My 2018 Personal Year in Review


This was a big and wonderful year for me. Here’s a recap:

My year, in pictures

Life can be a blur and gone in a flash. Before you know it a decade or more has passed. That’s why I think it’s important to look back and remember how far you’ve come.

It’s so easy to dwell on the negative things that happen in the world and to us personally, but how often do we stop and smell the roses? This has been a momentous year for me, so for the first time, I wanted to publicly review the last year and look at all the positive things that happened, goals that were met, and memories that were made.

Chances are most of you won’t be terribly interested to read about my year, but that’s ok. I did this for myself and those closest to me, and I hope to make this an annual tradition going forward. Maybe you’ll find some helpful nuggets.

Personal milestones:

  • Got engaged and married to the woman of my dreams

  • Bought land and began building a house

  • Became debt-free

  • Became an investor

  • Wrote a book

  • Read nine books

Business achievements:

To be clear, these aren’t things I did alone, this was a team effort. But as a company, I’m incredibly proud of what Proposify accomplished this year.

How I stayed productive

This year I evolved my methods of staying productive and organized. Here’s what I did:

I continue to use Google Calendar, Calendly, and Spark (the best email app in the world) to keep all of my meetings, calls, and events organized. I’d be lost without these tools. I continued using Evernote for notes, to-do’s, and recording ideas.

It was my first year having an assistant (Cavell) who booked my travel, printed, filled out and mailed things for me, ran some personal errands and generally made my life a whole lot easier.

People ask me how I was able to build a house, get married, write a book and build a company all in one year while still having lots of time for Christina and the boys. The real answer is, I hired and delegated. We hired Elegant Productions to plan our wedding, Bowers to build our house, and Scribe to help me write my book. I was obviously still heavily involved and had to make decisions, but these companies kept the project moving ahead.

On the personal side, I began using Productive and Calm apps. They have helped me be much more consistent with daily reading, meditating, stretching, eating healthily and exercising. I even use Productive to remember to listen to new music every week and go to the movies once a month. These activities allow me to unwind and keep me mentally stimulated, but I need a reminder.

The Five Minute Journal helps me begin the day on a positive, productive note, end the day reflecting on what went well and how I could have done better, and live an overall more mindful life.


I read more this year than any year prior. In addition to the usual books on business, I got some personal reading in, which is rarer for me.

I re-read JRR Tolkien’s, The Lord of the Rings for the first time since 2002, I read Lloyd Evan’s latest book, How To Escape From Jehovah’s Witnesses, which I designed the cover for, and I got to understand more about the science and philosophy behind Western Buddhism in Robert Wright’s, Why Buddhism Is True, which helped me gain a deeper appreciation for meditation as a way to override the evolutionary programming of the human brain.

Earlier in the year, Gino Wickman’s, Traction, and Simon Sinek’s, Leaders Eat Last helped me gain the mindset, strategies and processes needed to double our employee count, and From Impossible To Inevitable, Lost and Founder, The One Minute Manager Meets The Monkey, and The Hard Thing About Hard Things all helped me push through some major growth challenges.

Monthly highlights


  • Went on a romantic skiing getaway with Christina in Tatamagouche.

  • Had our first yearly planning offsite with the Proposify leadership team.

  • Went on a trip to Austin for Dan Martell’s SaaS Academy conference. It was surprisingly cold down there, and they even shut down the city the first day I got there all because of a tiny bit of snow. Silly Texans!


  • Travelled to San Diego for work (Traffic & Conversion and Social Media Marketing World conferences) and pleasure. Got engaged and closed the investment deal within same 24 hours!


  • Began writing my book, Free Trials (and Tribulations): How To Build A Business While Getting Punched In The Mouth. (launches January 29th)

  • Made my first angel investment in Cribcut.


  • I packed up my belongings and moved in with Christina. And surprisingly, we don’t get on each other’s nerves… too much.

  • I went to Toronto with Patrick and Ricky for Dan’s second SaaS Academy event of the year. Smoked my last cigarette and haven’t touched one since.

  • Christina and I bought land to build our dream house and began the design process.


  • Went on a trip to Florida with my family. We visited Disney World (first time ever for me) and then spent a few days in Tampa.

  • Proposify moved into the new office in the historic Morses’ Tea building in Halifax.


  • Christina and I went to a beautiful wedding (Natasha and Chris’) in Muskoka, Ontario (cottage country). The weather was gorgeous.

  • I was best man at Ricky and Allie’s wedding

  • Kevin hosted his Can Am party (July 4th weekend) at his new lakefront house

  • I bought my first surf board and wet suit (still working on the actual surfing part)


  • We saw Alvvays play during Halifax Jazz Fest.

  • Spent a week at the cottage with Christina and the boys. Got in lots of kayaking and standup paddle-boarding. Had our friends, Andrew and Cat and their girls down to the cottage.

  • For Micah’s birthday instead of buying him things, I took his friends to the waterpark for the day and then just the two of us went to Toronto for a couple of days. We visited the aquarium and saw a Blue Jays game.

  • Had our third annual Proposify cruise.


  • The biggest month yet. I enjoyed an incredible bachelor party hosted by Ricky and Kevin. Drinks were drunk, axes were thrown, and karaoke was sung.

  • Christina planned an amazing birthday party for me just a few days before the wedding.

  • The best day of my life happened: I married my best friend, Christina. It was a storybook wedding celebrated with our favourite people. We danced into the wee hours.

  • Went on a quick mini honeymoon at the mystical and luxurious Trout Point Lodge.

  • The weekend afterward, we went back to the same house where we got married to hang out with our friends, Bill, Meghan, Evan and Ashley.

  • I spent a week in San Francisco for Dan’s third event of the year. I went on an amazing hike near Golden Gate with Ricky, Jen and Lisa. The event was fantastic. We visited the office and met with Jeff Larson, CEO of Twilio, and went on a guided segway tour around SF at night.


  • I went on a business trip to Dublin to go to SaaStock and we turned it into our honeymoon. We rented a car and drove to the west coast of Ireland. Mountains were climbed, sights were seen, and Guiness was drunk.

  • We went to Jen’s epic annual Halloween party and I won best costume for the first time ever.

  • We visited the Annapolis Valley, picked apples, got lost in a corn maze, and visited a haunted house.

We ended the year with an amazing Christmas. Our year end Proposify party was a blast. Our house is nearly finished. My book is ready to launch in January. I invested in Concrete Ventures.

What’s next in 2019

I’m not a big fan of announcing New Years Resolutions, because by announcing it I kind of jinx myself. I prefer to announce things only when they are done or are well along the way to being done.

That said, next year I plan to take health and fitness to the next level, get more skiing and surfing in, see more of the world, read more books, speak at an event or two, write and record some music, and hit some ambitious business goals with Proposify. I hope you had a great 2018 like I did.

Happy New Year!

Kyle Racki