My 68 Most Powerful & Painful Business & Personal Lessons of 2013 (+ Costa Rica Photo Essay)

My 68 Most Powerful & Painful Business & Personal Lessons of 2013 (+ Costa Rica Photo Essay)

“There are no failures, only lessons.” – The Creed of Living Legends

Time Sensitive Note: We will be opening up our private How to Connect With Anyone course and community to a small number of new members starting on February 11th.

Enrollment will only be open for a few days and will be on a first-come, first-served basis. All of our past three CWA classes have sold out, so if you want to surround yourself with the people who won’t let you fail in 2014, be sure to get on our Early Access Insider’s List.

The power of surroundings was my single biggest lesson from 2013. I can’t wait to share that with some of you. Oh and next week we’ll be doing a fun contest to win a CWA Scholarship, so keep an eye out!

Now for the rest of the lessons…


If You’re Learning, There Is No Failure

That’s the beauty of life.

Which is why every Monday morning, as part of my weekly planning process, I spend a few minutes writing down any big lessons from the past seven days.

Then each January, as part of my annual goal setting and planning process, I go through each week’s lessons to be sure I live accordingly the following year.

It’s wild to see how much education a year of living can produce.

But if we don’t keep track and assimilate the lessons, it’s all for nothing. And making the same mistake twice sucks.

So I thought I’d share mine with you today.

But before I go through the lessons of each week or year, I always start with what I’m most proud of. Most of us tend to under-appreciate or forget to celebrate all that’s amazing – plus, starting with your wins puts you in a damn good state for building upon the future.

So here are a few of the fun things that are hard to believe happened last year:

  • Our community tripled in size to nearly 60,000 members.
  • We created Live Your Legend LOCAL and you all started hosting monthly events all over the world – 150 cities in 48 countries and counting!
  • I shut down my investment fund to go all in on our Revolution here. I also shut down my stand up desk project and have gotten more comfortable saying no.
  • I wrote the biggest check of my life – and it was to our partner charity impossible2Possible. We donate 5% of our income to support their amazing cause.
  • We did a massive update to our Live Off Your Passion course, turning it into its own members-only website.
  • Our revenue grew by over 300%!
  • I finally got some help! The team at LYL has grown to 14 paid rock stars (most are part-time) as well as a ton more volunteers. 18 months ago, it was pretty much just me. Thank you all for making this possible!
  • We launched group coaching for Connect With Anyone and Live Off Your Passion, and it has caused members to get more dramatic results than any other single thing we’ve done.
  • I ran (more like hobbled) my first 50 mile ultramarathon.
  • I got to explore some amazing parts of the world, including Thailand, South Korea, The Kamchatka Peninsula (Eastern Russia), Mexico, Montreal, Boston and Kona, Hawaii – and used those trips to take my photography a little more seriously. This pics in this post are all mine 🙂
  • Our TEDx talk somehow managed to break through 1,000,000 views and is currently #17 of over 37,000 talks on YouTube.
  • Thousands of you took the leap to start building things you actually cared about, and on top of that, over 500 started blogs and adopted a consistent writing and creativity habit. I love seeing that, because it’s where it all starts!

I can’t tell you how grateful I am to be able to list the above.

This list reminds me of something I learned from Tony Robbins a while back. It went something like this…

We Overestimate What We Can Do in a Day, but Drastically Underestimate What We Can Do In a Year

And even more so, we underestimate what we can do in a lifetime. Remembering that always helps when things don’t seem to be moving quite as fast in the short term as I’d like (which they never seem to do!).

Now, onto the lessons.

Since the list is rather comprehensive, I’ve decided to make this a bit of a photo essay as well – from my adventure in Costa Rica over the past few weeks. If you don’t have time to read all the lessons just stick to the parts in bold and the photos.


My 68 Most Powerful & Painful Business & Personal Lessons of 2013

Gate Open

On the Business Side…

1. The right people can (and will) change everything. This goes for business partners, friends, your spouse, you name it. The people around you will either kill your dreams or make them not only possible, but probable. That’s why connections are the core of what we do at LYL. And it’s why I’ve poured my heart and soul into our Connect With Anyone course and community that’s opening for the fourth time on February 11th. If you want to be guaranteed a spot (and early access), click here to get on the Insider’s List.

2. Character matters. It’s better to surround yourself with great people who have good businesses than not-so-great people who have great businesses.

3. Hanging around inspiring, accomplished people can inspire insane possibility. But it can also make you feel small, like you have nothing figured out. Let other living legends serve your progress, not hurt it.

4. Don’t worry about how much work you’re doing compared to others. Someone might spin their tires 80% of the time and work twice as much as you. That doesn’t mean you should feel pressured to waste your time the same way. Comparing yourself to anyone but yourself is almost always useless.

5. There’s a big difference between not doing your part and not doing the same amount of work. Always do your part. That’s the only amount of work that matters.

