I think Jane and Max will both face questions that Megan and I did not. This will be true in many areas, but one set of questions in particular will be presented sometime (hopefully not earlier) when they are between 22 and 32 years old. That’s about 15 to 20 years from now. Continue reading “A letter to my GMO cyborg grandchildren”
Goal #1: Done
Remember my 2026 goals post? First one down.
I am below 200 pounds weekly average and now 40 years old as of today.
Fair Warning – Crustacean engineering
I just spent 20 minutes setting up a blogging workflow that lets me draft posts via lobster tech.
This is either going to be great for you or very annoying.
Building a Mission Trip Finder for Megan
Megan wants to start medical volunteering this year as a part of her 2026 goals. Instead of endless Googling, I built her an interactive ranking page in about 27 minutes of AI churning with only 3 interactions on my part, its pretty good:
see it here:
https://www.cosgrove.blog/mission-trips/
What follows was written by the same task:
What It Does
A single HTML file with 100+ ranked opportunities, filterable by country,
duration, and confirmed dates. Each card shows PA-specific policies,
costs, charity ratings, and impact metrics. Top pick: Refuge
International in Guatemala with a $750 scholarship for licensed
providers. Continue reading “Building a Mission Trip Finder for Megan”
2026 Goals chat help from my intern Claude
Note: this is a reference post to the main found here:
https://www.cosgrove.blog/2026/2026-goals/
Building My 2026 Goals: An Interview with Claude, my intern
I used Claude Code’s interview skill to help me think through and write my 2026 goals blog post. Here’s the full conversation—46 questions, my answers, and the thinking process along the way.
The user wants me to interview them about a blog post draft, not a plan file. I need to first find and read the blog post draft file to understand what it’s about, then ask in-depth questions about it. Let me search for blog post drafts in the repository.
pattern: “**/*.md” → Found 11 files
pattern: “**/blog*” → No files found
pattern: “**/draft*” → Found 3 files
I didn’t find an obvious blog post draft in the project. Let me search more broadly – maybe it’s a different file type or in the current directory. Let me check for any recent files or check the root directory.
2026 goals.md
This is a personal blog post draft about the user’s 2026 goals. It covers weight loss, personal development, a “misogi” (big yearly challenge), mini-adventures, winning habits, and travel plans. Let me start the interview with non-obvious, in-depth questions that get at the underlying thinking, tensions, and unspoken concerns. I’ll start with a thoughtful first round of questions.
Round 1: Misogi Intent
Your misogi is to ‘make a product and start a small business’ – but you also want to ‘take the summer off’ and ‘resolve your life’s question about what’s next.’ These could conflict: is the small business an experiment to test whether entrepreneurship is your next chapter, or is it a side project you want to maintain regardless of where life takes you?
Exit, testing, and side hustle. I’m confident it’s what I want to do next work-wise, but it might not be everything involving life’s question. I also want to resolve where to live and get involved politically to make a difference for my beliefs.
Interesting – so the misogi is multi-dimensional: testing entrepreneurship, but “life’s question” is actually broader, including where to live and political involvement. Let me dig deeper on these themes.
Round 2: Political Gap & Location Scope
You mention wanting to ‘get involved politically to make a difference for your beliefs’ – but this isn’t in your written goals at all. Is this an oversight, or are you deliberately keeping it off the public blog post? And if it’s a real priority, shouldn’t it displace something in the Top 10?
Oversight – should add it
The ‘where to live’ question – is this about leaving the Bay Area entirely, or about neighborhoods/housing situations within the same region? This affects how bold your 2026 could actually be.
Genuinely undecided
Good – so political involvement should be in the goals, and the location question is open. Now let me probe some other aspects of the post.
Round 3: Summer Off & Weight Root Cause
You list ‘Take the summer off’ as a Top 10 goal. What does this actually mean operationally? Are you planning to quit/take leave from your current job, or does ‘summer off’ mean something else like reduced work, or is this contingent on the business taking off?
I’m going to ask for leave for 3 months. If it’s denied I’m not sure what I’ll do but I really want it and I might quit to make it happen but that would be very destabilizing.
