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.
Jon
/interview but not a plan, this blog post draft
Claude’s Thinking
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.
Claude
I’ll help you with an in-depth interview about your blog post draft. Let me first find and read the draft.
Claude’s Thinking
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.
Claude
I don’t see an obvious blog post draft file. Could you tell me which file contains your blog post draft, or would you like to paste the content directly?
Jon
cosgrove.blog/drafts/2026 goals.md
Claude
I see you have a blog post draft open. Let me read it.
Claude’s Thinking
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.
Claude
Excellent – this is your 2026 goals blog post. Let me start the interview with some probing questions.
Round 1: Misogi Intent
Question
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?
Jon’s Answer
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.
Claude’s Thinking
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.
Claude
Interesting – so “life’s question” is actually three intertwined threads: work (the business), location, and political engagement. Let me dig deeper.
Round 2: Political Gap & Location Scope
Question 1
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?
Answer
Oversight – should add it
Question 2
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.
Answer
Genuinely undecided
Claude’s Thinking
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
Question 1
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?
Answer
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.
Question 2
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?
Answer
I don’t care why, I’m making progress but want to finish. 207-202
Claude’s Thinking
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.
Claude
The summer leave is a pivotal moment – potentially destabilizing if denied. And congrats on the weight progress (207→202, 7 lbs to go). Let me probe some other areas.
Round 4: Megan’s Mirror & Bryan Johnson
Question 1
‘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?
Answer
Gift/relationship meaning
Question 2
‘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’?
Answer
Maybe a bit of all. I’m on a reasonable path now but want to iteratively improve and add things.
Claude’s Thinking
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
Question 1
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?
Question 2
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?
Answer
Haven’t decided yet
Claude’s Thinking
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
Question 1
‘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?
Answer
Aspirational, but I’ve been doing piano daily for a month and want to continue it, probably overcommitted though
Question 2
‘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?
Claude’s Thinking
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
Question 1
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?
Answer
Still exploring options
Question 2
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?
Answer
Ok with the mix, also ok with more than 6
Claude’s Thinking
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
Question 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?
Answer
Core trips survive
Question 2
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?
Answer
Need to define it, probably frequency based
Claude’s Thinking
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
Question 1
‘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.)?
Question 2
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)?
Answer
Existential/philosophical
Claude’s Thinking
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
Question 1
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?
Answer
I drafted quickly. Weight is super high priority, not sure it’s the ‘biggest’ item
Question 2
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?
Answer
That one is private
Claude’s Thinking
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
Question 1
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?
Answer
Link but don’t explain
Question 2
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?
Answer
Perhaps we can flesh it out more. [Provided detailed travel calendar through May]
Round 12: Summer Structure & Political Scope
Question 1
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)?
Answer
Hunting is Oct, boys trip TBD, summer trip is an undefined road trip w/ exception of June Colorado
Question 2
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?
Round 13: Unwritten Fears & Failure Scenario
Question 1
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?
Answer
The leave decision, also unknown unknowns
Question 2
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?
Answer
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.
Claude’s Thinking
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
Question 1
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.
Answer
Didn’t try is worse
Question 2
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’?
Answer
The practice faded naturally
Claude’s Thinking
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.
Claude
Key insight: “didn’t try” is worse than “tried and failed” – that’s important for how you frame the misogi. And the meditation risk is natural fade, not failure despite trying. A few more.
Round 15: Kids Balance & Unknown Unknowns
Question 1
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’?
Answer
Both equally at risk
Question 2
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?
Answer
I just mean I’m not sure I captured all my goals
Claude’s Thinking
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
Question 1
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?
Answer
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
Question 2
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?
Claude’s Thinking
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
Question 1
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?
Question 2
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?
Claude’s Thinking
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
Question 1
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’?
Answer
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.
Question 2
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’?
Answer
Image transformation
Claude’s Thinking
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
Question 1
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?
Question 2
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’?
Round 20: Birthday & Post Format
Question 1
When do you turn 40? This affects the weight deadline framing and potentially other timing.
Question 2
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.
Round 21: Vulnerability Level & Anything Else
Question 1
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.
Question 2
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?
Answer
Check the AI investing and tax note I just sent
Jon
I also want to make specific AI investments and be smart about taxes
Round 22: AI Investing & Tax Focus
Question 1
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?
Question 2
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)?
Round 23: Final Check
Question
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?
Claude’s Thinking
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.
Claude
Interview complete. Now I’ll write the comprehensive spec to the file, incorporating everything we discussed.
Writing the Spec & Blog Post
Claude
Done. I’ve written the comprehensive spec. Key additions from the interview:
- New goals surfaced: Marriage, political involvement, AI focus (building/upskilling/investing), taxes, alternative income stream
- Expanded to 15 goals (dropped the arbitrary “Top 10” constraint)
- Grouped by domain: Health, Family, Work/Life Direction, Hobbies, Financial/AI, Political
- Added “What Failure Looks Like” section based on your answers
- Added “Elephant in the Room” about the leave decision tension
Jon
Now I want you to write the actual blog post based on it and my original content. Make it in a new file.
Claude
Done. Created 2026-goals-post.md. What I did:
- Wrote it in your voice—raw, honest, first-person
- Reorganized for narrative flow rather than spec structure
- Led with the weight story (concrete, vulnerable) then pivoted to the bigger existential questions
- Cut the “Interview Notes” section entirely
- Kept the self-aware acknowledgment of overcommitting
- Ended with the public accountability framing
Jon
Now reformat it for WordPress
Claude
Done. Reformatted with WordPress HTML: <h1>, <h2>, <h3> for headings, <strong> for bold, <ul>/<li> for lists, <blockquote> for quotes, <hr /> for horizontal rules.
Round 24: Emergency Preparedness (Post-Interview Addition)
Jon
I want you to add emergency preparedness to the file
Question 1
What does emergency preparedness mean for you – natural disaster prep (earthquake kit, supplies), financial emergency fund, medical/health preparedness, or something broader?
Answer
Natural disaster prep
Question 2
Where should this live in the post – as a new goal under an existing category, or its own section?
Summary
Jon
How many questions did you ask here?
Claude
During the main interview for the blog post, I asked 44 questions across 23 rounds of the AskUserQuestion tool. Then 2 more questions when you asked to add emergency preparedness. Total: 46 questions.
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