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    <title>Taylor Jacobson — Articles</title>
    <link>https://taylorjacobson.org/</link>
    <description>Taylor Jacobson — Articles</description>
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    <lastBuildDate>Thu, 25 Jun 2026 14:30:14 GMT</lastBuildDate>
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      <title>Friends Newsletter — May 2026</title>
      <link>https://taylorjacobson.org/may-2026/</link>
      <guid isPermaLink="true">https://taylorjacobson.org/may-2026/</guid>
      <pubDate>Mon, 18 May 2026 12:48:16 GMT</pubDate>
      <description>In March , I gave myself permission to slow down my home search. Things came together quickly after that. I booked stays in Barcelona and Lisbon, and…</description>
      <content:encoded><![CDATA[<p>In <a href="/march-2026/">March</a>, I gave myself permission to slow down my home search. Things came together quickly after that.</p>
<p>I booked stays in Barcelona and Lisbon, and planned a US tour this summer. Then spring hit in Madrid. By the time I was scheduled to depart, I didn’t want to.</p>
<figure><img src="/cdn-cgi/image/width=800,quality=80,fit=scale-down,format=auto/_media/camphoto_1804928587.jpeg" srcset="/cdn-cgi/image/width=400,quality=80,fit=scale-down,format=auto/_media/camphoto_1804928587.jpeg 400w, /cdn-cgi/image/width=800,quality=80,fit=scale-down,format=auto/_media/camphoto_1804928587.jpeg 800w, /cdn-cgi/image/width=1200,quality=80,fit=scale-down,format=auto/_media/camphoto_1804928587.jpeg 1200w" sizes="(max-width: 700px) 100vw, 700px" alt="camphoto_1804928587" loading="lazy" decoding="async" style="max-width:100%;height:auto;display:block;" /><figcaption>Soaking up spring in Plaza Dos de Mayo, Madrid</figcaption></figure>
<p>The contrast — planning the trip, not wanting to go, and being excited to return — was exactly the data I needed to fully choose Madrid. Then, as though by divine affirmation, I found the perfect apartment within a week.</p>
<p>I&#39;ve been a master of forcing decisions and overriding intuition. Letting go and watching clarity arrive so fast was a poignant reminder of the power of non-forcing.</p>
<h3>🔹 Growing roots, finally</h3>
<p>For most of my adult life, I haven&#39;t been able to land. At first it was the wanderlust of a young man — an out-of-state school, a semester abroad, the India NGO chapter. </p>
<p>But over time a deeper pattern emerged: a yearning for something external to arrive and create a sense of home for me. I felt constantly compelled to keep moving, keep searching. </p>
<p>Until now. And I think it had to be this way; I needed the twists and turns, the working out of whatever kept me from really exhaling.</p>
<h3>🔹 The untold story of my health crisis</h3>
<p>Ending this search for home, finding a place to land, has created space to complete another process as well — putting the deeper, messier story of my health crisis into words.</p>
<p>Keeping this story private has been necessary, but also costly. It’s time to share.</p>
<p>It began on a normal-enough day in mid-June, 2020. I was watching a disturbing YouTube clip when my body erupted into uncontrollable sobbing. I had never experienced anything like it. </p>
<p>The following months were characterized by intense, debilitating dread. Picture the surge of panic you feel when you step in front of moving traffic — except constant, 24 hours per day, for <em>months</em>.</p>
<p>Within weeks at this stress level, I developed colitis (my gut was bleeding) and started losing hair and weight.</p>
<p>I told my best friend “I feel like I’m dying.” She thought I was being hyperbolic. My therapist assumed I was just struggling due to a recent breakup. I didn’t bother going to the doctor; I didn&#39;t want to be gaslit that this was a mental health issue, when I knew deep down that it wasn&#39;t.</p>
<p>This continued for <em>years</em>. I developed new symptoms — fibromyalgia, body tension, difficulty breathing, leaky gut, extreme chronic fatigue, and more. I tried dozens of treatments. None moved the needle.</p>
<p>Through it all, I had no way to relate to others. I had no real diagnosis. I looked healthy from the outside. Even my inner circle couldn’t understand. After all, I didn’t either.</p>
<p>Finally, in 2024-25 I got three critical diagnoses. </p>
<p>First, a scan of my airways revealed major breathing problems, likely caused by a bad orthodontic treatment when I was 11 years old. After reading my results, Michael Gelb, a leading specialist in New York, looked at me and said, “No wonder you’re having panic attacks — you can’t breathe.”</p>
<p>Five months later, I found myself in Coeur D’Alene, Idaho, meeting Dr. Tony Smith, a pioneer in the diagnosis and treatment of Lyme disease. Having potentially carried the infection for decades, I had Lyme in my blood, brain, sinuses, intestines, spleen, bladder, and lymph nodes. “One of the worst cases I’ve seen,” he said to me.</p>
<p>Then last year, Tim Frie diagnosed me with Prolonged Grief Disorder, a recent addition to the DSM-5-TR. Mine was triggered by a breakup in 2020, but the condition runs deeper than the loss of any specific person. This one has the been hardest to talk about, but I’ve learned to simply own it — I cry a lot, about everything.</p>
<p>So why am I sharing this? </p>
<p>Because I’m in a good place with this now, and holding back an important part of my life has been hard. Being known is healing unto itself and I deserve that. Maybe reading this will remind you that you do too.<br /><br />My core intention this year is grounding and rest. I&#39;m grateful to be landing in Madrid and completing these transition cycles, and to be able to share it all with you. Thank you.</p>
<p>Love,<br />Taylor</p>
<p>May/June<strong>📍</strong>— Madrid, Boston, Colorado, NYC, Florida, Madrid</p>
<h2>Did you enjoy reading this month&#39;s newsletter? Subscribe below!</h2>
<p>Or connect with me on <a href="https://www.instagram.com/taylorejacobson/">Instagram</a> or <a href="https://www.linkedin.com/in/taylorjacobson/">LinkedIn</a> for more.</p>]]></content:encoded>
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      <title>Friends Newsletter — March 2026</title>