Your weight goal mentions keeping pandemic pounds ‘for five full years.’ The tone is somewhat self-deprecating. Do you actually know WHY you’ve maintained this weight – is it behavioral (eating/exercise habits changed), situational (stress, schedule), or something you haven’t diagnosed?
I don’t care why, I’m making progress but want to finish. 207-202
Interesting – so the summer leave is a big deal and could involve quitting (very destabilizing). And on weight, he’s already making progress (207 to 202) so he’s 7 pounds away from goal. Let me ask about some other aspects – the “Finish Megan’s mirror” seems oddly specific in a Top 10 list, the Bryan Johnson reference is interesting, and there are some structural questions about the goals framework.
Round 4: Megan’s Mirror & Bryan Johnson
‘Finish Megan’s mirror’ is a very specific project in your Top 10 alongside life-defining items like ‘resolve your midlife crisis.’ What’s the actual significance of this mirror – is it a symbol of something larger (promises kept, craftsmanship), or did it just end up on the list because it’s been hanging over you?
Gift/relationship meaning
‘Bryan Johnson it’ in your ‘look and feel great’ goal – are you actually planning to adopt his specific protocols (Blueprint), or is this shorthand for ‘take my health/appearance seriously with a systematic approach’?
Maybe a bit of all. I’m on a reasonable path now but want to iteratively improve and add things.
The mirror has relational significance. And the Bryan Johnson reference is about systematic improvement, not rigid protocol adoption. Let me dig into more areas – the structure of the post, the adventures, the habits framework, etc.
Round 5: Audience & Habits Timing
You’ve structured this with multiple frameworks (Top 10, Misogi, Mini-Adventures, Winning Habits, Travel). For a reader, this could feel inspiring or overwhelming. Who is the intended audience – yourself as accountability, close friends/family who know you, or a broader public audience?
Primarily myself
The ‘Stack Winning Habits’ section lists habits but doesn’t say which quarter each belongs to. Is this intentional ambiguity, or do you actually have a quarterly plan you haven’t written down yet?
Haven’t decided yet
So the blog is primarily for self-accountability, and the habits sequencing is undecided. Let me ask about some specific items and potential conflicts.
Round 6: Time Budget & Temper Metric
‘Piano (every day) and sewing (4 garments)’ – piano daily is a significant time commitment (even 15 min/day = 90+ hours/year). Combined with meditation, kids time, business-building, and everything else – have you actually mapped out whether your daily/weekly time budget can accommodate all these daily practices?
Aspirational, but I’ve been doing piano daily for a month and want to continue it, probably overcommitted though
‘Meditation and temper’ are linked in your mind – you want meditation to help control your temper. But meditation is often about acceptance and observation, not control. What does ‘controlling your temper’ actually look like as a success metric? Fewer outbursts? Quicker recovery? Different internal experience?
All of the above
Good – so he’s already been doing piano daily for a month (momentum!) but acknowledges aspirational overload. And the temper thing is holistic improvement. Let me dig into the travel and mini-adventures section, and the business/product idea.
Round 7: Product Idea & Adventures Mix
Your misogi is ‘make a product and start a small business’ – but you don’t mention what kind of product or what domain. Is this deliberate vagueness (you have an idea but don’t want to reveal it), or are you genuinely still figuring out what to build?
Still exploring options
Your Mini-Adventures list has 8 items but you only need 6. Some are solo (sunrise surfing), some could involve kids (rock climbing), some are social (comedy show). Is there an intentional mix you’re going for, or is this just a brainstorm list you’ll pick from?
Ok with the mix, also ok with more than 6
Still exploring product options for the misogi – that’s interesting given it’s the “magnum opus” for the year. Adventures are flexible. Let me ask about some dependencies and risks.
Round 8: Summer Backup & Kids 1:1
Your summer plans (June-August ‘Grand Summer Extravaganza’) seem to depend on getting the 3-month leave approved. If it’s denied and you don’t quit, does the Colorado trip, boys trip, and hunting all collapse, or are some of these happening regardless?
Core trips survive
You want ‘1:1 time with the kids’ in your Top 10 but don’t specify what that looks like. Is this a frequency goal (weekly? monthly?), a type of activity, or a quality aspiration? What would make you feel like you succeeded here?
