The Surfer’s Guide To Entrepreneurial Bliss

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I spent a good chunk of the last week looking out over the ocean from a vacation house in the Outer Banks, reconnecting with the water, the sun and sand. But, I never expected a set of killer business and marketing lessons to be revealed by surfers catching early morning waves.

1. Go Where the Waves Are – If you love to surf, but you live by the bay, you don’t just walk out and ask for waves on demand. You’ve got to go where the waves are. And, that’s in the ocean, not the bay. In fact, many surfers travel the world to find the best waves. Same thing applies to starting a business.

You don’t just decide you like building surfboards, then open a surf shop in downtown Chicago and expect people to start swarming in. You go to the waves. The places where your customers already congregate, share experiences and look for solutions. Not too long ago, this meant relocating to the coast. But, with the internet, you can now literally find the places your customers hare hanging out online, go to those places, build relationships and serve their needs in the communities they already participate in.

2. Survey the Sets – Before you paddle out, spend some time just sitting on the beach watching how the waves are breaking. Do your research to find the location of the best swells and the easiest openings to paddle out without getting crushed.

Similarly, in business, passion is not enough, you’ve got to do your research, look at the waves, understand the nature and nuances of the market, the easiest points of entry and the places where the greatest opportunities lie.

3. Wait for Your Wave – Once you’ve made it off the beach, rather than jumping on the first wave that comes along, you’re often better off sitting and observing from your new vantage point point…being in the waves…before choosing the best one to ride.

Same thing in business. The landscape often looks and feels very different from the inside looking out. Take the time to understand how the your observations and assumptions have changed, reexamine the players and the culture and observe from the prospective of someone who’s in the mix before deciding which wave, person, project, vendor or initiative to attach yourself to.


4. Don’t Wait Forever – If you keep letting solid waves pass you by, because you’re waiting for that one epic swell, you may well end up losing out on a lifetime of wonderful waves…and that epic one may never come.

At some point, you’ve just gotta take action on what’s in front of you, rather than sitting around all day, hoping something better will come along. Wait a while, do what you can to prepare, look as far out as you can to estimate the quality of the sets that might be rolling in. But, after a while, if nothing comes along, take the wave that’s before you. Even if it’s the wrong one. Even if it causes you to miss the one epic wave of the day. Because…

5. As long as You Stay in the Water, They’ll Be Another Day – Their are few true once in a lifetime opportunities. Opportunities are all around us all the time…if we’re willing to stay in the game and keep working for the big hit after days, months or even years of satisfying, but not epic opportunities.

The moment you pull yourself out of the mix, the minute you stop repeatedly trying and exploring, you eliminate of the opportunity to be in the game when circumstances converge to create magic.

6. Size Matters. If the wave is very small, you’ll never be able to gather the momentum to have fun. And, if it’s too big, for all but a few storm surf riders, the risk of death is just too great. But, then there’s that middle area, the 4 to 12 footers, the ones that seem to roll along the shelf for miles before they hit the shore. They may not be fodder for stories or once in a lifetime rides, but they’re often a source of sustained ear to ear smiles.

Same thing with starting a business. Skip the small waves. Find a big and hungry enough market to support what you’re trying to sell, to hit critical mass and turn a jones into a source of income and momentum. Without that, you’re never even in the game.


7. Start With the Long, Slow Rollers and Use a Big Board. No doubt, the big waves, the epic rides always require the most skill and the greatest risk. Played well, they can lead to massive success. Played poorly or too aggressively, you end up going “over the falls” and that can be catastrophic.

Find the long, slow 3 footers and use a big stable board to learn the craft, master that level, then move slowly into bigger surf and shorter boards.  Pay your dues. Take your time to build your knowledge base, skills, abilities and relationships. Master your current level, then when you’re competent, take it to the next level. And, don’t look to others to know when the time to make the jump is. We all go at our own, often radically different paces. Honor that.

8. Be Ready When the Big One Takes You By Surprise. No matter how much you try to read what’s coming in, there will be times where you blink and find yourself seconds away from an epic tube. Don’t ask why you never saw it coming, just get on your feet and ride.

Same thing in business. Plan well, but don’t allow your plan to become your master. Opportunities come along, often out of nowhere. You can sit there and analyze why you never saw it coming. You can say, “but this doesn’t fit with our original plan and projections.”

