25 Things Swimming Taught Me About Small Business (or, How To Escape Alcatraz) | Dr. Isaiah Hankel | Focus, Create and Grow Your Way To Intelligent Achievement 25 Things Swimming Taught Me About Small Business (or, How To Escape Alcatraz) | Dr. Isaiah Hankel | Focus, Create and Grow Your Way To Intelligent Achievement

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25 Things Swimming Taught Me About Small Business (or, How To Escape Alcatraz)

“Believe in yourself, not only in swimming, but in life itself. You always have to have fun. You have to have an open mind. If you’re not enjoying it, don’t do it. Life’s too short.”

Debbie Meyer (3X Olympic Champion; Freestyle Swimming)

“On matters of style, swim with the current, on matters of principle, stand like a rock.”

Thomas Jefferson (2nd President; United States of America)

“Only when the tide goes out do you discover who’s been swimming naked.”

Warren Buffett (Chairman & CEO; Berkshire Hathaway)


The only person who can get you across a dark body of water and back on solid land is you.

I was never a very good swimmer. Growing up, I must have looked like a drowning monkey when I swam because lifeguards would always watch me extra closely. In 6th grade I (illegally) dove under one of the docks on Lake Pend Oreille in Sandpoint, Idaho and the lifeguard on duty didn’t see me come up on the other side. Five minutes later I was laying on the beach drying off when a loud siren started to sound. Nearly a thousand people evacuated the lake and a chain of 20 lifeguards started to sift carefully through the water. Volunteers were running up and down the beach asking people questions. Who were they looking for?

One of the volunteers ran up to my parents and asked if they’d seen a kid named Isaiah. I was standing right next to them. I meekly raised my hand and said, “I’m right here?” The search was called off. I was grounded and banned from the beach for the rest of the summer. I learned two important lessons that day; first, know the consequences of the rules you break before you break them, and second, stay visible to the people who have power over you.

Train Early; Succeed Often

In college, our wrestling team trained twice a day during the season. One practice was at 4:30PM and the other was at 5:00AM in the morning. The only other people that were up training at 5:00AM were the swimmers.

Competitive, individual sports like wrestling and swimming teach people 3 traits critical for business success: self-reliance, self-discipline, and self-awareness. Studies show that elite athletes like wrestlers and swimmers make more money and are happier than non-athletes. I understand why wrestlers are successful in business and entrepreneurship (and I wrote about it here), but I never understood why swimmers were also successful in these areas. So, I turned to my friend Sarah Kathleen Peck to find out.

Sarah is a 20-time NCAA All-American swimmer who has also successfully swam from Alcatraz to San Francisco 9 different times. She is an award-winning designer and storyteller who spent the better part of the past decade building communications, marketing and PR campaigns for small to medium companies. Today, she teaches writing and storytelling workshops to help people discover their voice and share their stories with the world. Sarah is also a prolific writer who has been featured in The Huffington Post, Psychology Today, Fast Company, and Lifehacker. Her blog is called It Starts With as was recently ranked on Problogger’s 20 Bloggers To Watch List.

Enter Sarah: Swimming From Alcatraz

I tried not to think about it. 56 degrees. 5AM. Naked.

Chilly toes and frozen skin against the dark murky bay as I pulled hundreds of strokes to move my body from one place to another. I was fulfilling a promise I had made to hundreds of people. A promise that if we raised enough money for charity: water for my 29th birthday, I would swim from Alcatraz back San Francisco—with a slight twist. I promised I would wear nothing but a swim cap if we managed to raise more than $29,000 for clean water.

We raised $33,298.

I swam as fast as I could to the edge of the island, crawling up the slippery moss-covered rocks in the misty morning. Against the concrete slab and the sign warning all prisoners not to jump, I limbered up and into the air. I stood up and turned around and waved back at the boat that had dropped me off. I ducked back into the water as quickly as I could and pushed off, looking out briefly at San Francisco, so far off in the distance. The water was choppy and the wind a bit gusty, but not too bad. I needed to get moving.

I started swimming, just like I’d always done.

One stroke at a time.

25 Lessons Swimming Taught Me About Business

I’ve been an open water swimmer for a little more than five years, and a swimmer for most of my remembered life. Without swimming, I wouldn’t be who I am.

Swimming taught me how to be present, embrace fear, and take calculated risks. Swimming also showed me how to get results. Squeezing six hours of training into each day, somehow, made me more productive, not less. Here are 25 things swimming taught me about being successful both in business—and life:

1. Cold is a sensation that lasts for a few minutes.

Just like nerves on stage or flutters during an interview, once you jump in and get started, you can usually find your stride. In the water, cold is a sensation that you can immerse yourself within or detach from—and it gets easier to deal with each time you jump in. Don’t stand on the edge of the pool and wait. Keep jumping in.

2. Something always breaks.

Always. There is no perfect. There is no one ideal moment. When you step up to the blocks, jump in the water, try a new experiment, or make a new product, something always gets a little screwy. Or it gets a lot messed up. If I threw in the towel every time my goggles broke, my toes got cold, or when I felt bad, I’d be sitting on the sides the entire time I could be swimming.