      <link>https://taylorjacobson.org/march-2026/</link>
      <guid isPermaLink="true">https://taylorjacobson.org/march-2026/</guid>
      <pubDate>Thu, 26 Mar 2026 12:36:09 GMT</pubDate>
      <description>I’m writing from Madrid, where Homequest 2026 has officially commenced. And yes, it is a quest — equal parts adventure and challenge. My brother pointed…</description>
      <content:encoded><![CDATA[<p>I’m writing from Madrid, where Homequest 2026 has officially commenced. And yes, it is a <em>quest</em> — equal parts adventure and challenge.</p>
<p>My brother pointed out that I’ve been rushing the decision of where to live, because I need stability to heal my body, which remains my core life focus and obstacle. But, the right environment is just as critical as stability. So, I’m slowing things down and shifting the context from &quot;moving&quot; to &quot;exploring&quot;.</p>
<figure><img src="/cdn-cgi/image/width=800,quality=80,fit=scale-down,format=auto/_media/hike-with-friends.png" srcset="/cdn-cgi/image/width=400,quality=80,fit=scale-down,format=auto/_media/hike-with-friends.png 400w, /cdn-cgi/image/width=800,quality=80,fit=scale-down,format=auto/_media/hike-with-friends.png 800w, /cdn-cgi/image/width=1200,quality=80,fit=scale-down,format=auto/_media/hike-with-friends.png 1200w" sizes="(max-width: 700px) 100vw, 700px" alt="hike with friends" loading="lazy" decoding="async" style="max-width:100%;height:auto;display:block;" /><figcaption>Cute Spanish village. Off to hike with new friends.</figcaption></figure>
<h3>🔹 Iboga nights: the full story</h3>
<p>In February, I spent a week working with a plant medicine called Iboga, known for telling you the truth you need to hear, and for healing the body (PTSD, addiction, nervous system).</p>
<p>My “retreat” was just me being hosted by a husband-wife Bwiti* facilitator duo at their home, complete with 8-year old boy and baby girl.</p>
<p><em>*Bwiti is the millennia-old wisdom tradition that has been cultivated by Gabonese people in collaboration with the plant itself.</em></p>
<p>I went in looking for nervous system healing, and that’s what I got. It’s been a month and I’m sleeping better than I have in years. TMI alert: I used to pee 5-15 times per night. Since the retreat, 1-2 times. This is huge.</p>
<p>The underlying conditions, especially sleep apnea (technically UARS), are still a thing and will have to be addressed for my body to truly heal, but this was a real step forward.</p>
<p>Candidly, I was hoping for some message-in-the-sky moment too, and that did not happen. In a way, I was surprised how little the Iboga communicated directly with me.</p>
<p>FAQs</p>
<ul><li><strong>Was it scary/intense? </strong>Not really, and much less than I expected.</li><li><strong>Was there vomiting? </strong>Yes, but IMO this is not the big deal people make it.</li><li><strong>Was it healing? </strong>Yes. The plant medicine, being taken care of by a loving family, hanging out with an angelic baby.</li><li><strong>Are you a new, enlightened person now? </strong>Please, I was already perfect.</li></ul>
<p>Verdict: Recommend 9/10.</p>
<h3>🔹 Things I&#39;m digging this month</h3>
<p><strong>Freedom app blocker</strong> (7/10). I lose way too much sleep with TV and scrolling. So, I finally installed an app blocker, <a href="http://freedom.to/">​Freedom.to​</a>. It took an hour to properly set up; annoying but 100% worth it. If you have an app blocking system you like, I&#39;d love to know about it.</p>
<ul><li>My setup: ~10pm cutoff for everything except audio books until ~8am so that I can sleep longer if my body wants. I also block distracting apps during key work hours, ~11am - 2:30pm.</li></ul>
<p><strong>Yuka ingredient scanner</strong> (10/10). A few years ago, someone put the fear of God in me about most sunscreen being horrible for your skin (even high end ones). Since then I’ve been trying to find effective sunblock that isn’t toxic. <a href="https://yuka.io/en/">​Yuka​</a> finally solved this problem for me. Just scan a barcode and get an instant quality rating on any beauty or packaged food product. What&#39;s your go-to skin-safe sunblock?</p>
<p><strong>Books! </strong><a href="https://www.brandonsanderson.com/pages/the-mistborn-saga-the-original-trilogy">​<em>Mistborn</em>​</a> by Brandon Sanderson is a fun adventure-fantasy novel, and <a href="https://www.nirandfar.com/beyond-belief/">​<em>Beyond Belief</em>​</a> by Nir Eyal explains the staggering science of limiting beliefs and how to actually change them. Loving both.</p>
<p>Thanks for reading. Challenges abound. Homequest continues. Let&#39;s see what happens next. I&#39;d love to hear how you&#39;re doing.</p>
<p>Love,<br />Taylor</p>
<p>April<strong>📍</strong>— Spain, Portugal, then TBD.</p>
<h2>Did you enjoy reading this month&#39;s newsletter? Subscribe below!</h2>
<p>Or connect with me on <a href="https://www.instagram.com/taylorejacobson/">Instagram</a> or <a href="https://www.linkedin.com/in/taylorjacobson/">LinkedIn</a> for more.</p>]]></content:encoded>
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      <title>Friends Newsletter — January 2026</title>
      <link>https://taylorjacobson.org/january-2026/</link>
      <guid isPermaLink="true">https://taylorjacobson.org/january-2026/</guid>
      <pubDate>Wed, 07 Jan 2026 01:20:20 GMT</pubDate>
      <description>Fun fact: If I start writing my newsletter but don’t finish within ~48 hours, I start over. I like the feeling that what you’re reading is a transmission…</description>
      <content:encoded><![CDATA[<p>Fun fact: If I start writing my newsletter but don’t finish within ~48 hours, I start over. I like the feeling that what you’re reading is a transmission of what I’m experiencing right now.</p>
<p>The last 5 weeks have been dynamic.</p>
<p>I nixed my Denver plans in favor of a more committed trial run of Madrid. Despite being the rational choice, Denver just hasn’t felt right. While Madrid feels “far” to my American psyche, it checks almost every box I have. I’ve never been so excited about a move.</p>
<p>This has also been a time of momentum around my chronic illness healing journey. Diagnostic pieces are clarifying and fitting together in new ways. This doesn’t mean rapid progress—if anything, the opposite—but it does bring more confidence about the path forward, which is a relief.</p>
