Lessons learned from getting married

Hi my name is Roslyn, I’m a 2x founder and executive coach. I share actionable ideas you can use to build with integrity, live a meaningful life and achieve sustainable succcess without burning out. I also work with founders & leaders 1:1, which you can learn more about here.

Hi there,

I’m so happy to be back in your inbox today after taking a break for my wedding. It was sooo magical and I’m incredibly happy with it. Here’s a pic from our ceremony. 

I also experienced a major post-wedding crash (fatigue, sickness, etc.). It’s taken me a full two weeks to feel like myself again. Over these last couple of weeks in moments of stillness and rest, I’ve been reflecting on the lessons I learned from my wedding.

A few themes have emerged that I’m excited to talk about today because their relevance extends well beyond getting married.

Today I want to get into the light and dark sides of weddings:

• Dark side: wedding perfectionism

• Light side: purpose and intentionality

• Lightest side: love and life partnership

🎙️ Before we get into it, I had so much fun chatting with Kirsti McNabney on her podcast about burnout, breaking free from hustle culture, and redefining success in a way that prioritizes your energy, creativity and wellbeing. Check it out here.

Alright, let’s dive in.

🌊 Where we go deep on how to build with integrity and live a meaningful life.

THE DARK: WEDDING PERFECTIONISM

Imagine you’ve spent the better part of the year, tens of thousands of dollars and many conversations with your partner, family and friends about this one day that is meant to be the most important day of your life (no pressure). And on that day, while incredible in so many ways, you find it hard to be as fully present as you want, to receive all of the love coming your way, because there is this tiny little critical part of you saying things like “My hair is flat”, “That speech went over time”, and “The DJ is NOT sticking to my playlist”.

I call this wedding perfectionism, and define it as the need or desire for everything about your wedding to be perfect. (You might notice it’s similar to general perfectionism, where you could replace the word “wedding” above with “life”.)

From my own personal experience I’ve divided it into three tiers:

1. HOW IT LOOKS

First of all, how do I look? We put SO much pressure on brides to be looking the most beautiful they ever have and ever will in their lives, investing thousands of dollars on dresses (these days multiple), accessories, hair and makeup, fitness in the months leading up, beauty treatments (hair, nails, brows, skin, botox & filler… the list goes on and on). And so yes, with all of that money invested and such high expectations it can be hard not to have thoughts like “Oh no, my curls are falling out” and “Is my dress fitting properly?”. 

Then there’s not only how did I physically look, but how did I act? Was I welcoming and inviting enough? Did I talk to enough people for long enough? Oops I missed a step in our first dance, did they notice? Did I get too drunk at the afterparty?  

There’s also the issue of how the whole wedding looks. You’ve been working with wedding vendors — your venue, flowers, lighting — for months but you don’t get to see how it all comes together until the day of. Unfortunately in this day and age, it can be hard not to at least have the thought “How will it look on Instagram?” flit through your brain.

2. EVERYONE ELSE’S EXPERIENCE

Next is worrying about how the experience of your wedding is for everyone else. Are they warm enough? Did they like the food? Oh no, that table looks a lot farther away than it did in the seating diagram, I hope they’re not offended. This speech is going very over time, I hope people aren’t bored! This song sucks, does everyone else think it sucks? I should’ve added it to my “do not play list”.

What an impossible task to try and keep every one of your wedding guests happy at all times! (People-pleasers will try though.)

3. MY EXPERIENCE

And finally, there’s the perfectionism I extended to how I experienced my own wedding. I judged the fact that I wasn’t fully present, peaceful and grateful 100% of the time (kind of high expectations for myself right?). I noticed when I was worrying about what others thought instead of “being in the moment” and beat myself up for it. Because I’ve been doing a ton of inner work over the past year, part of me expected that I was going to be this fully healed, enlightened person at my wedding. But that’s just not realistic. Especially in the high pressure setting of a wedding, with last minute planning, lots of family time and little space for myself leading up to it. 

