Write It Down. Make It Real.

My 2026 Personal, Family, and Professional Goals

Every year, I take a personal trip to read, reflect, and write down my goals for the coming year. Last year I went to Austria, and this year it was Paris. I preferred the loud silence of the Austrian Alps to the Parisian bustle, and next year will be someplace with fewer distractions.

I am sharing this personal goals and planning template because I believe deeply in the power of writing things down.

Every meaningful outcome in my life, from my career to my family to rebuilding after failure, started as words on paper.

Planning is not about perfection or rigid timelines. It is about clarity, intention, and giving your future self a fighting chance.

This template is not meant to tell you what your goals should be. It is meant to help you slow down, think honestly about what matters, and put it into writing so it has weight. My hope is that by sharing how I plan, it helps you (and your kids) plan your own path with more confidence and purpose.

2025 Reflection

The Past Year: Things of Significance (Family, Business, Personal):

What aspects were the most important to you in the following areas last year? Which happenings or events were the most significant? Summarize briefly.

Family

Spending time with the kids in Capri, Italy, with them and their friends. Living in the same city with my oldest son has been an incredible gift, plus we have two brother poodles from the same litter, which has been a great excuse to get together weekly to let the dogs play. Seeing all the kids charting their own course in life, school, and career has been amazing.

Another big event that caught me off guard was getting an 18-page letter from my father airing a lot of grievances about the past between us, especially about my memoir, The Red Circle.

He was triggered by a book excerpt that ran about me leaving home at sixteen on Father’s Day this year.

My team ran it on SOFREP.com, and I had no idea. He thought it was me writing something new.

The letter hit me like a sledgehammer to the head. I was angry at first, then sad that a father would say these things to his son.

I was also a bit frustrated because I’ve put in a lot of work into our relationship over the past five years and thought we were in a good place.

It did make me appreciate that I broke the pattern and that I now have a much healthier relationship with my own kids. Short version is I reached out and said I would be open to reconciling in joint therapy, which he seems open to.

Personal

Feeling a sense of accomplishment in the sense that I’ve reinvented myself after my Navy SEAL career and now doing exactly what I want to do on my own terms, and that’s a great feeling.

It was a huge challenge to build new friendships and relationships outside of the military because I lost so many friends in the war, and due to professional jealousy.

I realize I need to stop chasing the dating scene and just be open to meeting someone in my natural circles of activity. Sometimes it feels like I’m forcing things, so I’m committed to being more relaxed and open to meeting someone who is more in harmony with where my life is at right now.

Hobbies

Continuing to fly my RV6 in Portugal and Spain this year has been amazing. Getting to ski in the southern Alps with my son and my OPM friend Romain and his wife was a great end to 2025.

Health & Fitness

Stem cell treatment at BioXcellerator took away my constant joint pain, and I no longer have shoulder issues, but my hip joints are still in bad shape. I’m thankful to have found an amazing pilates studio in Lisbon, which has been keeping me in functional shape. I’m going to have to explore other treatments because my hip mobility from overuse injuries in the Navy is affecting my other hobbies, like surfing, which I really want to keep doing.

Friends & Community

I took a break from YPO this year because of some local chapter politics I didn’t agree with. I got dragged into a fight between two board members. It was the first year I felt YPO took more from me than I got. I was also disappointed that no one from YPO Global followed up with me about it. This was significant because I’ve been in YPO for over 8 years.

Towards the end of the year, I really reflected on how much I appreciate the caliber of people in New York, and from my Harvard Business School OPM alumni group.

Another substantial event was seeing a close friend I’ve had for twenty years take money (hundreds of thousands) from a military charity for his own use.

It ruined our friendship, and it reminds me of what money does to some people. I tried to focus on the positive outcomes and use it as a teaching point for my own kids, but this was someone I really thought would be a friend into old age, and it knocked the breath out of me.

Belongings

I bought a few investment-grade watches and a small Banksy, which was fun. I’m focusing on saving for a blue-chip art piece because it’s a more stable long-term investment.