<p>Lastly, I’m working on some shiny new projects. I became a minor partner in Club Reset, a pickleball, coworking and wellness space in the heart of Mexico City. I’m also hosting a retreat this weekend in Valle de Bravo combining pickleball and men’s work.</p>
<figure><img src="/cdn-cgi/image/width=800,quality=80,fit=scale-down,format=auto/_media/Untitled-1024x1024.jpg" srcset="/cdn-cgi/image/width=400,quality=80,fit=scale-down,format=auto/_media/Untitled-1024x1024.jpg 400w, /cdn-cgi/image/width=800,quality=80,fit=scale-down,format=auto/_media/Untitled-1024x1024.jpg 800w, /cdn-cgi/image/width=1200,quality=80,fit=scale-down,format=auto/_media/Untitled-1024x1024.jpg 1200w" sizes="(max-width: 700px) 100vw, 700px" alt="Untitled-1024x1024.jpg" loading="lazy" decoding="async" style="max-width:100%;height:auto;display:block;" /><figcaption>After a recent pickleball tournament with my friend Charlie</figcaption></figure>
<h3>🔹 My biggest unlock of the year</h3>
<p>To my surprise, my biggest “aha moment” of the last year came from an astrology-based personality test called Human Design.</p>
<p>During a retreat, I watched each of the 4 men in attendance get deep, actionable insight from an aspect of Human Design called Motivation.</p>
<p>Learning my own Motivation, “Hope”, and how it works, was like being given permission to do life my way, and stop forcing myself to be someone I’m not.</p>
<p>Human Design has insight into essentially all aspects of our lives: how to best use our energy, where to live, romantic dynamics, and much more.</p>
<h3>🔹 Using personality tests with AI</h3>
<p>One of my favorite applications of Human Design and other personality tests has been adding them to my ChatGPT account&#39;s saved memory.</p>
<p>I then use the Personalization setting to ask Chat to take these insights into account.</p>
<p>These are some of the tests I’ve done and how I rate their usefulness (⭐️ out of 3):</p>
<p><em>Attachment Style</em> ⭐⭐⭐— how your system responds to intimacy and your path to healthier relationships. Ask ChatGPT to help you figure out yours.</p>
<p><em>Human Design</em> ⭐⭐⭐ — how best to use your energy so you can make decisions, relate, and live in alignment. I recommend the paid report on IHDSchool.com.</p>
<p><em>Wealth Dynamics</em> ⭐⭐⭐— learn your gifts, deficits, and ideal role within a team or business.</p>
<p><em>Enneagram</em> ⭐⭐— reveals your unconscious motivations and defense strategies; how you act and why. Note: I have not found the test to be an accurate diagnostic. Consider reading the book or asking ChatGPT to help.</p>
<p><em>Galactic Signature</em> ⭐⭐— a powerful, poetic set of “codes” on what moves you, your effect on others, and more.</p>
<p><em>DISC </em>⭐⭐— what values you unconsciously prioritize in communications and group dynamics. Great workplace tool.</p>
<p>What is your favorite personality test and why?</p>
<h3>🔹 A wish for you for 2026</h3>
<p>To me, personality tests are useful only insofar as they help us to discover how we want to be and do life.</p>
<p>The reason I described my Human Design insight as “my biggest aha of 2025” is that it gave me permission to own something I had known for ages but felt too guilty to embrace.</p>
<p>The truth is that there is no playbook for being ourselves. No one has ever been you before.</p>
<p>Personality tests can help validate what we already sense is true, and this is profoundly valuable. But ultimately, learning to be you will always come down to self-trust:</p>
<p><em>In that place beyond fear, emotion, the body, language, right and wrong, societal norms… what persists? What feels true?</em></p>
<p>My wish for you in 2026 is to know that part of you and trust it unconditionally.</p>
<p>Love,<br />Taylor</p>
<p><strong>📍in January/February:</strong> Mexico City, North Carolina, Boston, Spain</p>
<h2>Did you enjoy reading this month&#39;s newsletter? Subscribe below!</h2>
<p>Or follow me on <a href="https://www.instagram.com/taylorejacobson/"><em>Instagram</em></a> or <a href="https://www.linkedin.com/in/taylorjacobson/">LinkedIn</a> for more.</p>]]></content:encoded>
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      <title>Friends Newsletter — November 2025</title>
      <link>https://taylorjacobson.org/november-2025/</link>
      <guid isPermaLink="true">https://taylorjacobson.org/november-2025/</guid>
      <pubDate>Sat, 29 Nov 2025 21:10:51 GMT</pubDate>
      <description>It’s been tough to find time to write this month. I had wrist surgery last week—a second attempt to repair an old climbing injury—so I had to pack up and…</description>
      <content:encoded><![CDATA[<p>It’s been tough to find time to write this month.</p>
<p>I had wrist surgery last week—a second attempt to repair an old climbing injury—so I had to pack up and move out of my Cambridge place before the procedure.</p>
<p>Then on Monday, I hit the road for the 30-hour drive to Denver. Sitting down now to write feels like a deep breath after a sprint.</p>
<figure><img src="/cdn-cgi/image/width=800,quality=80,fit=scale-down,format=auto/_media/IMG_1474.jpeg" srcset="/cdn-cgi/image/width=400,quality=80,fit=scale-down,format=auto/_media/IMG_1474.jpeg 400w, /cdn-cgi/image/width=800,quality=80,fit=scale-down,format=auto/_media/IMG_1474.jpeg 800w, /cdn-cgi/image/width=1200,quality=80,fit=scale-down,format=auto/_media/IMG_1474.jpeg 1200w" sizes="(max-width: 700px) 100vw, 700px" alt="IMG_1474" loading="lazy" decoding="async" style="max-width:100%;height:auto;display:block;" /><figcaption>Fuel-up #5, middle of Nebraska</figcaption></figure>
<h3><strong>🔹 The spiritual weight of our stuff</strong></h3>
<p>The process of purging possessions and moving stirred up a lot of emotion, but has also opened up more excitement about the future.</p>
<p>In <a href="/october-2025/">my experience</a>, each of our possessions, even our home, has a psychic cost—an open loop our unconscious minds are always tracking, as well as a tether to an outdated version of us.</p>
<p>Like relationships, possessions have their chapters. Some are meant to stay for a lifetime. But in general, we hold onto things for too long.</p>
