On Friday, July 24th, I successfully swam 5.25 miles in the ocean non-stop as part of the Maggie Fischer Memorial Cross Bay swim. It was the culmination of 20 months of hard work and it was incredibly satisfying. I have been writing somewhat random posts talking about the events and training leading up to the swim and my reflections afterward. This article is a bit of a summation and aggregation of articles I wrote about how I did it and what I learned. Enjoy!

Introduction to the Cross Bay Swim

If you’re new here, you might be wondering ‘What is the Cross Bay Swim?’ Here’s a brief article I wrote just before leaving for the swim. An assembly of photos of the swim course can help you visualize the race and the scale.

I wasn’t alone in my efforts. I had a team backing me up.

Step 1: Get the Motivation

First off, you might like an introduction and overview of the Maggie Fischer Memorial Cross Bay swim found in Who’s the Guy in the Wetsuit. The swim website has a great article here on getting the motivation to do an event like this. My motivations were a little bit different.

I answer the question, ‘Why enter a 5.25 mile swim’ in this earlier article. While it seems like I was born knowing how to swim, not everyone is. Chris Gulliebeau writes about living with the regret from not learning how to swim. Even though I was comfortable with swimming in most situations, 5 miles in the ocean is a long, long way. But once I found out about the race and I learned that someone I knew did it, I couldn’t – not – try (double negative intended there!) Chris uses learning to swim in a metaphor for living a life without regrets. I echo his sentiment; “If there’s anything I don’t want, it’s a life of regrets.”

Step 2: Do the Training

Hey, 5.25 miles is along way, but it’s not as difficult as swimming the Amazon River.

I started off slowly. The hardest part was getting myself into the pool. I had to rely on a trick I used to do a body building show in college; Tell everyone you know you are going to do something and then be too embarrassed not to make every attempt to do it.

The first year I trained at the YMCA triathlon and around my buddy’s wake boarding boat. The second year, I was able to get a little more serious. Kevin moved to Charlotte and that offered the opportunity for me to swim while he kayaked along side me during the summer months. Let me tell you, swimming in open lakes for miles is very, very different than swimming in the pool! No matter the medium or your challenge, you have to get started. While I was training, I wrote this article on How to swim 1 Mile. I think the advice is good for swimming in particular and goal setting in general. Remember “A journey of 1000 miles begins with the first step.”

“You don’t want to know what we see swimming next to you.”

Step 3: Overcome Hurdles

The 2008 Debacle

Nothing ever goes according to plan. Not even Big Rocks like the Cross Bay Swim. You get obstacles. There are hurdles that need to be overcome. There’s no such thing as a free lunch.

I started training for the 2008 cross bay swim after returning from Israel in the Spring of 2008. The race I wanted to enter was never to be. I learned of the cancellation reading this post via my iPhone waiting for 8 hours on a plane that would never take off. Here’s a video of the race day conditions. I had trained and trained hard for 5 months for nothing. There was to be no race at all. I had to make a decision, would I give myself a mulligan for that goal or would I man up and decide to train even harder for the 2009 race? After about a month of feeling sorry for myself, I re-invented F-Club, and trained lights out for the 2009 Cross Bay Swim.

The 2009 Debacle

While I was training for the 2009 swim with renewed vigor I came to the harsh realization that the corrective foot surgery that I had been putting off had to get done. I had bent my big toe backwards 180 degrees the wrong way when a 250lb tight end fell on me while playing flag football (if anyone ever tells you flag football is non-contact, they lie!) This combined with a previous football injury collapsing the arch in my other foot had led to me wearing a foot cast and carryign crutches around for the better part of 3 years. That sucked. I had to end that cycle. The trouble was that the injury wasn’t interfering with my training (just all other aspects of my life.) Should I have the surgery? Would I be able to recover in time to train myself back into elite shape to do the swim? Was I just procrastinating because I was terrified of surgery? In the end, I had the surgery. It was awful, but I got through with it with tremendous help from my friends. And then we trained harder than ever to get in shape for the swim.

The week before the 2009 swim a giant shark washed up on shore. YOU DO NOT WANT TO MISS THE VIDEO HERE.. Sure, that kind of shark doesn’t eat people. But no one on those beaches thought they were bathing next to a prehistoric beast, either! Gut check time. Those shark images reminded me of the stories Long Island pilots would tell as they flew over area beaches. “You don’t want to know what we see swimming next to you” they would say. No, no sir I don’t. I pulled up my ‘big boy pants’ and decided to cowboy up.

Step 4: Get the Job Done!

In the end, there’s nothing left to do but swim. The event took me 3 hours. It felt like an eternity. If you’re interested, here’s an account in 3 acts of the swim day.


In the end this swim was more than about traversing 5+ miles in the ocean. Aside from the ego trip and validation of completing a long distance swim,I found there were many, many ancillary benefits, too. Sure, I picked up a bunch of practicle skills, but there were unintended, in tangible lessons learned as well. Some like weightloss were expected. Others like a change in psychology or help ending insomnia were not.

Abbreviated List of Benefits Derived from Long Distance Swimming

  • Learn how to swim in Open Water.
  • Learn how to cope with the unexpected.
  • Unforgettable experiences with good friends.
  • Weight loss.
  • Injury rehabilitation.
  • Drastically improved my insomnia.
  • Controlled my temper.
  • More productive at work.
  • See new places, and swim them!

I could continue rambling on about each item listed above, but that’s not my point. My motive in this article was to describe what it is like to set your sites on some foreign, larger-than-life goal, work yourself senseless to achieve it, and then enjoy the fruits of your labours. There were many times I wondered to myself if the efforts I was putting in were worth it. Many people thought I was crazy for attempting the swim. Others saw no point and no value in this kind of a goal. I hope that I’ve made a case here for setting your own hugely aggressive goal, and for following through.

At this time of year (January) there is no shortage of people wishing to make themselves over in a more ideal image. What separates the success stories from those people who will be making those same resolutions again next year is the ability to follow through. What’s your next life-changing goal? What will you do to get there?

Comments (7)

Great job! I appreciate you sharing this accomplishment and the analysis. No brag just fact and encouragement to others to do the same. Good going.

Thanks so much, Andrew!

Certainly, that’s the idea here on Cubicle Warrior. That while each of our goals and circumstances are different, patterns for success emerge that we can all apply to our own cases.

The nearly 2 years of training that I did for the swim taught me so much that it directly influenced my success in all the other areas of my life. Similarly, I was able to learn from success stories in disparate industries that helped me get through my goal.

Thanks for commenting!

Congratulations on the success! The steps you’ve listed here are not just great but can also be applied in other areas of life. A very big thanks for sharing your story. We sure learned much.

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