As I get older, I appreciate super high-quality products that last decades and am not afraid to pay the money, especially for luggage and clothing.

I did have a contractor re-paint my concrete floor in my Lisbon loft, and his worker got paint on my expensive Roche sofa, which was such a bummer, especially because they tried to shift blame and gaslight me over it, which made it worse.

The one thing I don’t like about Portuguese culture is the lack of accountability among trade workers. I had the same thing happen last year when the airport damaged my plane's wing and didn’t take responsibility.

I love living in Lisbon, but this type of thing really bothers me.

Thankfully, I found an incredible personal assistant, Filipa, who has been protecting me from a lot of this bullshit.

Intellectual

This year, the most significant thing that happened was noticing I wasn’t being intellectually stimulated, so I started thinking I need to spend more time in New York and also make a better effort to attend some business school alumni and YPO events.

Finances

I paid off an SBA loan for the business, and that felt good.

Getting my daughter through undergrad with no debt and into her Master’s program in London, was a great feeling. Since the Pandemic I’ve made a conscious effort to get my personal expenses very low. Having my home paid for and no personal debt is a huge relief.

I’m at a point where I don’t have to work anymore, but I am still motivated to work and build a higher passive income that lets me give back more and share in more fun experiences with my kids, friends, and family.

Also grateful for my YPO forum mates and what they’ve done to expand my view on investing and long-term thinking about finances. Our retreat this year in Madrid was epic.

Emotional/Spiritual

Been listening to a lot of Alan Watts on Spotify, which has been amazing. This is one area of my life where, while I still feel a sense of wonder in the Universe, and I feel very satisfied with where I’m at in life spiritually.

Bucket List Items

Fly in space, trip to Japan, Antarctica, and Mongolia. Own and fly my own turboprop or small business jet. Build and design my own house. Own a small airport and a boutique hotel.

Six sentences about last year.

Wisest decision I made: My new literary agent, David, and partnering with Author’s Equity on my new parenting book, Puddle Jumpers. Super excited about the book launch this year.

Biggest Lesson Learned: Environment matters, and I need to surround myself with my people more often. I found that if I don’t, I just hide out at home and read.

Biggest Risk: A confidential business move (I know!)

Biggest Surprise: A former friend misappropriating funds from a military charity.

Biggest thing I completed: My parenting book, Puddle Jumpers.

Most important thing I did for others: Supporting my kids and replying to every request from kids through my author site and socials. I get a lot of strange messages and requests, but I always respond if it’s a kid or young adult.

Six Questions about the past year

What am I most proud of? Being a great dad to my children.

Who are three people who influenced me most? My mom is always an inspiration, whether she knows it or not, and my YPO forum mates. So thankful for this group.

Who are three people I influenced the most? My children.

What was I able to accomplish? Last year was mediocre for my media digital business, but I made some much-needed personnel and organizational changes. 2026 is looking good. My biggest accomplishment was doing the Puddle Jumpers book deal with Author’s Equity. Madeline’s (the CEO) team is amazing to work with.

What is the biggest thing I discovered about myself? I’m an optimist, but even optimists need help to stay positive.

I’m also proud of myself for prioritizing my physical and mental health and letting go of people who drain energy or don’t reciprocate.

What am I most grateful for? My mom, my kids, and my YPO forum.

The Best Moments

Describe the greatest and most memorable, joyful moments from last year.

YPO retreat in Madrid, such an amazing time with the guys, and getting a behind-the-scenes look at Real Madrid stadium, a custom car fabrication shop, and the Royal theatre was incredible. Not to mention the deep conversations we had as a group.

The Italy trip with the kids and their friends.

Getting my little dog Apollo, the brother of my son’s dog, Atlas.

Letting Go

Is there anything else I need to say? Anything I need to let go of before I can start my next year?

Goodbye, friend. I hope you find peace with what you did. I believe in forgiveness, but what you did ruined a twenty-year friendship, and there’s no going back for me.