<p>Purging and moving can help us feel, process, and make space for who we want to become.</p>
<h3><strong>🔹 Comfort vs truth — the battle royale</strong></h3>
<p>Being human as I am, I am often present to my desire for more comfort and permanence—rooting in one place, building community, all that.</p>
<p>But as I complete this move, close a connection I’d been exploring, work to heal my body—it’s helpful to remind myself that misalignment with inner truth is more painful than change.</p>
<p>On that note, my ongoing palate expansion has improved my breathing slightly, with signs that my resting heart rate and pain levels may be dropping. I’m also testing out a treatment called Frequency Specific Microcurrents, and next week begin a heavy metals detox in Mexico City.</p>
<h3><strong>🔹 What draws others close? Lessons from hard times</strong></h3>
<p>One of the gifts of enduring a multi-year crucible is that you change. A lot.</p>
<p>Some people seem to like me less now. I’m more honest and less people-pleasery, which ruffles feathers sometimes.</p>
<p>Yet in general, people trust me more with their most sensitive bits. And I find this infinitely more gratifying than being liked.</p>
<p>How did this happen?</p>
<p>First, I’m safer: less judgmental, more validating. Breaking down so many times in my 30s decimated any illusions of superiority. Unsurprisingly, people prefer less arrogance.</p>
<p>Second, I do boundaries better. This one is counterintuitive—but when we’re clear about what does and doesn’t work for us, in a gentle manner (a big unlock for me), people know where they stand. They have the playbook to navigate in and out of our good graces. Mystery is scary. Clarity is safe.</p>
<p>And third, I’ve become a fiercer champion of others. When you’re at your weakest, you don’t just need safe people—you need champions. People who accept you exactly as you are, while also celebrating your steps forward and lovingly challenging you to rise.</p>
<p>The through-line in all this has been facing shame. Shame is tricky. It speaks to us through the voice of pride—spinning our toxic traits into “strengths”. Indignation, to avoid vulnerability. Controlling, instead of revealing. Being hard, when softness would be more effective. That was me across the board.</p>
<p>When we face our frailty and flaws, without self-reproach, we become humbler and more self-confident—a magnetic combination.</p>
<p>I am far from mastery. But if you want deeper connection, this work is fundamental.</p>
<h3><strong>🔹 What is life asking of you? A New Year’s workshop invitation</strong></h3>
<p>I want to know, what do you yearn for?</p>
<p>What part of you is done waiting?</p>
<p>And what if your anxiety, depression, procrastination—even your physical ailments—were just symptoms of misalignment?</p>
<p>I am collaborating with my friend Chetan Jhaveri to offer a <a href="https://luma.com/u32p0gk6">New Year’s workshop</a> centered on heeding our intuition—breaking through our conditioning and fears to create goals that align with our soul’s longings.</p>
<p>Early bird discount + limited spots. Please <a href="https://luma.com/u32p0gk6">join us</a>!</p>
<h3><strong>🔹 Things I liked this month</strong></h3>
<p><em>»</em> <a href="https://www.amazon.com/gp/video/detail/B0FNNHM1MT/ref=atv_dp_share_cu_r"><em>House of David</em></a><em> on Prime</em> — A retelling of the David and Goliath story that portrays God not as a distant authority, but as a force drawn into us when we act from deep, courageous truth. Inspiring and resonant. (10/10)</p>
<p>​<em>»</em> <a href="https://a.co/d/dUwf7x3"><em>The Way of the Superior Man</em></a><em> by David Deida</em> — In a society with no elders or masculine wisdom tradition, this book lays out a much-needed growth path for men. Rocked me as much as it did 10 years ago. (10/10)</p>
<p>​​<em>»</em> <a href="https://www.untoldapp.com/"><em>Untold</em></a><em>: AI Journaling App</em> — You speak, it listens and reflects insights back to you, drawing from psychology, science, and ancient wisdom. My main complaint: like ChatGPT, it won’t challenge your BS, but it’s a solid supplement to human support. (7/10)</p>
<p>That’s it for now. Until next time, be fierce—but gentle.</p>
<p>Love,<br />Taylor</p>
<p><strong>📍in December/January:</strong> CDMX, Chapel Hill, Charlotte, Boston</p>
<h2>Did you enjoy reading this month’s newsletter? Subscribe below!</h2>
<p>Or follow me on <a href="https://www.instagram.com/taylorejacobson/"><em>Instagram</em></a> or <a href="https://www.linkedin.com/in/taylorjacobson/">LinkedIn</a> for more.</p>]]></content:encoded>
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      <title>Friends Newsletter — October 2025</title>
      <link>https://taylorjacobson.org/october-2025/</link>
      <guid isPermaLink="true">https://taylorjacobson.org/october-2025/</guid>
      <pubDate>Mon, 06 Oct 2025 16:32:34 GMT</pubDate>
      <description>Hello from a family gathering in Charlotte. I re-read my first few newsletters and they feel a bit intellectual and impersonal. September&apos;s email felt…</description>
      <content:encoded><![CDATA[<p>Hello from a family gathering in Charlotte.</p>
<p>I re-read my first few newsletters and they feel a bit intellectual and impersonal. <a href="https://preview.convertkit-mail2.com/click/dpheh0hzhm/aHR0cHM6Ly90YXlsb3JqYWNvYnNvbi5vcmcvc2VwdGVtYmVyLTIwMjUv">September&#39;s email</a> felt more real. Let’s see how this one lands.</p>
<figure><img src="/cdn-cgi/image/width=800,quality=80,fit=scale-down,format=auto/_media/IMG_0956-1024x768.jpeg" srcset="/cdn-cgi/image/width=400,quality=80,fit=scale-down,format=auto/_media/IMG_0956-1024x768.jpeg 400w, /cdn-cgi/image/width=800,quality=80,fit=scale-down,format=auto/_media/IMG_0956-1024x768.jpeg 800w, /cdn-cgi/image/width=1200,quality=80,fit=scale-down,format=auto/_media/IMG_0956-1024x768.jpeg 1200w" sizes="(max-width: 700px) 100vw, 700px" alt="IMG_0956-1024x768.jpeg" loading="lazy" decoding="async" style="max-width:100%;height:auto;display:block;" /><figcaption>The Jacobson men in Charlotte, NC</figcaption></figure>
<p>This month: a parasite, a plant medicine invitation, why you’re not happy, and a crazy story about the wisdom of the heart.</p>
