40 under 40 Action Plan

Full timeline of activities to reach my 40 under 40

Random Observation/Comment #879: Do with intention. I feel like AI will give us the ability to create and build anything. Now we just need to decide for ourselves what the focus will be.

//AI Generated with ChatGPT4o through a series of prompts from building this action plan

Why an Action Plan?

I have around 1.5 years left to finish my 40 under 40 list. That’s not a lot of time! To keep myself in check, I used deep research and reasoning with ChatGPT to help me map out my goals and how to approach reaching my goals.

Summary: Out of 40 goals, 18 are fully completed. The remaining 22 goals are either in progress, in planning, or ongoing habits that need to be accomplished or maintained by Dec 2026. These remaining goals will be the focus of the action plan below.

Action Plan by Category

To tackle the diverse goals, we’ll group them into categories by type: Travel & Adventure, Fitness & Physical, Learning & Creativity, Financial & Career, and Personal Growth & Relationships. For each category, we outline the remaining goals, practical habits/routines to adopt, an approximate timeline, and prioritization tips. This plan is personalized to your life (e.g. incorporating family) and designed to help you complete everything before your 40th birthday.

Travel & Adventure Goals

Goals in this category (Incomplete):

• Visit 50 Countries (Goal #1) – 5 countries left to visit.

• Cross-Country Road Trip (Goal #2) – Plan and execute a coast-to-coast RV trip. We may alter this to going to more National Parks.

• Attend 20 Weddings as a Guest (Goal #25) – Attend ~13 more weddings (currently at 8). (This depends on external invitations, but we include it here since it may involve travel and adventure.)

  • This is probably the hardest one because I can’t force my friends to get married. Realistically, I have 1 more wedding to attend before I’m 40 that’s already planned.

Challenges: These goals require significant time and planning (and, for weddings, some luck and social opportunity). Visiting 5 new countries and doing a long road trip in ~1.5 years means you’ll need to actively plan travel. Attending weddings is partly out of your control, but you can position yourself to not miss any opportunities.

Habits & Routines:

• Travel Planning Routine: Allocate time every month to plan upcoming trips. For example, set aside one weekend a month to research destinations, check flight deals, and coordinate schedules. Regular planning ensures you’re ready to seize holidays or breaks for travel.

• Travel Savings Habit: Continue contributing to a “travel fund” each paycheck to finance these adventures. This ensures you have budget set aside for flights, lodging, and the RV rental for the road trip.

• Stay Socially Engaged: Keep in touch with friends (ties into Goal #19) and be active in your social circles so you’re naturally invited to events like weddings. When someone mentions an engagement or an upcoming wedding, express your enthusiasm—be genuinely supportive and ready to attend.

Timeline & Pacing:

• 2025: Aim to visit 3 new countries by the end of 2025. Plan one trip in Summer 2025 (perhaps a family trip or solo adventure abroad), another in fall (maybe a shorter international trip or a combo if work travel can be leveraged), and one around the December holiday season (could be tied into a vacation or visiting family overseas). Spread them out to have recovery and planning time in between.

  • Japan with family isn’t a “new” place, but I consider it a fruitful family trip

• 2026: Plan to visit the remaining 2 countries by mid-2026. For instance, one in spring 2026 and one in summer 2026. This leaves some buffer in case any plans slip. By fall 2026, you should have hit 50 countries.

• Cross-Country Road Trip: Schedule the road trip for summer 2026 if possible (or spring 2026). That gives you time to plan the route and logistics in 2025. It could be a two- to three-week trip. If work schedule is a concern, consider splitting it into segments taken over a couple of long holiday periods (e.g., part during a July 4th break and part later). Ideally, doing it in one continuous journey is most fulfilling. Have a concrete date by early 2026 to start the trip.

• Weddings: You can’t fully schedule these, but you can anticipate a few. In 2025 and 2026, aim to attend any wedding invitations you receive. Given many friends are already married, this goal is a stretch. If by mid-2026 you are short, consider broadening the scope: perhaps attend a wedding of a more distant acquaintance or accompany your spouse to any of her friends’ weddings. Each opportunity counts. (Ultimately, don’t worry if the number doesn’t reach 20 exactly. We should focus on cherishing the ones you do attend.)

