Last weekend, I joined a sailing flotilla traveling from Portland twenty nautical miles down the river and back on an overnight trip. Originally, I planned on taking a 22′ Catalina as the skipper with another sailor in my sailing club as crew. I’ve never sailed that far as the captain of a boat.

To prepare, I had to buy nautical charts of the route, a VHF radio, and create my first sail plan with three different options for different sail speeds. The sail plan lined out the hazards on the river and where we should be when. I checked the bridge heights for the bridges we would cross against the height of the boat’s mast and determined that I should be able to sail underneath them.

I was anxious about returning up river on day two. My experience sailing upriver, especially in the morning, has been that it can be so slow that you creep along at less than a nautical mile an hour. At that rate, we would have had to anchor an extra night and spend two days returning to the marina. Which was a terrible scenario because I had a deadline on Monday and still had work to complete to make it. I was also concerned about motoring on the river and, if there was no wind, how long our little outboard motor could push us before it sputtered out of gas.

The day before the trip I lost my crew member. I didn’t even know if I could join the flotilla, because I wasn’t going to sail solo, but I gathered my gear and food and showed up to the marina with the hope that the flotilla commodore could put me on someone else’s boat as crew.

The commodore put me on his boat and we spent two days motoring up and down the river because there wasn’t enough wind to sail. I had a great time, but more than that, it was a rewarding trip because I learned about sail plans, boat speeds, how to radio in to a local railroad bridge to get the operator to open it, nautical chart symbols, marina fees, outboard range, travel distances on the river, radio protocol, and some of the local conditions not on the charts.

It wasn’t a perfect trip: we didn’t sail, I didn’t skipper my own boat, and we had a little drizzle of rain both days.

This is typically how it works when you invest in something new in your business. There are hurdles to start, internal (anxiety about speed on the river) and external (losing a crew member at the last minute). The new endeavor doesn’t end up working (crewing someone else’s boat under power, not sail). However, it provides resources and intelligence for something that will work.

Because of this, when you make an investment in something new, at a minimum, you should consider that you’ll make not one, but two or three investments before you generate a return (time, money, energy).