Michael Phelps won a gold medal and broke a world record—with broken goggles.

3. Do it anyway.

When you realize that each moment has its own unique set of screw-ups, you can stop waiting for the perfect moment. Learn to smile and do it anyways. Every time I’ve launched a product (not one time, every time), something breaks. A website goes down. My link is screwed up. A video fails. Someone else’s website goes down. It’s all part of the process. So what? We carry on and we continue (and we start to laugh at all the ways things can go wrong).

4. Honesty and apologies go a long way.

When that something does break, I email people and admit what’s going on. When the website breaks, I email people and I say, “Whoops, sorry! I’ll have it back up in a moment!” If I panic, I just spend more time panicking. Instead, I spend time fixing it and getting back to the business of my work—or my swimming. It’ll break. Learn to roll with it and carry on.

5. Build in flexibility.

Knowing that things break can either make you pissed off—or more strategic. I build in buffer times to let the boat idle, I have a backup set of goggles and caps, I carry an extra pair of warm socks and a warm water bottle—but I don’t count on any of it. I’ll swim without any of it if I have to. In your life, build in flexibility whenever you can. Know that you might be up all night. Dealing with things that break creates resilience. Resilience creates agility. Agility and flexibility are critical for creation and innovation.

6. First times are everything.

Your days and your weeks should be filled with first times. If you’re not doing something new, you’re stagnating or getting boring. Get in the pool, already. Push yourself to try something new. Write a bigger essay, publish a book, learn a line of code, write a thank-you note. Go after new things before you think you’re ready.

7. You’re never really ready.

If you wait until you think you’re ready, you’re just waiting. The thing about starting blocks and timers is that somehow you’ve just got to get on with it—and before you’re aware of it, you’re off the blocks again, trying another time. Deadlines, habits, and accountability partners help us get over the hump of getting started. One of the reasons I sign up for so many triathlons and open-water events is because they get me to actually do the things I say I want to do—if it were up to my mind, we’d be sitting on the sidelines for a lot longer.

8. Stop thinking already.

Most of procrastination is over-thinking. Whether you do it now or later is a matter of how much time you spend thinking on it. The quicker you can get to action and the less time you spend thinking, the more time you’ll spend having fun.

Action teaches us everything. Figure out what you’re doing by doing it, not thinking about it. Whenever you get stuck, pick something and test it. Iterate.

9. Lean into the fear.

Fear doesn’t disappear. It’s always there. It’s your relationship with it that changes.

Fearlessness isn’t the absence of fear—it’s the ability to walk towards it and embrace it. It’s knowing that even if it knocks you down, you’ll find a way to get back up.

10. Everyone has something.

Just like you are afraid or scared, so too are the people around you. We’re joined together by networks of experience, history, and patterns. Many of us have lived strange lives. Be gentle with each other.

11. Every drop of water counts.

It may seem insignificant—but each drop, each action, is extraordinarily powerful. The work effort in a single day may seem unremarkable, but the cumulative effect of a month’s worth of days is powerful. Each footprint matters. Just like every person who donated $1 and $10 and said, “I’m not sure this will make much difference,” your work will build and accumulate over time with enough steady application.

12. Develop massive respect for the larger system.

We are but one drop in the ocean, one person among many, one piece of the puzzle. In the water, the ocean is big, brutal, handsome, and terrifying. The massive depths and powerfully crushing waves are nothing to mess around with—one slip-up, one screw-up, and you could be toast. Seemingly simple tides move at speeds far faster than I can swim against. The curls and riptides sweep bodies away from the shore like bits of timber against the surface: if you screw up, you lose. Yet even amidst this mountainous backdrop, you can do remarkable things.

I take the ocean very, very seriously. I prepare extensively, mapping and mitigating against risk—we chart the tides, have experienced boat captains, I drink plenty of fluids to hydrate (and prevent cramping in the water), and I listen to the rhythm of the ocean. I also check my ego at the door—it’s not about pushing through when the conditions aren’t right. I’ll be the first to call off a swim if it doesn’t feel right—call it intuition or respect, but you’ve got to be careful. I treasure the gift of life, and I do this not with recklessness, but with awe and humble respect for the ocean’s depth and velocity.

We carry man-over-board flags, two radio sets (to talk to the coast guards), and I have signals to notify my board crew of what needs to happen next. (Pull me out of the water is me just putting my hand on my head. Simple as that. Come get me.) We don’t mess around.

In work, the systems and structures and networks are equally powerful.

13. Know when to call it.

With bigger risks, the ego can get in the way. CEO’s will push agendas and ideas forward out of fear of appearances; testosterone-fueled aggression will hinder good decision-making.

In the water, my life is at stake. Making bad calls can mean I’ll get swept out to sea or lost in the giant crush of the ocean. Each decision is critical.