Long-term vs. One-off: Visiting each country is a one-off event, but achieving the total of 50 is a long-term goal requiring multiple events. The road trip is a one-off experience (though a big one) – it requires long-term preparation but is achieved in one multi-week effort. Attending weddings is event-based, but the “long-term” aspect is maintaining your social network (overlap with personal relationships) to be invited. Prioritize locking in the trips (which you can control) early, while staying flexible for weddings.

Tips for Tracking & Motivation:

• Use a travel checklist: Maintain a list of countries with checkboxes. Mark off each new country visited (and maybe write a one-line highlight of the trip to make it memorable and motivating). Seeing 45/50 progress become 50/50 will be highly motivating.

• Calendar blocking: Put tentative travel dates on your calendar now. Having “Trip to [Country]” penciled in for specific weeks in 2025/2026 makes the goal real and keeps you accountable to plan around it.

• Visual motivation: Put up a world map at home and pin the countries visited (and maybe mark the ones left to visit). This visual reminder in your daily environment keeps you excited about filling in the map.

//Kept building on this since around 2009. My Mom made all the pins with wax on the top so it’s easier to see.

• For the road trip, outline the route on a US map and track planning milestones (route finalized, RV reserved, key stops identified). Treat it as part of the fun! Each planning session is bringing you closer to the dream.

• For weddings, keep a list of friends who haven’t married yet (or who might have upcoming ceremonies). While you can’t control this, it helps to know whom to congratulate when the time comes. Celebrate each wedding you attend by maybe writing a short reflection afterward – it will help you value the experiences even if you don’t reach 20.

Fitness & Physical Goals

Goals in this category (Incomplete):

• Learn 5 Fun Dances (Goal #22) – In progress.

• Achieve Table Tennis 1900 (IRL) / 3100 (VR) (Goal #26) – In progress (VR ~2900, physical game improving but might be getting worst as I get better in VR).

  • [ALT Goal] Achieve a consistent 250ft backhand disc golf drive (Goal #26B). Get a par on Owl’s Den front 9 holes - Current personal best is a +2. All progress recorded on UDisc. Drives are around 200ft.

• Do a Handstand (Goal #28) – In progress (working on strength and balance).

  • [ALT Goal] Palm the floor or do a split (Goal #28B) - Currently my flexibility is awful, but I can commit to doing flexibility exercises.

(Note: These are the explicitly physical goals. Other goals like the cross-country road trip involve stamina but are covered under Travel. Cooking or brewing were physical but already done.)

Challenges: These require regular practice and training. They are skills that improve gradually: dance techniques, sports ability, and strength/balance for a handstand. The key challenge is staying consistent with practice amidst a busy schedule.

Habits & Routines:

• Weekly Dance Practice: Choose specific dances you want to master (e.g. Moonwalk, salsa step, a popular TikTok dance, etc.). Dedicate 2 short dance practice sessions per week (say 30 minutes each) to learning and refining one dance at a time. You might use online tutorials or even take a fun dance class for a style you’re interested in. Rotate through different dances to keep it interesting, but ensure you can fully perform five distinct routines by the end. Perhaps focus on one new dance every 2-3 months.

  • In the next month, I’ll figure out which dance moves are best. I like the moonwalk and a better common dance move.

• Table Tennis Training Schedule: For VR table tennis, you’re already close to the 3100 rating – continue to play a few matches each week to keep sharp. For physical table tennis, consider joining a local club or finding a practice partner to play with weekly or biweekly. Even 1 hour of real table tennis practice every week can dramatically improve your skill over a year. If possible, enter a local amateur tournament by mid-2026 to gauge your rating progress and get competitive experience.

  • This might not be as realistic based on the time I’ve been spending on disc golf and how much I’ve been training in person. I’m going to revisit this in 6 months after I’ve done a full year of disc golf.

• Handstand Exercises: Incorporate a short daily fitness routine focusing on upper body and core strength (10–15 minutes a day). Key exercises: wall-assisted handstands, shoulder strength drills (like pike push-ups), and core workouts (planks, hollow holds). Additionally, practice the handstand itself 3-4 times a week against a wall for balance. Gradually increase the time you can hold it. Also, work on flexibility in wrists and shoulders to prevent injury.

