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I have a question. What do you do once you've already reached the summit? What then?
I'm 50yrs old. Spent most of my adult life working hard to earn financial freedom, often 6 or 7 days a week (I made sure to have fun along the way, though). But I recently achieved my financial target and don't really need to work anymore. Not super rich, but enough to not need to worry anymore. The problem is, I've been so focused on hitting that goal that, now that I've hit it, I don't know what to do with myself. It's true what they say, "be careful what you wish for"
Originally I had thought I would just spend more time with friends and travel. But, it's clear now that, at this age, most friends are busy with kids, career, and life. I've thought about starting a new business, seems a waste to not use all of the skills/experience/network that I've accumulated, plus it will be more social (but I start to think of Brookes from Shawshank Redemption. He became "institutionalized". He was in the prison (no doubt a metaphor for normal work/life) but he couldn't handle being "retired" from the prison and actually wanted to go back in. Just like the guy who wanted to be put back in the matrix, even though he knew it was an illusion)
The main problem is that, being so focused on achieving financial independence for so long and putting all I had into it and the sacrifices it takes, now that I've hit it, I feel emotionally drained and unable to get the drive to do any of those side projects I told myself I would do one day, or to start a new business.
So, that's the question. Once you've worked so hard and hit your financial freedom (or primary goal), what then? How to refocus or find the next stage of fulfilment (especially when most people you expected to be around aren't around or available)?
My almost 5yo has been sneaking into my room at night to snuggle with me. Sometimes it’s just a little before dawn, and sometimes it’s several times at all hours of the night. If I’m conscious enough I’ll tell her to go back to bed or even walk her back myself, but often I will wake feeling completely beat up because she’s 45lbs and clambering over me all night. We’ve had lots of talks about needing rest (both of us!) She isn’t having nightmares or terrors or sleepwalking. She just says I’m more comfortable than her bed. Is this a normal developmental stage, like one last game of being a toddler before she moves on to little kid-hood? Or is this a sign of distress of some kind? Other possibly pertinent info: She is generally very clingy (I don’t like that word but don’t know another to describe how she likes to “stick with me” a lot of the time) but can still happily play by herself or with her sister and friends as long as she knows I’m nearby. She doesn’t like people to leave the house without a goodbye “ritual” (she makes pretend snacks to give to the person leaving) but with me it is the most heightened- she will often cry. She has never been in daycare and I breastfed her until she was three (she protested and still tries to nibble me every now and then.) Stable home, loves her daddy and sister. Guidance please!
hi Stef, whenever politically charged topics come up in conversation with people I don’t know well (those at work, school, etc) I get quite anxious. I have a very good grasp of the issues and can argue well, however I still get very nervous and feel very stressed out. What do you think is going on here?
what to do about in-laws that are well off and insist on purchasing gifts for you? What is the appropriate level of receiving gifts? I feel compelled to earn what I keep in life and am uneasy about simply receiving things just because I happen to marry the right woman. The father in-law and I don’t see eye to eye on a lot of issues (manly socialism vs capitalism. Though I realize it’s a false dichotomy) and if I were to accept any gifts, would it mean I could no longer express myself due to our different world views? Is this a subtle form of manipulation?
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Wednesday Night Live 18 June 2025
In this episode, we examine the dynamics of conversation and the importance of honesty in relationships. I critique a recent discussion between Tucker Carlson and Ted Cruz, highlighting the challenges of maintaining reason in political discourse. Through audience questions, I reflect on accountability in politics and personal responsibility, sharing my own struggles with these concepts. We also explore the impact of artificial intelligence on creativity and the necessity of honest communication. I justify my return to X (formerly Twitter) and encourage listeners to consider their experiences with truth in relationships. Ultimately, this episode emphasizes the vital role of honesty in sustaining connections.
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In this episode, I explore the complexities of morality and ethics with a guest, reflecting on societal behavior changes since 2016. We discuss the relationship between tyranny and technology, stressing the importance of individual liberty and personal accountability. Our conversation covers individualism versus collectivism, the need for accessible ethical principles, and the potential of innovations like Bitcoin to enhance freedom. This dialogue invites listeners to thoughtfully engage with their moral beliefs in a transforming technological landscape.
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