2024 Annual Review

The Year of Kaia

Hey friends,

Tomorrow marks five years since I quit Google to embark on this journey of entrepreneurship and a self-directed path. As I reflect on this milestone and the transformative year that was 2024, I'm excited to share my annual review with you.

Before we dive in, I wanted to ask for your help.

Over the last five years, my work has been focused on helping leaders and teams at companies like YouTube, L’Oréal, and Squarespace to create healthy, high-performance work cultures. Working with organizations has been fun and rewarding, but lately I’ve felt called to go deeper into the work of personal transformation with a small group of curious humans.

So this year, Claire and I are cooking up a new offering and we need your help.

I’m opening up 1:1 conversations for those who want a more intentional, fulfilling life but feel trapped in cycles of overwhelm, exhaustion, and reactivity.

If you are…

• Constantly reacting, feeling like you have no control over your time

• Spread too thin, overwhelmed by endless demands

• Feeling unfulfilled and discounted, despite achieving success

• Struggling to set boundaries, work always bleeding into personal life

• Running on stress, feeling exhausted, but afraid to slow down

…then I’d love to chat with you!

👉 Click here to book a call.

(Or if someone in your life comes to mind, please forward this along to them ♻️)

This is not a sales call and there is zero cost or commitment—just an open and honest conversation for me to learn what’s holding you back and share some tips that I hope can be helpful for you.

In exchange for your time and help, I’m happy to share my knowledge and answer any questions you have about focus, energy optimization, stress management, etc.

Now onto my 2024 Annual Review.

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2024 Annual Review

Overview

2024 was a year of intensity, beauty, love, caregiving, parenting, difficulty, and joy. Looking back, it feels like several years compressed into one.

Here are some of the big things from the year:

• We welcomed Baby Kaia into the world

• We spent our first full year in Portugal

• I was diagnosed with a rare autoimmune disease and learned my DVT destroyed the valve in my leg

• We slowed the business down for parental leaves

• We renovated our first home (it’s nearly done!)

• We went on two long trips to visit family in the US and Malaysia

Reflections on My Personal Life

FATHERHOOD

The biggest transformation for me, obviously, was becoming a father.

A friend once told me nothing prepares you for being a parent, but that you’ll be ready when the time comes. I found that to be true. Adjusting to the new role of a parent was simultaneously challenging and natural.

It was challenging because who I used to be died. For 10 years, if not longer, I’ve thrived as an independently-minded, freedom-loving guy. I’ve moved from city to city, taken on different careers, traveled extensively, and enjoyed an adventurous lifestyle.

Getting married obviously changed my orientation to the world, but I still operated with a sense of freedom and flexibility that was familiar. Do I want to spend the morning reading, meditating, and drinking coffee? No problem. Should we book a weekend getaway on a whim? Not much holding us back.

Can I still do these things as a dad? Of course, but it all takes more planning, preparation, and being accepting of the trade-offs.

As much as I was truly excited to become a dad, I also wrestled with feelings of sadness and grief in the months leading up to Kaia’s birth. It was hard to identify the mixed emotional experienced I was going through, and that I now know so many men also experienced.

Luckily, I was blessed to have the support of my friend Brandon who offered to host a Fatherhood Ceremony for me. In the calls leading up to the ceremony, he held space and allowed me to be with all of those feelings. Excitement. Sadness. Curiosity. Worry. Joy. Grief.

I’m so grateful to have had the time and support to process the experience as I feel this helped me make the transition with more awareness and ease.

TRANSFORMATION

Becoming a parent changes your life forever. Personally, it wasn’t an overnight change, rather I’ve experienced it is an ongoing process of transcending my own self-interest. My sister told me, “Having a child is like having your heart walk around outside your body.” Every day, I feel less and less attached to my own preferences and more strongly connected to what’s best for my child, my wife, and our family.

While Brandon’s help and the support of my friends at the ceremony was wonderful, nothing has been as helpful in navigating this transition as the relationship I’ve built with Claire.