WEDDING PERFECTIONISM: APPLICATION TO REAL LIFE

When I reflect on the root of this perfectionism, it’s this deeply rooted, mostly subconscious feeling that if everything at my wedding wasn’t perfect and if anyone had a bad time, then people would judge me, reject me or not like me. If I did anything to offend anyone or was anything less than a perfectly poised, beautiful, caring, considerate, intentional, graceful bride, then I wasn’t safe. If my wedding wasn’t perfect, then I wasn’t perfect and therefore not lovable. 

And this is what’s at the root of perfectionism broadly for me and for many people: a fear of criticism, failure, rejection, disappointing others, being seen as incompetent and feeling like you’re not good enough.

I know that just because my wedding is over, it doesn’t mean my perfectionism is. That these fears will just manifest in other areas of my life. 

So here are the ways that I’m actively working with my perfectionism, that you’re welcome to use if you experience it too.

1. Gratefulness. Reflecting on the moments, big and small, that I loved about my wedding. Writing them out in a big list. Calling up friends and family and debriefing with them what we loved most. Rereading or rewatching speeches and soaking up the love.

I’ve also been reflecting on all of the moments that I did embody presence, joy, peace, and gratitude in the moment. It turns out there were several, that I was in that state most of the time, but unfortunately my brain tends to zero in on the few moments where I was stressed.

Whatever aspect of life you’re trying to be perfect in, intentionally bring attention to the ways in which you’re already crushing it. 

2. Journaling. For a few days after my wedding I allowed all of my thoughts to swirl around in my head, causing anxiety, worry and guilt to emerge before attempting to stuff them back down. I finally sat down and journaled things out, identifying stories that had been bothering me, giving a voice to my inner child to express her emotions and concerns without holding back, giving myself compassion, and allowing the possibility of new perspectives to emerge.

I also did some “Internal Family Systems” journaling aka “Parts Work” which can be incredibly helpful for perfectionists who have very active inner managers. I won’t go too deep into it in this newsletter but if you’re interested, check out the book No Bad Parts by Dick Schwartz.

3. Shadow work. At the core of my perfectionism is my inability to accept certain parts of myself that I learned were bad or unlovable, from my upbringing and throughout life, and from the media and our culture broadly. Shadow work suggests that we need to fully own and accept the qualities about ourselves that we’ve disowned, hidden and suppressed, and to see the gift in them, in order to fully accept ourselves. I’m currently reading and working through the exercises in “The Dark Side of Light Chasers” by Debbie Ford. It’s awesome so far, highly recommend.

4. Nervous system work. When our nervous systems are activated, our brains actually search for a story to explain why we’re in fight-or-flight. I think this has been the case for me. I’ve noticed that as I’ve felt less sick, my perfectionism and rumination have lessened dramatically.

Part of what’s been helping me regulate my nervous system is intentionally engaging in practices like body scans and body mapping, resting, breathwork and walking outside. I can’t understate this enough, that now that my nervous system is regulated, I’ve pretty well forgotten the things that were stressing me out a week ago.

Find a nervous system regulation practice that you like and that works for you, and give it a try when you find yourself going down the perfectionism spiral.

THE LIGHT: PURPOSE & INTENTIONALITY

Now on to what I loved and think we did so well with our wedding. 

The first thing is that we were incredibly purpose-driven and intentional with our wedding planning process. In fact, we took Priya Parker’s Artful Wedding Planning course 15 months out from our wedding. 

One of the most important parts of the course was the idea of defining the purpose of our wedding and allowing that purpose to guide our decisions — around guests, location, venue, wedding events, food, music, all the way down to the little details. 

Our purpose was: 

Aside from the purpose, we also really wanted the wedding weekend to feel authentic and an expression of who my partner Callum and I are, individually and as a couple. 

Here are a few of the intentional decisions we made in service of our purpose.

LOCATION & TIMING

We decided to host our wedding weekend in Sarasota, Florida, in March, thinking a tropical weekend getaway would be welcome towards the end of winter for our guests coming mainly from Canada and the northeast. We chose to host our wedding events on Siesta Key & Longboat Key since my family had been going there for many generations and it’s a very special place to me and Callum. Our intention was to give our guests a 3-day tropical vacation, leaning into the fun and relaxation that the beach and warmth provide.