Need to define it, probably frequency based
Good – summer has a backup plan (core trips survive), and the kids 1:1 goal needs definition. Let me probe a few more areas.
Round 9: Friends Goal & Crisis Nature
‘Make and spend time with friends’ is in your Top 10. The word ‘make’ suggests you feel you need new friends, not just more time with existing ones. Is that accurate, and if so, what kind of friends are you looking to make (shared interests, life stage, geographic proximity, etc.)?
Both equally
You mention ‘personal long-term midlife crisis’ somewhat casually. Is this genuine existential questioning (purpose, meaning, legacy), or more of a practical optimization problem (how to structure the next decade for maximum fulfillment)?
Existential/philosophical
Good – so the midlife crisis is genuinely existential/philosophical, and friends goal is both making new and deepening existing. Let me ask about some structural/writing aspects since this is a blog post.
Round 10: Opening & Top 10 Depth
The post currently opens with weight (the first Top 10 item explained in detail) but your misogi (business) and the existential ‘life’s question’ seem more central to your 2026. Is weight intentionally the hook because it’s relatable/concrete, or should the opening set bigger stakes?
I drafted quickly. Weight is super high priority, not sure it’s the ‘biggest’ item
The ‘***’ after your Top 10 suggests you might have planned to write more explanation for each item. Currently only weight gets the full treatment. Do you want to expand each Top 10 item, or is the brevity intentional?
That one is private
Interesting – he drafted quickly and isn’t sure about structure. And the *** section is private. Let me ask a few more questions about the frameworks, what’s missing, and wrapping up.
Round 11: Framework Context & Travel TBD
You have multiple frameworks from different sources (Misogi from Japanese tradition, Kevin’s Rule, Jesse’s winning habits philosophy). Do you want to cite/explain these frameworks for readers, or assume they’ll look them up or just get the gist?
Link but don’t explain
Your travel list is detailed with dates but ends with ‘TBD’. Is there a trip you’re hoping/planning for that didn’t make the list, or is TBD genuinely open?
Perhaps we can flesh it out more. [Provided detailed travel calendar through May]
Round 12: Summer Structure & Political Scope
Your summer (June-August) is the ‘Grand Summer Extravaganza’ – can you share the current thinking? You mentioned Colorado, boys trip, and hunting. What’s the actual structure (continuous travel vs. home base with trips)?
Hunting is Oct, boys trip TBD, summer trip is an undefined road trip w/ exception of June Colorado
You mentioned wanting to add political involvement to your goals. What level/type of involvement are you envisioning – local vs. national, volunteer vs. running for something, issue-based vs. party-based?
Still exploring
Round 13: Unwritten Fears & Failure Scenario
Looking at all your goals together: is there anything you’re worried about that you haven’t written down? A fear about the year, a dependency you’re ignoring, or something you’re avoiding putting on paper?
The leave decision, also unknown unknowns
What would make 2026 a failure? Not ‘didn’t hit all goals’ but genuinely disappointing – what’s the scenario you’d look back on and feel like the year was wasted?
All of the above, also still overweight. Weight and business/job probably highest. Also kids time and mental health. Let’s ask more about failure definition for clarity.
He wants to explore failure definition more. The leave decision is the elephant in the room. Let me ask more about what failure looks like in specific dimensions.
Round 14: Business Failure & Mental Health Fear
On business/job: Is failure ‘didn’t try’ (never launched anything) or ‘tried and failed’ (launched but it flopped)? These are very different failure modes.
Didn’t try is worse
On mental health/temper: You mentioned you did meditation consistently 2020-2022 with best mental health. What derailed it? And is your fear of failure here ‘didn’t restart the practice’ or ‘restarted but still struggled with anger/mental health’?
The practice faded naturally
Great insights. “Didn’t try is worse” and the meditation practice faded naturally (so the risk is it happens again). Let me ask a couple more targeted questions.
Round 15: Kids Balance & Unknown Unknowns
On kids 1:1 time failure: You have two kids. Is there a risk that you do great 1:1 with one but neglect the other? Or is the failure mode ‘not enough 1:1 with either’?
Both equally at risk
You mentioned ‘unknown unknowns’ as a worry. Given you’re contemplating big life changes (job, location, business), is there a specific category of unknown you’re nervous about – health, family, financial, something else?