  • The dancing and general reduction in drinking should help with this. I may also replace this with a rock climbing/bouldering goal, but this is TBD. I may also do an ALT exercise related to flexibility and palming the floor or doing a split

Timeline & Pacing:

• By end of 2025: Aim to have 3 out of 5 dances learned and be able to perform them confidently (perhaps show them off at holiday parties or family gatherings – fun and accountability!). Also by late 2025, reach the VR table tennis 3100 rating (at your current pace, likely attainable well before then) and be noticeably closer to the physical 1900 rating (maybe in the 1700+ range, depending on opportunities to play). By this time, you should also be able to kick up into a handstand against a wall and hold it for a few seconds.

• By mid 2026: Learn the remaining 2 dances (perhaps one in early 2026, one by mid-year). Achieve the physical table tennis 2000 rating by mid 2026 – this might require regular competitive play, so plan to consistently train and possibly participate in a league or ladder in early 2026. For the handstand, by mid 2026 you should aim to hold a free-standing handstand (even if briefly).

• By Dec 2026: Be performance-ready with all 5 dances (maybe record yourself doing them for fun or perform at your 40th birthday!). Maintain table tennis skills – by this time you should have hit both rating targets (celebrate this, perhaps by hosting a VR TT match with friends or a real-life ping-pong party). For the handstand, aim to hold a handstand for at least 5 seconds unassisted by your 40th birthday. This is a clear, attainable marker of success.

Long-term vs. One-off: These are long-term skill-building goals that require steady progress. None of them can be done in one sitting; they need continuous effort over months. The one-off “completion” moments will be: being able to bust out a dance routine, hitting the rating, and executing a handstand. Prioritize regular practice (long-term habit) over any cram sessions. Consistency beats intensity here.

Tips for Tracking & Motivation:

• Use a Habit Tracker: Log your practice sessions for dance, ping-pong, and handstand exercises. For example, use an app or a journal to tick off each day you practiced. This helps you see streaks and stay accountable.

• Set Mini-Milestones: Break each goal into sub-goals and celebrate when you hit them. E.g., “Learned the full footwork of the Moonwalk” or “Held a handstand for 1 second” or “Increased ping-pong rating by +100 points”. Treat yourself with small rewards (like a relaxing evening or new ping-pong paddle) when you hit these mini-milestones.

• Find a Community or Buddy: It’s more fun to practice with others. Maybe get your spouse or a friend to join a dance class with you, or have a weekly ping-pong game with neighbors. This adds social motivation and accountability.

• Visual Progress: Record short videos periodically – e.g., your dance practice or your handstand attempt each month. When you look back, you’ll see the improvement. This can be incredibly motivating on days when progress feels slow.

• Stay inspired: Follow a couple of dance or fitness content creators who are around your age or also learning new skills. Seeing others achieve these skills can inspire you to keep at it.

Learning & Creativity Goals

Goals in this category (Incomplete):

• Record an Audiobook (Goal #5) – In progress (narrating your books).

• Create a 5-minute AI-Generated Video (Goal #9) – In progress (several shorter AI videos done; goal is a full 5-min video).

• Publish 30 Video Workshops/Lectures (Goal #16) – In progress (25/30 done; 5 more to record and publish).

• Learn 5 Card Magic Tricks (Goal #24) – In progress (learning tricks via saved videos, not all mastered yet).

• Play a Full Two-Handed Piano Song (Goal #23) – In progress (learning piano; can play bits, but not a full song smoothly yet).

• Learn 5 Fun Dances (Goal #22) – In progress. (Listed under Fitness, but also a learning goal. Already covered in Fitness, so we’ll focus here on the others.)

(These goals involve acquiring knowledge or creative skills and producing creative outputs. They require practice, learning, and content creation.)

Challenges: The main challenge is time management and skill development. Recording an audiobook and finishing video lectures are big time commitments that also require creative energy. Learning piano and magic tricks from scratch requires consistent practice and possibly instruction. The AI-generated video needs both creativity and technical work with AI tools. Balancing these creative projects with work and family is tricky, so planning and perhaps combining efforts will help (e.g., some goals might overlap or help each other).

Habits & Routines:

• Audiobook Routine: Treat the audiobook recording like a mini-project over a set period. For example, schedule 2 recording sessions per week (1-2 hours each). Perhaps early morning or late evening when the house is quiet. Aim to record one chapter or a set number of pages per session. Build a ritual: warm up your voice, set up equipment, and record in a quiet space regularly. Consistency will help you chip away and not strain your voice by doing too much at once.

  • This is an interesting one because it’s just reading. Maybe I’ll just turn the audiobook into a podcast.