6. The more you succeed, the more you have to lose, and the more you might fear of it not working. It seems counterintuitive that success can create more fear.

7. Strive to spend your time on one of two things: what you’re incredibly good at or what you absolutely love. Ideally, they are one in the same. Find team members who enjoy the rest – and are awesome at it.


8. There are people who can help your community a lot more than you can in certain areas. Find them, swallow your pride and share their expertise with those who trust you.

9. You may think you know your audience, but you don’t. Don’t assume. Always ask and interact and expect to be wrong. Then build what you learn.

10. Keep learning and growing as if you’re just starting out. After all, everyone is always just starting out…

11. An awesome way to help people “above” you is to offer to mentor and help their kids with your area of expertise or passion.

12. Focus is the key to the world!

13. Take time to step away from the emotional and reactionary part of business (and life) to slow down and see the full picture of what you’re building. Do this each day, month, quarter and year.

14. Have fun with the ups and downs of business. Know there will be a lot of both, and don’t bitch during the slow times.

15. Stop letting stats and metrics control your life. Even if you do the right thing, they won’t always go up. Don’t let that frustrate you from staying committed to a process you know is consistent with results.

16. Measure success by how well you stick to the process – not the day’s outcome. Or as the surfers say, learn to love the paddle…


17. The biggest difference between lasting and successful business and movements and everything else is the quality of the systems and processes in place.

18. Nothing beats genuine, in-person connection. Nothing. Reserve time and money to attend a few relevant events and conferences each year.

19. You have to match and mirror in every situation. If you want to genuinely connect, you must show up on the level of the person on the other side.

20. One of the biggest reasons people don’t buy or do things is because they forget. Find courteous and clever ways to remind people to do things they already know are important to them.

21. Business is not about getting all you can out of someone else. Don’t charge for everything just because you can. Business is really about adding unbelievable value to the community you serve and finding a way to be fairly rewarded for it.

22. Make more decisions about what people want and need, instead of what’s best for the business. This way of making decisions feels so much better.

23. Even though we chase money, the money is not what we’re after. It’s the feeling we believe the money will produce.

24. When you do too much, you get lost in checking the boxes and lose site of the intangibles and the bigger vision – the stuff that actually matters.


25. Find a specific, hands-on way of helping people. Don’t be a generalist. For LYL, this was when we went beyond helping people find and do work they love, and focused more specifically on building the genuine connections with the people who make it possible.

26. Most people and especially new community members are not at the same place I am. Go back and cover the basics from time to time.

27. Everyone needs something to do – autopilot income does not create fulfillment. And passive income really is a myth.

28. Recognize the pattern of doing too much. It’s natural to keep doing new things because at first you have to so you can see what works. But once something starts to get momentum, you have to start calming down and decide to focus where all the action is – and where you can have the biggest impact.

29. As sad as it is, honesty, integrity and trust can become your most powerful differentiators. Hopefully that won’t always be the case. I’d much rather trust be the rule, not the expectation.

30. I get excited when I have a good potential solution to something. I get anxious when I have no potential solution. When overwhelmed with a project, step back, lay out a plan and start problem solving.

The office

31. Engagement is everything. Study and practice ways to engage the people you want to serve and move them to action. Become an unbelievable storyteller.

32. My single most powerful action of my career was being on stage, giving an 18-minute talk. Notice your 80/20 outputs and give them attention.

33. Don’t expect everyone to “get you” and your approach. When taking the road less traveled, most people won’t. That’s why your core tribe is even more important.

34. Spend some of your profits on giving back to your customers, who are the people who make it all possible. We’ve given thousands of dollars of books, prizes and gifts to our community, and we plan to do a lot more in 2014. Include a scholarship to CWA next week!

35. Everything I learned at World Domination Summit in 2013.

36. Spend time promoting the tools and content you already have. It’s not all about constantly creating new things. Be sure your best stuff gets seen by the people who need it most.

37. When dealing with decisions that could possibly have huge results with very little risk, just say yes. Do them. Sure they might turn out to be a waste of time or money, but it’s worth finding out. Take good bets. But probably not this one…


On the Personal Side…

38. I want my life and this community to be about adventure, exploring and discovery. That guides my daily decisions.

39. Giving to people and causes you believe in feels amazing. Find a cause you believe in and find a way to help them grow. Our relationship with impossible2Possible has been incredibly rewarding. I’m constantly thinking about what I could do to prop them up.

40. There are two sides to EVERY story – often, two very different sides. I don’t care how much you know and respect the person on one of the sides. Find the other story. Understand it. Then do your best to be objective.

41. Do unto others as they would want you to do unto them – not as you want them to do to you.

42. I’ve recently discovered one foundational secret to life: Never be in a hurry, but always live life knowing that it’s incredibly short. Yes, I know – much easier said than done.