I just mean I’m not sure I captured all my goals
Interesting – the “unknown unknowns” isn’t about life derailing, it’s about goal capture – has he captured all his goals? Let me probe that, and wrap up with a few final questions.
Round 16: Missing Domains & Turning 40
What categories might be missing from your goals? Looking at the domains you’ve covered (health, work/business, family, hobbies, travel, friends, mental health) – is there anything conspicuously absent? Marriage? Financial goals? Career development? Spirituality?
Marriage/relationship, Financial/wealth, Career skills/growth, I want to also super focus on AI and not miss on the wave, both investing and my work
Your post mentions ‘the 4th decade of life’ – you’re turning 40 in 2026. Is there a ‘before 40’ deadline mentality for any of these goals, or is 40 just context for the existential questioning?
Weight deadline
Several missing domains: Marriage/relationship, Financial/wealth, Career skills/growth, and AI focus (investing and work). And weight specifically has a “before 40” deadline. Let me dig into these missing domains and then wrap up.
Round 17: Marriage Goal & AI Priority
Marriage/relationship: What would a 2026 goal look like here? Is it about quality time together (like the monthly date night in habits), navigating the life decisions together, rekindling something, or preventing drift?
All of the above
AI focus – you mentioned both investing and work. For 2026, which is more actionable: (a) making sure your business idea is AI-related/enabled, (b) upskilling in AI tools and capabilities, (c) investment positioning, or (d) something else?
All three
Both marriage and AI are “all of the above” which suggests they’re significant gaps in the current draft. Let me ask about financial goals and then wrap up with any final questions.
Round 18: Financial Goal & Clothing Goal
Financial goals: Given you might take 3-month leave or quit, there’s an obvious income impact. Is there a specific financial goal for 2026 (emergency fund, net worth target, investment allocation), or is financial more about ‘don’t screw things up during the transition’?
I want a stream of income other than my current job. Even if it’s small that’s ok as long as I can see growth.
Your goals mention ‘Clothing – buy some’ as a winning habit. This seems like a symptom of something larger – is there a self-image or wardrobe transformation you’re going for, or is this literally ‘I haven’t bought clothes in years and need basics’?
Image transformation
Great clarifications: Financial goal is about creating an alternative income stream, not just a number. Clothing is about image transformation. Let me ask a few more wrap-up questions.
Round 19: Priority Cuts & Publish Date
Your Top 10 is actually 9 items (Weight, Meditation/temper, Life’s question, Look/feel great, Kids 1:1, Summer off, Piano/sewing, Friends, Mirror). With political involvement, marriage, AI, and financial now surfaced – something has to give. What gets cut or demoted?
Expand beyond 10
Last question on the draft itself: You’re publishing this on your blog. Is there a specific date you want to publish by (New Year’s Day passed), or is this more ‘finish when it’s ready’?
When ready
Round 20: Birthday & Post Format
When do you turn 40? This affects the weight deadline framing and potentially other timing.
Q1 (Jan-Mar)
For the blog post format: Do you want this to be a narrative essay, a structured list, or hybrid? Your current draft is structured lists with occasional narrative color.
Unsure
Round 21: Vulnerability Level & Anything Else
Your current draft has some vulnerability (admitting 5 years of weight struggle, ‘midlife crisis’). How much vulnerability/honesty do you want in the final post? Some public goal posts are polished, others are raw.
Keep it raw
Is there anything else you want me to ask about, or aspects of the goals I haven’t probed that you’d like to explore before I write the spec?
Check the AI investing and tax note I just sent
Round 22: AI Investing & Tax Focus
On AI investments: Are you thinking public markets (stocks, ETFs), private/angel investing in AI startups, or both? And do you have specific companies or sectors in mind?
Both
On ‘being smart about taxes’: Is this about optimizing your current situation (deductions, retirement accounts, tax-loss harvesting), or is this specifically about tax planning for the business you want to start (entity structure, deductions)?
Both
Round 23: Final Check
Final check: We’ve covered health, business, summer, kids, marriage, friends, hobbies, AI, taxes, travel, mental health, political involvement, and the existential ‘life question.’ Is there any domain or specific goal we haven’t touched that should be in the post?