• Video Creation Routine: For the remaining 5 video workshops, schedule a bi-weekly or monthly filming day. For instance, plan to film one video lecture on the first Saturday of each month until done. Prepare slides or notes in advance (perhaps during weekday evenings). This way, you’ll finish the 5 by ~5 months. For the AI-generated 5-min video, break it down: script writing (one week), gather media or generate assets (another week), then editing. You could dedicate a month of part-time effort for this: e.g., May 2026 – “AI Video Month” where you spend a few hours each week on it.

  • This might not be too bad because I need to release videos for the DIN YouTube Enablement Series.

• Practice Schedule for Piano & Magic: Carve out 15-30 minutes a day for skill practice (either piano or magic tricks). Perhaps alternate days: e.g., piano practice Monday, Wednesday, Friday; card trick practice Tuesday and Thursday (and maybe a weekend session for whichever you prefer). Little and often is effective for building muscle memory for piano and sleight-of-hand for magic. Keep a keyboard accessible at home so you can sit for a few minutes anytime. Keep a deck of cards on your desk to fiddle with during breaks – practice shuffles or a trick sequence to keep it fresh.

  • I need to consider which two handed songs I can remember to play that might be a fun popular song.

  • I think I need to figure out the magic trick I want to do. I’ll create a folder in YouTube Shorts or Instagram Reels that shows the magic trick reveal and the dance move.

• Leverage Family Time: Some of these can be made family-inclusive. For example, perform simple card tricks for your daughter Evie – kids are a forgiving audience and will be delighted, which motivates you to get better. Or involve her in the AI video (maybe she can appear or help pick the theme) to make it a fun joint project. If Evie is learning an instrument or loves music, practice piano while she practices something, turning it into a family “music time.” This can help you stick to the routine.

Timeline & Pacing:

• Audiobook: Depending on book length, aim to complete recording by end of 2025. If you start now with two sessions a week, you could finish recording in a few months. Allow time for editing the audio as well (maybe by early 2026 have the final audiobook ready). This will be a huge accomplishment to check off well before the deadline.

• Video Workshops: You have 5 left. You can finish these by mid-2025 if you do one per month, or by end of 2025 at a slower pace. Certainly, plan to complete all 30 by 2025 so that in 2026 you’re done with this goal and can perhaps shift focus to promoting them or your subscriber goal. Mark the calendar for each of the 5 videos (e.g., one per month May through September 2025) and stick to it.

• 5-min AI Video: Set a goal to have this finished by mid-2026. Perhaps allocate a specific timeframe like April–May 2026 to devote to it (after you’ve done the video lectures). Because you already have experience with shorter AI videos, you can build on that. Having it done by mid-2026 gives you time in late 2026 to share it (maybe premiere it on your 40th birthday as a fun celebration!).

• Piano Song: Choose the song you want to perform ASAP (if you haven’t already). A realistic timeline: learn to play with hands separately by mid-2025, hands together (slowly) by end of 2025, and polish it to performance level by mid-2026. If you practice consistently, a year or so is reasonable for an amateur to learn a moderate-difficulty piece. Consider scheduling a little “recital” for yourself in mid-2026 – e.g., plan to play the song for your family or friends (or record a video) by that time. That event on the calendar will motivate your practice.

• 5 Magic Tricks: You could tackle roughly one new trick every 2-3 months. For instance, master one trick by June 2025, another by late summer, etc., and all five by end of 2026. Magic tricks often require practice to perform smoothly and confidently. By planning one at a time, you won’t overwhelm yourself. Perhaps aim to have 2–3 solid tricks ready by end of 2025 and all 5 by fall 2026, so you can even perform a mini magic show during the holidays or at your 40th birthday party!

Long-term vs. One-off: Recording an audiobook and creating the AI video are one-off projects – they have a clear end product, but need sustained work over weeks or months. Publishing video workshops is a series of one-offs that form a larger body of work (almost done!). Piano and magic are skills (long-term learning) but have specific one-off completion criteria (perform a song, do 5 tricks). Prioritization: It might help to tackle one big project at a time in this category to avoid overload. For example, focus on finishing the audiobook while casually practicing piano/magic on the side (as a break). Once audiobook is done, focus on finishing video workshops, then the AI video. Skill goals (piano, magic, dance) can be ongoing in parallel since they require daily small practice rather than large blocks. Be careful not to push all creative projects to the last minute—spread them out and perhaps alternate technical/creative tasks to keep your enthusiasm high.