43. Happiness = Reality – Expectations. Have high standards and expectations for yourself but low expectations for the things you can’t control. You’ll be happily surprised to see how things work out.

44. Changing your expectations does not have to mean lowering them. Those are two VERY different things.

45. Don’t confuse complacency with contentment. Avoid complacency at all cost, but if you link happiness and contentment to complacency, then you’ll be unhappy with happiness. Talk about a mess!

46. Stop getting frustrated when someone is consistently negative or pessimistic. It’s their pattern. What else can you really expect?!

47. Travel hacking is so worth it – and a ton of fun! It encourages travel and adventure and makes so much more possible. Plus, the experience of flying Business Class for 20%  the price of coach is pretty unbelievable. I’m actually writing this from seat 1E on a flight back from Costa Rica as I drink a free glass of red wine next to a bunch of consultants and business folks who quite possibly paid the full $5-8k fare for their ticket. 😉 Chelsea and I paid only $92 each for our business class flights.

48. If you get creative, cost is not an excuse for not traveling. I’m so glad I met Travis Sherry, my travel hacking ninja, who’s helped make this stuff incredibility simple. You’ll hear a lot more from him this year as he helps us plan our around-the-world trip for 2015. This is the best table ever btw…


49. The goal does not always have to be to improve. It can just be to do it and be. Embrace and build upon what you have right in front of you.

50. Work out because you enjoy moving and breathing, not because you want your body to look a certain way. It all comes back to process over outcome.

51. Do whatever you can to avoid losing momentum. So many people focus on how to regain momentum, but if you find a way to keep the snowball rolling (however much it may slow down at times), the compounded progress becomes unreal. There’s also a ton less resistance.

52. Things almost always take longer than expected. Plan accordingly.

53. It’s one thing to have all the time, freedom, flexibility, resources to do anything you could ever want, but another thing to live life without feeling rushed, stressed, anxious and pressured. That is the real mastery.

54. The number one biggest cause of my stress and discomfort is not feeling that I have enough time to do the things I have to do or want to or feel I need to do. I can control that with better planning and expectations.

Tabacon Spring

55. Stress is one of the biggest causes of disease and illness. Having a supportive community and loving your work are two of the biggest cures. Thanks to Lissa Rankin for writing Mind Over Medicine – the book that woke me up to how deadly important it is to get a handle on stress.

56. Almost nothing is worth worrying about. NOTHING. Except for the health of you and those around you. The thought of death removes any reason to be concerned about anything else. Just charge forward and make your damn impact.

57. It’s not always about what’s next. Everyone loves to ask that. What’s next for me is giving deeper focus to what I’m doing right now. We don’t have to always be looking ahead. All the good stuff is usually right here anyway.

58. Starting with someone else’s point of view tends to help a person open up and allows for a deeper connection.

59. Help first. The rest follows.

60. Use freedom wisely. Endless planning, doing and traveling cripples me, stresses me out and runs me down. No one can do it all. And that’s a good thing.

61. The key to balance and focus is not on doing more of something, but just bypassing distractions and having space.

reading chair

62. Celebrate EVERYTHING. Pat yourself on the back. Do a happy dance. Hardly anyone gives themselves the credit they deserve.

63. Just follow the trail of excitement and energy and keep building upon things.

64. When I have energy, excitement and inspiration, life is WAY better and I feel unstoppable. And that can change in an instant with my thinking or a new idea. No matter how challenging something might feel, it’s incredibly empowering to know it can change immediately and that it’s often more in my control than I’d like to admit.

65. Not standing firmly for things I believe in kills my energy. If you don’t stand for something, you’ll fall for anything.

66. Confidence is at the root of fulfillment, happiness and enjoyment. Without it, it’s tough to be fired up to do anything and be who you really are. Oh and be sure to smile…


67. You can almost always take another step, whether it’s an actual step that’s 13 hours into a 50-mile race or a metaphorical one in the pursuit of what matters.

And finally…

#68. Relentlessness is what gets results. 

There’s not some specific technique that always works – it’s just persistence. Dedication is the best and only real technique worth practicing.

It blows my mind the difference a year can make.

And more than that, it’s amazing to see what’s possible when tens of thousands of people from every country in the world come together to stand behind a common belief: That we can all do work that makes us come alive and embrace work that actually matters – to us and to the world. With the right tools and surroundings, it’s not only possible, but incredibly likely.

You all created this. I have you to thank for what this Revolution has become.

I saw the below sign as I walked out of a surf bar in Nosara. Together we are making these words so much more real for so many people…

Livin the dream

Now how about you?

Tell us one of your big lessons in the comments. We all have at least one!

There’s so much to experience – so much to learn  – so much adventure to be had.

The future looks bright, my friends –


P.S. Remember, Connect With Anyone opens its doors in 12 days. If you think you might want to check it out, be sure you get on the early access list here.