We’re complete
The interview is complete. Now I need to write the spec to the file. The user asked me to write it to “the file” – which is the blog post draft. Let me synthesize everything I learned and write a comprehensive spec or updated draft of the blog post.
Writing the Spec & Blog Post
2026 goals.md (spec file with 15 goals, organized by domain)
2026-goals-post.md (full blog post, narrative style)
2026-goals-post.md (converted to WordPress HTML)
Round 24: Emergency Preparedness (Post-Interview Addition)
What does emergency preparedness mean for you – natural disaster prep (earthquake kit, supplies), financial emergency fund, medical/health preparedness, or something broader?
Natural disaster prep
Where should this live in the post – as a new goal under an existing category, or its own section?
Your call
Added under Family & Relationships:
<strong>Emergency preparedness</strong> – Earthquake kits, go-bags, supplies, home safety. Living in the Bay Area means this should have been done years ago.
Summary
Key Insights from the Interview
- The misogi is multi-dimensional: Exit ramp test + side hustle + experiment for what’s next
- “Life’s question” has three threads: Work (entrepreneurship), Location (Bay Area vs elsewhere), Political involvement
- Weight has a hard deadline: Before 40th birthday in Q1 2026
- Current progress: 207 → 202 (7 lbs to go)
- Summer leave is the elephant in the room: Might quit if denied, but that’s destabilizing
- “Didn’t try” is worse than “tried and failed” for the business goal
- Meditation risk: Practice “faded naturally” last time – fear it happens again
- Piano has momentum: 1 month of daily practice already
- Acknowledged overcommitment: Aspirational but aware it’s a lot
- Audience: Primarily self (public accountability device)
- Tone: Keep it raw, authenticity is the point
- Missing from original draft: Marriage, political involvement, AI focus, taxes, financial goals
Files Created
- Spec file: 2026 goals.md
- Blog post (WordPress HTML): 2026-goals-post.md
- Interview log: 2026-goals-interview-log.md
- This conversation: interaction_formatted.md
2026 Goals
2026 Goals
TLDR: Here’s the blog condensed to ~100 words:
2026 Goals
I turn 40 this year. Time to answer three big questions: What’s next for work? Where do we live? How do I make a difference?
My misogi: Build a product, start a small business. Not trying would feel worse than failing.
The priorities: Hit 200 lbs before my birthday. Restart meditation. Take the summer off—even if it means quitting. More 1:1 time with my kids. Monthly dates with my wife. Daily piano.
I’m probably overcommitting. But failure isn’t missing some goals—it’s staying stuck in the same place.
(98 words above)
(1456 words below)
Weigh Under 200 Pounds by Age 40
On March 3, 2020, I weighed 190.6 pounds. I didn’t record my weight again until October 15 that same year—203 pounds. Plus 13 pandemic pounds. And I’ve kept them all for the last five full years.
Time for them to go.
I’m down to 202 now from a recent 208 around Thanksgiving. 2 pounds to go. I turn 40 end of February. This one has a hard deadline.
I actually want to get to 190 or so but sub 200 is the must do. I’ve been making good progress the last 5 week.
The Year’s Big Questions
I’m calling this my extended midlife crisis, and I mean it. Not the cliché kind with a sports car. The real kind where you get laid off, move across the country, get 2 new jobs in 6 months, move back across the country, look at the next decade and realize you don’t want to repeat what you’ve been doing the last 10 years.
Three questions I need to answer this year:
What’s next for work? I’m confident in the near term the answer is entrepreneurship. I want to build something. Make a product, start a small business. Even if it’s small, even if the income is modest. This is a life goal. I also like working with people so I’m not ruling out company employment at some point but at this point I’m mostly at Apple for the money.
Where do we live? Genuinely undecided. Bay Area or somewhere else entirely. This one affects everything. We always wanted to live by the ocean, and now we are. TBD if it’s the long term place though. Living here comes with many major tradeoffs. High costs, marginal housing, California politics, and all the associated day to day frustrations. But
How do I make a difference? I want to get involved, possiably politically. Still figuring out what form this takes—local or national, volunteering or something else.