Or, you can get on the damn thing and ride it to glory.

What do you guys have to add?

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31 responses

31 responses to “The Surfer’s Guide To Entrepreneurial Bliss”

  1. Well done Jonathon,

    It’s amazing how when you’re aware–or AWAKE–how the metaphors for a successful life are all around. And really, because business tends to be so much less clear (and more messy), it’s easier to find inspiration and guidance for action outside, in simpler activities, as in the case of surfing.

    I love it! It really does help me to see the patterns, to guide my actions. I find myself doing the same sort of thing with sports or other physical challenges. I like to think I’ve done a post as clear as this but I may be kidding myself.

    Either way, I don’t want to start trying to add anything to your work here. I think it’s perfect as stands. It’s just enough wisdom to act on.


    • Jonathan Fields says:

      Absolutely, the patterns really are all around us when we pause long enough to see them.

  2. Great post. I moved to the beach about 5 years ago with the intention of learning to surf. I started my small business 2 years ago with the hopes to go “Renegade”.

    For most people, myself included, getting in the water has always been the hard part. Too cold, too rough, sharks, etc. That was just the business side of things.

    In a moment of sheer frustration, I hired an instructor, a coach. Fear is a funny animal. It will keep you from the true fulfillment of riding the wave. Do whatever it takes to get out there and surf! You can’t imagine the bliss while standing on the beach watching. Just as you can’t enjoy the successes without launching. Get in and paddle out.

    My surfboard, and my business are getting more use these days, even if it is only in a learning aspect. I’ve had a lot of sand and salt in my nose thus far, but I haven’t lost my board. Im finding the learning more enjoyable than I thought. Its hard work. The cold goes away, and the bruises heal. Come on in, the water’s fine. Besides, do you see the girls that hang out with surfers?

    Thanks Jonathan

    • Jonathan Fields says:

      No doubt, if you have the ability to tap a trusted mentor, it can make the process way more enjoyable and also provide an incnetive to act and a source of accountability

  3. Srinivas Rao says:

    Hey Jonathan,

    My friend sent me this article. It peaked my interest immediately because I’m an avid surfer. The funny thing is I finished graduate school in April and in my struggles to find a job, surfing has been the one thing that has kept me going with a smile on my face. I went from being an occasional surfer to surfing about 6 hours a day about 5 times a week. Needless to say I’ve gotten a hell of alot better. What’s interesting is I also wrote blog posts about the 7 Life Lessons I’ve learned from Surfing and Why Surfing makes the world a better place. Stop by and check them out :). I’ve just subscribed to your RSS feed.

    • Jonathan Fields says:

      Hey Srinivas, I’ll stop by and check out your post. Man, you must have some serious chops after that much time in the waves!

  4. Mike CJ says:

    Jonathan – I loved this – I’m a surfer and a blogger! It’s a dreadfully overused phrase, but this really resonated with me.

    I’d add only one thing: “Treat every wipeout as one step closer to the ultimate ride.”

    • Jonathan Fields says:

      Thanks for that, no doubt it resonates in entrepreneurship, too…as long as you learn from your wipeouts

  5. I’m a surfer too and also loved this story. So true. Don’t forget the most important rule though. You’re going to have wipeouts, make mistakes, judge the wave wrong or get caught on the wrong side of a big one. Ouch. But never mind, just get back on your board, get back out there and try again. Practice makes perfect!

    Surfing definitely holds a few keys to happiness for me. It keeps you totally in the moment. Thank you:)

    • Jonathan Fields says:

      Glad to see it’s resonating with my surfer family! And, great addition with the wipeout rule.

  6. Jim Valeri says:


    I can totally resonate with this. I have a friend who sees opportunity waves all the time, but more often than not, uses the wrong board and wipes out.
    Then he quits, until he gets excited about the opportunity waves again, and continues to use the wrong board for him.

    Part of this is just recognizing that you need to get comfortable with the beginner board, then stay in the water long enough to catch the wave you need. I’ve been using the same board for a while (counseling) and I think I’m ready to move onto a different one (writing).

    Thanks for the great analogy. I gotta go talk to my friend now… 🙂

    • Jonathan Fields says:

      So true, you can be in the right place at the right time, but if you choose the wrong approach in relation to your experience and abilities, it’s game over

  7. Adalia John says:

    I am not a surfer, however, I appreciate the use of surfing as a metaphor for life in general. You have a gift with the pen. I am inspired by this writing to keep on keeping on. Sometimes even those who inspire others, have moments when they too need to be inspired, for me this is such a moment.