<h3><strong>🔹 Chronic illness updates and oddities</strong></h3>
<p>I flew to Charlotte to visit my dad but checked into a hotel after a clash with his girlfriend about my health-related needs. Chronic illness is difficult, but the social dynamic makes it harder. I’m using the extra space for writing and reflection.</p>
<p>Meanwhile, I have a new 1.5mm gap between my front teeth, indicating that my palate expansion is underway — step one to healing my sleep apnea and breathing issues. I feel relieved to be on a path to improvement.</p>
<p>Lastly, my six weeks of fever turned out to be a parasite. My medical mage Roberto in Mexico City diagnosed me just by looking at my tongue. Legend.</p>
<h3><strong>🔹 Revealing hard truths with Iboga: A plant medicine invitation</strong></h3>
<p>I’m co-organizing a small Iboga retreat, to be led by a trusted facilitator.</p>
<p>I learned about Iboga years ago but lately feel more eager to work with it. It’s a tree bark originally cultivated as sacred medicine in Gabon, Africa, known for illuminating inner truths with a clear and direct voice. Whatever discomfort may arise in the process seems a small price to pay for that kind of insight.</p>
<p>NB: This is not a commercial endeavor—just something that feels right. If you’re curious, reach out.</p>
<h3><strong>🔹 Why you’re not happy &amp; other wild insights from attachment theory</strong></h3>
<p>I cannot recommend highly enough <a href="https://preview.convertkit-mail2.com/click/dpheh0hzhm/aHR0cHM6Ly93d3cueW91dHViZS5jb20vd2F0Y2g_dj1fdXZ3aDl4X01RMA==">this interview</a> on attachment theory with Adam Lane Smith.</p>
<p>Attachment theory explains how childhood bonds shape our behavior as adults. It has given me a life-changing roadmap for better relationships.</p>
<p>Some highlights from the interview:</p>
<ul><li>Folks with an insecure attachment style do not experience serotonin at healthy levels, and are therefore more depressed and susceptible to dopamine addiction.</li><li>Smart phones are exploding insecure attachment. The parental bonding required to cultivate secure children is now constantly interrupted by phone usage. Then as kids age, bonding with friends is displaced and intermediated by dopamine-feeding social media.</li><li>Modern society rewards repeat relationship offenders. Tribe life didn’t. If you acted badly towards someone in a tribe, everyone would find out, incentivizing <em>maturation</em>. These days, if you act badly, you can just find new people, rinse and repeat.</li><li>Dating apps really do suck. Because secure attachers tend to link up and stay together, the online pool is mostly insecure attachers. Being more insecure, they position themselves for <em>matches instead of relationships</em>. They get a quick dopamine hit but repel the right people.</li></ul>
<p>​<a href="https://preview.convertkit-mail2.com/click/dpheh0hzhm/aHR0cHM6Ly93d3cueW91dHViZS5jb20vd2F0Y2g_dj1fdXZ3aDl4X01RMA==">Listen to the interview</a> and then let me know, what stood out to you?</p>
<h3><strong>🔹 Your heart knows where to go: stop complicating it</strong></h3>
<p>My friend Hannah has launched many businesses over the years, but none of them really felt right.</p>
<p>The truth?</p>
<p>Her heart has always called her to something wilder (keep reading).</p>
<p>But there was no clear business model, so she kept talking herself out of it.</p>
<p>Finally six months ago, she said screw it and <a href="https://preview.convertkit-mail2.com/click/dpheh0hzhm/aHR0cHM6Ly93d3cuaW5zdGFncmFtLmNvbS9oYW5uYWhleHBsYWluc2l0Lw==">started posting</a> about her passion: the intersection of behavioral psychology and ancient mystical wisdom.</p>
<p>Last week she crossed 50,000 followers.</p>
<p>The business model? Still forming. But she’s lit a fire with a fast-growing following and the possibilities are palpable.</p>
<p>If your heart holds a pregnant desire like Hannah’s did, perhaps now is the time to give it birth.</p>
<p>And if so, I’d love to hear about it (even just one line).</p>
<p>Also, you should <a href="https://preview.convertkit-mail2.com/click/dpheh0hzhm/aHR0cHM6Ly93d3cuaW5zdGFncmFtLmNvbS9oYW5uYWhleHBsYWluc2l0Lw==">follow Hannah</a>. She is a genius with a big heart.</p>
<p>That’s it for this month.</p>
<p>Love,<br />Taylor</p>
<p><strong>📍in October</strong>: Charlotte, NC » Mexico City » Long Island, NY » Maine » Colorado</p>
<h2>Did you enjoy reading this month&#39;s newsletter? Subscribe below!</h2>
<p>Or follow me on <a href="https://www.instagram.com/taylorejacobson/"><em>Instagram</em></a>, <a href="https://x.com/taylorjacobson/"><em>X</em></a>, or <a href="https://www.linkedin.com/in/taylorjacobson/">LinkedIn</a> for more.</p>]]></content:encoded>
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      <title>Friends Newsletter — September 2025</title>
      <link>https://taylorjacobson.org/september-2025/</link>
      <guid isPermaLink="true">https://taylorjacobson.org/september-2025/</guid>
      <pubDate>Tue, 09 Sep 2025 16:05:01 GMT</pubDate>
      <description>A hard truth about chronic illness: sometimes you just don’t have the energy to write your August newsletter. I had a bunch of travel last month: Idaho…</description>
      <content:encoded><![CDATA[<p>A hard truth about chronic illness: sometimes you just don’t have the energy to write your August newsletter.</p>
<p>I had a bunch of travel last month: Idaho for a Lyme clinic follow-up, Colorado for my 40th birthday, Mexico City for a romantic exploration, Vermont to have my palate expander installed—and my body just couldn’t handle the load.</p>
<figure><img src="/cdn-cgi/image/width=800,quality=80,fit=scale-down,format=auto/_media/Celeb-1024x768.jpg" srcset="/cdn-cgi/image/width=400,quality=80,fit=scale-down,format=auto/_media/Celeb-1024x768.jpg 400w, /cdn-cgi/image/width=800,quality=80,fit=scale-down,format=auto/_media/Celeb-1024x768.jpg 800w, /cdn-cgi/image/width=1200,quality=80,fit=scale-down,format=auto/_media/Celeb-1024x768.jpg 1200w" sizes="(max-width: 700px) 100vw, 700px" alt="Celeb-1024x768.jpg" loading="lazy" decoding="async" style="max-width:100%;height:auto;display:block;" /><figcaption>Celebrating 40 w/some bros</figcaption></figure>