The foundation of love, respect, honesty, and collaboration that we’ve worked to create together was—and is—our saving grace. Every Relationship Meeting we’ve held, every deep discussion we’ve had, every ounce of love we’ve shown each other over the past 5 years helped us navigate this transition.

It was honestly the most difficult, trying year of our relationship on so many levels, and at the same time, it was undeniably the most beautiful and bonding. Looking back, I can only see how it’s made us stronger. So thank you, Claire, for being the most loving, caring, and supportive wife and mama a husband could ask for. <3

Reflections on My Work

WORK-LIFE INTEGRATION

My relationship to work was also more complex and challenging than ever before.

I started off the year with a roar of passion and energy. I had a lot to give. I worked nights and some weekends (rare for me) and loved being in the flow. I think the baby coming inspired a sort of protector-provider energy I haven’t experienced before.

Then Kaia was born, and my relationship to work changed. Every minute I spent at the office was a minute I’d miss something at home. I felt sad and guilty when I was away from Kaia and Claire, but then I felt overwhelmed and behind when I wasn’t putting time into the business.

Claire and I talked about this a lot in the lead up to Kaia’s birth, and we agreed that our business needed at least one of us running it, so I took on that responsibility. But I wasn’t great at it.

Even though we intentionally lowered our expectations around revenue and growth, I struggled to keep all the balls in the air. Project deadlines were extended, a lot of work had to be put on pause, and I rarely felt in-the-zone with the business overall.

I felt grateful for all the freedom that self-employment provided. It gave me the flexibility to set my own schedule, attend every check-up with Claire and every doctor’s appointment for Kaia, and take time off for paternity leave, but I still felt a constant tension trying to decide how and when I wanted to work.

On top of that, all the habits, routines, and structure I had built over the past 5+ years to stay healthy, fit, and energized had too change, and adjusting to the new norm took time, thoughtfulness, and constant experimentation.

Even as I write this, I’m still navigating this new reality.

Despite all the challenges, it was a beautiful year. We started our own family unit. We renovated our first home. I made new friendships. And we settled deeper into Lisbon, growing a new community of friends and feeling more and more at home.

HIGHLIGHTS FROM 2024

QUICK HIGHLIGHT REEL FROM 2024

Countries Lived In: Portugal

Homes Lived In: 6!

Countries Visited: France, US, UK, Spain, Malaysia, Indonesia

New Countries Visited: Zero!

Places Visited: Comporta, Paris, Barcelona, London, Minneapolis, Kuala Lumpur, Bali

Books Read: 22 (see the full list on Goodreads)

Favorite Novel: Red Rising trilogy by Pierce Brown

Favorite Nonfiction: Conquerors: How Portugal Forged the First Global Empire by Roger Crowley

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PERSONAL HIGHLIGHTS

OH BABY, BABY

This was the best. The most challenging, the most beautiful, the most rewarding. I’m now the parent that’s trying to convince my other friends to hurry up and have kids already.

THE BIRTH

Holy smokes, this was miraculous to witness. I mean miraculous in the truest sense of the word. This was a singular experience that I will never forget. Witnessing Claire’s strength, determination, and grace throughout 36 hours of labor left me speechless. I see, and women in general, with a whole new level of reverence. I’m very grateful for the support of our doula who guided me in how to show up and support Claire throughout the process. Highly recommend support like that for any expecting parents reading this!

PATERNITY LEAVE

As I mentioned earlier, I took 3-4 weeks off after the birth, then about a month when Kaia was 3 months old for a trip to the US and again when she was 7 months old for a trip to Malaysia. These were such special moments of the year when I was able to drop fully into dad-mode, help balance the load with Claire, and soak up so many cute moments with Kaia.

THE ‘IN-BETWEENS’

One of my favorite parts of being a dad are the little “in-between” moments in our days. Waiting to check out at the grocery store and dancing for Kaia in the stroller for a laugh. Rolling around on the floor and blowing raspberries on the little one’s belly to get her in a good mood before an outfit change. Riding up an escalator and pulling a face to get Kaia’s attention and if I’m lucky, a smile. These moments are indescribably beautiful. They make all the hard shit so much easier to handle.

