were both at peaks of our careers that demanded everything we had. The right person at the wrong time is still the wrong person. Not because they’re flawed, but because relationships require bandwidth, attention, and emotional availability that you might not have during certain uh phases of your life. Lesson three, you can’t love someone into being different. Every divorce taught me this lesson in a different way. You can’t love Justine into grieving the way you
grieve. You can’t love Tula into being comfortable with your work intensity. You can’t love Claire into wanting the same daily life structure you want. When you find yourself constantly trying to convince someone to want what you want, to value what you value, to approach life the way you approach life, you’re not in a relationship. You’re in a renovation project. And people aren’t houses. They don’t get better when you fix them. Lesson four, divorce can be an act of love. This is the hardest lesson,
but maybe the most important one. Sometimes the most loving thing you can do is admit that you’re not right for each other and set each other free to find someone who is staying in a relationship that doesn’t work isn’t noble. It’s not honorable. It’s not proof that you’re committed. It’s just two people slowly diminishing each other instead of admitting that love alone isn’t enough to bridge fundamental incompatibilities. Um, each of my divorces was painful, but
they were also honest. There were admissions that we had tried our best and it wasn’t working and that continuing to try would only hurt both of us more. Lesson five. Multiple relationship endings don’t make you a failure. Society treats divorce like evidence that you’re bad at relationships. Three divorces must mean you’re really bad at them, right? Wrong. Multiple relationship endings can mean you’re good at recognizing when something isn’t working and brave enough to do something about it. They can mean
you’re not willing to settle for mediocrity just to avoid the discomfort of starting over. They can mean you understand that finding the right person is worth the risk of being wrong several times first. The deeper patterns, looking back at all three relationships, I can see patterns that I couldn’t see while I was in them. Patterns that might help you avoid some of the same mistakes. Pattern one, I kept choosing based on attraction rather than compatibility. In each case, I was drawn to something about the person, Justine’s
intellect, Tula’s lightness, Cla’s creativity. But attraction isn’t a strategy for building a life together. What I should have been asking, do we handle stress the same way? Do we want the same things from day-to-day life? Do we approach problems similarly? Do we have compatible energy levels and social needs? Pattern two, I underestimated the importance of shared life philosophy. I thought if we loved each other and respected each other’s goals, we could figure out the details later. But the
details are everything. How much time do you spend together versus apart? How do you handle money? How do you make decisions? How do you deal with extended family? How do you approach parenting? These aren’t small details. They’re the foundation of your daily experience together. Pattern three, I kept trying to fit relationships around my work instead of integrating them in each relationship. I approached it like here’s my mission to change the world and here’s this other important thing
called love that I need to fit into the margins. But love isn’t something you fit into margins. It’s something you build into the structure. And if you can’t build it into the structure, if your life mission is incompatible with deep partnership, then you need to either change your mission or accept that you’re not designed for traditional relationships. Pattern four, I confused intensity with sustainability. All three relationships had incredible highs. The conversations with Justine, the romance
with Tula, the creative connection with Claire. But intensity isn’t the same as sustainability. Real love isn’t a series of peak experiences. It’s a system that works during ordinary Tuesday afternoons. It’s something that functions when both people are tired, stressed, and dealing with mundane problems. What I know about love now. At 52, after three divorces, and multiple other relationships, here’s what I understand about love that I didn’t understand at 30. Real love is
quiet. It’s not dramatic highs and lows. It’s not constant intensity. It’s not needing to prove anything to anyone. Real love is two people who genuinely enjoy each other’s company, who handle problems as a team, who want similar things from life and are willing to work together to build them. Real love is based on choice, not feeling. Feelings change. Chemistry fades. The person who makes your heart race at 30 might bore you at 40. But if you choose someone based on shared values, compatible
goals, and mutual respect, that foundation can support a lifetime. Real love requires two complete people. You can’t use a relationship to fix what’s broken in you. You can’t expect someone else to provide what you’re not providing for yourself. You have to come to love whole, not looking to be completed. Uh, real love accepts trade-offs. Every choice you make in love is a trade-off. If you choose someone stable, you might trade away some excitement. If you choose someone creative, you