<p>As a result, I’ve had some form of a fever for at least half of the last month and have been doing the bare minimum.</p>
<p>So, here we are, in September. I asked ChatGPT how to make this process easier, especially when my health is on the ropes. Let’s see how this goes.</p>
<h2>Life updates</h2>
<p>I’m leaving Boston. I got hives and rashes all summer there (the nervous system under heavy chronic load can produce many other symptoms), so, after consulting with doctors and the internet, I’m heading to Denver.</p>
<p>I still plan to test drive Málaga, Spain, for a month during the depths of winter. And I anticipate I’ll continue spending time in Mexico City too.</p>
<p>Is this overly ambitious given my health? Perhaps. But it’s hard to keep the adventuring spirit locked away entirely.</p>
<h2>On being soul-blocked</h2>
<p>What do you do when you have lofty goals for your life, but some obstacle is in your way? Caregiving an elder. An unexpected child. Being sick, like me.</p>
<p>It’s fun when life gives you a clear vision and a wide-open lane to run towards it. But a lot of the time, we just aren’t in that position.</p>
<p>I launched Focusmate in 2016 and went hard until 2020 when my health crisis began. Since then, I’ve had to dramatically change how I lead that business, in order to do it in just a few hours per week. Needless to say, that isn’t the best way to grow a young startup.</p>
<p>But Focusmate is far from my only dream. I’ve also had to shelve or slow-roll other desires like learning guitar and writing. Even dating is dramatically harder when you’re sick, let alone hopefully starting a family, one day.</p>
<p>So, what do you do when you’re blocked like this?</p>
<p>You can’t force it, but you can’t repress your dreams either.</p>
<p>You have to live in the in-between: holding the vision, chipping away when possible, and continuously challenging your assumptions about what’s possible… while also validating the difficult reality you live in, and sometimes accepting that it’s just not going to happen right now.</p>
<p>I’d love to hear—what have you learned about navigating difficult circumstances and in-between times?</p>
<h2>A truth-centered approach to love</h2>
<p>A little-known secret about me: I’m more mystical than I sometimes let on.</p>
<p>In fact, the book that’s had the most influence on my life is Carol K. Anthony’s esoteric <a href="https://click.convertkit-mail2.com/wvudg0g4p5cghkq97z2i7hn6gpxxxh8hnl5rl/6qheh8hl7v48kmao/aHR0cHM6Ly9hLmNvL2QvZ1dTd09UZg==">guide</a> to the 5,000-year-old Taoist text, the <em>I Ching</em>.</p>
<p>Her core teachings are on living your life in alignment with your inner truth—aka the Tao, the flow of the universe, or, if you prefer a more western angle, God’s will.</p>
<p>Recently I learned that she wrote a concise aside on what the <em>I Ching</em> has to say about romantic love. I devoured it whole on my last flight.</p>
<figure><img src="/cdn-cgi/image/width=800,quality=80,fit=scale-down,format=auto/_media/image-648x1024.png" srcset="/cdn-cgi/image/width=400,quality=80,fit=scale-down,format=auto/_media/image-648x1024.png 400w, /cdn-cgi/image/width=800,quality=80,fit=scale-down,format=auto/_media/image-648x1024.png 800w, /cdn-cgi/image/width=1200,quality=80,fit=scale-down,format=auto/_media/image-648x1024.png 1200w" sizes="(max-width: 700px) 100vw, 700px" alt="image-648x1024.png" loading="lazy" decoding="async" style="max-width:100%;height:auto;display:block;" /></figure>
<p>I’ll be honest, <a href="https://click.convertkit-mail2.com/wvudg0g4p5cghkq97z2i7hn6gpxxxh8hnl5rl/kkhmh6hnlgp0dxal/aHR0cHM6Ly93d3cuaWNoaW5nb3JhY2xlLmNvbS9ib29rcy1tb3JlLTEvMmxwN200Z282Z3I4eDM3M2M1dHRsenUzOWE5amk2">this little book</a> brought me back from the depths of cynicism about modern love. But not because it has anything to do with modern love (it was written pre-internet).</p>
<p>This book is a vivid transmission about staying rooted in the deepest places within yourself. Refusing to play games. Living for the innate reward that is doing what your heart desires, so that you can detach just a little bit more from the outcome. And how much more attractive all of that makes you.</p>
<p>As I read, I found myself breathing easier about my romantic future and ability to find happiness.</p>
<p>Whether you’re single and in despair or 30 years deep in a rewarding marriage, this 148-pager is absolutely worth your time.</p>
<p>Or you’ll read it and think I’ve gone off the deep end. But I’m okay taking that risk.</p>
<p>And that&#39;s a wrap for this edition!</p>
<p>Love you,<br />Taylor</p>
<h2>Did you enjoy reading this month&#39;s newsletter? Subscribe below!</h2>
<p>Or follow me on <a href="https://www.instagram.com/taylorejacobson/"><em>Instagram</em></a>, <a href="https://x.com/taylorjacobson/"><em>X</em></a>, or <a href="https://www.linkedin.com/in/taylorjacobson/">LinkedIn</a> for more.</p>]]></content:encoded>
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      <title>Friends Newsletter — July 2025</title>
      <link>https://taylorjacobson.org/july-2025/</link>
      <guid isPermaLink="true">https://taylorjacobson.org/july-2025/</guid>
      <pubDate>Thu, 10 Jul 2025 15:41:46 GMT</pubDate>
      <description>Hello from the pickleball court — where else? 🙂 Life updates: For the past year, I have been investigating treatment for sleep/airway issues that have…</description>
      <content:encoded><![CDATA[<figure><img src="/cdn-cgi/image/width=800,quality=80,fit=scale-down,format=auto/_media/24AF42B7-D031-452D-8D23-8A0E32916315-576x1024.jpeg" srcset="/cdn-cgi/image/width=400,quality=80,fit=scale-down,format=auto/_media/24AF42B7-D031-452D-8D23-8A0E32916315-576x1024.jpeg 400w, /cdn-cgi/image/width=800,quality=80,fit=scale-down,format=auto/_media/24AF42B7-D031-452D-8D23-8A0E32916315-576x1024.jpeg 800w, /cdn-cgi/image/width=1200,quality=80,fit=scale-down,format=auto/_media/24AF42B7-D031-452D-8D23-8A0E32916315-576x1024.jpeg 1200w" sizes="(max-width: 700px) 100vw, 700px" alt="24AF42B7-D031-452D-8D23-8A0E32916315-576x1024.jpeg" loading="lazy" decoding="async" style="max-width:100%;height:auto;display:block;" /><figcaption>Hello from the pickleball court — where else? 🙂</figcaption></figure>
<h2>Life updates:</h2>
