Sailing Away While Teaching


Learning and Teaching – Always

In recent columns, we have profiled former teachers and administrators who have continued to teach after leaving the mainstream education sector. Robert Bateman chose to change his field of mentorship, while Michael Munro moved on to a completely different country to continue his teaching, and Barbara Allisen found a new and interesting format in which to pass on her expertise. Their choices were very personal, but consistent with wanting to continue to impart knowledge and to helping students learn. This decision to continue to teach in some way isn’t surprising given that teachers enjoy passing on information and eagerly look for new challenges as a way to keep themselves involved and active.

In this article, you’ll meet Tony Dobson who has combined his lifetime hobby with skills he’d honed during twenty-three years in the field of education to create a new and exciting challenge teaching something that had been a passion for him— sailing. When contemplating retirement, Tony decided to take his hobby and run with it; but he had to overcome some personal challenges first in order to meet the rigorous standards of the Canadian Yachting Association. Having done this, Tony has spent his retirement teaching a new subject to a very different age group, all the while hoping for fair winds and following seas in his new classroom.

Although Tony’s retirement plan is very much his own, we hope that by reading his answers to our questions, you will see how a hobby, a passion, an interest can become a satisfying way to take those myriad skills that you have developed during your career and use them in a new and interesting way after retirement.

What was your original area of work in education?

I taught Grades 7 to 10 English, Math and Science.

How long did you teach?

I was a teacher in the education system for 23 years.

What type of education focused work/volunteering are you now involved in?

I currently teach sailing to people who have purchased, boats but haven’t yet acquired the skills necessary to sail and cruise them safely. The lessons can be spread over several days or weeks of cruising aboard the client’s vessel.

What were your reasons for deciding to continue to actively work after retirement from your primary career?

Wanting to stay busy doing things that I love to do was and is the prime motivator.

What made you decide on this particular type of post-retirement work?

Sailing is a passion for me, and since I had, many years ago, qualified as a Sail Canada Instructor, I decided to renew that qualification. The added advantage is that I have access to first-class sailing vessels and get all the sailing time that I would like to have, without the costs of owning my own boat while continuing to teach.

What challenges did you encounter in your new endeavour that you did not expect and how did you deal with them?

First, I had to upgrade my Sail Canada instructional qualifications so that I could teach sailing. Given my background I did not expect to be challenged so much; but at one point my skill level was seriously challenged and felt personally affronted. However, I decided to practise diligently and was able to overcome the initial failure to qualify.

What have been the rewards of your new endeavour?

I get to meet new and interesting folks, I get out on some very beautiful sailing vessels in some very beautiful sailing country, and I make some mad money. AND I get out of the yard work that my wife looks after while I am gone!

What impact if any has your choice had on your life in general?

Course bookings usually occur weeks in advance, so I have to plan my summer camping trips around them. Sometimes, I have to cancel other plans due to changes in sailing contracts. The extra money coming in from this hobby, however, helps to pay for expenditures in my other hobby—woodworking.

Where you ever worried that you might have made a mistake in your choice? If not why? If yes, did you have a Plan B – what was it?

Not at all! I didn’t really have a Plan B.

Did your new position require special training and if so what was it?

Yes—Instructor qualification from Sail Canada (formerly Canadian Yachting Association).

Has your background in education aided you in what you are now doing?

Absolutely! Lesson planning and preparation is essential, especially when it is expanded to the business of running a sailing charter from five days to several weeks of 24-hour contact with clients and their needs.

How long do you intend/hope to be doing the type of work you are now doing and why?

Probably another year or so; then I plan to move on to online teaching for DIY Investors. The investment counselling and teaching interest arise out of my own confusion about the world of finances, and a recognition that Canadians must begin to control their own financial futures, starting with debt management.

What advice would you give to other educators interested in pursuing the same type of work/ volunteering that you are involved with?

If you are a sailor, enjoy meeting new folks and you aren’t fed up with teaching and you also don’t mind earning some spending money—go for it! Take the Instructor course from Sail Canada.

Do you have any further thoughts or comments about your retirement choice?

I can’t think of a better way to spend summers— earning money doing the hobby I love most! A caution must be considered: no matter how enjoyable the work is, at some point the attraction of earning extra money, and the imperative of conducting a sailing course/charter must be balanced by protecting the other part of your life that you worked hard for—RETIREMENT.

As has often been pointed out, teachers are innovative and creative in their careers and their approach to life. In our recent articles and those yet to come we hope you will find something that will help you make your retirement plans, whatever they are, satisfying and unique.


Carol Baird-Krul & Enise Olding
Carol and Enise ( are the creators of a series of pre-retirement and post-retirement planning workshops: Transition to Retirement: The Uncharted Course©, Recently Retired: Charting a New Course© and Ideas… Enhanced and Advanced©, and authors of Transition to Retirement: The Uncharted Course. Previous articles on retirement may be viewed in back issues at

This article is from Canadian Teacher Magazine’s Nov/Dec 2013 issue.

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