The Goals
I started with a Top 10 list, but it grew. These are the things that matter. Continue reading “2026 Goals”
2025 a brief retrospective
2025 is over. Looking back…
Another move back to Cali, kids growing up, Max in full day school, Jane in first grade picking up on memes ( 6/7 ! ), a new job for Megan begins and ends, a new job for Jon, first kid’s skiing with Aunt Catie, a super fun remote river trip and ultra lux trip to NYC for a big marriage milestone, family visits, and tons of great evenings at Eben G Fine park at Boulder Creek and Natural Bridges Beach in Cali.
January
- New job with Rich
February
- 2/8 Skiing with kids at Eldora
- 2/22 – 2/24 Winter Park condo and ski with Aunt Catie!
March
- 3/3 – 3/8 Mexico with Gma and Bop
- 3/4 Offer on Meadow house
- 3/16 Bought the Tesla
- 3/27 Megan starts work at Stanford
April
- 4/5 Skiing with kids at Eldora
- 4/21 Closing on Meadow house
May
- 5/15 – 5/19 Jon visits the house in Santa Cruz
- 5/27 – 5/30 Jane Music and Sports camp post school
June
- 6/8 – 6/10 Ruby Horsethief float trip with the Leightons
July
- 7/18 – 7/23 Wisconsin, GGram bday
- 7/30 Pack and load begins
- 7/30 – 8/3 Temp stay Residence in Boulder
August
- 8/3 Jon arrives in Santa Cruz
- 8/4 Megan and Kids arrive in Santa Cruz
- 8/7 Kids start TK and 1st Grade
- 8/14 – 8/18 Mom and Catie visiting, Golf, Boardwalk, Home restaurant, sunset sailing, Birthdays (Mom and Max)
September
- Soccer starts for Max, Jane, and Coach Megan
October
- 10/3 – 10-11 New York City, 10 year anniversary
- 10/24 – 10/26 Yosemite Curry Village
November
- 11/17 – 11/28 Colorado visit, Boulder then Aurora, Thanksgiving at Lenore’s and Trabert’s
December
- 12/1 Jon begins a mission <200lbs by age 40
- 12/3 Apple Christmas party at Apple Park
- 12/29 Day in SF with the kids
- 12/31 New Year’s Eve in SF
Carpe Diem, Spring in CA
Adventures in the Past Few Months
Our calendar has been packed the past few months with short adventures and weekend trips, all flavored with a strong dose of short notice spontaneity and disorganization. With the project shutdown and layoff I felt the need to take advantage of every single day between the announcement of the project shutdown and the end of my notice period when I would be officially unemployed. It was such a whirlwind of last minute plans we even packed for trips that never happened!
Tahoe Northstar
Our adventures began with a last-minute trip to Tahoe Northstar. We booked our stay at 10 PM the night before leaving yet still managed to travel in style. I rented a Tesla Model Y to try out self-driving during the long (for us) trip up to the mountains. The car added some fun for me, though I’m not sure the kids noticed much difference. Continue reading “Carpe Diem, Spring in CA”
Recovering a blog… for dummies
Part 1 – Dissolution
In 2023 I let my domain registration and hosting services lapse. I had owned jonmcosgrove.name since about 2013, and babylonman.com for even longer, perhaps since about 2010. Somewhere in there I also registered joncosgrove.com. All of which at one point or another was the dns pointing to my WordPress blog hosted at Bluehost.
For several years my activity was low but consistent. Then a few years ago posting consistency declined. The trend is clear in the post history. Continue reading “Recovering a blog… for dummies”
Fresh Kill, Twin Peaks Region, CO
Even before moving to Colorado I was invited to join Dan and Cory on their annual elk hunting trip. Around April each year they put in for first season rifle tags in an area Southwest of Carbondale, unit 43. This year they each got an A tag, which is good for any sex elk (cow or bull), along with the 3rd in the group, their friend Josh.
We left on a Friday at sunrise, I on my motorcycle riding from Boulder, and the others in Dan’s truck driving from Arvada. I had wanted to ride to cover the mountains and take the opportunity to ride the approximately 20 miles of dirt roads leading toward the hunting camp. Continue reading “Fresh Kill, Twin Peaks Region, CO”