COUPLES THERAPY

After more than a year of saying we wanted to do couples work, we finally dove in. And what an amazing investment it has been. So many times, our session would roll around and I’d be asking myself, “Is this really worth it? I don’t think we have any issues to discuss.” Then we’d have this great session, tears would flow, connection would ensue. And I’d remember, “Oh yeah, that’s why you do therapy.”

FRIENDS & FAMILY IN LISBON

Some of my favorite moments of the year were hosting friends and family in Portugal.

Claire’s mom and my mom came in the first 1-2 months after Kaia was born, and that was incredibly helpful and fun. Plus, Claire’s sister came with her husband and two kids, which was such a memorable trip.

Two of my best friends came over from the US and my mate Oli came down from Glasgow. Claire hosted some of her close pals as well, and these moments were wonderful.

FAMILY TRIPS

We took Kaia on her first trip to Minnesota in August. It was such a special month, especially because Kaia got to meet three (!!!) of her great-grandparents! Nothing really compares to seeing your child spending time with multiple generations of family. On top of that, my sister’s third baby was born within weeks of Kaia, so it was super cute to see Kaia and her cousin hanging.

BABYMOON

I had never heard of a “babymoon” until Claire was pregnant, but now I’ll recommend this to anyone expecting! We went to a beautiful hotel a couple hours south of us in Comporta and did a mini-retreat filled with morning journaling, sauna and spa sessions, long walks to the beach, and incredible food. I’ll always treasure this trip.

LOW BACK TRAINING

I’ve had on-again, off-again low back pain ever since an injury I suffered while getting hazed in college (oh did I not tell you I was in a fraternity? How…embarrassing.). I tweaked it again quite badly in the fall of 2023, and then my brother hurt his back early in 2024, so I finally decided to go deep on solving this issue. I put aside all other exercise and movement (no yoga, no lifting, no tennis, no padel) for the first 6-weeks of this Low Back Ability program, and I’ve continued the work up until now. Not only does my back feel stronger and more resilient, it was such an interesting educational journey.

HEALTH EXPERIMENTS: GROUNDING & CARNIVORE DIET

As I mentioned at the top, and you’ll read more about below, I have an autoimmune disease. This past year, I tried some new stuff to heal my inflammation. In July, I did a full 30 days of the carnivore diet (and recorded a YouTube Short each day of the challenge). In August, I started grounding regularly, meaning I’d go chill in a park barefoot. Both seemed to have made a positive impact and my flare-ups have been very minimal and infrequent since the summer. Things are tracking in a good direction.

PERSONAL LOWLIGHTS

Now, let’s look at some of the challenges I encountered in 2024.

ENERGY

As someone who has spent many years obsessively optimizing my life for great energy, I definitely felt the pain of less sleep, less exercise, less time for self-care, etc. I was amazed at how well Claire managed with so little rest, and honestly I felt so fragile compared to her at the start. As time went on, I did learn that I can still function without a great night’s sleep, or a perfect morning routine, so I think there is a silver lining here.

HOME RENOVATION

This was tough on many levels. We started the project around Christmas 2023 and the original timeline for completion was the end of April 2024, just before Kaia’s due date. As I write this in early 2024, we’re still not done. Don’t get me wrong, it’s been a huge privilege to get to design our own home, and lots of the process was cool, but it has taken a toll mentally and emotionally. So much time. So many decisions. So much stress. The hardest part for me was that Claire had to do a lot of work on this during her mat leave, and I wish she would have been able to fully unplug and be without work stress in that precious newborn period.

MOVING

Related to the above, we had to move a lot this year. We stayed in our original rental until August, when we then packed up everything, put it in a storage unit, and went to the US to visit my family. We were hopeful we might move in upon returning, but that wasn’t the case.