Tips for Tracking & Motivation:

• Project Plans: For the audiobook and AI video, create a simple project plan or checklist. List all chapters to record or all steps of the video project, and check them off as you complete them. This gives a sense of progress and accomplishment at each step.

• Public Accountability: Leverage your blog or newsletter. Announce that you’re working on an audiobook version of your book or a special AI video project for your 40th. Regularly updating your readers on progress can motivate you to avoid procrastination (plus it builds excitement among your audience).

• Learning Logs: Keep a small notebook or digital note for piano and magic practice. Jot down what you practiced and any breakthroughs or lingering challenges each week. Looking back at entries like “Week 1: can barely coordinate left-hand on piano” and later “Week 12: played through entire song slowly” will show progress.

• Celebrate Creative Output: When you finish each video workshop or complete a chapter of the audiobook, allow yourself a bit of celebration – maybe a nice dinner or an evening off to watch a movie. Creative work can be draining, so acknowledging each finished piece will keep you energized for the next.

• Stay Curious and Have Fun: Remember why these are on your list – they’re fun and fulfilling! If a particular trick or song frustrates you, switch to a different one for a while to keep momentum. Perhaps involve friends – e.g., have a friend who plays guitar accompany your piano, or exchange magic tricks with a colleague who is also learning. Keeping it fun means you’ll be more likely to stick with it even on busy days.

Financial & Career Goals

Goals in this category (Incomplete):

• Explore 5 Streams of Income (Goal #12) – In progress (experimenting with side-income ideas).

• Maintain a Profitable Company (Goal #30) – Ongoing (company is profitable; goal is to sustain and grow it).

• Reach 2000+ Subscribers/Connections (Goal #17) – In progress (currently ~400 newsletter subscribers).

(These goals relate to financial stability, career/business growth, and personal brand/audience – which can tie into financial success. Some of your other career achievements, like breaking into AI (#3) and advisor roles (#18), are completed – congratulations! Now the focus is on diversifying income, sustaining your business, and growing your platform.)

Challenges: Time and focus are limited resources. Testing multiple income streams while running a company and also producing content to grow subscribers is a juggling act. There’s a risk of stretching yourself thin. The key is to integrate these goals with each other and with your existing work where possible. Also, growing subscribers from 300 to 2000 in 1.5 years will likely require consistent output and marketing – something you noted you haven’t focused on yet.

Habits & Routines:

• Income Streams Experimentation: Dedicate a small, regular time block to exploring new income ideas. For example, every two weeks, schedule a 1-2 hour “income stream lab” session. In these sessions, pick one idea from your “30 Streams of Income” list and work on it – this could mean setting up a small experiment or researching and taking a concrete step. For instance, if one idea is affiliate marketing, one session might be signing up for an affiliate program and adding links to your blog; another session might be creating a simple digital product to sell. Treat these like mini-hackathons for personal finance.

  • This might be an app that I’ve been building. It’s actually pretty nice that the company is fully setup so it’s just setting up the SaaS.

• Business Health Check-ins: For your company, institute a routine of monthly reviews. In a short monthly meeting with yourself (and any partners or your spouse if she’s involved), go over key metrics: revenue, expenses, any new opportunities or risks. This habit ensures the company stays on track. Also, set aside time each week (even just 30 minutes) to address something that will keep the business healthy – e.g., following up on invoices, exploring a new client lead, or improving a product. Maintaining a profitable company is about vigilance and continuous improvement, not just hitting a number once.

• Audience Growth Routine: To reach more subscribers, consistency is key. Commit to a content schedule for your Life in Lists of 30 blog/newsletter – e.g., publish at least 1 quality post per week (or 1 every two weeks, whatever is sustainable). After publishing, spend another hour on promotion: share the post on social media, engage in a relevant community or forum, or reach out to other bloggers for cross-promotion. Additionally, consider adding a habit: “Every week, do one thing to promote or improve the newsletter” – this could be as simple as inviting friends to subscribe, or as involved as running a small ad campaign or writing a guest post on a related publication.

Timeline & Pacing:

• 2025: Use 2025 as a year of experimentation and steady growth. By the end of 2025, aim to have tried at least 3 out of 5 new income stream ideas in some form. They don’t all need to be successful, but you should have some data on a few. In parallel, by end of 2025 try to increase your newsletter subscribers to, say, 500-600 through the consistent posting + promotion strategy (that’s roughly doubling your current base, a realistic interim target). Also, in 2025 focus on consolidating your company’s profitability – for example, increase net income or secure a couple of new contracts to ensure revenue for 2026.

