A New Chapter : Service & Self

"By seeking and blundering we learn."
— Johann Wolfgang von Goethe, German Philosopher

Photo: Nanny & Granddad’s cottage in Chezzetcook, NS. About 6 years old.

I’m getting ready to start a significant new chapter and project.

First, I want to chat about how I’ve landed here.

The last 10 years have been amazing.

They’ve been full of:

Beauty & pain.
Joy & sadness.
Frustration & growth.
Struggle & transformation.
Achievement & failure.
Fear & love.

A lot of love.

I’ve learned many things the hard way, and I wouldn’t take any of it back. Despite numerous challenges and setbacks, I’m learning to love myself more and more each day. Most of the time, I love my life more than I ever have. It feels pretty incredible to say that. It has not been easy getting here.

I grew up playing sports and though there was never any chance of me playing professionally, I felt an immense pressure to prove myself and to earn my right to exist through performance and competition. This stayed with me for a long time and caused a great deal of pain and suffering. It’s still an ongoing battle.

Between ages 19 and 23, I struggled to find my place in the world. I felt lost, confused, hopeless, and deeply unhappy. Many times, I seriously considered taking my own life, because I hated myself. I hated my life.

Today, I am beyond grateful for the people, events, and influences that steered me onto a different path.

With no real sense of direction other than a nagging belief that life could and should feel different––that there must be more––I promised myself that I would not succumb to these thoughts. I decided that I would do everything in my power to make real change. And I did. I made the difficult decision to shed my identity as an athlete and quit football half way through my fourth year of university with no idea what would come next.

I picked up books, tried my hand at coding, built a blog website and wrote on there for a while. I would walk and bike around the city to new coffee shops, and even though I felt intimidated, I forced myself to sit down and introduce myself to people in hopes of making new friends. It felt scary, but I was starting to see that there really was more out there.

At 23, my brother sent me a video by Casey Neistat, the renegade NYC filmmaker who launched a daily vlog about his life, espousing the value of hard work, determination, raw creativity, and fearlessness. These videos and this message spoke to me on a visceral level.

I had a strong feeling that this might be it. That this could serve as the vessel to pour all of my chaotic energy into, and begin making my new life. A life filled with discovery, passion, creation, and connection.

When I began to explore this new interest, I was ridiculed and discouraged by almost everyone in my life. They didn’t understand the sudden change in direction. It’s challenging for me to remember how hard that actually was for me at the time, but that judgement was devastating to my already fragile self esteem, and I’m sure my insecurity made that resistance feel 100x stronger.

I battled to find the motivation to actually get out and create videos consistently, and to find the courage to put myself out there for the world to see. I would gain a bit of momentum, then it would fizzle out. I let myself down over and over again and was incredibly hard on myself for that. Eventually the pain of not doing, of suppressing myself, of not making steps toward the life I wanted, became greater than the fear of failure, or of what others might think.

On June 3rd, 2015, I was sitting with my friend Pat at a panel event, and instead of listening to the brilliant speakers, I was daydreaming about making more videos. An idea came to me. I’d seen my friend Dennis Stever complete a project, honing his craft in photography by shooting and sharing a single photo everyday for a year. I thought, what if I did that with video?

I looked at Pat and said:

“I’m going to shoot and edit a 1-minute video every day for a year and see what happens.”

I started the next morning. This project changed the trajectory of my entire life in ways I couldn’t have imagined. I explored my home (Halifax, Nova Scotia, Canada) and fell in love with it. I made lifelong friends and connections. I spent a lot of time alone, shooting, exploring, and editing, and began the process of knowing myself in that solitude. I probably shaved a few years off my life, sleeping about 3 hours per night, but I felt I had to do this or I was destined to live out a miserable life. It was the best decision I ever made.

Nearly halfway through the project, I was able to raise $5,000 from my community via GoFundMe to buy my first real camera kit. I landed a few contracts with local businesses and left my full-time job about 200 days into the project. I spun this into a freelance business for a year, backed only by my personal credit card.

After that year, by recommendation of a close friend and mentor, Robert Zed, I started my first production company, threesixfive, with Gavin Hatheway. We’d only met once, but having followed my daily video project, he reached out to me and mentioned that he’d just graduated from the honours physics program at Queen’s University and that he was interested in pursuing work in the video production space. Knowing very little about who he was, I must have had a good feeling, because I told him about my plan and he was crazy enough to come sleep on the futon in my shitbox apartment for a few weeks as we kicked things off.