BRANDING & COMMUNICATION

To further drive home the feelings we wanted our guests to experience with us, we playfully branded our wedding weekend as “Spring Break” and had a lot of fun coming up with a brand identity that we’d use for our website, communications, decorations, flowers and signage. We picked fun and vibrant colours that conveyed the more playful, tropical, non-traditional vibe we were going for.

We sent all of our save the dates and invites digitally (hard copies weren’t a priority) and gave our guests all the information we felt they’d need to enjoy their time in Sarasota and the wedding events: from accommodation, restaurant and activity recommendations to weather and appropriate attire (I even had fun sending a vision board for attire inspiration lol).

REHEARSAL DINNER

We hosted our rehearsal dinner at the beach, with tables right on the sand, in part because that was the original vision for our wedding (before we had to pivot to a new venue). 

We gathered everyone for sunset and before dinner we held two cultural ceremonies. The tea ceremony, led by Callum’s dad (who is Chinese), was about us honoring our elders, and them inviting us into each other’s respective families. 

The Scottish Quaich ceremony, led by Callum’s mother (who’s Scottish) and which involved drinking Scotch from a quaich together, symbolized our commitment to sharing everything in life and sealing our bond. 

Because I LOVE speeches at weddings but didn’t want to have too many for the wedding night itself, we invited anyone in our bridal party to speak that wanted to and had five very sweet, moving and funny speeches which was just the best. 

WELCOME BEACH DAY / VOLLEYBALL TOURNAMENT

Callum and I are both very active people that love sports (he was a national record-holding swimmer, I was just a normal competitive soccer player), so naturally, instead of a welcome drinks we decided to host a beach volleyball tournament for our guests the day before the wedding. NGL it was intense. We have a lot of athletic friends, and they leaned in! There was some stiff competition, which was exactly what we wanted. It was SO fun and so very us and our guests loved it too.

CEREMONY 

Since neither of us is particularly tied to a religion, we basically designed our own ceremony and had it right on the beach with the ocean as the backdrop. I asked one of my oldest and dearest friends, Sarah, to be our officiant and it was so comforting and special to have such a close friend up there with us for our ceremony. We found an outline off the internet and wrote her a script and asked her to insert her own speech about us (see how I snuck one more speech into the itinerary!), which was absolutely beautiful, and personal and wise.

We also made the unpopular (these days) decision to do our photos right after the ceremony so that Callum’s first look of me was coming down the aisle, which was super worth it for the emotion it elicited in the moment.

RECEPTION

We wanted the reception to really lean into our values of connection, love and fun so there were a few fun things we did to facilitate this:

1) DANCE BREAKS: Between our cocktail hour and dinner, we did our first dance (to Holy by Justin Bieber!) and then to set the tone of fun for the evening, we invited everyone onto the dancefloor to dance for a few songs before sitting down for dinner. We then proceeded to have another dance break in between the 2nd and 3rd speeches to get people up and moving and having fun (and not feel like they were stuck sitting through all the speeches).

2) SMALL TABLES & TABLE TOPICS: We chose smaller tables of 6 people instead of slightly bigger 8 tops to facilitate more connection and easier conversation across the whole table. The flipside of the menu contained table topics with questions like “What’s something one of your loved ones does for you that makes you feel special?” to encourage deeper conversation.

3) SPEECHES: We had four speeches, one from each set of parents, my sister (my MOH) and Callum’s brother (his Best Man). This felt like the right amount and all of the speeches were beautiful and touching. As mentioned, we were able to add more in through the ceremony and rehearsal dinner.

AFTER PARTY

Finally, because we’re the type of couple that enjoys a great dance party late into the evening, we transported our guests off property to a very old, kind of divey bar with a dance floor for our afterparty. 

PURPOSE & INTENTIONALITY: APPLICATION TO REAL LIFE

I was so incredibly happy with how everything turned out at our wedding and I know that a major reason for that is the purpose and intentions we set at the beginning of the planning process. 

