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.

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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.

Health & Appearance

Weight – less than 200 pounds before my birthday. Non-negotiable.

Meditation – I did this consistently from mid-2020 to 2022 and had the best mental health I’ve had in years. Then the practice just lapsed in favor of day to day stuff. I want it back.

Look and feel great – I’ve been anticipating this 40 year b-day for months now. I’ve grown out my hair and have a bit of a hairstyle, I’m losing weight, and plan to buy some non threadbear clothing. Sounds simple, but it’s an image transformation grasping onto my last decade of ‘youth’ 🙂

Family & Relationships

1:1 time with the kids – 1:1 time with the kids is always the best for both Megan and I. We want to make this more frequent.

Marriage – Monthly date nights. This one was Megan’s suggestion and I think it’s a great one. We even have a babysitter now

Friends – Make new ones and invest in the few I have.

Emergency preparedness – Earthquake kits, go-bags, supplies, home safety. We used to have this in place and lost it in all the moves. Should be an easy win this year.

Work & Life Direction

Take the summer off – I’m requesting three months of leave. If it’s denied… I’m not sure what I’ll do. This matters enough that quitting is on the table, though that would be extremely destabilizing, again. The plan is a grand summer road trip with a stop for June in Colorado.

Build an alternative income stream – Connected to the business goal. Even small is fine if I can see growth.

Hobbies & Crafts

Piano – Every day. I’ve got about 2 months of momentum already and I want to keep it going.

Sewing – Four garments this year. Including matching shirts for Max and Dad.

Finish Megan’s mirror – Long overdue. 10 years in fact.

Financial & AI

AI – I don’t want to miss this wave. Three dimensions: build something AI-related or AI-enabled (the business), upskill in the tools, and position investments in both public markets and private opportunities.

Taxes – Be smarter about them. Current optimization and future planning both.

Choose Your Misogi

“A misogi is an old Japanese ritual… you do one big year-defining thing every year.”

This is your magnum opus for the year. The biggest thing you have to show for it.

My Misogi: Make a product and start a small business.

I’m still exploring what to build, but the constraints are clear: it needs to ship and make money. This serves as an exit ramp test, a side hustle, and an experiment for what’s next—all at once.

Schedule 6+ Mini-Adventures

Kevin’s Rule: Every other month, do something for one day that breaks your routine. Six times a year minimum. I’m okay with more.

  • Sunrise surfing
  • Sailing on the bay (deckhand in a race?)
  • Rock climbing outside or mountain biking with the kids
  • Trail maintenance / volunteer day
  • Mountain bike race
  • Culinary week
  • Comedy show
  • Concert

Mix of solo, family, and social. The list has eight items because I don’t need to limit myself to six.

Stack Winning Habits

Jesse’s philosophy: “We are basically a product of winning habits, winning routines, and a winning mindset.”

Add one winning habit each quarter. Haven’t decided which quarter gets which yet.

  • Brush teeth (2x a day) and whiten
  • Buy clothes and spend at least a minute looking presentable each day
  • Computer / education time with the kids
  • Monthly date night

Travel

Here are our high level travel plans for the year.

January – Snow trip (long weekend)

February – Mom visit, LA, Channel Islands, or Hawaii? Kids are off the 13th through 17th.

March – Camping, and maybe a Disney cruise around the 15th when there’s no school.

April – Spring break desert trip with the Leightons

May – More camping, then Missouri for Catie’s graduation

Summer – The Grand Summer Extravaganza. Contingent on the leave approval, but the structure is an undefined road trip anchored by Colorado in June. Fingers crossed…

October – East coast, plus hunting trip (Jade’s wedding?)

TBD – TBD guys trip

What Would Make This Year a Failure

I thought about this carefully. 2026 would be a failure if:

  • I’m still above 200 pounds.
  • I didn’t launch anything (didn’t try is worse than tried and failed)
  • I’m still in the same job, same place, same routines—nothing changed
  • The existential questions are still unanswered, still stuck in the same crisis
  • My family and relationships suffered because I was chasing goals
  • My mental health declined and the meditation practice faded again

The Elephant in the Room

The summer leave decision is the thing I keep circling back to. There is a book titled 18 summers. I haven’t read it, and don’t know for sure what it’s about, but my take away from reading (the cover) is that time is going quick with the kids. I’ve been working full time in a corporate job for 15 years. I want a break and our kids are in their prime time that tons of older parents say they miss. I’ve wanted a summer off for 2 summers in a row now. If the time off is denied and I quit, that destabilizes everything again for us and it’s been a long 18 months already. It’s not an easy call.

The interplay between the work transition, the location and cost of living decision, and wanting to get involved—they’re all connected and all unresolved.

I’m also aware I might be overcommitting. Piano every day, meditation, building a business, summer travels, 1:1 time with both kids, date nights, friends, sewing, political involvement… it’s a lot. I’ve got momentum on piano and weight loss. The rest… we’ll see what sticks.

I’m publishing this mostly for myself. Public accountability. If you’re reading this and we know each other, feel free to ask me how it’s going.

I used Claude code to interview me after making an initial draft of this and then mades subsequent revisions. Super helpful. Here’s the command and link to the full chat in another post

https://www.cosgrove.blog/2026/2026-goals-chat-help-from-my-intern-claude/


---
description: Interview me about the plan
argument-hint: [plan]
model: opus
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Read this plan file and interview me in detail using the AskUserQuestionTool about literally anything: technical implementation, UI & UX, concerns, tradeoffs, etc. but make sure the questions are not obvious.

Be very in-depth and continue interviewing me continually until it’s complete, then write the spec to the file.