As of April 2025, we’ve been in business for 7.5 years and have worked with some of the biggest brands in the world like Puma, Oakley, eBay, Amazon, Sherwood Hockey and many more. We opened an office in Toronto, survived a pandemic, and we went from $100k in sales in year one to a seven figure business in our fourth year. It has been a journey of constant ups and downs, of hard lessons learned, and of pushing ourselves, each other, and our team to rise to each new challenge and grow.

We’ve created hundreds of thousands of dollars worth of pro-bono content for deserving organizations and individuals in our community, and have been able to provide meaningful employment, internships, and other opportunities for young creatives.

We’ve built our dream production studio, the first of its kind in Halifax, where we’re pushing the boundaries of what’s possible from little Halifax and bringing global brands to us.

This business has allowed me to achieve many of my dreams. I’ve travelled across the world. I work with people I love. I get paid to think and be creative.

I have been challenged in ways I couldn’t have imagined. I have bent, broken, and pieced myself back together several times. We’ve taken big risks in order to grow. Some have paid off, others have not. Some are still yet to be determined.

These past 3-4 years have been especially challenging. I’ve had to make terribly difficult decisions in the business, and I haven’t always made the right ones. This has cost me friendships, hundreds of thousands of dollars, an immense amount of anxiety, and a lot of sleep.

This brings us to now.
May, 2025.

As my role and life have changed, I’ve become less active on social media. In my 20’s I was out there almost every day, sharing my journey, thoughts and feelings openly. I was consistently connecting—on a deeper level—with myself, my community, and the world around me. These last few years there has been less and less of that. These days, I tend to share more business-related content on LinkedIn, and cute photos of my puppy on Instagram. I’ve still shared glimpses of the journey, but I miss that more consistent and thoughtful engagement with both myself and my community.

I love my job and our company. I’m proud of the work we do. I love my friends and my life so damn much, truly. But something has been missing and it’s been gnawing a hole in me, exposing a dissonance between how I’m living and how I know I want to.

When I haven’t had the energy or interest to try to fill that void with creative projects, I’ve sought change, challenge, knowledge and growth in other ways.

I’ve read tons of books (psychology, buddhism & spirituality, memoirs, shadow work, personal development etc.). I’ve done about 4 years of consistent therapy (which has been transformative––please do it!). I've filled the pages of about 25 journals, participated in peer support groups, and I’ve shared my struggles with friends (and complete strangers). I trained for and ran my first marathon in a hollowed-out Toronto during covid. I finally learned to swim and completed a half-ironman shortly after.

While acknowledging all these great things happening in my life––this dissonance and inability to lean into the next chapter has left me feeling lost, again, but in a different way. Back in 2014-2016 I felt completely lost, and like I had nothing. Today, I have almost everything I need or want except whatever that one thing is that feels like it’s been missing.

In my lostness, I have also sought comfort and escapism in many forms. Some of which are relatively harmless (but still insidious), like indulging in laziness, snacking, scrolling, or binging TV shows. Others have been more harmful, to my body and to my self-esteem. For a string of about two years, I managed to keep up appearances and show up for my business (albeit not as well as I would have liked), my friends, family, and community, while simultaneously running myself into the ground. I thought I could run from my problems. The same way I gritted and grinded myself into my career, I thought I could simply pave over my deepest struggles and hurts with sheer willpower.

In my exhaustion, I refused to listen to the signals my body was sending.

Feeling anxious?
Just fucking do it anyway.

Lonely?
Seek connection and go on gazillions of dates that don’t actually feel right.

Chemistry’s not there?
Make the chemistry be there. Be better. Find a way.

Red flags in a relationship?
You can change them. You can change you.
Make yourself as small as you possibly can, contort yourself however you must in order to make it work, because being alone is hard and scary and being wanted makes you feel like you deserve to exist.

Too tired to go out on the weekend?
Push through it.

Anxious once you’re out?
Have some drinks and make it go away.

Want to make change?
Well it’s really hard now, because you’ve leaned on these crutches too hard and now we’re talking about addiction.

