Author: jon cosgrove

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?

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?

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.

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?

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?

‘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?

‘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’?

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?

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?

‘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?

‘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?

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?

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?

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?

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?

‘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.)?

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)?

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?

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?

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?

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?

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)?

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?

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?

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?

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.

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’?

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’?

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?

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?

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?

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?

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?

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’?

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’?

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?

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 do you turn 40? This affects the weight deadline framing and potentially other timing.

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.

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.

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?

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?

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)?

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?

What does emergency preparedness mean for you – natural disaster prep (earthquake kit, supplies), financial emergency fund, medical/health preparedness, or something broader?

Where should this live in the post – as a new goal under an existing category, or its own section?