<ul><li>For the past year, I have been investigating treatment for sleep/airway issues that have been the cause of brutal chronic symptoms, some for over a decade. I am relieved to share that last month, I chose an orthodontist in Burlington, Vermont, to work with on a palate expansion procedure that should help, using a new technology called the Facegenics Midface Expander. It’s a 24-month process, so I’m buckling up psychologically, but am so excited to finally be approaching the “starting line” to make this better.<br /></li><li>Update on June’s 500 pull-up challenge: I knocked out 448 pull-ups in just 21 days, but an wrist injury flared up and I had to stop. Still, I went from a 6-repetition max set on the first day, to doing 11 repetitions in a single set a couple weeks later, and I loved the process. I may invite folks here to join me next time. Let me know if you’d like that.</li></ul>
<h2>A few nuggets from my world:</h2>
<h3><strong>​#1 What if the subconscious mind IS the body?</strong></h3>
<p>I’ve operated for most of my life with the heuristic that the subconscious is part of the <em>mind</em>, connoting something cerebral and even mystical in nature.<br />​<br />But recently I heard something new:<br />​<br />What if the subconscious is actually just the <em>body</em>, doing its best to communicate to us in the only languages it has?​<br />​<br />Consider that our entire organism is a well of information and experiences. It’s well-known for example that traumatic experiences get stored in the tissues of our body. ​<br />​<br />But the body cannot “speak” to us in a language that we easily understand. ​<br />​<br /><em>​That fear in your hips… That grief in your lungs… </em>How does the body tell us what to do with it? ​<br />​<br />In short: It’s hard. ​<br />​<br />Especially while the conscious mind is trying to help us get through the day. ​<br />​<br />Maybe our so-called subconscious “mind” is just the body trying to share its knowledge and needs in the only language it has: intuition, emotions, dreams, pain, and the like.</p>
<h3><strong>#2 I am lonely. Are you lonely?</strong></h3>
<p>I swap daily WhatsApp notes with a friend on the other side of the country, someone who has also suffered a lot in recent years.<br />​<br />We talk about crawling through our respective “shit pipes,” a reference to Andy Dufresne’s prison escape through a narrow, 500-yard long sewage pipe in the classic 1994 film <em>The Shawshank Redemption</em>.<br />​<br />That is: sometimes life finds us crawling through our own personal shit pipes, and we don’t know how long they are — just that our best option is to keep on crawling.​<br />​<br />I would do almost anything to get out of a shit pipe. But absent that, having a cherished friend in there with me — to cheer each other on and validate the pain — is more precious than words can say. ​<br />​<br />Extending this notion more broadly, I feel an almost-daily, primordial drive to sit around a campfire with loved ones, alternately talking and singing and crying and sitting in silence, taking in the stars.​<br />​<br />Something about that combination seems to be a balm for the human condition: steady connection with a small tribe to which we deeply belong, alongside the rooting perspective of staring out into the expanse of space — a place to be tenderly yet firmly held in the depths of pain and heights of exuberance that life sends through us.​<br />​<br />Instead, we have a society that seems designed to make us feel frantic and fractured. Too many responsibilities sitting on our shoulders alone. Too many sources of distraction pulling us away from this moment. Access to too many dang <em>people</em>, so many that we struggle to properly value and cherish any single one.​<br />​<br />I am not saying anything new. ​<br />​<br />Yet, some part of me feels that this loneliness thing is the most fundamental challenge I will face in this life; that it sits beneath all the health crises, all the brokenheartedness, all the grief and loss, and more.<br />​<br />Because while we may not be able to avoid life’s shit pipes, we shouldn’t have to crawl through them alone.​<br />​<br />I’m curious to hear from you. What do your cravings and deep connection fantasies look like? Is there a way that this newsletter can help you feel less lonely?​<br />​<br /><em>[Next month, I may continue in this vein by writing about community-centric businesses — why they’re the future, and what I’ve learned about them after 9 years running Focusmate.]</em></p>
<p>That’s all for now—thanks for reading and have a great month.<br />​<br />Taylor<br />​<br />Current📍: Cambridge, MA, with no travel planned in July 😅</p>
<h2>Did you enjoy this newsletter? Subscribe below to get it every month</h2>
<p>Or follow me on <a href="https://www.instagram.com/taylorejacobson/"><em>Instagram</em></a>, <a href="https://x.com/taylorjacobson/"><em>X</em></a>, or <a href="https://patronview.com/patrons/"><em>Patron View</em></a> for more.</p>]]></content:encoded>
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      <title>Friends Newsletter — June 2025</title>
      <link>https://taylorjacobson.org/june-2025/</link>
      <guid isPermaLink="true">https://taylorjacobson.org/june-2025/</guid>
      <pubDate>Sun, 01 Jun 2025 18:04:42 GMT</pubDate>
      <description>Life updates: I’m in Mexico City this week, taking full advantage of $35 private pickleball lessons. I haven’t felt this excited to develop a skill since…</description>
      <content:encoded><![CDATA[<h2>Life updates:</h2>
<ul><li>I’m in Mexico City this week, taking full advantage of $35 private pickleball lessons. I haven’t felt this excited to develop a skill since I was in 4th grade practicing trumpet 3 hours a day.<br />​</li><li>I’m doing a 500 pull-up challenge for June. This coincides with being at my heaviest weight ever (~197 lbs). After being weak, tired, and in pain for so long, I’m grateful this feels attainable. As of day 1, I could do 6 pull-ups from a dead hang in a single set. Let’s see where I land at the end of the month.<br />​</li></ul>
<h2>A few nuggets from my world:</h2>
<h3><strong>Is emotional resilience the #1 life skill?</strong></h3>
<p><strong>​</strong>I’m starting to think it is. </p>
