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Business Lessons from a Failed Vacation

Business Lessons from a Failed Vacation: What the cancellation of my dream trip taught me

For the past couple of years I’ve been wanting to go on this mind-blowing trekking trip through the mountains of the Oaxaca region in Mexico. You start at the peak of a mountain, descend 70km by foot while visiting indigenous communities where you learn about their sustainable way of living, and finish off with a 30km whitewater rafting trip until you arrive at this amazing beach. I never shy away from something as exciting as this and I booked my trip two months ago. This was going to be my reward trip for working non-stop during COVID…something to really look forward to!!

And then…a week before my departure, the trekk got called off by the organizers. I was shocked, disappointed and felt helpless. The new Delta variant in Mexico made it too risky to bring a group of trekkers to these vulnerable communities. It was also risky for us as travellers. After basking in my frustration and drama for 24 hours, I realized that I could still manage to do something – perhaps not as big. I had the time booked off anyway.

I went back to a fundamental question: why did I want to go in the first place? The core of my decision was “because I want to have something to look forward to – I want to have ‘some’ sort of adventure.” So on a whim, I looked at other (less risky options). In a moment of clarity, I turned to my husband and said firmly: “let’s go to New Brunswick.”

In less than two hours, we had booked the flight, found a car rental and planned a loose itinerary for a last-minute, one-week family trip. I found myself gaining that giddiness back and still getting excited about having something to look forward to. Of course, it’s not the amazing 100km trekk through the mountains in Mexico, but I was still really, really excited because I dug deep into why I wanted to go in the first place.

Don’t get me wrong – that trekk to Mexico is still in the cards. It is going to happen, but it will just take a little longer. Which will give me more time to train, get in better shape and perhaps travel in a time when the pandemic is (hopefully) behind us.

This brought me back to advice I give over and over to my clients that want to start a business. They have an idea to start a huge restaurant, beautifully adorned, with a sparkly kitchen and bells and whistles. Or those that want to start the multi-faceted platform that includes an app and a double-ended marketplace. Or those who dream of becoming a residential developer, buying land and building homes.

Unfortunately, as they start doing the research of the costs associated with all of this, the struggles of getting financing and the many skeptics that squash their dreams, they give up.

If you have faced this situation, I challenge you to dig deep and ask yourself “why do you want to do this in the first place?” And my second question, and perhaps the most important one:

Is there anything you can do NOW in a smaller, less capital-intensive or risky way that will get you closer to your big dream?

To test the market, sort of speak.

For restaurant dreamers: could you start by renting a commercial kitchen and creating a ghost kitchen following? Then you could potentially do pop-ups at strategic venues, then move to a food truck and eventually a place of your own.

For platform dreamers: maybe you could start by developing a good looking landing page, using templated software, gaining a few customers and tweaking as you go. Iterate continuously until you find the sweet spot that will get you to the next big step.

For residential developers: maybe you can start by flipping homes (which by the way, that was my first business venture in Canada!) – buy a small home with good bones, do impactful esthetic renovations and sell it just before a year later (to avoid capital gains taxes). Then the profit gets reinvested into purchasing a bigger home, flipping it and so on. (Side note: I remember doing this through three different homes that I lived in, renovated them while living there and sold them 350 days later. It was a crazy time in my life, but it’s what helped fund my first pet retail store)

Here are some tips if you are faced in a situation where your big dreams seems almost impossible or too far away:


Ask yourself “why do I want this?” Then after you answer yourself, ask yourself why again to that answer, then do it again. Do this three times and you will start discovering the root.

Why do I want to go on this Mexico trek? Because the adventure sounds unreal
Why does the adventure sound unreal? Because discovering the hidden roots of my heritage is important
Why is discovering the hidden roots of my heritage important? Because COVID has put a wrench on my plans and I need something to look forward to


Another analogy you can visualize: you want the “Tesla version” of your business. But you can’t afford it right now. What can you start doing now equivalent to the Ford Fiesta of your business but that will get you closer to where you want to get?


Sometimes our friends and family mean well, but at times they don’t ‘get’ our entrepreneurial mind. Being an entrepreneur can be lonely, but community support (either through Facebook groups, Meetup groups, LinkedIn groups, or *gasp* in-person stuff) will be important to stay motivated and feel supported. Remember, celebrating those small wins (as tiny as they may seem) and feeling that moral support, will get you closer to your big goal.

Life has a funny way of doing things on your behalf for a reason. Sometimes it doesn’t go according to OUR plans, but the new journey we take can lead to better adventures, more learning and a different sense of accomplishment.

And now, I will start packing for New Brunswick, because I’m really looking forward to this little adventure.

Has this ever happened to you? Or do you have a big business dream that you could start NOW in a smaller version that will get you closer to it? Let me know!

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