Many sociological studies show that, at the end of life, there’s no mystery about what’s real and important. Whether it’s professionally or personally, most of us want to contribute to the world in a way that’s meaningful to us. This is what remains when we reach the end.

There’s this split consciousness we have between getting caught up in the daily details of our lives while also trying to maintain a long-term perspective about ourselves, the world, and our contribution to it. We want to be in community and help alleviate suffering, but we also deal with our own humanness every day. 

On this Greatest Hits episode, I’m sharing my thoughts on how I navigate holding both a commitment to acknowledging my life experience while not getting lost in the day-to-day minutia. I’m offering the most important question you can ask yourself about your life, and how this is a powerful tool that keeps you oriented toward the kind of life you want to live. 

Joining The Clutch is easier than ever! Text your email address to 347-934-8861 and we will text you right back with a link to all the information you need. Hope to see you inside The Clutch soon!

What You’ll Learn From This Episode:

  • What the most important question you can ask yourself about your life is. 
  • How this question puts you in touch with what truly matters. 
  • Prompts to help you orient your values, decisions, and the way you live your life. 

Listen to the Full Episode:

Featured on the Show:

Full Episode Transcript:

Welcome to Unf*ck Your Brain, the only podcast that teaches you how to use psychology, feminism, and coaching, to rewire your brain and get what you want in life. And now here’s your host, Harvard Law School grad, feminist rockstar, and master coach, Kara Loewentheil.

Hello my chickens. So last night I was watching a movie called The Swimmers on Netflix and it is about this incredible kind of true story of two sisters who were swimmers who were refugees from Syria, who left Syria and traveled in very dangerous ways to Germany. And then eventually their whole family was able to get out and to escape Syria. But it’s just an incredibly powerful film about their journey and their swimming careers as well as the complexity of the human and refugee experience.

And it was such a fascinating thing to watch my brain because obviously moves are created in such a way as to be emotionally moving and there’s also just inherent emotionality to learning about and thinking about the experience of being a refugee or of any kind of really life disrupting challenging hard experience that humans may have. And watching my brain it was like this sort of split screen in which in one half of my brain I saw that sort of that experience you have when you just are like, “Holy shit, none of my problems are really problems.”

I mean we all know on a sort of, whether you call it spiritual or kind of thought work or whatever level we know that what we decide are our problems are problems. And sometimes other people would all agree with us and sometimes they wouldn’t. But there is a sort of just that perspective that you get from seeing an experience that this for many of us, not everybody, there are people listening to this podcast who have been through this kind of thing.

But certainly I have never let’s just say, I have never had to be a refugee. I have never had to cross an ocean in an inflatable boat hoping I don’t drown to get to the next shore. I have never gone through many of the things that these people went through. And I could see the sort of one side of my brain just being like, wow, that was a dose of needed perspective. Not that, the movie is in no way kind of like, I don’t what you would call it, suffering porn sort of. It’s actually a beautiful film. And the purpose of it isn’t to make people with privilege feel better about their lives.

The movie itself is a work of art. It’s well worth watching. But it’s impossible to watch the movie for me and not in addition to appreciating it as a work of art, also have that perspective check. So I had that happening in one half of my brain which was the things that I was worried about this morning just really don’t seem that important right now in light of my reminder of how unbelievably fortunate I am. Those of you who have been listening to me for a long time know that I don’t believe in gratitude spackling.

I don’t believe in Olympics of suffering, emotions happen inside your body and they are hard for you if they’re in your body regardless of the cause. And at the same time it’s a beautiful gift to me to be able to get my head out of my own ass, look at the world and see how fortunate I am. And for me it really renews my commitment to giving back to the world. So I’m having that happening on one side of my brain.

And on the other side of my brain I just sort of know that my perspective isn’t transient but my emotional connection to it is transient because I also just live in my daily life where I have a bunch of stuff happening in my own life that I am trying to figure out. And I think that this is a long way of getting to this point but I think a worthwhile journey.

But what I’m trying to describe is the split consciousness that most of us have, or at least a good portion of us have between being all up in the daily details of our lives and trying to maintain a big picture or long term perspective about ourselves and the world and our contribution to it. Now, I think there are people on either extreme also. Some people just don’t ever give a fuck or think about anything that’s happening in the world or in history or in a historical perspective or in a global perspective or anything beyond themselves.

Some people sort of become so caught up in and obsessed with that that it becomes their life. So there’s sort of both extremes. There’s people who give away all their possessions including their kidneys to strangers. And there’s people who don’t ever think about other people. Most of us are in the middle trying to be good citizens of the world, not citizens in a nationalistic political way but just be a participant in our communities and the world.

We want to contribute and be of service and help the world. We want to try to help alleviate human suffering. And we are also stuck in the bullshit of our own lives, some of which is bullshit, some of which is extremely serious for us. And we are also dealing with our own just suffering from being a human which is part of the human experience. So this episode today is an episode that I recorded a while ago but one that I think really speaks to this question and it’s one of our most listened to episodes precisely because I think it is so important.

And I think for me the way that I try to navigate this holding both of these things, this sort of commitment to not ignoring or trivializing my own life and my own experience and my own challenges and my own goals because this is my life and I’m the person in it and I want to make it matter.