<p>If we accept that:</p>
<ol><li>Relationships are the most important part of life, and</li><li>Every relationship is essentially a negotiation, then</li><li>Acting out emotions is sabotaging these vital negotiations</li></ol>
<p>If, however, you can sit through <em>burning emotional discomfort</em> without reacting, you can engage more honestly, assertively, and strategically—making requests, being persuasive, holding your ground, walking away when appropriate, and so on.<br />​<br />If that sounds cold or calculating, you’ll hate Orion Taraban’s new book, <em>The Value of Others</em>. But I think it’s brilliant—an unflinching, behavioral economics + evolutionary psych take on romantic relationships. Highly recommend it if you’re up for a bit of uncomfortable truth.</p>
<h3><strong>If you want to accomplish anything, kill your darlings.</strong></h3>
<p><strong>​</strong>In my 20s, I was proud to be an “idea guy.” I also got very little done. Not a coincidence.<br />​<br />By 30, when I had the idea for Focusmate, I’d failed enough to know that building something meaningful would require focus. That meant cutting off everything—even good ideas—that didn’t serve my mission.<br />​<br />Saying no to those “darlings” was scary. But not as scary as repeating my old patterns. For the next few years, I asked myself one question constantly:<br />​<br />“Will this help me build my business?”<br />​<br />No rationalizations. No “maybe I’ll meet someone useful at this party.” Just no.<br />​<br />This principle extends beyond distracting ideas to friendships, social obligations, unnecessary spending, and more.<br />​<br />Most distractions are just echoes of an identity we’re clinging to—like being an “idea guy” or a “good friend” or “a fun person” or or or.<br />​<br />Since letting go of the “idea guy” identity, I have felt so much lighter and more powerful.</p>
<h3><strong>Neuronutritionist </strong><a href="https://www.timfrie.com/"><strong>Tim Frie</strong></a><strong> has changed my relationship to food.</strong>​</h3>
<p>Food and eating has been probably my most significant coping and self-soothing mechanism.<br />​<br />In a case like mine, where food isn’t just fuel but is actually deeply entwined with my trauma, you can’t just turn a few knobs to find the ideal diet.<br />​<br />Neuronutrition is an approach to food and eating that centers the nervous system.<br />​<br />A core principle, therefore, is that a healthy diet is one that doesn’t stress you out, because stress is far more damaging than virtually any unhealthy food.<br />​<br />This one idea blows up about 90% of nutrition content online imploring us that <em>this</em> superfood or <em>that</em> fasting regimen is the silver bullet.<br />​<br />I’ve spent so much of my life stressing about diet. For the first time in my life, my mental chatter about food is gone. I feel peaceful and empowered.<br />​<br />Follow Tim on Instagram, work with him, or train with him at the National Academy of Neuronutrition.<br />​<br />P.S. Tim doesn’t know I’m sharing this. He’s just one of those people worth amplifying.</p>
<h2>Join my newsletter for more content like this.</h2>
<p>Or follow me on <a href="https://www.instagram.com/taylorejacobson/"><em>Instagram</em></a>, <a href="https://x.com/taylorjacobson/"><em>X</em></a>, or <a href="https://patronview.com/patrons/"><em>Patron View</em></a> for more.</p>]]></content:encoded>
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      <title>Friends Newsletter — May 2025</title>
      <link>https://taylorjacobson.org/may-2025/</link>
      <guid isPermaLink="true">https://taylorjacobson.org/may-2025/</guid>
      <pubDate>Thu, 01 May 2025 15:31:00 GMT</pubDate>
      <description>Some quick life updates: In December, I moved to Cambridge, Massachusetts, to focus more seriously on some chronic health issues. I love Mexico City, but…</description>
      <content:encoded><![CDATA[<h2><strong>Some quick life updates:</strong></h2>
<ul><li>In December, I moved to Cambridge, Massachusetts, to focus more seriously on some chronic health issues. I love Mexico City, but navigating health care en español wasn’t ideal.</li><li>I’m still running Focusmate. We hired our 10th team member — our first growth hire — to help us deepen our reach in the ADHD community, where Focusmate has had the strongest impact and clearest product-market fit. I’m almost 10 years into this journey and still fired up about what’s coming, and I’m grateful for that.</li><li>I am newly obsessed with pickleball and playing as much as I can handle :)</li></ul>
<h2><strong>Some interesting tidbits from my world lately:</strong></h2>
<h3>#1: <em>&quot;Attention = no tension&quot;</em></h3>
<ul><li>I love how this phrase conceptualizes paying attention as a physical experience of relaxation. For example, when I’m listening to someone but thinking about my response, I can feel that as tension in my neck, face, etc.<br />​<br />Related to this, if I notice tension in my body, I use that a potential sign to <em>not</em> say what I’m considering saying.</li></ul>
<h3>#2: Money mindset</h3>
<ul><li>In my younger years, some serious &quot;wealth is bad&quot; conditioning unconsciously drove my life choices in the direction of poverty. Two new narratives helped up-end that: First is that money can facilitate ease in life, so not having enough sabotages your ability to share your gifts with the world. Poor = selfish (?!)<br />​<br />Second is that wealth can mean stewarding resources that aren’t yours per se, but which you can put to work in service of others or your purpose.<br />​<br />Together these helped me stop martyring around money and get excited about welcoming wealth in my life.</li></ul>
<h3>#3: Sustainable &gt; Ideal</h3>
<ul><li>When I was considering this newsletter, my brilliant friend Blake Smith asked me: <em>What topics can I easily write about? And what frequency can I easily maintain?</em><br />​<br />I used to set goals based on what seemed ideal, which often led to failure. I’m loving the context of setting goals based on what I can easily <em>sustain</em>, rather than what seems <em>ideal</em>.</li></ul>]]></content:encoded>
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