40 Thoughts On Turning 40 | #287
February 10th, 2025: Greetings from Oaxaca. What a beautiful place. We took some fun pictures. and oh, and I turned 40.
If you’re stumbling upon this post from the web, hey! I’m Paul and I have built my life around writing things like this on the internet. If you enjoy this post, you might like my books The Pathless Path and Good Work.
I decided to riff on thoughts racing through my head over the past week.
I don’t have a good reflection on what it’s like to be 40 yet as I’m only a few days into this thing.
For now, these 40 thoughts will do:
On Change & Transformation
Blowing up my life and walking away from a successful career to embark on something much more uncertain was the most important decision in my 30s. It led to so many great things. At the time, it felt scary and foolish. Now I wish I had done it earlier.
You can reorient your life in a new direction quickly but the underlying rewriting of scripts and rewiring of your nervous system takes much longer than you would ever expect.
Following your “bliss” as Joseph Campbell has put it, is one of the most worthwhile things to do with your life. But I wouldn’t recommend it to anyone. Following what truly matters means you must walk away from parts of yourself that you love and parts of yourself that others love. This can be quite the roller coaster of emotions.
“The moment” when people take bold action is often a post hoc fabrication. Real change is slow and confusing, I want more people to know this so that they might feel permission to embrace the slow and more confusing journey of going after things that matter to them.
We unconsciously adopt narratives about the shape of our lives from previous generations, movie plots, and our peers. These “scripts” are often useful but tend to outlive their purpose as we age. Much of life is about figuring out which stories to discard as you age.
I have two regrets from my twenties: not living in another country and not taking more risks career-wise. Both would have pushed me out of my comfort zone. It seems that life will eventually push you out of your comfort zone whether you want it or not, so you might as well do it intentionally as early as possible.
I’ve never looked back and regretted being more adventurous with my life. Assuming this is true still now it means I can probably be more adventurous than I feel comfortable with right now too.
There are many rules worth paying attention to but many more are negotiable. We live in weird times and thriving in life likely requires weird approaches. If you aren’t shaking things up in random ways, you are missing out.
On Work
The desire to escape work is pervasive and keeps far too many stuck in less-than-ideal situations. People dream of one day becoming financially free. This is a mistake. You can’t escape work, you can only transcend it, something that becomes obvious upon leaving employment. Once I realized there was no escape, I could soften into the more human impulses to create, contribute, and be useful. This seems to be universal across people and time. Can this make you enough money though? I can’t promise that.
Finding your “good work,” the work that feels satisfying at the moment and satisfying upon reflection, can take years to find. But once you find it, you’ll be happy you never gave up.
Relatedly, the 14 months I spent writing my first book was the most satisfying work experience of my life. If that is the only thing of note I create for the rest of my life, it will have been worth it. The combination of intense challenge, creative work, and doing something I cared about was a perfect trifecta. It made the ten years I made making PowerPoint slides seem incredibly silly.
A “good job” can still be bad work. It’s easy to confuse a life that makes sense on paper with one that fills your heart and soul.
More people should try self-employment or freelancing for at least a year of their adult life. Having to make money “on your own,” and understanding how to be productive and motivated without a boss and other subtle coercive forces is immensely valuable. They also give you “eff you” courage, being able to walk away or dismiss any absurdity at work if you return to such an environment in the future.
Time for tinkering, following my curiosity, and reading about things that interest me can feel like “wasting” time but these periods tend to lead to interesting opportunities. This is because it's a way of getting in the flow with my nature and optimizing for energy first. This ends up being a great hack for avoiding starting things you’ll want to quit later.
Burning out happens faster when working for yourself because there are no limits on how much work you can do. This can be a hidden positive because you’ll waste fewer years doing work you ultimately don’t care about. In a more formal job, you can spend years, if not decades doing things you don’t care about. The limits on hours worked and hidden camaraderie of others disengaged with their work can convince you this state is normal, keeping you in a state of low-grade burnout without ever really burning out for a long time.
Money & Success
Attaining impressive achievements feels great and I wish people would stop pretending otherwise. But this is not the problem with such achievements. The problem is that you’ll get addicted to the feeling and will be surrounded by other addicts too. As you grow older and people opt out of this kind of path, it will be hard to see how this chase shaped everything around you.
Defining success on your own terms will create tension with those around you who don’t value the same things. It is easier to succeed like those around you but more satisfying to make progress against your own secret mission over the long-term.
Having success early in life is a blessing and a curse. It can show you that many achievements leave you feeling empty and craving more. But if you move away from this kind of path, you will see your peers achieve things you know you were capable of. It takes a lot of inner work to deal with this.
Having an impressive job or career is the easiest way to run from both your inner world and outer world responsibilities while still being seen as a respectable adult.
Money is one of the most powerful forces in the world. Never underestimate its role in shaping all of your decisions as well as everyone around you.
Making less after making a high income is a cheat code for figuring out what you value. When I went from making six figures to $30k after quitting my job, I saw how little of my previous spending was on things I valued. I knew this, but seeing my bank account shrink meant I couldn’t bullshit myself anymore.