Your discipline, self-esteem, and momentum have eroded.
And what makes it even harder is that people keep telling you what a great job you’re doing.

You’ve created an image of yourself in the eyes of others.
Even though you do share some of the struggles, everyone sees you succeeding. They say “I see your content online, you guys are killing it!”, to which you reply, “Thanks! I’m glad it looks that way!”, disguising real pain with a distorted false humility.

You manage to put on a good face (most of the time).
You don’t need to change yet.
You can push a little harder, a little longer.
And when you feel like you can’t, there are dopamine pings available to you in abundance that––for a moment––make you feel like you can.

I stayed in this spincycle, flying back and forth between my two apartments––my two lives––in Halifax and Toronto without a semblance of a break.

Until I broke.

After my second out-of-body panic attack in a single week, I called my brother, told him what was happening and that I was coming to his place. I laid on his floor and couldn’t move. I felt like I might never get up again. My skin started breaking out in hives and it got worse and worse to the point that I couldn’t function, and I couldn’t sleep a wink.

As our business faced a handful of intense (to put it mildly) challenges, I went a month and a half with a maximum of 5 minutes of sleep per night, and was absolutely riddled with anxiety. Doctors couldn’t figure out what it was, and began testing me for some very serious illnesses that you do not want to have. I wrote more about this specific experience here, if you’re curious.

At my absolute lowest, while withering away on my couch in my underwear and watching an episode of Avatar: The Last Airbender, I was struck by a scene where the show’s antagonist, Zuko, has also pushed himself past the brink, and goes into a catatonic state where he is forced to learn, the hard way, that the only way to heal, and to truly love himself, is to begin by slowing down and taking basic care of himself.

In this moment, a wave of understanding washed over me.

All these things that I understood, intellectually (because I’d heard them and read about them and therapied about them and journaled on them hundreds of times), but could never bring myself to actually feel, just clicked.

In that moment I learned how to love myself, and what that actually means.

I realized that self-love is not just a feeling, but an action that can lead to a feeling.

I realized that self-love means:

Taking care of yourself.

Listening to your body and honouring its needs. Rest. Nourishment. Kindness.

Accepting yourself, not out of complacency, but in acknowledgment of that fact that nothing else works. It might work for a time, but denying our demons and hurts only makes them stronger.

Honouring all of your feelings and emotions, and feeling them fully.
Without judgment or suppression.

Treating yourself with the same kindness that you know your favourite people deserve.

Living authentically and in alignment with your own values, rather than trying to live up to others’ expectations.

Cultivating quality of attention and presence, so that you can be with yourself, rather than constantly being off somewhere else in your mind.

Setting boundaries, and saying no when something doesn’t serve you.

Being accountable. Not in a harsh, punishing way, but in a way that nurtures growth and integrity, allowing you to build real self-esteem.

Putting yourself and your needs first. Not out of selfishness, but in recognition of the fact that you cannot pour from an empty cup.

Forgiving yourself, and relieving yourself of the guilt and shame that weigh you down.

Accepting that you don’t have to justify your existence and joy. You can just be, and be happy without having to “earn” these things.

It means being your own best friend.

Once you show yourself care and compassion, once you act lovingly toward yourself, then you will feel love for yourself.

Eventually I got a diagnosis and treatment for my skin, but I’ve had lingering effects for about seven months now. This is causing me a great deal of discomfort, lost sleep, and stress. Thanks to some advice from my friend Mark Brand, I cut out coffee, gluten, dairy, and alcohol. That helped a bit but it seems that other foods are still causing issues. Most recently, I’ve started following the AIP (autoimmune protocol) diet, and it’s been helping.

It still sucks. I love food. All of it. I miss my coffee rituals. I miss being able to share a meal or a drink with friends.

These past few years, I’ve struggled to cultivate discipline and consistency, and to commit myself to the lifestyle required to meaningfully explore the kind of things that really light me up and fill me with a sense of purpose. I’ve failed to develop a consistent writing practice, through which I can actively investigate my deepest interests and curiosities.

Things like….

• Spirituality, psychology & philosophy.

• Constructive frameworks for modern, healthy masculinity.

• Leadership, coaching & personal development.

• Mindful entrepreneurship & business with purpose.

• Community building.
  
  
  

Now, I find myself in this situation where, in order to be healthy again, I have no choice but to re-establish discipline, routine, and mindfulness. It is, and it will be, challenging, but I want to choose to see this as an opportunity.

