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 am 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)


500 am wake (yep, still on EST)

500 to 800 wish I was still asleep

800 to 915 client call with client in Poland (I miss her!)

915 to 1045 call with my own coach — my head spins for at least an hour after! WOW!

1045 to 1100 snack

1100 to 1200 emergency call with client in Virginia — she’s up to great things down there!

1200 to 100 lunch and stare at the mountains from my condo

100 to 300 working, emailing, client delivery, marketing…I bang out a ton of stuff!

300 to 330 nap

330 to 500 client meeting online

500 onwards chilling out in front of the fire


6 am wake up

700 to 800 travel to Banff Springs Hotel to meet Favourite Calgary Client  One

800 to 1130 get wrapped in mysterious nice-smelling stuff, exfoliated, steamed, and “hot-springed”

1130 to 1215 lunch at Banff Springs Hotel with Favourite Calgary Client One

1215 to 100 return to Canmore with Favourite Calgary Client One

100 to 300 work my ass off with Favourite Calgary Client One

300 to 500 meet with marketing team for Favourite Calgary Client One

500 onwards dinner and chilling with said Favourite Calgary Client and marketing team

Thursday (today)

6 am wake up

800 meet Favourite Calgary Client Two at the condo

800 to 6 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 pm onwards relax with Favourite Calgary Client Two


6 am wake up

800 to 900 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

900 to 1200 meeting with Local Consultant that will, I am sure, give us precisely what we need

1200 to 200 long leisurely lunch and farewell to Favourite Calgary Client Number Two

200 to 500 client emails, quick calls, and few house keeping items

500 onwards relaxing, staring at the fire, recharging

Saturday and Sunday

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 am wake up

600 to 830 packing up and preparing to depart

830 to 930 drive to Calgary

930 to 1030 meet and connect with Favourite Calgary Client Three (it will be so good to see her again)

1030 to 1100 travel to Nadine’s

1100 to 1130 visit, catch up, and say my good-byes

1130 depart for airport

1230 drop rental car and hope to not argue with rental guy (again) and check in

200 depart Calgary

800 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!

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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.