I spent too little when young and took too few risks. If that was true then, it’s probably true now. If you are good at saving money when 23 you are probably still good at it at 40. Fears can protect us, but they can also confine us.
Money fears are the home of the deepest anxieties of life: dying, belonging, being loved, and being accepted. The happiest people I know have decided to tango with these fears directly. The upside to being able to exist with your fear, uncertainty, and discomfort and not needing to make it go away is the ultimate path to freedom
On Relationships
I’ve always been fascinated by relationship advice that married people give because it was never useful. “Communicate,” people would say. Sounds great. Five years into a happy marriage I understand why it's hard to give advice on relationships. Everything is unique to the little world that you build with this person. So perhaps the best advice is to find someone who you are excited to world-build with.
Meeting Angie felt lucky and I don’t know what to tell people still searching for someone other than “don’t give up.” While single from 27 to 34 I was frustrated, confused, and full of app disappointment. Then I met someone who was perfect and my life changed in an instant. I’m glad I never gave up because the upsides to a good relationship are so high.
Marrying someone from another country adds permanent tension to a relationship. In my observation, a failure mode in this kind of setup is when one person tries to “solve” this discomfort by defaulting to one country's way of living, the more familiar default path. For me, the bigger upside seems to be embracing this tension and committing to never being able to perfectly solve the challenges of families living on two sides of the planet, different foundational understandings of the world, and language and cultural differences. I’ve found that when I embrace these things with curiosity, it can lead to more interesting possibilities for life.
Becoming A Parent
I had some theories about parenting and how to raise kids. And then I had a child.
Becoming a father is the most humbling thing I have experienced. The first two years of this journey have forced me to admit “I don’t know and it’s okay” more times than I can count.
Anxiety about your kids is probably the most acceptable kind of worrying. This can be useful in protecting your kids from harm but it seems that a failure mode can be developing intense expectations for your kids (and worse, yourself). If I see everything my child does as an indication of being a good or bad parent, I’ll undermine the sense of connection that I hope to have with them in the first place. I like to remind myself that I’m the result of hundreds of generations of parents raising children in much more challenging environments. If my kids have a little too much screen time or junk food, everything will probably be fine.
I’ve never experienced more moments of joy and love than I have while spending time with my daughter. It’s probably the best way to reawaken your inner child. I’m still gradually re-learning how to play, not take myself seriously, and be silly. My daughter is my greatest teacher.
I suspect having a child toward the end of my 30s makes it a lot easier than if I became a dad in my 20s. Despite this, I am a bit sad that I’ll have “less time” with my children than a younger parent will.
The returns to having a great spouse with a young child are incredibly high. As a parent, you’ll face all sorts of questions, tips, advice, and even unintended criticism. People will have thoughts, and having someone you can laugh about it with later is priceless.
It’s been sad to see so many people in my generation opt out of becoming parents. I’m lucky that I grew up in a big extended family where having kids was “high status.” However, I understand where people are coming from. If I hadn’t met Angie I don’t know if I would be a parent now. I also think I could still be happy. But now that I have a child, I couldn’t imagine any other life path.
Parenting has added hard constraints to my life and I would be lying if I said I “had it all.” I’ve sacrificed a lot of time working over the past two years, and this has been hard. We don’t live in a culture where this is a normal thing to do, especially for dads. But I don’t regret this one bit. Every time I’ve felt the pull to “do more,” I try to think about the end of my life, realizing that I won’t regret this time one bit.
Happiness, Life & Misc…
There is a state of alignment you can reach in which magical things will start happening to you. I would have rolled my eyes at this ten years ago but now I have fun thinking about how to continue inviting this kind of serendipity into my life.
I’ve never seen a single person become happier by spending more time following politics or the news.
Reading history gives you more appreciation for the present by helping you see how consistently crazy humans have been at all times in history and how much more comfortable and safer the world has become.
Leisure and deep rest, the kind that recharges our soul is a practice, one that is incredibly hard to commit to in a world that celebrates, hustle, action, and achievements.
“Have you tried doing less on the problem?” is an underrated strategy to get unstuck. Most people try to do more.
Writing is one of the most powerful acts in the world. It’s never too late to start. But beware of its power in exposing you to what you truly desire.
hey
I’ve been having fun and hanging out online since 2015. I’ve somehow figured out how to hack a living doing things like this for more than seven years. Wild.
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"I’ve never seen a single person become happier by spending more time following politics or the news."
I remember seeing an interview with Prince. He started crying when he was talking about the violence we are exposed to through the news and tv in general. He said humans shouldn't be exposed to it. I *felt* that.
Excellent reflections my friend. Obviously you know I love this point you made about living in alignment and inviting serendipity:
"There is a state of alignment you can reach in which magical things will start happening to you. I would have rolled my eyes at this ten years ago but now I have fun thinking about how to continue inviting this kind of serendipity into my life."
Reminds me of this great Charles Bukowski quote - "The free soul is rare, but you know it when you see it – basically because you feel good when you’re with them."