Preface

This is not a learn-to-sail book. There are plenty of learn-to-sail books. I have written a few myself. But this is not one of them.

It is a book about starting and running a small enterprise.

Mine happens to be a sailing school.

One need not necessarily be in the sailing business to find something useful here. Much of running any business is the same, regardless of what goods or services it offers. The parallels are self-evident.

I expect no one to read this cover to cover, nor to read the chapters in order. There is no plot. There is no beginning nor any particular end. Each chapter addresses a separate element of running a small business. Similar to most manuals or reference books, a reader can zero straight in on topics of immediate interest and save the rest for another time.

There are synergies and cross-connections in any small business operation. Each element affects another in some measure. So, my advice is to skip around as need and curiosity dictate. There are many crosslinks (in the digital version) to assist in finding further context to topics of keen interest.

The book’s point of view is that of a present-day older me, somehow going back in time and counseling a younger me. The reader is invited to eavesdrop on that imaginary tutorial.

I would categorize this as part handbook and part memoir. It recounts some encouraging successes, dispiriting defeats, endless surprises, and the many lessons learned.

Personal anecdotes, tips, and observations are sprinkled throughout. Many are intentionally obfuscated. I do not name names where it serves no purpose. This is intended to be a resource, not a tabloid.

I have been privileged to be able to pursue my passion – designing, growing, and managing public sailing programs. For me, it has always been a vocation.

In hindsight, I guess I was pioneering. There were no “how-to” references available when I started. I was feeling my way into an emerging new field which, much later, came to be known as community sailing.

Having few mentors or role models for guidance, I learned mostly by trial and error. By necessity, I discovered my own “best practices” as I went along. During my half-century or so in the trade, I accumulated some opinions, based on my experiences. I share many of them here.

I am sometimes asked for advice – and am happy to oblige. But, as age has caught up with me, it seemed time to write down some of what I have learned, to preserve it for when I am no longer able to respond. Perhaps it will serve as some help to those who follow.

I began drafting this tome many years ago. It started with stray thoughts scribbled on scraps of paper and stuffed into a folder for safe-keeping. Eventually, I knitted those disjointed thoughts into prose. Then, countless times, I revisited each topic to add nuance, further reflections, and anecdotes.

The vast majority of workers in the sailing instruction business are summer job people – high school and college students mostly. They come and go seasonally.

Almost none think of it as a “real job”. To many it is simply a respectable and defensible way to pass the time between academic years.

A very tiny number of them find it a career vocation – as I did. They are, in part, my target readership. I write these words encouragingly, to offer them a head-start, a short-cut; so, they do not have to learn the ropes as I did – from scratch.

– JK