And also not becoming solecistic and not only thinking – it’s not even about solecism, it’s really more not getting lost in the day-to-day and maintaining a big picture vision for my life and how I’m going to be in this world and how I’m going to interact with and affect people around me. Whether that’s just my family and friends or on a global scale, for me I’m somebody with a big picture mission. You don’t have to be to use these tools. One of the ways I do that is to think about the question that I talk about in this episode which I call the most important question you can ask yourself about your life.

And this is a sort of a question that you can use any time you need to zoom out. That’s sort of what that movie prompted for me was just a moment in which I zoomed out to sort of see what mattered and see where I was. And so the question that I talk about in this episode is a question you can use to zoom out at any moment. It’s not about seeing the enormity of suffering in the world and being disempowered. It’s not about guilting yourself for any privilege that you have, neither of those are useful. Those don’t help the world at all and they’re not fun for you.

It’s about zooming out to get a bigger picture so that you know when you’re making decisions, when you are taking actions, when you are choosing how you spend your time that you are doing it from a place that takes a step back from the day-to-day. So with that introduction, I invite you to listen to this episode and consider this question and return to it as many times as you need.


So, I just watched the Netflix movie, Don’t Look Up, which is meant to be satire more or less. Was an amazing star studded cast. I was just weeping at the end and not out of sort of depression at the bleakness and trueness of the satire but because it made me think about what I think is the most important question you can ever, ever ask yourself.

In some ways this is all of coaching and philosophy rolled into one and it is the most direct line to the part of you that truly knows what matters and truly knows your own kind of essential worth, and goodness, and capacity for humanity. And this is something I think about all the time and that is when I am trying to decide anything and I think there are decisions that we know are decisions like should I take this big risk with my job? Should I try to fall in love again? Should I buy this house or whatever?

But there are so many little decisions on a day-to-day basis especially in our relationships I think that we don’t even know are decisions. We don’t even realize that in the moment we’re deciding whether to offer something to someone, whether to connect with someone, whether to choose love, whether to choose forgiveness, whether to give someone the benefit of the doubt, whether to turn towards them or away from them. Or decisions with our own selves, whether to turn towards what we truly want and believe or away from it and turn our face towards the illusory approval of other people.

And this is a question I always ask myself is will I regret this when I’m dying? And even asking that question feels so emotional to me. I might cry recording this podcast because I know it sounds like a depressing question but I actually think it is. It’s the deepest most important question you can ask yourself because especially if you are doing thought work and trying to connect to what you truly believe and what you truly value. And you are trying to live the kind of life that matters to you.

That question is going to put you so in touch with what truly does matter. When we talk about the coaching exercise of trying to communicate with your future self. It’s not psychic, we don’t really know what your future self is like. Who knows? The world could go through an apocalyptic event and future you is radioactive. We have no idea who the future you really is. But what we are really connecting to is the part of you and for some people they would feel that’s their spirit or their soul. For some people it’s their mind, a part of their prefrontal cortex, whatever it is.

It’s the part of you that can see beyond the ego, and the pride, and the small addictions of our lives, and the moments we are small in our ego, and the moments that we are in love with our own suffering. And the moments where we care more about what society thinks of us or other people think of us than we do about what our true longings, and values, and aspirations are. That knowledge, that power is already inside of you. That’s how we can access it. That’s how we can speak to your future self. It’s already in you.

And to me when I ask myself, what will I regret when I’m dying, on my deathbed if I make this decision, will I regret this? It gives me this long perspective on my life. And it shows me what is in alignment with my highest values, my deepest priorities, the kind of person I want to be, the kind of life that I want to live. I will never regret choosing to feel love for myself most of all, the choice that honors and loves me the most. I’m never going to regret feeling love for someone else.

And if your thought is immediately, but that about if it makes you do these things? Then we have episodes about how loving someone isn’t the same as doing any specific thing towards them. And I’m never going to regret trying to help and serve as many people as I can. I’m never going to regret failing because I really tried. There are so many things that I would regret if I were to get to the end of my life and look back and see that I had cared more for what other people thought of me than what I thought of myself.

If I were to look back and see that I had chosen what felt safe and comfortable over what I truly wanted. If I were to look back and see that I had turned away from love, turned away from loving the people in my life because I didn’t want to feel vulnerable, or I wanted to feel safe, or I wanted them to love me first or better. So, I think that when you can access this part of you that can imagine what will truly matter at the end, that is such a powerful tool to keep you oriented towards the kind of life you want to live.

And so, then we can look at the sociological studies which I’ve talked about on the podcast before. And they show people’s regrets are pretty consistent at the end of life. People regret working too much when their job was not something that they particularly cared about. Or even if they did, if there was some workaholism going where they were working compulsively out of a feeling of scarcity, and overwhelm, and ignoring the rest of their life. So, people regret working too much. People regret not spending enough time with their loved ones.