Like running a business, or a household or anything worth doing, there are going to be tons of decisions, big and small, easy and hard. Having a vision that’s inspiring and rooted in values makes it easier to make the hard decisions and stay motivated to see it through.

THE LIGHTEST OF ALL: LOVE & LIFE PARTNERSHIP

So much goes into planning a wedding and it can kind of feel like this big show you’re putting on for everyone. But underneath the orchestration of it all, is what it’s actually all about, which is committing to a life partnership, in front of your closest people. 

People say deciding on your life partner is one of the most significant decisions we make in life and plays a major role in our overall happiness. I would tend to agree.

As I settle back into my life in NYC with Callum, I couldn’t be more grateful to be doing life with him. 

Writing my vows really forced me to reflect on what I value most about him and our partnership and why I’m so excited for our future together.

Some of the things that I love and value the most (which I shared in my vows) are:

HIS CHARACTER

I deeply respect and admire the man that Callum is. He is an incredibly kind and tender soul. The curiosity, playful and childlike joy he has makes our everyday life more vibrant and precious. He brings excellence, brilliance and devotion to everything he does, from sports, to leadership to creativity and entrepreneurship. And he is so brave, having faced his fears to honor his truth time and time again. What’s also so important to me is that he’s committed to his own growth and evolution, that he’s willing to face himself and do the work required to grow as an individual and in our relationship.

OUR PARTNERSHIP

Callum truly makes our home a place that I want to be, where I feel safe and loved and cherished. He’s a natural nurturer, a fantastic cook, and incredibly thoughtful and considerate. If you’ve been reading this newsletter a while you know my last couple of years have come with major life challenges and transition. And throughout it, Callum has held me, seen me and empowered me (and picked up the extra slack in our home when I’ve been unwell).

As someone who is entrepreneurial, intent on healing and growing, and wanting to make the most out of life, I go through a lot of ups and downs and set a pretty big vision for our life… and Callum has never shied away from any of it. He truly believes in the highest vision for me, as I do for him, has supported me in finding my voice and given me the courage to step into my authentic self and my purpose.

OUR SHARED VALUES AND VISION

We envision a future together that is full of growth, adventure, meaning, abundance, impact, creativity, freedom and also presence, peacefulness, and gratitude for life’s simple moments. We also both want to have kids and raise a family together in a very conscious way. 

CONFLICT MANAGEMENT

Obviously, everything is not perfect all the time. We’re both human beings, with different life experiences, perspectives, triggers and limiting beliefs. And so naturally we experience conflict and sometimes hurt each other. What I love about our relationship (something we’ve definitely had to actively work on over our five years of being together), is that these days we’re able to approach our conflicts with more emotional awareness, compassion for each other’s inner child and a desire to understand one another and ourselves more deeply, rather than to win or be right.

LOVE & LIFE PARTNERSHIP: APPLICATION TO REAL LIFE

Whether you’re choosing your life partner, or the people to surround yourself with in your life more broadly — friends, chosen family, coworkers, community — choose people who make you feel safe to be who you are, that accept you where you’re at but that expand you and inspire you to manifest your greatness, and who you can have fun being in the present moment with. 

🪞 Your turn to reflect. Take these prompts to your morning journal or talk it over with a friend or coach.

• What’s at the root of my own perfectionism? What am I scared people will see if I’m not perfect? What am I scared will happen?

• What in my life do I want to bring more purpose or intentionality to?

• What are the qualities in a life partner, or the people in my life, that are most important to me? 

• Who in my life allows me to feel most like myself? Who expands me and inspires me? Who gives me energy when I spend time with them?

• 1:1 Coaching: I have a few spots left for 1:1 coaching. If you’d like support in building with integrity and living more meaningfully, book a free strategic coaching consultation.

• Let’s be friends: If you want to see the BTS of building Within and receive more tips and ideas on building with integrity, connect with me on LinkedIn and Instagram.

Thanks so much for reading today.

With love,
Roslyn 💚