• 2026: In the first half of 2026, experiment with the remaining 2 income stream ideas from your list of 5. By mid-2026, identify which of the 5 streams seem most promising or enjoyable to continue. The goal isn’t necessarily to have all 5 running actively, but to have explored them and ideally have 1-2 additional steady income sources established (even if small). By end of 2026, you might have, say, a rental property venture started, a monetized blog, a side consulting gig, or some investment income – whatever aligns with your interests.

• Subscribers Goal: Ramp up efforts in 2026 to hit the 2000 subscriber mark. Growth can be exponential as you get more content out and word-of-mouth spreads. Consider a mid-2026 checkpoint: ~1000 subscribers. Then intensify marketing the last 6 months (maybe around the time you launch your next book or some big event like your 40th birthday, which could attract attention to your story). Aim for 2000 by Dec 2026 by possibly doing a “road to 40” campaign or special series of posts that draw in new readers.

• Company: By the time you turn 40, the aim is that Wanessa Labs, Inc remains profitable for the year and ideally has grown. You might set a measurable target like “maintain profitability with at least X% profit margin in 2025 and 2026” or “achieve $Y in revenue by end of 2026.” Having a target will help you know what “maintain” means. Timeline is ongoing, but the key is to not neglect the business while chasing other goals – hence the weekly and monthly routines to keep it on track.

Long-term vs. One-off: Maintaining a company is clearly a long-term continuous effort (no real finish line, just don’t let it falter by 40). Growing subscribers is also a gradual process – there isn’t a single action that achieves it; it’s the accumulation of consistent content and engagement. Exploring income streams has elements of both – each stream idea might be a one-off project to set up (e.g., create a small online course, or start renting out something, etc.), but you want to end up with sustainable streams that last. Prioritize building habits that drive these goals (because small actions done regularly will compound financially), but also knock out one-off tasks like setting up accounts, creating products, attending networking events to seek advisory opportunities, etc. Balance is key: don’t start all streams at once; do them one by one. And allocate specific periods to focus on subscriber growth (like a marketing push when you have new content or around events).

Tips for Tracking & Motivation:

• Financial Tracking: Keep a simple spreadsheet or dashboard for your new income streams and company finances. Update it monthly with revenue from each stream (even if $0 for some months while experimenting) and company profit. Seeing the numbers (even small ones growing) can be motivating and keeps you informed. It’s encouraging to watch a side project go from $0 to, say, $50 a month to $200 a month, etc.

• Use OKRs or SMART Goals: Consider setting specific quarterly goals for these. E.g., “Q3 2025: Launch one new income stream (Etsy store or ebook) and gain first $100 from it” or “Q1 2026: Reach 500 subscribers”. These give you shorter targets to hit on the way to the big goal, which helps maintain momentum.

• Accountability Partner: If possible, find a colleague or friend who is also working on a side hustle or growing a blog. Do brief monthly check-ins – share your subscriber count and income experiments, and they share theirs. Encouraging each other and maybe even friendly competition can light a spark to keep pushing.

• Educate and Inspire: Keep yourself motivated by learning about others who achieved similar goals. Maybe listen to a podcast about entrepreneurs building multiple income streams or read a newsletter about growing an audience. This not only gives you new ideas but also reinforces that the effort pays off.

• Tie into Personal Mission: Remember that your financial and career goals feed into providing for your family and enabling your adventurous life. When motivation dips, think about how an extra income stream or a robust business will give you freedom (maybe funding those trips or ensuring security for Evie’s future). Keeping that “why” in mind makes the grind feel worth it.

Personal Growth & Relationships Goals

Goals in this category (Incomplete/Ongoing):

• Stay Meaningfully Connected (Goal #19) – Ongoing (weekly messages to old friends).

• Volunteer with Evie’s School (Goal #20) – Ongoing (help out with school events regularly).

  • This has been fun for the runs and Dragon Dads

• Special Gift for Parents (Goal #21) – In planning (yet to decide/execute a meaningful gift).

• “Taskmaster”-like Competition (Goal #31) – In planning (idea for a fun competition, possibly on 40th birthday).

• Teach Evie to Cook a Meal (Goal #34) – In progress (introducing cooking to your daughter).