So we found a temporary home for September, then another for October, then another for November, each time hopeful it would be the last temporary home. Then we packed up everything into storage before going to Malaysia in December, then we came back to Lisbon in January and had to find another new home. Phew. This was a lot of admin and stress. We are really good at packing now though. And it was cool to get to live and explore a ton of different Lisbon neighborhoods.

HEALTH

Some of you know I was hospitalized with a blood clot (DVT) in November 2022. As a healthy young-ish adult, the doctors were as perplexed as I was about the cause. So I went on a journey, hiring a functional medicine doctor, trying an elimination diet, going to a Traditional Chinese Medicine (TCM) doctor, researching and talking to specialists, and on and on.

Finally, after nearly two years, I was diagnosed in September with a rare autoimmune condition called Behçet's disease.

Additionally, I learned that the clot destroyed the valve in my leg. This means the blood flows down, but not up my leg like it should. And the vascular specialist I saw told me I need to wear compression socks for the rest of my life, elevate my leg daily, and be mindful that long-term complications could include swelling, discoloration, and nasty ulcers on my leg.

That was devastating. I struggled a lot in the weeks and months after that diagnosis, and it’s something I’m still processing.

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BUSINESS REVIEW

While our business took a backseat to family priorities this year, I'm proud of what we maintained and the foundation we've built for future growth. Below is a snapshot of our business activity in 2024, followed by key highlights and lessons learned.

In past years, I’ve done more comprehensive business reviews (see Year Three, Year Two, Year One) but this year I’m more time-constrained and not feeling it, so I’m just going to lay out a few highlights and lowlights.

As always, my inbox is open if you have any questions about the business!

CLIENTS SERVED IN 2024:

• Google gTech

• L’Oréal USA

• Google Security

• Biotherm

• L’Oréal Europe HR

• L’Oréal DACH

• Welsh Government

• DreamBank Academy (American Family Insurance)

• Centers for Disease Control and Prevention (CDC)

• L’Oréal Italy

• Wisconsin Credit Union

BUSINESS HIGHLIGHTS

FREEDOM & FLEXIBILITY

I felt extremely grateful last year for the life our business affords us. Being self-employed is hard, don’t get me wrong. But owning my time and being able to decide when I worked was a huge privilege with all the personal stuff that happened this past year.

MAKE TIME UNIVERSE

This is both a highlight and lowlight. I wanted to go all-in with Make Time this past year, and to a certain extent, I did! I sent 25 “Time Dorks” newsletters, we hired a growth marketing agency that helped us consistently post and grow on LinkedIn, we completed an in-depth insights & copywriting project with a brilliant copywriter, hired a website developer to overhaul the site, and delivered Make Time workshops to Google, L’Oréal, the CDC, and more.

But I also failed a couple fronts. I didn’t launch the new Make Time course we had been planning on, which was a big part goal of mine. And we haven’t launched the new website (although it’s nearly there!). Ultimately, I overestimated how much energy I’d have for these projects after Kaia was born. It was a lesson for me in focus, prioritizing, and doing too much at once.

BODY-BASED PRODUCTIVITY

I teamed up with my friend Charlotte Grysolle to develop a new series of workshops around the concept of body-based productivity. Most productivity advice is focused on cognitive strategies but we believe it misses an incredibly crucial point: your mind is connected to your body. If you want to be more creative, focused, and resilient, the best way is to start by taking care of your body. Our first workshop with a team at Google received overwhelmingly positive feedback, with one executive messaging me weeks later saying, "For the first time in my career, I don't feel guilty about prioritizing movement during my workday - and I'm actually getting more done.” You can read more about this in one of Charlotte’s Stretch newsletters here!

WORKING ALONGSIDE FRIENDS (…ESP AT THE BEACH!)

We rented an office next to our friend Kelsey and I really enjoyed having those easy social interactions during the week. I also developed a new series of workshops with my friend Charlotte, and that creative collaboration was a blast. Claire helped start a weekly ritual of coworking with friends at the beach on Fridays, which was so fun. We are leaning into this in 2025 and it brings me a lot of joy.

