Navigating the Winds of Career Change

SailingThis summer while on the water, I was struck with how managing our career path requires us to be aware of the conditions around us and be ready to quickly adjust when our environment changes – much like sailing.

During the summer I enjoy recreational sailing at our family cottage in the beautiful Muskokas, but navigating our cottage’s lake can be tricky as the winds are very gusty and unpredictable. There are times that the wind shifts so suddenly that it sends me scrambling to adjust the sail and shift my weight so that I don’t capsize. At other times I can be going full speed ahead and within seconds I am becalmed (stalled with no wind). The very nature of sailing involves making many small adjustments and sometimes some large adjustments. But that’s all part of the fun and the challenge of sailing.

“The only thing that is constant is change” Heraclitus, Greek Philosopher

In this day and age, the winds of career change are more unpredictable and gustier than ever. If we try staying on the career path that we charted at the beginning of our career, or we get caught daydreaming while at the helm, we can easily find ourselves off-course or dead-in-the-water – like the time that I grounded my friend’s yacht because I was watching the scenery instead of keeping my eye on the depth finder. Layoffs and rapid technological changes require us to be alert and responsive or be left behind. It’s a human tendency to wait until we HAVE to act – usually making it more difficult to recover than if we had acted proactively.

“If you want something new, you have to stop doing something old” Peter F. Drucker, Business Management Expert  

Throughout our career journeys, we often need to make small adjustments along the way – attaining certifications, obtaining training, taking on new responsibilities or adapting to new methodologies. Sometimes larger interim career changes are needed to get us to the desired end-destination (tacking in sailing terms) – like additional education or a job change. And other times the end-destination itself needs to be completely reassessed. There isn’t an auto-pilot for managing our careers – we need to take the helm ourselves!


As you chart your career course and set sail, here are some steps to consider:

  1. SearchingIdentify your destination. What are your aspirations? What are your career goals? You might have a 5-year goal or a 10-year goal. If you have a career goal that matches your strengths, passions and work style, then you are more likely to enjoy the voyage…and enjoy the destination when you arrive.
  2. If it’s a challenge for you to identify a long-term career goal, I encourage you to look for help from someone who can help you explore your long-range goals…for example a Career Coach or a mentor.
  3. If identifying a long-term career goal is still a struggle for you, try to identify a shorter-term goal – your NEXT waypoint in the journey. Sometimes we only have enough light to illuminate our next step. Given your CURRENT skill set and experience level, what is one short-term action that will likely open the most doors for you? When you arrive at your interim waypoint, you will likely have a different perspective and vantage point in which to make the next decision.
  4. Chart your course. Determine what path lies between your current position and your end destination. Navigating - MapThere might be a couple of hops necessary to get you to your desired career! You don’t necessarily need to get there in one leap. It might require some courses, another degree or some additional job experience. What is YOUR next step?
  5. Don’t let obstacles deter you from setting a worthwhile goal. When charting your course, there will very likely be some obstacles in the way of your dreams. Worthwhile change usually comes with challenges, but many times obstacles that may seem like mountains are merely speed bumps when we examine them as part of the bigger picture. When you see obstacles that are in the way, instead of throwing the dream away, ask yourself, “What would it take to get around this obstacle?”
  6. Watch and be prepared to make adjustments along the way. Conditions are certain to change along your career journey. You have a choice to be proactive or reactive. Not choosing, by default, is actually choosing to be reactive. Block off time in your schedule to read career-related materials, attend seminars, network, listen to podcasts, and watch related videos. By watching the conditions around you, you are more likely to notice when you will need to make adjustments!
  7. Get on board! You can have your end-destination planned and your course charted, but unless you get in the boat and start to set sail, it does you no good at all! Once you embark and cast off, the journey will most certainly be more exhilarating than standing on the dock.
  8. And don’t forget to enjoy the ride along the way!


What simple change can you make now to help you move one step closer closer to your career destination?

Who can keep you accountable for that next step?


Kevin Schafer is the founder of Cardinal Career Management Services,
focusing on Career Improvement, Leadership Development, Retirement Planning & Job Search coaching for clients across Canada and world-wide. (


If you need help in establishing your long-term career goals, in determining some intermediate waypoints, in adjusting to the environmental factors around you, or in just getting off the pier, I would be happy to assist you.

Call for a FREE, 15-minute, no-pressure assessment:

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