• Family Dinners Together (Goal #35) – Ongoing (regular family meals at the table).

• Enjoy Evie’s Childhood (Goal #36) – Ongoing (be present and cherish moments).

• Build a Loving Community/Neighborhood (Goal #37) – Ongoing (fostering friendships and community traditions).

• Stay Happily Married (Goal #40) – Ongoing (nurturing your marriage).

(These goals center on relationships – family, friends, community – and personal character/happiness. Many are ongoing habits rather than finite tasks, so the focus is on maintaining consistency and depth in these areas.)

Challenges: The primary challenge here is that these are important but never “urgent” things. It’s easy for work or other goals to consume your time, leaving relationships inadvertently neglected. Also, some are a bit vague (e.g. “enjoy childhood” is abstract) or one-time events that need planning (the gift for parents, the Taskmaster party). Ensuring you give adequate time and heart to these amidst everything else is key. The good news is many can be integrated into daily life and even overlap with each other (family dinners help you enjoy your child’s company, volunteering at school builds community, etc.).

Habits & Routines:

• Weekly Connection Habit: You’re already sending a message to an old friend or “blast from the past” weekly. Keep this up and maybe formalize it: e.g., every Sunday evening, send a thoughtful note or make a call to someone you haven’t seen in a while. Create a list of people you want to reconnect with over the next 18 months. One idea: combine this with Goal #25 (weddings) – by staying in touch, you’ll naturally be top-of-mind for invites.

• Family Time Rituals: Continue and strengthen routines that foster family bonding: for example, family dinner at the table a certain number of nights a week (Goal #35). If currently it’s sporadic, aim for at least 3-4 times a week where everyone sits together with no devices, sharing the day. Maybe introduce a fun dinnertime question tradition (“best part of your day?”) to make it something Evie looks forward to. Also, perhaps institute a family game night or outing once a week or biweekly – this helps “enjoy Evie’s childhood” (Goal #36) by making memories together.

• Date Nights and Marriage Check-ins: To stay happily married (Goal #40), prioritize your relationship with your spouse. Set a habit of a date night once a month (more if possible) – just you and your wife, doing something you both enjoy (dinner, movie, hike, etc.). Also, a habit of short daily check-ins can be great: e.g., a walk together after dinner or a few minutes chatting before bed about the day, maintaining emotional connection.

• Volunteering and School Involvement: Since you’re already helping at Evie’s school, consider taking on a slightly bigger role for a specific event or committee in the upcoming school year. For example, if there’s a school fair or PTA committee, volunteer to lead or co-lead a portion. This will fulfill the volunteering goal (Goal #20) with more impact and also strengthen ties with other parents (feeding Goal #37, community). Make it a habit to ask the school or teacher every few months, “How can I help?” so you consistently contribute.

• Cooking with Evie: Make weekend cooking with your daughter a routine. For instance, every Sunday afternoon, have a “Daddy-Daughter Cooking Hour.” Start with very simple things (scrambled eggs, sandwiches, baking cookies) to build her confidence and interest. Over time, let her take the lead more and more. By doing this regularly, you’ll achieve Goal #34 organically – one day she’ll surprise you by making a simple meal almost on her own.

Daddy-Daughter Cooking Challenge

• Planning the Special Gift for Parents: Schedule some time in the next month or two to brainstorm and decide what that special gift (Goal #21) will be. Perhaps it’s something like compiling a video of their life stories, organizing a surprise family reunion, or creating a photo book of memories. Once you have the idea, break it into steps and maybe work on it a little each week. For example, if it’s a video, each week in the fall of 2025 you could interview a family member or collect old photos. Treat it as a project with a deadline (maybe present it to them at a holiday in 2025 or on one of their birthdays/anniversary).

  • I should present this as a spreadsheet

• “Taskmaster”-like Competition Planning: Since this is envisioned around your 40th birthday, you have time to plan. Make it fun by involving friends early. Perhaps make a habit of brainstorming ideas for tasks/challenges whenever you gather with the “Northend Beefcakes”. You could even do a mini-trial run at a smaller party in 2025 to test the concept. As your birthday nears (summer 2026), start formally planning: venue (maybe your backyard or a park), list of challenges, invites, etc. This doesn’t need a frequent routine, but mark key planning milestones on a calendar so it doesn’t get forgotten.

