How I Swam 5.25 Miles in the Open Ocean

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?

How to Swim One Mile Nonstop

On the flight back from Tel Aviv in the spring of 2008 I decided that for my next adventure I was going to swim 5.25 miles in the ocean. I had no idea how but I knew there were people I could count on to help me through. My own ego and force of will featured prominently in this decision, too. Now April, I had 14 weeks to learn to swim 5.25 miles non-stop in the ocean by mid-July. In pool terms, that is 324 25-meter-pool-lengths or 162 laps. When I made the decision I could do only one without stopping.

One Down, 161 left to Go.
The stroke of choice for long distance swimmers is American Freestyle. In New York where I grew up learning the stroke, it is referred to as ‘crawl.’ For the sake of this blog assume that these terms are interchangeable.

Crawl is difficult. Disconcerting for beginners, your head is in the water so that your face is down. You breathe by rotating on your body axis trying not to get a mouthful of water. This is very difficult if you aren’t what I call ‘swim flexible.’ Also complicating matters is the fact that you can’t really see straight ahead to where you are going – in the pool you must rely on bottom markers to know how close to the wall you are. Finally, crawl is very easy to do if you are efficient and have excellent form. It is exhausting if you are not. The more tired you get, the worse your form providing an asymptotic decline in performance.

The first thing I needed to work on was my breathing. After 1 lap of crawl I was panting for air. A decade of bench presses left me muscle bound – not muscular but literally inflexible to stretch well enough to rotate and breath. I practiced stretching constantly. In the pool, out of the pool, morning, noon, and night.

In the ocean I assumed that I would need the ability to breath as well on my right side as well as my left so I would alternate lengths of the pool breathing on my right side with a length breathing on my left. This also forced my to work both my right and left shoulders evenly further helping me strengthen the muscles around the previously torn rotator cuff.

5.25 miles is a long, long way. Especially in water when you can do only 1/162 of the distance without stopping. I created an incremental improvement program to get better.

Basic Program
I knew that a mile was 64 lengths of the pool. I was determined that no workout would ever be less than one whole mile. My first sets of workouts were dividing that into 7 sets like I would in the gym. My first 6 sets would be 10 lengths of the pool. Not much but better than 2. At the end of that, I would rest for a bit. The rules were simple, do 10 laps, of any stroke, kick board or not without stopping. I think my first workout took my entire night.

Basic Plus
Once my body adjusted to swimming for a mile a night, every other night, I stepped up the intensity. Breaststroke has always been very easy for me as is sidestroke. I would swim one set with only crawl and breast stroke and the next set after a short rest with the kick board and sidestroke. The focus was on getting as many laps of crawl in as possible.

The Breakthrough
After I knew that I could swim a mile without issue, albeit very slowly, I eliminated all rests between the sets. Now I was doing 64 straight lengths with no stopping. My next step was to eliminate the sidestroke and kick board laps making the entire workout only breaststroke and crawl.

At this point I would alternate every length or every lap of crawl with breaststroke. Eventually I was able to be more consistent with my freestyle numbers. I would swim 1 lap of crawl for every 1 lap of breast, then 2 laps of crawl for every one of breast. I had worked up to 5 crawl laps to every one breast when I decided to go for broke and do 8 laps of crawl – the equivalent of a quarter mile without stopping. I was overjoyed when I realized that I could! I remember the rest of my workout being an absolute joy I was so proud of myself!

After that progress came quickly. A quarter mile of crawl became a half mile of crawl. I would alternate a ‘fast quarter mile’ with a long, slow quarter mile. The night I did a full mile of freestyle without stopping I was criminally insane from the effort and oxygen deprivation but I grinned ear-to-ear! I think I told everyone about my accomplishment that I could reach via cell phone. I slept the sleep of the dead that night.