The Connection 008 - 2026 Goals & 2025 Recap

Hi there 😄 

This is my friends & family newsletter. You probably signed up after reading one of my articles, a LinkedIn post, or after we met. You'll get a monthly email.

It was only after Chris died last November that I finally got a reply from an old friend. I’ll call him “Alex”.

Eight years of emailing Alex, with no response. Birthday messages. Life updates. The occasional "thinking of you, man." I never got anything back.

It took a message about the motorcycle accident to break the radio silence.

It keeps me up sometimes. Because there were times I wasn't a great friend. There were times (cringey, crawl-into-ball-and-die moments) where I chose convenience over loyalty, where I let him down. And I think maybe I earned the eight-year silent treatment.

But there were good moments too. Times I showed up when it mattered. I want to believe it balances out. I’m not sure it does.

The only move left: look at where you failed, and try to fail less. Look at where you succeeded, and do more of that.

That's what these reflections are for. Once a year, once a month, every day… the frequency is a detail. But you have to look. Reflection is how you steer instead of drift.

This is a review of my 2025 and a public sharing of my 2026 goals.

At the end, I share why I do this and how I review the year.

To summarize: This helps me look back at what worked, what didn't, and what I want to focus on in 2026.

🎩 2025 Recap

🌎 Remote Life OS

What I said:

Move RLOS from the back burner to the main focus. Grow RLOS to $100K in revenue. Launch three 30-day LARJ cohorts. Continue offering coaching and self-paced tiers.

What happened:

I reached 10% of the revenue goal.

RLOS quickly became not the main focus (more on that below), but I still managed to chip away at things. The email list grew from 2,000 to 8,000+ subscribers. I re-set up a Solo 401 (k) for the business. Small win, but it felt like leveling up.

The bigger shift: I completely moved away from the cohort model. When you think about it, the promise was broken from the start: "Hang out with me for four weeks, and you'll learn how to get a job…then you might still have to go get that job" just isn't a very good offer. The job search is too variable. Unlike physical training, where you can track reps and weights, the ups and downs of looking for work don't fit neatly into a four-week sprint. Some people need two weeks. Others need six months.

So I tweaked the offer. More one-on-one and group coaching, which gave me the flexibility to meet people where they were. I also developed a service I call Land The Interview: I analyze and break down resumes, cover letters, and LinkedIn profiles so people can land more interviews. The value is clearer, and the promise actually delivers.

💼 Consulting

What I said:

Consult for 15-20 hours per week. Build enough pipeline so you're not chasing work. Use consulting to replace W-2 income while building RLOS.

What happened:

This ended up being a much larger share of my time, resources, and energy than I thought (in a good way).

I checked all the boxes. Consulting fully replaced my W-2 income. I didn't have any W-2 for 2025.

I worked with four different companies this year: I Will Teach You To Be Rich, Clay, The Rundown, and OpenAI. Each one taught me something about where I'm best suited for this type of work and what kind of clients I'm looking for.

Going deep on it this year made me realize I'm ready to start writing about solopreneurship. I've been doing it—either full-time or on the side—for most of my career. In the last ten years alone, I've done it while moving five times, going through two international relocations, and raising four kids. There's a story there. And lessons learned. I'm ready share it. More on that below.

🏘️ Family

What I said:

Get involved with kids' extracurriculars (coaching BJJ or soccer). Schedule more date nights with Amy. Take more pictures. Be less petty.

What happened:

I coached Jiu-Jitsu until summer, then coached Oliver's soccer in the fall. Date nights happen—Amy mostly initiates them, and I haven't been as proactive as I could be. I did not do a good job taking pictures this year. I still catch myself being petty at times, especially with the kids and especially at night, when I’m tired. It's something I try to be mindful of. Sometimes, I’m able to stop it.

The biggest surprise: finding out we were pregnant in February and having Madeline in November. That and the house (more on that below).

So yeah, major updates on the family front that didn’t make it into last year’s planning session 😅

Briefly, on the kids: Oliver and Annabel now walk to school with their friends now. They continue to be their own little team. Theodore is coming into his own. He may be our best chance to have a professional athlete in the family. And Madeline Mei Jing is adjusting to the chaos.

I thought for sure Deefer was going to die this year. He started struggling in March and April. He was diagnosed with an adrenal gland tumor and a blood clot in his leg. We thought we’d only get another month with him. But he's doing well on medication and palliative care. Every day, I’m so glad I get to see his face 🐶

🤝 Friends & Network

What I said:

Keep building relationships in Philadelphia. Restart soft networking in a sustainable way. Use upgraded Calendly with different calendars for catch-ups, work, etc. Stretch goal: host work and networking events in Philly.

What happened:

I did okay building relationships in Philly. Between school drop-offs and soccer Mondays, connections happened. But I want to be more deliberate now. We bought the house, so we're here for the next ten years, maybe more.