RENTING AN OFFICE

As I just mentioned, we got an office for the first half of the year, primarily to get outside the home, socialize, and mix up our routines. This was a great investment for mental and emotional health.

BUSINESS LOWLIGHTS

VIRTUAL ASSISTANT(S)

One of my goals over the past two years was to off-load some of the tasks in the business that aren’t in my zone of genius. So we took a leap and hired our first full-time virtual assistant towards the end of 2023.

We quickly learned the first hire wasn’t a fit, so we hired a new VA a month or so later. There were a few bumps early in the process with our second hire, but Claire really leaned in and helped train them up. It was going pretty well for most of the year, but then while we were away in the US in August, our VA put in her 30-day notice, then ghosted us the next day. It caused some headaches as I had to take on a lot more admin + ops work, and I didn’t properly maintain our systems from August-December, so there has been a lot of backlog to catch-up on now that Claire is back.

LACKING CREATIVE FOCUS

I spent a lot of the year in a more reactive mode. With limited time and low energy, it was harder to be creative and focus on the bigger projects. It was a lesson in remembering that the days where I start by something generative, like writing, learning, researching, creating, etc. are just better days. As the saying goes, it’s better to “make before you manage” and I started too many days last year managing all the random bits in the business and this was an energy drainer.d

MONEY

Although we intentionally lowered our revenue expectations with the maternity and paternity leaves in mind, it was still hard for me to adjust to not making the same amount of money we had done in previous years.

PERSONAL WRITING

With the pivot towards going All In On Make Time in 2024, I stopped writing this newsletter and honestly, stopped writing for myself. I missed this, and it’s something I’m hoping to revitalize in 2025.

INTENTIONS FOR 2025

As I look ahead to 2025, I'm setting a few intentions that build directly on what I've learned through the challenges and joys of the past year.

These aren't big goals but rather lightly-held personal commitments grounded in the realities of my new life as a father, husband, and entrepreneur.

LOVE

I started 2024 deeply connected to living a life through love. Every day, I was meditating on love, listening to music filled with love, and trying to make love the lens through which all my decisions were filtered. And it was wonderful. I’m reconnecting to this value in 2025.

In practice, this means setting aside 10 minutes each morning to meditate specifically on love and gratitude before checking email or starting work. It means creating dedicated "love rituals" with Claire and Kaia - like our Sunday morning pancake tradition or bedtime stories that have become sacred moments in our home.

PRESENCE

Zen teacher John Tarrant says, “Attention is the most basic form of love.” Presence is directing your attention to the present moment. I want to be more present in all moments of my life, but most especially, in those special moments with my daughter.

To cultivate greater presence, I'm re-committing to a “phone-free morning " - not checking my phone for at least the first each day. I’ve found that starting the day like has a positive snowball effect on my attention and presence throughout the day, and it ensures I can soak up those special morning moments with the family.

SURRENDER

Letting go of my desires, preferences, and attachments and putting more trust into the flow of the universe, collective consciousness, whatever you want to call it…this is a beautiful practice. It’s a constant work-in-progress, but I’m leaning more into letting go this year.

The autoimmune diagnosis taught me that some things simply aren't within my control, no matter how optimized my habits or how disciplined my approach. In 2025, I'll practice surrender by keeping a journal where I document the outcomes of situations where I chose to let go rather than force my will. I suspect this record will show me that the universe often has better plans than I do.

THANKS FOR READING!

If you made it all the way down here, thank you!

1) If anything resonated, or if you have questions, feel free to reply directly to this email or drop a comment on Substack.

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Hugs,

Connor

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PAST REVIEWS, TEMPLATES, & RESOURCES

BUSINESS REVIEWS

You can read my previous business annual reviews here:

• Year One (2020-2021)

• Year Two (2021-2022)

• Year Three (2022-2023)

PERSONAL

You can read my previous personal annual reviews here:

• 2019

• 2020

• 2021

• 2022