Deeper Weekend 2014

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bryanWe can often picture where we’d like to go with our businesses, whether that’s a revenue goal, a certain lifestyle, or a level of power and prestige. The problem is: we don’t always know exactly how to get there. So, sometimes you just have to keep sailing.

If you’re not familiar with how a sailboat works, it’s pretty straightforward. Rather than using a motor, the boat is propelled by the wind pushing on your sail. Makes sense, right? But you can see where you might run into problems if you’re trying to get to a specific destination.

What happens when your destination is where the wind is coming from? See the problem? For the wind to push you forward, it needs to be behind you – or at least at enough of an angle to catch the sail.


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When this happens, you often have to sail past your destination and turn back to catch the wind. The first time this happens can be defeating because it seems like you’re losing progress by moving away from your goal, but don’t lose hope. Consider this: when we focus too narrowly on one goal, we lose sight of the big picture; we may even overlook a bigger goal. Remember that time Columbus kept sailing? That worked out pretty good.

Here are a few lessons from sailing that we can apply in our businesses:

Keep Moving. Just because the course isn’t clear from the start doesn’t mean you should stop. Keep using your momentum to achieve new things. If your goal is growth, keep up your marketing and networking efforts until something new presents itself. You never know where your next lead will come from. So keep moving; there’s a reason they call it “dead in the water.”

Figure It Out Along the Way. You may not know exactly what’s going to happen next. Let’s face it, you’ll probably never know what’s going to happen next, but as a business owner you have to be able to figure it out along the way. That’s how you got this far. Uncertainty is something we have to live with, but when new opportunities present themselves you have to be ready to act.

Adjust Course. Now that you’ve made some headway, you can start to determine if you’re in a position to head towards your goal. A new position means new perspective. You’ll use that to make changes in your short-term strategy to work towards the long-term goal. This new perspective may even reveal new goals.

Remember, just because you may not be headed directly towards your goal today doesn’t mean you should stop everything you’re doing. Keep moving, pick up speed, and make adjustments as necessary.


Bryan is a recent cliff jumper looking forward to running a firm his own way.  He aims to catalog his experiences here for future generations of cliff jumpers to learn from. Starting in January 2015, he will also be the Visiting Instructor in Accounting at Assumption College located in Worcester, MA. Bryan is also the co-host of a new podcast, Ctrl Alterego, which follows the saga of two new businesses in different stages of development.  He has joined forces with Barrett Young of The Green Abacus for this adventure. Follow along

  • On 06-16-2015 at 5:46 pm, Adrian G. Simmons said:

    Great encouragement — thank you Bryan!

  • On 06-29-2015 at 8:38 pm, Jim Bell said:

    “You may not know exactly what’s going to happen next. Let’s face it, you’ll probably never know what’s going to happen next, but as a business owner you have to be able to figure it out along the way.” Well spoken Bryan. Not knowing can be disabling as we venture out of a comfort zone. Certainly the reminder is well served for me personally.


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