Soft networking fell off the list until December, when I realized I hadn't reached out to anyone in months. More on this below.

Lastly, hosting networking events didn't happen in 2025, and it’s not a priority for 2026.

❤️‍🩹 Health

What I said:

BJJ 2x per week. Weight train 3x per week. Start incorporating cardio. Focus on consistency, not intensity. Don't compete in tournaments.

What happened:

I did okay. Gym 1.5x and BJJ 1x per week. I got injured a few times but never let it spiral: I kept eating in check, got back into it, bodyweight training as soon as I could. I started doing Peloton. I stopped doing it.

I’m still finding consistency, especially with the house and now, with Madeline.

💸 Money

What I said:

Save enough for a down payment on a house ($160,000 for an $800K house). Sell crypto holdings. Keep up automatic investments. Get business finances to improve tax and investment efficiency.

What happened:

We saved up a down payment on a house so we could buy one in a year or two, as planned… then we bought one.

The saving was easy enough. But between having the baby and running out of room in the apartment (I could change Theodore’s diaper while brushing my teeth and join a Zoom seated at my desk, and Annabel and Oliver were sharing seven square feet of floor space) this house checked so many boxes. Good location. Parking. Actual bedrooms for actual kids.

Looking back on it now, it's like:

Even after buying, we don't think about the mortgage. It hasn't touched our day-to-day finances.

We just needed to get into a place we loved. Every time I walk in, I find something new. The foyer fits two strollers. The garage that doesn't require a parking spot prayer every time we turn the corner. The high ceilings make the chaos feel less claustrophobic.

I sold half of my crypto holdings to cover the down payment, in an exercise of half relief, and half treasure hunt. See, my Ledger kicked the bucket sometime after the Dublin move, and I had no idea how to recover the crypto on it. It took me four hours at the end of one night: laptop open, ChatGPT running, digging through exchanges I'd forgotten existed… but I got it out.

In more fiscally responsible moves, I continued with automatic investing. Got financial planning advice from my friend Joe Shure, took a tax planning course from Ankur Nagpal’s Silly Money, and I’m trying out Carry.

🧳 Leisure & Travel

I visited my brother’s family when they had their first baby. We celebrated Theodore's first birthday. Hosted a triple karaoke birthday party for him, my sister, and me.

In the summer, went to Denver for Scott’s wedding. Took a family trip to the Poconos. Amy and the kids went to Dublin, and I set up the new house.

I wanted to go back to Nashville, but punted for 2026.

Kept reading and watching movies (move on that below). Kept playing poker, stopped playing chess (not sure why).

🗺️ 2026 Planning

My 2025 theme was: Take risks under your name.

The 2026 theme is: Consistency is a super power.

Showing up isn’t enough. You need to show up in a way you can sustain for an unreasonable period of time. Obsess over this. Build the systems and habits to make this a competitive advantage.

Summary of 2026 goals: Split RLOS into two brands. Grow consulting income; make product income 30% of the mix. Be present for the family. Take more photos. Build friendships deliberately. Train 4-5x per week. Pay down the mortgage faster. Stretch: Start Philly newsletter.

🌎 Remote Life OS

I'm splitting Remote Life OS into two different verticals.

RLOS Jobs Newsletter: The focus is on landing remote roles. I’ll keep the newsletter running weekly. The Land The Interview service stays: resume, cover letter, LinkedIn teardowns that help people get interviews.

The operational goal: improve operations so I can increase cadence to 3x per week (e.g. use an agentic browser, Notion Agent, etc. to make publishing stupidly simple). Start paid acquisition once I've reached 10,000-12,000 subscribers. Then monetize with partnerships, no ads. For Land The Interview, optimize my inbound process: better segmenting of leads, better follow-ups.

RLOS Solopreneurship Newsletter: Solopreneurship is the next vertical for Remote Life OS. Like landing a remote job, solopreneurship is a tool; another way to design your life around what actually matters to you.

I've been doing solopreneurship on and off for seven years. I've been quiet about it because I was focused on the jobs side. But going all-in on consulting this year reminded me I have a story to tell here (e.g., I chipped away at this while working for four companies, moved five times, and had four kids).

Revenue goal for Remote Life OS: $100K and make this a larger part of the overall income mix.

Stretch goal: Launch a local Philadelphia newsletter. I’ve wanted to do this for the past year and haven't prioritized it yet.

💼 Consulting

Goals:

• Grow consulting income by 50%

• Double down on this niche I’m carving out for myself

• Squeeze more out of each opportunity and client. Go to the office. Meet more people. Add more value.

🏘️ Family

One of the BJJ coaches asked me what it was like having 4 kids. I told him it was fun. He replied:

Goals:

• Keep it fun.

• Take more photos.

• Consistency is king: with activities, schedules, and family traditions. Prioritize spending time with family.

