Why I Pay Money to Get Lucky

In Chronicles of a CEO by Rebecca Liston

Oh I know I lured you in with that rather intriguing article title, didn’t I? There’s a small part of you that thinks I just might disclose a penchant for visiting a certain district in Amsterdam or maybe I will confess a secret passion for roulette…

Alas, no such luck! But I do have a great story to share! Stay with me! This past Sunday I flew to Calgary to spend two days before driving up to the mountains and spending a week at my dear friend’s condo in Canmore. My itinerary looked something like this:


  • 4:00 am wake up
  • 7:00 depart London for Calgary!
  • 9:05 arrive Calgary airport
  • 9:30 to 11:30 argue with Enterprise car rental about my car not being ready (long story)
  • 11:30 hop in a town car (Enterprise is paying!) and race across town to my friend Nadine’s house
  • 12:10 arrive at Nadine’s, lug luggage into house, change, make self presentable (not easy given my last several hours were spent on a plane and fighting in a parking garage)
  • 12:30 get picked up at house by New Contact Number One for lunch
  • 12:30 to 3:30 pm have lovely lunch and great conversation with New Contact One
  • 3:30 to 7:30 pm spend time with Nadine and family (Derek cooks…it’s awesome)
  • 7:30 fall into exhausted sleep


  • 6:30 am wake up
  • 6:30 to 8:30 email and text replies, client support, etc.
  • 8:30 to 9:00 get ready
  • 9:00 to 9:15 attend an online Prosperity Playground with Nadine’s fab coach and feel very inspired as a result!
  • 9:15 to 10:00 finish getting ready
  • 10:00 drive to New Contact Number Two coffee meeting
  • 10:30 to 12:00 spend incredible 90 minutes engaged with amazing woman – delightful!
  • 12:00 to 12:30 drive downtown Calgary
  • 12:30 to 2:30 have fabulous lunch with one of my favourite Calgarians (okay, okay, he was born in Edmonton but whatever…LOL)
  • 2:30 to 4:00 drive to Canmore
  • 4:00 to 6:00 unload car and take long leisurely walk through Canmore to get a few groceries
  • 6:00 eat cereal for supper (because I can)
  • 7:00 to 8:00 chat with friends online
  • 8:30 bedtime (I am still on EST)


  • 5:00 am wake (yep, still on EST)
  • 5:00 to 8:00 wish I was still asleep
  • 8:00 to 9:15 client call with client in Poland (I miss her!)
  • 9:15 to 10:45 call with my own coach — my head spins for at least an hour after! WOW!
  • 10:45 to 11:00 snack
  • 11:00 to 12:00 emergency call with client in Virginia — she’s up to great things down there!
  • 12:00 to 1:00 lunch and stare at the mountains from my condo
  • 1:00 to 3:00 working, emailing, client delivery, marketing…I bang out a ton of stuff!
  • 3:00 to 3:30 nap
  • 3:30 to 5:00 client meeting online
  • 5:00 onwards chilling out in front of the fire
  • 6:00 am wake up
  • 7:00 to 8:00 travel to Banff Springs Hotel to meet Favourite Calgary Client One
  • 8:00 to 11:30 get wrapped in mysterious nice-smelling stuff, exfoliated, steamed, and “hot-springed”
  • 11:30 to 12:15 lunch at Banff Springs Hotel with Favourite Calgary Client One
  • 12:15 to 1:00 return to Canmore with Favourite Calgary Client One
  • 1:00 to 3:00 work my ass off with Favourite Calgary ClientOne
  • 3:00 to 5:00 meet with marketing team for Favourite Calgary Client One
  • 5:00 onwards dinner and chilling with said Favourite Calgary Client One and marketing team

Thursday (today)

  • 6:00 am wake up
  • 8:00 meet Favourite Calgary Client Two at the condo
  • 8:00 to 6:00 pm; we work and we discuss and we plan and we strategize and I anticipate we will have many breakthroughs! (And yes, we will go for walks, eat, and take quiet breaks during the day — balance is everything and I am in the mountains, after all, so I am going to enjoy them!)
  • 6:00 pm onwards relax with Favourite Calgary Client Two


  • 6:00 am wake up
  • 8:00 to 9:00 prepare for Big Meeting with Local Consultant who Favourite Calgary Client Number Two and I are bringing in to help us with some pieces we know we need support with from someone who knows things we just don’t
  • 9:00 to 12:00 meeting with Local Consultant that will, I am sure, give us precisely what we need
  • 12:00 to 2:00 long leisurely lunch and farewell to Favourite Calgary Client Number Two
  • 2:00 to 5:00 client emails, quick calls, and few house keeping items
  • 5:00 onwards relaxing, staring at the fire, recharging

FREE TIME — oh yeah — I am OFF and the Mountains are my playground! The Bow River at my doorstep, I will wander off, explore, and soak it all in. I am in my happy place.


  • 6:00 am wake up
  • 6:00 to 8:30 packing up and preparing to depart
  • 8:30 to 9:30 drive to Calgary
  • 9:30 to 10:30 meet and connect with Favourite Calgary Client Three (it will be so good to see her again)
  • 10:30 to 11:00 travel to Nadine’s
  • 11:00 to 11:30 visit, catch up, and say my good-byes
  • 11:30 depart for airport
  • 12:30 drop rental car and hope to not argue with rental guy (again) and check in
  • 2:00 depart Calgary
  • 8:00 EST arrive home to my chiclets — hooray!

Now, why on earth did I just give you a blow-by-blow of these last few days and the next ones to come? And what does any of that have to do with paying to get lucky?

Well remember back on that first Monday, I had lunch with one of my favourite Calgarians (yes, the one born in Edmonton!). Well during that lunch he asked me about my week and what I had planned, and he said, “Seems to me like a great way to spend some money to me!” And I grinned and said, “Yes, yes it is!”

Because you see, it wasn’t FREE to come to Calgary. The condo isn’t free. The food isn’t free. The gas, the car rental, the park pass for Banff, the spa treatment, the souvenirs for the kids: it all costs money.

But look how lucky I got! This is something that my lunch date on that Monday understood, just as I do: That spending money to do what I did this week would result in greater “luck,” greater prosperity, better relationships, more clients, deeper connections (to my own self as well as to them), than I could ever have gotten by sitting in my own home office.

I met two new amazing potential clients/referral partners. I had lunch with someone I truly respect and enjoy. I spent time with my girlfriend and her family. I had several days of deep and intense working time (and relaxation time — recall the spa?) with favourite clients. And I got time on my own to unwind and enjoy the mountains and this place that feels so much like home to me.

Yep, I paid money to get lucky. My secret is out. And I have to say that I hope you pay money to get lucky yourself one day soon — and tell us all about it when you do!


                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                                Did you enjoy this post? You can have articles like this, insights, and opportunities sent directly to your inbox each week. Click here to stay connected.


Rebecca Liston helps her clients predict, pivot, and compete in an increasingly complex global marketplace. Her clients quickly uncover the root of their challenges and know the actions to take to overcome them. A six-time nominee for the RBC Canadian Woman Entrepreneur Award, Rebecca combines business strategy with intuition, giving her clients the edge on forward-thinking, elegant answers to their most complicated problems. Her clients are entrepreneurs with CEO-mindsets and executives with entrepreneurial instincts. She is based in London, Ontario. What if you could get the answer to your biggest business challenge, in one sitting? Visit rebeccaliston.com to find out more.