In pursuit of clarity on what kind of work I want to do (outside of threesixfive), I’ve considered blogging more seriously, writing a film or book, starting a YouTube channel, and several other ideas.

All with a similar angle: How to help others understand and love themselves and their lives by sharing the most important lessons I’ve learned.

My two biggest challenges/fears in making this happen have been:

1) A form of imposter syndrome, which causes me to ask the question “who am I to act like I have all the knowledge, expertise, and answers people need?”. The world, and social media, are now filled with the ‘life coach’ types. Many of whom are wildly successful and accomplished (especially in a traditional sense), so why would anyone be interested in what I have to say?

2) Deciding how I want to position myself. Ryan Holiday is the Stoicism guy. Seth Godin is the godfather of marketing. Esther Perel is the world’s relationship guru. Tony Robbins has a deep, rumbling voice and massive hands.

They have well-defined angles. Schticks, if you will.

I can’t just be the “spirituality, psychology & philosophy, modern/healthy masculinity, leadership, coaching & personal development, mindful entrepreneurship and business with purpose, and community building” guy.

Or can I?
For now at least?

I actually just read this paragraph by one of my new favourite writers, Craig Mod:

Maybe ‘schtick’s aren’t all they’re cracked up to be?

Back when I created that original daily video project, I learned that people weren’t interested because I knew everything. They were interested because I was trying. Because it was relatable, and because it was compelling to witness the process of someone learning, stumbling, and growing.

I am still learning, stumbling and growing. Just in new ways. I’m working on new problems, with a better set of tools and with a lot more experience behind me.

Rather than taking a hard stance and saying, “this is what I am, this is who I am, and this is what you should do”, I just want to get back to sharing my journey and inner world publicly. To say “this is who I am becoming, this is what I’m thinking about, this is what I’m trying, and here are a few things that have worked (or not), for me.”

I definitely don’t have all the answers, and I don’t want to pretend to, but I have developed some knowledge and tools that I believe could be helpful to a lot of people.

As I’ve moved out of my 20’s and into my 30’s, I’m feeling a call away from constant pursuit of personal gain, and toward service of others, especially younger generations. You might call this growing up?

I recently heard Arthur Brooks, on the Rich Roll Podcast, say that one of the most powerful tools for healing is to help others heal. So many times, when friends have shared their own challenges, I’ve jumped to give what I do believe to be great advice, only to realize it’s actually the exact same advice that I need to hear, because I’m not embodying it myself.

Change can be scary. Change is hard. But I really believe that the best way to help others make change is not to preach from above, but to do the work and model the behaviour yourself.

So now I’m asking myself:
Can I be a model? An example?

Can I help others make positive change, by going inward? By doing the messy work required to make my own change, and by sharing my own truth, trials and triumphs, publicly and vulnerably?

I’m going to try.

I will start by writing and sharing one* short piece of writing per week, indefinitely. I’ll begin sharing them on my blog and on Instagram, and see where that takes me, allowing for adaptation to the format if this one ceases to serve me.

*I want to thank my new friend Adam Cotterrill, a beautiful human I just recently befriended on the internet, who helped me be a bit smarter, and kinder to myself, adjusting from five posts per week, down to three, then down to one.

I’m thinking of this as creating a mental gym for myself, where I can hone my writing, thinking and perspective. Process my ideas, experiences, and feelings.

I’ve been searching for this next step for years now, but I’m already finding myself in the grocery store writing down thoughts and ideas I want to write about, drawing connections between them, and building on them in my head and notebooks. When I sit down to start writing, I don’t want to stop.

It still feels scary, but in my experience, when something feels scary and hard, but it also feels right, that’s usually a sign you should keep moving in that direction.

I’m looking forward to seeking, blundering, and learning.

I’m excited to go inward, and to share this process with anyone who cares to follow along or join in.

If you’d like to be one of those anyones, you can scroll down and subscribe to my newsletter.

I’ll be sharing my daily posts on here and on Instagram, and I’ll compile my writing into a weekly newsletter with a few extra thoughts tying them together.

If you have any topics, ideas, or questions you’d like me to write about, now would be a good time to share them to dave@threesixfive.ca.

Sending love.

Here goes.