• Hold the standard. Keep reminding them: this is how we behave, especially as they're exposed to more outside influences.

🤝 Friends & Network

Goals

First, more soft networking.

I used to be better at this. I thought technology could help me get back on track.

At first, I built an elaborate Clay table to help me do more: automated email finding, research scraping, and an apparatus that’d make Rube Goldberg blush. And then I never deployed it. It sat there, pristine and untouched, like a Planet Fitness membership.

My friend Scott is really good at this type of networking. I asked him what his process looked like.

I used to do exactly this. Then somewhere between kid two and kid three, between the moves and the sleep deprivation, it slipped. One of those habits you stop doing and don't notice until it's been gone for months.

So now that it's top of mind again. I stripped out the friction. I deleted the Clay table. I’m focusing on three principles:

1. Think it, do it

2. Add value

3. Volume

Others goals:

• Have people over to the house for dinner or drinks, 1-2x per month.

• Have a monthly lunch with friends

• Start attending Philadelphia networking events

❤️‍🩹 Health

Goals:

• Weight training 4-5x per week.

• BJJ training 2x per week

• Better meal planning

• Start seeing a doctor again; get regular blood work

💸 Money

Make no major moves. Focus on making more money with more consistency, changing up income mix (more products, fewer services), and tax optimization.

Other goals:

• Continue with tax optimization, e.g. Solo401k and backdoor roth.

• As income increases, increase mortgage payment; pay down in 6-7 years.

• Move towards a 10-year plan of buying a house in Ireland.

🧳 Leisure & Travel

Goals:

• April: Nashville.

• May: My 40th birthday.

• Summer: Beach holidays & more beach tips.

🛝 Fun Stuff

I watched 39 movies this year. Up from 38 last year, though this year included a lot more with the kids. Annabel loves watching movies; Oliver covers his ears at moments of high narrative tension.

Random standouts: Relay, Furiosa, Dazed and Confused, Wake Up Dead Man.

I read 19 books. Up from 18 last year.

Some gems in no particular order: Both of Chris Whitaker’s books All the Colors Of The Dark and We Begin At The End were haunting and riveting and I can’t wait to re-read them. Anthony Mara’s Constellation of Vital Phenomena was terrific. I was pleasantly surprised how much I enjoyed Sally Rooney’s latest, Intermezzo. Finally, I started re-reading Dennis’s books.

🤔 Why Do This At All?

Writing this takes about 20 hours in December. Twenty hours of scrolling through Google Photos, reading old notes in Roam, and deciphering my own handwriting. Then another five hours typing out what I did and didn't do over the past 365 days, while Oliver and Annabel have their screen time and Theodore shouts at me, demanding a bottle or a bagel or scrambled eggs

To be honest, the whole exercise is so strange and narcissistic navel-gazing. It’s like writing a year-end performance review for a job, where I'm both the employee and the manager and the only person who'll ever read it.

Especially when, in my completely non-biased opinion: I already won. I won this game.

I met, married, and am building a life with the love of my life. My family is healthy and beautiful and they love one another. We have our home—the one with the foyer and the garage and the high ceilings—where we'll spend at the next decade (probably more). Every morning, I wake up and do work I find challenging and enjoy, with full autonomy over when and where I do it. I spend no time thinking about things I want. Zero calories on coveting anything, other than more hours in the day. (And a home sauna. That’d be dope. Would love that.) But that’s it. That’s the whole Wi$h Li$t.

So why spend 25 hours doing this every year? Why bother?

Two reasons.

First, the Bill Gates quote sums it up:

We're capable of great things. They just take time.

Second, having joy—treating things joyfully in what's considered mundane.

Chris Bailey wrote:

In other words: there's joy in looking back.

⏪️ How I Review My Year

My process:

1. Review and retrospective on the last year.

I review:

• Photos

• Swarm check-ins (yes, I’m the guy still using Swarm)

• Instagram

• Google Calendar

Then, I review my notes on Roam. I put these in six buckets: Long-term projects, Career, Relationships, Health, Finances, and Leisure. For each bucket, I think about: (1) What went well (2) What could be improved.

2. Plan the next year.

I review notes about (1) my long-term goals and (2) my Perfect Tuesday. These are my North Star metrics as I plan what I want to accomplish in the new year.

Finally, I keep the following in mind:

Success is measured by inputs and intention, not blindly following a set path.

🙏 The End

Here are my reviews of 2024, 2023, 2022, 2021, 2018, 2017

How was your year? If you did an annual review, LMK. I'd love to read it.

Ending Note

If you're enjoying The Connection, I'd appreciate you sharing it with a friend. They can sign up here. This is the same email I sent to friends & family, so I hope you like it.

And if we haven't connected in a while, please hit reply and give me an update on your life! I've found this is the best way to stay meaningful in touch -- better than social media.