Timeline & Pacing:

• Ongoing (Always): Goals like staying connected (#19), family dinners (#35), enjoying Evie’s childhood (#36), community building (#37), and your marriage (#40) are continuous. The aim by Dec 2026 is simply to have kept these up consistently. However, it might help to have some reflective checkpoints. For example, every 3 months, do a quick self-assessment: Have I been connecting with friends lately? How many family dinners did we manage? Are my wife and I feeling connected? Use these reflections to adjust if you’ve been slipping.

• 2025: By the end of 2025, try to complete the special gift for your parents (#21). That gives you plenty of time to plan something truly meaningful. Perhaps aim to give it to them for Christmas 2025 – a heartfelt holiday surprise. Also in 2025, make sure you are on track with volunteering (e.g., participated in multiple school events during the year). If by late 2025 you realize you haven’t done much at the school, that’s a cue to ramp up involvement in 2026 (maybe chaperone a field trip or start an after-school club).

• 2026: Host the “Taskmaster” competition around your 40th birthday in Dec 2026. Start concrete planning by mid-2026: set a date, inform friends to save the date, and prepare the tasks by fall 2026. This can actually serve as a grand finale celebration of completing the 40 under 40! Also, by 2026, hopefully the habit of cooking with Evie will have paid off – perhaps by summer 2026 she can independently cook a simple meal for the family (with supervision). If she does, that’s a perfect occasion to celebrate Goal #34 – maybe have her cook her grandparents a dish (combining with a family dinner).

• Milestones: While these aren’t easily quantifiable, you can still set a few targets to ensure progress: e.g., Number of school events volunteered in (aim for at least one per school semester), Cooking milestones with Evie (make breakfast together by mid-2025, let her take charge of a dinner by mid-2026), Friend connections (work through your list of old friends to message so that by 40, you’ve reconnected with, say, 50 people you care about). Setting these little targets can prevent complacency.

Long-term vs. One-off: Most of these are long-term lifestyle goals – you don’t really “finish” staying happily married or enjoying time with your child; you continually do them. The one-off items are the gift for your parents and the Taskmaster party – those you can plan and execute on specific dates. Prioritize the daily/weekly family and relationship habits above all, because they’re the heart of life. But also schedule the one-off special events (parents’ gift, birthday event) well in advance so they don’t get lost in the shuffle. The special gift for your folks might be the easiest to procrastinate – try to tackle that in 2025 so it’s not last-minute in 2026. The party will be a fun capstone – prioritize doing it even if some other goals slip, because it celebrates whatever you have achieved and brings your community together (which itself fulfills goal #37 in spirit).

Tips for Tracking & Motivation:

• Journal or Diary: Consider keeping a simple journal to record memorable moments in these personal areas. Jot down when you had a great family dinner conversation, or when Evie said something that reminded you why you’re savoring her childhood, or when you had a great date night. Reading back through these entries will motivate you to keep creating such moments, and it’s a treasure trove of memories.

• Habit Tracking for Habits: Use a calendar or habit-tracker for things like weekly friend reach-outs or family dinners. For instance, mark an “X” on days you have a family dinner. Try to maximize those X’s. Or keep a list of names of friends you’ve contacted and the date, aiming not to repeat the same few people too often.

• Feedback from Loved Ones: Ask your spouse occasionally how they feel about your work-life balance and family time. Ask your parents if they’d like to see you more or less of something. Sometimes a gentle outside perspective (“we’d love to have you over for dinner more often” or “it was great when you helped at the school event”) can motivate you to keep it up. Knowing that your efforts make others happy is a strong driver.

• Combine Goals for Motivation: Notice how many of these goals interconnect. Use one to motivate another. For example, involve your community friends in your family traditions (maybe a neighbor joins your family for dinner occasionally – mixing goal #35 and #37). Or involve Evie in preparing the gift for her grandparents (she could draw a picture or help pick photos – combining goal #34 with #21). When you combine them, you get double fulfillment and it reinforces why you’re doing this.

• Celebrate Relationships: While other goals have obvious celebrations (trip completed, product launched), don’t forget to “celebrate” relationship goals too. Maybe throw a summer BBQ for your neighbors to celebrate your awesome community (goal #37), or a special dinner date to toast to your strong marriage on an anniversary (goal #40). Recognizing these successes will remind you that these are as important as any career or adventure milestone.

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I fully intend to write a retro of following these habits and see how I do by 40.

~See Lemons Complete his 40 under 40