When I’m afraid and my emotional fear winds up, I push through. But when the real risks become too great—the waves are choppy, the boat’s not working correctly, the tide is pulling faster than the charts predicted—I’ll call it. We’ll hop out. “Today’s not the day,” we’ll say, and we’ll bring the boat back to shore.

I work very carefully to understand the difference between emotions, intuition, and real risk. Understanding the difference between ego and safety, between wisdom and fear, is the mark of a great leader in any business. “Calling it” is about the humility to know when you need to change your mind or your course of action, even if it feels bad to your ego. Do the right thing.

14. Every day, every practice, is different.

Some days I show up and I glide through practices, other days it’s nearly impossible to finish the circuit and my arms wobble through the weights. The same goes for my business: some days I nail it, crafting content and copy and wowing my clients; other days, I barely get through a pile of emails. Each day you just do the best you can.

15. You have more grit inside of you than you think you do.

In a recent yoga class, the teacher held us in warrior pose for nearly ten minutes. Students moaned, people crumbled, legs wobbled. At minute five the teacher set our perspective again: Nelson Mandela, he said, was in jail for decades. Do you mind holding the pose for just a few more minutes?

We straightened up immediately.

You are capable of incredible things: if you’ll let yourself.

16. Your body is a fluid, living, breathing machine.

You’re brilliantly designed, full of trillions of cells each packed together in a rhythmic working, breathing, functioning system. The rhythm of the day for an athlete is punctuated with precision: I know the windows of times to eat, what fuel to feed my body, when to rest, and when to push.

In life, your business efforts and teams each have their own dynamic pulsations. Studying how these systems organize, how to feed them, and when to push them lets you build the best possible system—for you and your team.

17. Pay attention to your strengths and your weakest links.

People say focus on your strengths—I agree—but you also need to know where your weakest links are. What’s the point that will break you?  You have to carry yourself through all of it, and propping up the weakest links (or specifically focusing on two key areas to improve)—actually create a framework to ALLOW for you to shine in your strengths.

For me, my business weaknesses are remembering certain calendar dates and getting buried in email. As a result, I focus both on improving my writing skills AND on developing skills and tools to help improve my weakest links.

18. Respect the grace and beauty of being alone.

In silence we learn the true nature of our thoughts, of our fears, and what patterns we’ve embedded within our bodies. Disappear into the silence of consciousness. Being present—without distraction, without a crutch of stimulation or media attention—is one of the most difficult things to do. In the water and in writing, I find periods where I lose track of time and sink into the deepest parts of my intelligent consciousness. We need more alone time, and less loneliness.

19. Your edge of discomfort is your area of growth.

Most of my best ideas come from the edge of discomfort—either in the water or within an idea. Push into it.

20. We’re smarter when we move.

Exercise has been shown to improve our smarts and reasoning skills, yet many people sit for upwards of 10 hours per day. Sometimes the smartest thing you can do for your business is go work out.

21. Asking for what you want.

This the biggest thing you can do to change your outcome. Sitting in silence in the ocean of talented people and connections is amateur at best. When we learn how to ask others for what we need, and learn how to ask well, we can move our businesses forward quickly.

22. Know your boundaries.

Leaning into your edge teaches you where your boundaries are—what’s okay and what’s too much for you. Know what you’ll be willing to do and when you need to protect your time, energy, or heart with appropriate boundaries. Most creative people say no to almost everything. Saying no is a boundary. In the pool and ocean, my boundaries come in the shape of what time I go to bed, what I do on Friday evenings, how I behave with alcohol, and who I allow to come out on the water with me.

23. Listen to the little feelings.

Learn what your gut is telling you. There’s a time to push beyond the fear, and there’s a time to listen to your intuition. You get better at it with practice, and action teaches you everything.

24. Each voice is unique and meaningful.

You don’t get written out of the journey if you don’t come in first place. Every single swim matters. In business, every voice matters. When I get frustrated that I’m not matching up to people I’d admire, or when I work with clients who are afraid to write—I realize that we have got to stop comparing ourselves and our work if we want to actually get to the business of making things. Even if a hundred people say the same thing, you’ll still be telling it to someone else for the first time. There are 7 billion people in the world. We’re going to repeat each other. Might as well join the chorus.

25. Distance creates perspective.

Out in the calm oceans beyond San Francisco, a mile and a half out in the middle of the black, dark sea, I get to turn around and look back at the city that makes up so much of my life. In a swimsuit, in the ocean, the city looks small, dots of light flashing on hillsides with a smattering of buildings. Many of my friends and I get lost in it, worried about the hour’s work. With distance comes perspective.

Have you ever participated in a sport, competitive or otherwise? If so, what lessons did your sport teach you about business or life?

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And don’t forget to visit Sarah here: It Starts With

Sarah is a 20-time NCAA All-American swimmer and an award-winning designer who has been featured in The Huffington Post, Psychology Today, Fast Company, and Lifehacker. Currently, she teaches writing and storytelling workshops to help writers, entrepreneurs, and thought leaders discover their voice and share their stories with the world.



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