might trade away some predictability. The question isn’t whether there are trade-offs. It’s whether you’re making them consciously and you’re happy with what you’re getting in exchange. Real love is rare. Most relationships are compromises. Most marriages are two people who decided they’d rather be together than alone, but who aren’t actually that compatible. real love. The kind where you genuinely prefer each other’s company to anyone else’s. Where you’re better together than apart, where
you’re building something neither of you could build alone. That’s rare. And maybe that’s okay. Maybe it’s better to have three relationships that taught you something than one mediocre marriage that teaches you nothing. The questions you should ask. If you’re in a relationship now or thinking about getting into one, here are the questions my divorce has taught me to ask about compatibility. Do we handle stress the same way? Do we have similar energy levels and social needs? Do we want the same amount of
together time versus individual time? Do we approach conflict resolution similarly? Do we have compatible relationships with money, work, and ambition? About values? Do we agree on how to raise children? Do we have similar definitions of loyalty, honesty, and commitment? Do we want the same things from family life and social life? Do we have compatible spiritual or philosophical beliefs about vision? Where do we see ourselves in 10 years? And are those visions compatible? What does a successful relationship look like
to each of us? How do we each define love, partnership, and marriage? What are we each willing to sacrifice for this relationship? And what aren’t we about timing? Do we both have the emotional bandwidth for a serious relationship right now? Are we both in a place in our lives where we can prioritize partnership? Are we choosing each other or are we running from something else? The hardest truth. Here’s the hardest truth I’ve learned. Some people aren’t designed for traditional relationships. Not because
there’s something wrong with them, but because their life mission, their personality, their way of moving through the world doesn’t fit into conventional partnership structures. I might be one of those people. My work isn’t just what I do for money. It’s my calling, my identity, my contribution to humanity’s future. It requires 80our weeks, constant travel, enormous stress, and total focus. It’s not compatible with romantic dinners and weekend getaways and the kind of daily attention that
makes someone feel cherished. That doesn’t make me a bad person, but it might make me a bad partner for someone who wants a traditional relationship. And maybe that’s okay. Maybe it’s better to be honest about who you are and what you can offer than to keep trying to force yourself into shapes that don’t fit. Maybe some people are meant to love humanity more than they love individuals. Maybe some people are meant to change the world instead of building a perfect marriage. Maybe the goal isn’t
to find someone who completes you, but to become complete enough that you can love without needing, give without depleting yourself, and choose based on what you want to build together rather than what you’re afraid to face alone. What this means for you, if you’re divorced, don’t let anyone make you feel like you failed. Divorce can be courage. It can be clarity. It can be choosing growth over stagnation, truth over comfort, possibility over security. If you’re in a relationship that isn’t
working, don’t stay just because leaving feels hard. Hard isn’t the same as wrong. Sometimes the the most loving thing you can do is admit that you’re not right for each other and set each other free. If you’re single and people are pressuring you to find someone, remember that being alone is better than being with the wrong person. Use your single time to become the kind of person who attracts the kind of love you actually want. If you’re looking for love, look for compatibility. As much as
chemistry, look for someone whose way of living fits with yours, whose approach to problems complements yours, whose vision for the future aligns with yours. And remember, love isn’t about finding someone who meets all your needs. It’s about finding someone whose needs you enjoy meeting, whose growth you want to support, whose presence makes you a better version of yourself. The final lesson, three divorces taught me that love isn’t about finding the perfect person. It’s about becoming the kind of
person who can love well, who can be honest about their needs, clear about their boundaries, generous with their attention, and brave enough to leave when staying would hurt everyone involved. My divorces weren’t failures. They were education. Expensive education, painful education, public education, but education nonetheless. And now at 52, I understand love in a way I never could have at 30. I know what I need, what I can offer, and what I’m not willing to compromise on. I know that being alone is better
than being wrong together. I know that love is a choice you make every day, not a feeling that happens to you. Whether I find that rare real love again remains to be seen, but I’m no longer willing to settle for anything less. And neither should you. Share this with someone who needs to hear that divorce isn’t always failure. Sometimes it’s wisdom. Subscribe if these conversations help you think differently about love and relationships. And remember, your relationship status doesn’t define your
worth. Your willingness to be honest about what you need and brave enough to pursue it. That’s what defines your character. Love well, choose wisely, and don’t be afraid to start over if you need to. Three divorces taught me that sometimes the most loving thing you can do is let go, and sometimes the bravest thing you can do is try again.