    Thank you,

    • Jonathan Fields says:

      Thanks, adalia, It’s amazing how many life and business lessons exist in nature all around us when we stop long enough to see them

  8. A few years ago I was talking with my brother who still surfs at the age of 62. That conversation also led to a great metaphor for entrepreneurs. He said, “You know, I surf better now than I did when I was thirty.” Then he added, “You gotta ride more waves. It all goes in the bank.”


  9. Tisha Morris says:

    Great article, Jonathan! Would make a great book!

  10. Kyle Hansen says:

    Great post, and I love the analogy to surfing as I never thought of business this way even though I’ve been a surfer for about 35 years. I think people underestimate how hard it is to really truly learn to surf. It’s the same way in business, it takes time and persistence. I don’t know of any other sports that require this in order to learn the sport, just like in business actually.

  11. This post made me smile because it is a mini-version of the lessons I was trying to teach my seven year old son at the beach earlier this summer. He had his first boogie board and wanted to go crashing into the ocean with it. I told him to slow down and just sit onthe beach with me for a few minutes. He tried, but the tempatation was too great. He did go crashing into the ocean with his boogie board, and the waves ate him alive. After enough wipe outs, he drug his little body out of the water, sat down with me and said “Now what were you saying Mom?” With a little observation and some advanced planning, our ride can be so much easier – and WAY more fun!

  12. Vincent says:

    Hi Jonathan,

    These are some great ideas for entrepreneurs. If you want to be in the game, you got to first start surfing the waves. Most people fail to start and hence they are always out of the game.


  13. Daniel says:

    I learned to surf (badly) in Hawaii, and I’d add one more rule:

    Share. There will be plenty of waves for everyone, so give up a wave here and there to another surfer.

    The business analogy is that there is plenty of opportunity out there for everyone.

    Dan, from the Casual Kitchen Blog

  14. I don’t surf but it’s good metaphor. But I learn one stuff for swimming. Success and progress start in a moment when you think: “I can’t do it any more”. If you continue after that you make progress, if not you stagnate.

  15. Dan Holloway says:

    Great post, Jonathan, but I’m not surprised surfing has lessons to offer. Just think of the film Big Wednesday – about al you need to know in life summed up in a hippy surfer flick.

  16. Naomi says:


    I’m Sooooo glad you wrote this post. I love surfing, and I’m constantly explaining everything in life and marketing in terms of surfing. There are so many parallels.

    In fact, I recently wrote and article on this:

    Worth a look – when it comes to positioning and snagging that perfect ride, surfing can teach you a lot about business.

  17. Fiona Boyd says:

    This is a great set of metaphors Jonathan, really useful. Have made all the mistakes and come to the same conclusions you do here. Except I wish I’d done mine in the water and not in business. Jumping in too early or being pushed to start is hazardous, but waiting around too long is more hazardous. Research is key, but too much is debilitating. Everywhere it seems to be about finding that little magic bit in the middle and mining it for everything it’s worth. Thanks for this- you’re reminding me of some lessons learned and some hard won insights, too easily overlooked.

  18. […] Watching the surfers revealed a connection between surfing, business, and life in general.  […]

  19. Wayne Key says:

    If I going to add anything to your list it would be if you know you love it, just get in the water Now and get going. We can never loose time, we just loose bits of ourselves. Sadly it cost me quite a bit of time to learn this…

    anyway… another excellent post. Thanks!

  20. Jonathan, Great metaphor for business. Too many people look for the “perfect wave” and never seem to get started. The trick is to find the one that is good enough to get started and build from there. Pick your spots and expand. Great post as this made sense to me.

    — Dan

  21. Mouli Cohen says:

    I love it! I just started surfing in the last year and your metaphors are perfect!

  22. Rob Beedie says:

    Just Paddle Out / Drop In / Wipe Out & Do It Again, Again, & Again

    ENJOY EVERY MINUTE, every single minute……

  23. […] post was inspired by an article Jonathan Fields wrote, The Surfer’s Guide To Entrepreneurial Bliss.  Jonathan Fields is the author of, Career Renegade, and his blog, Awake At The Wheel, has amazing […]