Business planning and a cross-country trip

My cousin (pictured second from right) and 3 of his friends are biking across Canada to raise money for cancer care. (Sorry I don’t have a bigger picture).

Because of the oddities of the Canadian landscape, my house marks the geographic halfway point of their trip but only one-third of the distance they have to travel on their trip. In the month or so they’ve been on the road, they’ve been stopped by snow (unseasonal even in Canada) and unbelievably torrential rain… and one of them ran into a car and spent 2 weeks recovering.

The 2 days they spent at my house were a whirlwind of high-protein foods, bike repairs, and planning. It was interesting to watch how they planned and I thought it was worth blogging about because there was a good business-planning lesson.

You see, a lot of businesses fall on either end of the planning spectrum: Some are over-planned and some are never-planned. The over-planned ones spend a lot of time and money and effort on setting a course and creating strict steps to get through that course. The never-planned businesses basically just hope for survival and a vague sense of profitability. Both types of businesses will sputter along: The over-planned business will invest heavily to meet its plan but will be unresponsive to evolving marketplace demands. The never-planned business will bend and sway and never really push forward effectively.

But my cousin and his Biking4Change colleagues were a model of planning: They had a clear goal (get across Canada) and timetable (do it in 2-3 months) but they recognized that the day-to-day changes (like weather or running into a car) would impact their trip. So every checkpoint necessitated a readjustment of their situation: They couldn’t pack food for the entire trip, for example, so they had to build food-buying into their plan. They’ll be traveling through some pretty remote areas, too, so they have to think about drinkable water and bears. (And for those of you who aren’t familiar with Canada, please don’t think that I live in that kind of environment… I wouldn’t survive a day). They rely on local help as well as the tight-knit community of cross-country cyclists to get a quick idea of what’s ahead and how they can meet their needs for the week or so until their next checkpoint. They look at what’s ahead, they assess the situation, and they develop contingency plans in case of headwinds or inclement weather.

The over-planned business isn’t flexible and the never-planned business is too flexible, but this plan-to-the-next-checkpoint model works for businesses. You need some clear goals and plans but you also need checkpoints along the way where you can reassess. Don’t try to plan out your entire journey in excruciating detail at the very beginning: You can’t accurately foresee everything and you can’t possibly carry everything for the entire trip. Instead, have a bold, over-arching vision for the full trip but create a clear plan just to your next checkpoint and carry just enough to get you there. Get the help of people (like colleagues and coaches) who are “local” to your situation and can help to propel you forward to your next checkpoint.

This approach will help you act faster. You’ll be more agile to act quickly (and you’ll be more likely to act!).

This approach will save you money because you don’t have to invest in more infrastructure than you actually need right now. You’ll grow incrementally this way rather than risking your business with high expenses and insufficient cash flow at the very beginning.

This approach helps you to respond to the demands of your marketplace better, which ensures survival in all kinds of market conditions.


  1. Create a vision for your business that takes you from where you are today to a highly successful ideal in the future. Set an end date but give it some flexibility.
  2. Set up checkpoints along the way, much like my house was a checkpoint along my cousin’s journey. Make these checkpoints measurable points along your route and assess your situation whenever you arrive at one. You might consider basing these checkpoints on revenue earned or time in the business or a product release (like 1.0, 2.0, 3.0).
  3. Create a list of things you need to have in place to take you from today to your first checkpoint.
  4. Create a list of detailed tasks to take you from today to your first checkpoint. If possible, make them as sequentially step-by-step as possible. And, of course, just do those steps in order.
  5. Identify a couple of people who are familiar with the route and “local” to the situation (they are doing the same thing now or have done this before) to help you. Get in touch with them.
  6. Get started on your step-by-step process, keep your eyes on the overall vision but don’t worry too much about the details later on the journey. Just work on making the current leg of your trip as successful as it can be.

Published by Aaron Hoos

Aaron Hoos is a writer, strategist, and investor who builds and optimizes profitable sales funnels. He is the author of The Sales Funnel Bible and other books.

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