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A look back at 2019

December 31, 2019 7 Comments

Happy New Year!

I’ve had the past 12 days off, which has given me an ample amount of time to reflect and recharge for 2020. And recharge I must. This past year was filled with CHANGE. In today’s post I’m taking a look at some memorable moments from 2019, before starting off this new year – and decade – with some strong resolutions.


2019 started off with a flurry of wedding planning! Azim proposed at the end of October in 2018, and after deciding on a venue later that year, and some preliminary research, we put a hold on planning to enjoy our time being engaged.

Wearing my wedding veil and pyjamas

Once 2019 started, I hit the ground running. I am unapologetically one of those women who had a wedding VISION, and I put a lot of love and energy into bringing it to life. I really enjoyed the planning process, especially with the help of my planner. Here’s a link to my wedding vendor post 🙂


By far, the highlight of February, and one of the highlights of the year for me was visiting New Orleans around Mardi Gras. I went with my cousin (and favourite travel buddy 🙂 ).

New Orleans Sazerac Bar

It was an incredible trip because we planned out so much, but still managed to find lovely surprises around every corner. Read all about it here!


In March I began my secondment at my company’s innovation lab. After nearly three years in my job, I had been starting to feel stuck. This opportunity was eye-opening for me, and helped me more than I could have imagined. Little did I know at the time, my career was about to shift.


In April I turned 29, and celebrated by spending lots of time with family and friends. I had plenty of meals out, went to the symphony, visited the TIFF picture palace, had afternoon tea with my mom, and went to a ROM speaker series. Azim and I also continued with wedding planning, and by this time had most of the big details sorted!


In May, I remember work feeling overwhelmingly busy. It kind of never slowed down for the rest of the year! I had shifted my job search into high gear – which can often feel like a full time job, on top of a full time job. I was also organizing a big charity event for Dress for Success, which had a lot of logistical challenges. It was rewarding, but hectic!

At the same time, the world was in an uproar over the Game of Thrones finale, and Canada was going crazy with Raptor mania 🙂


June marked the start of the busiest summer of my life. In this month alone I managed to pack in our engagement photoshoot, my bridal shower, a truly astonishing number of job interviews, and a trip to Sweden to attend our dear friends’ wedding. Phew!!

A couple of my favourite humans 🙂


Another huge month, as I arrived back from Sweden and started my new job almost immediately. As the countdown to the wedding started to crunch, and my brain worked in overtime to adjust to my new role, I barely had time to say goodbye to my old work family. I had been with them for 3 years, so the sudden change – although necessary – was a challenge.

The challenges I faced were made a little easier with continued wedding celebrations. I had the BEST bachelorette party I could ever have dreamed of 🙂


After nearly a decade together, I was honoured to marry the love of my life.

And we snuck away on a mini-moon to Prince Edward County 🙂


As soon as we returned home from our “mini-moon”, Azim packed his bags and we whisked off to Michigan to move him into his new home for the next couple years. I am so proud of Azim for persevering, following his dream, and going to grad school. Being apart is hard, and was especially so right after the wedding, and as my new job became increasingly intense.


October is when the crash happened. I won’t call it a quarter-life crisis…but it was kind of a quarter-life crisis.

I had been going on a very steep upward trajectory from the beginning of the year. Work was busy, as I managed my day job, a secondment, work on our women’s committee, networking, job searching, and job interviews…which ultimately ended up in career shift.

Add wedding planning and getting married to the mix, and I barely had time to register that the next few years of my life would be radically different than what I had imagined. Azim moved to the U.S. days after we returned from our mini-moon.

As I started to get the hang of my new role, and life without Azim, I realized a few things that hit me in the gut.

I would be turning 30, and had hit every goal on my “Plan A”. What’s a “Plan A”? Plan A is the plan you make while you’re young, and haven’t quite figured out where life will take you. Most people de-rail from their Plan A and end up on Plan B, C, D or even farther along by the time they reach their 30s. They take risks, or things go wrong and they choose a new path.

But I didn’t do that. I didn’t take risks, and when things had gone wrong, I just grinded it out and stuck with what I knew. I had found a job after university and moved up the corporate ladder. I moved out in downtown Toronto, and I married the love of my life. Although my new job came with a wealth of opportunities to learn new things…I still felt/feel unfulfilled.

Forgive my navel-gazing…but I wanted to share because I’m sure I’m not alone in feeling like this.

Living at home with my parents at 30, away from my spouse, and uncertain of what I want to make of myself feels simultaneously like a new beginning and a heavy weight.


Prince Edward County

In November I really tried to wind down and reflect, while managing the new and intense schedule at work. I went to therapy, stayed home more often, and enjoyed spending a lot of time with my mom.

We had gone to Prince Edward County together, and she spent a lot of time with me to help me through my funk.


This past month has been amazing. I went to all the Christmas parties! I caught up with friends I had been neglecting over the past two months. I went to Niagara-on-the-Lake with my family, and took the longest break from work I’ve had since 2016.

I’m ready for the next year, and the next decade.

Not mentioned in this post are all the lovely moments that truly bring joy and make my days so beautiful. My fun (and weird) outings with my best friends, celebrating birthdays, engagements, and new life. Reading incredible books, or seeing movies and shows that moved me. I am so grateful for my loved ones, who have made this year the most incredible one yet.

Thank you so much for reading xox!


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  • Lillian January 1, 2020 at 8:43 am

    I am so so proud of you. You had a real busy year and came through many many turmoils and made you a stronger person.
    I love you so much.

  • Angela Liang January 1, 2020 at 10:04 am

    Thanks for sharing your incredible year. 🥰

    • jocelyncaithness January 1, 2020 at 8:11 pm

      Thank you so much for reading Angela ah-yee <3

  • Nabila Islam January 1, 2020 at 6:22 pm

    Hey Jocelyn,

    It sounds like you’ve had a full year, filled with a lot of change. I think you’ve experienced a lot of wonderful things in 2019, but it’s been very go, go, go.. so the downtime was much needed. It sounds like it’s helped you to refocus/recharge, and I’m excited to hear what 2020 is like for you. I myself have been in a funk since October. Lots of health issues cropped up, I’ve been uninspired at work, my inbox has been accumulating, etc. I’ve become more of a homebody and it’s helped a bit. Happy New Year to you and your loved ones. I look forward to reading about more adventures!

    • jocelyncaithness January 1, 2020 at 8:11 pm

      Thank you so much for sharing, I really love reading comments like this! I’m sorry you’ve been in a funk, and that you’re experiencing health issues 🙁 Sending good vibes your way <3 I'm glad that spending time at home has helped a bit, and I hope it continues to!!

  • Laura January 3, 2020 at 8:24 am

    Thanks for being so transparent about your ups and downs. It’s been a year of change for you and I can relate to the unsettling feeling of “what’s next”. Wishing you the very best in 2020! I’m here for you always. Xoxo

    • jocelyncaithness January 4, 2020 at 6:08 pm

      You’re the best <3 I'm so lucky to have you!!

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    About Me

    About Me

    Hi, Friend!

    I'm Jocelyn: a daydreamer and fashion lover disguised as a finance professional. My head may be in the clouds, but my stilettos are firmly planted on the ground ;)

    Jocelyn Caithness

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