People regret not having told the truth about who they were or how they felt. People regret the things they left unsaid. I’m sure people regret some things they said, if they were said out of anger or cruelty. But we could even look at that and see there’s no mystery really about what’s important. It’s pretty consistent across people. It’s doing, whether it’s work or outside of your professional involvement, but it’s contributing to the world in a way that’s meaningful to you. It is spending time and connection on your loved ones. It’s telling people the truth about how you feel.

It’s being truthful about who you are and living the life that felt authentic to you. I think when we reach the end that’s what remains. And all the small pieces of us that are trying to conform, trying to be safe, trying to have the last word, trying to feel superior, trying to feel righteously indignant, trying to hold grudges. I think that fades away. And what’s real and important is what matters.

And so, I really want to encourage all of you as you are thinking about this coming year, and we’re still early in the year, as you are thinking about the decisions you make, as you are thinking about how you relate to the people in your life. Start asking yourself that question. Ask yourself that question as much as you can. I think that I have lived a life that allows me to feel in a way that probably a lot of people my age don’t which is that if I died of course there are things I want to experience left. I want to grow old with my partner. I want to meet my to be born nephews and nieces.

I want to go on epic trips. I want my book to be a bestseller. I want to reach every woman in the world with this work. I want to blow my own mind with what’s possible. I want to be an example to others. There’s so many things I want to do. But I would feel like I’ve done what I needed to do. I would feel like I had been who I really am and I had let people see who I really am, and I had lived a life that is in alignment with what I truly want. And I think that comes from asking myself that question all the time.

We, I think especially in contemporary America, we don’t have a good relationship with the idea with death, with the idea of the end of life. We have this culture that is really focused on eternal youth and sort of immortality. It’s like you’re supposed to be young until you can’t possibly fake it anymore and then you’re just supposed to disappear and never be heard from again. And we don’t have the social safety net and structure that allows a lot of people to stay intimately involved with their aging loved ones, to care for them in their home if they want to.

We don’t have a culture that sort of is in touch with our own mortality. In some ways that’s probably because of some good things like lifesaving medications and vaccines. We just have a lot less death all around us than people used to. Life expectancy is longer, child and mortality has plummeted in the last 150 years. So those are good things but it means that we are not really in touch with that part of life.

And so actually I had a custom ring made with a friend of mine who’s a jeweler and we made it in the style of what used to be called Momento Mori which was jewelry style that was meant to remind the wearer that life is short and that death is always coming. And that sounds macabre, but it’s actually meant to be inspirational to remind you to live your life the way that you want to. I mean historically probably it meant live a certain kind of Christian life but we get to reclaim the symbolism however we want.

And so, I had this ring made that is two, there’s what’s called a star sapphire and a spindle and then it’s a gold band that is engraved with lots of flowers. But then there is two little skulls hidden in it. And to me that is sort of my reminder that life is beautiful and life also is painful and it always ends in death. And so how can I let that reality not be something to fear and try to avoid, but something to welcome, not just as the conclusion to life as it has to be but as something that gives life its contrast and its meaning? Constraint is what gives meaning.

I’ve always thought, who would want to be immortal because then nothing really matters? You can redo everything a million times. You don’t have to make any choices. You don’t have to have any priorities. Death is the constraint that gives life the chance to be meaningful and to matter. So, what I recommend if this podcast resonated with you is that you start asking yourself that. It doesn’t always have to be in a moment of decision. You can ask it in a more general way. You can write about it.

If I were to find out that I had only six months to live, or three days to live, what would I think about the way I’ve lived my life? If I were to get that second chance, what would I change? What can I say I know I will not regret doing whenever that times comes? I think that is the single most important question you can ask yourself to help you orient your decisions, and your values, and the way you live your life.

It’s not about perfection. That’s why that long term view is so helpful I think. Because if I just say to you, well, what kind of person do you want to be? And you say, well, I just want to be someone whose always loving and kind, and always forgiving, and always whatever. That’s a perfectionist fantasy. Nobody does that. But when you think about it from the perspective of that deathbed moment or question, of course you’re not thinking well, I wish 35 years ago I hadn’t snapped at my partner in the supermarket checkout line. You don’t remember that shit at the end.

It’s an accumulation, it’s an overall orientation, an overall alignment. It’s an overall moving towards the kind of person you want to be, the kind of life you want to have even though of course there’s going to be moments along the way that aren’t in alignment with that, or where you aren’t able to be that person. So, it’s more effective than just asking yourself, who do I want to be because you can come up with a perfectionistic unrealistic answer to that question.

But when you think about it from the perspective of I’ve lived hopefully a long life, I’m looking back, what will I regret? What will I not regret? What will I feel was a life well lived? I think that’s the most important question any of us can ask ourselves.

If you’re loving what you’re learning in the podcast, you have got to come check out The Clutch. The Clutch is the podcast community for all things Unfuck Your Brain. It’s where you can get individual help applying the concepts to your own life.

It’s where you can learn new coaching tools not shared on the podcast that will blow your mind even more. And it’s where you can hang out and connect over all things thought work with other podcast chickens just like you and me. It’s my favorite place on earth and it will change your life, I guarantee it. Come join us at www.unfuckyourbrain.com/theclutch. That’s unfuckyourbrain.com/theclutch. I can’t wait to see you there.

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