UFYB 227: THE MOST IMPORTANT QUESTION YOU CAN ASK YOURSELF ABOUT YOUR LIFE

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, often I really plan my podcasts out ahead of time of course. But I am actually recording this one just spur of the moment because I feel so compelled to share this with you. 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 whose 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. So, I recommend that you ask yourself that today and I’ll talk to you next week.

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