3 Words that describe the past year

Learning, reprioritizing, and appreciation.

The Year Ahead in 2026

Theme: Growth

What does the year ahead of you look like? What will happen in an ideal case? Why will it be great? Write, draw, let go of your expectations, and dare to dream.

My Next Year will be about:

Define the most important aspects of next year in the following areas*. Which events

will be the most important? Summarize briefly.

Work Studies, Professional

I’m going to make an effort to attend at least one professional learning class or conference and read at least four books on leadership and coaching.

Belongings

Upgrade my airplane and purchase another self-storage or parking garage for passive income.

Relaxation & Hobbies

Take each of my children on an individual trip in addition to our family trip in Italy.

Health & Fitness

Going to schedule a consultation with a top sports orthopedic surgeon and decide what action to take with my joints. Continue to do yoga and pilates weekly, find a pool, and schedule that works so I can swim 2x per week or more.

Friends & Community

Attend one OPM or YPO professional development event. Check in monthly with my existing friends, with no agenda other than to see how they are.

Intellectual

Take at least one online class. Read four books on coaching or leadership. Continue my chess coaching with James.

Emotional-Spiritual

Explore an Ayahuasca retreat.

Finances & Bucket List

Purchase an income-generating property. Go to Japan, which is on my bucket list.

Magic 3 of 2026

These are the three things I admire about myself

I am ready to let go of these three things

1. Drinking. I love great wine, but am cutting way back because alcohol causes inflammation in my joints. I can literally feel the difference when I wake up.

2. Negative people

3. Too much time on dating apps. It was better than last year, but really want to meet a life partner organically or through my normal activities. The dating apps have turned into a dumpster fire at a Trump rally.

Three things I want to achieve most this year

1. # 1 Bestselling book with Puddle Jumpers

2. Explore the sale of my digital media business

3. One bucket list item checked off

People (at least 2-3) who will be my pillars during rough times

1. YPO forum (6 great resources)

2. Mom

Three things I will dare to discover

1. Language

2. New Culture

3. Ayahuasca

Three things I will have the power to say no to

1. Anything or anyone that makes me unhappy

2. Unreasonable requests

3. No-win media interviews like the Russia Today interview request…

Three things that will improve my surroundings

1. New York or London for 2 months out of the year

2. Family & friends

3. The Harvard Business School OPM community & YPO forum

Three things I will do every morning

1. Journal

2. Work out and stretch

3. Be grateful (Journal)

Three things I will pamper myself regularly

1. Weekly sports massage

2. My chef, Migue,l who does meal prep

3. Flying when the weather is good

I will connect with my loved ones in these ways

Travel, and experiences. Regular weekly check-ins.

Three presents to myself if I hit my financial goals

1. Income-generating property

2. Blue-chip art piece

3. Porsche Restmod from the company in Madrid

Six sentences about my next year

This year I will not procrastinate any more on…making better relationship decisions.

This year I will draw my most energy from…my surroundings.

I will be the bravest when…confronted with bad people.

This year I will always say yes when…it’s a fun experience and aligns with my goals.

This year will be special for me because…My new book is coming out and I believe it will help a lot of parents.

My word for the year ahead: Progress

Secret Wish: Find a life partner

Specific goals 2026

Business

1. Puddle Jumpers #1 on the New York Times Bestseller list.

2. Double revenue this year & explore a sale to a strategic media company or private equity.

3. Turn Puddle Jumpers into an ongoing business.

Family

1. Take one solo trip with each of the kids (New York, Alps Ski, Maldives)

2. Trip with mom somewhere she wants to see.

3. Reconcile either direction with my father.

Personal

1. Japan trip, settle on dates by end of February

2. Ortho Consultation by end of February

3. Start swimming again

5-year outlook: I own an incredible loft apartment in New York and a waterfront home on the Mediterranean Sea. Managing my family office and continuing to run Puddle Jumpers and write.