Forty Lesson Learned The Hard Way—So You Don’t Have To

One of Jimmy Buffett’s best songs is “A Pirate Looks At Forty”. It’s about a friend of his (Jimmy insists he is NOT the pirate) who could not find his place or make his mark in the modern world. I turned forty-years-old this year and I sometimes feel like I am just now getting it right. (Hey, forty is the new thirty, right?) I recently had some time to reflect on what I have learned during my forty (and a half) years on this planet. In the past four decades I have had some stunning successes, and struggled at times, too. I often wish I could go back and slap my younger self and then share the life lessons I learned later (the hard way.) Since that isn’t possible, I’ll share some suggestions with you. I came up with the following forty things I wish I knew when I was younger. (I suffered so you don’t have to.)

1. Practice No Regrets Living. Don’t wait to do the things that you want to do. It seems that the older I get the more complicated things become. It was easier to travel, experiment and take risks when I was younger.

2. People Matter Most. No matter how much money you make or success you have, it’s always more satisfying to share these moments with family and friends.

3. If You Have An Addictive Personality, Pick Something Positive. Yes, “everything in moderation” is good advice, but there are times when a person is so over-the-top-excited about something they will want to jump in with both feet. This is great when it’s something healthy, positive and productive.

4. Don’t Waste Time Worrying About The Past (or The Future). How many minutes have been wasted worrying about things that may-and more likely may not-ever happen. My advice, expect the best but be prepared for the worst. Try not to worry about things you feel guilty about from your past. Either fix them, or forget them.

5. Don’t Worry What Others Think. Peer pressure and the need to fit in don’t just keep kids up at night. Life is so much easier when you live it for yourself, free of the pressure of worrying what others think. Do what YOU want to do.

6. Take Risks When You Are Young. It’s easier to recover from a bad decision when you are younger. It is also true that “what doesn’t kill you makes you stronger.” To try to go beyond what you think is possible and to take some chances is healthy and leads to learning experiences that prove invaluable later in life.

7. Starting Your Own Business Is The Best Way To Get Rich. Yes, real estate and the stock market have made many people wealthy, but building a business is also one of the better ways to create wealth. Plus, there is nothing like being your own boss. I have started five businesses and highly recommend entrepreneurship.

8. Live For Today, But Plan For Tomorrow. Living in the moment is one of the ways to be truly happy. Doing so without any plans or provisions for the future is foolish. Yes, live like there is no tomorrow, but save for the future and take care of yourself physically, too.

9. Your Time Is Your Life. Frittering away hours may seem like no big deal when you are young. However, when you start to realize that you have pissed away a good portion of your life, the concept of time shifts. Your time is your life energy. You have a limited amount to squander. Being more aware of where your time goes and how you spend it is one of the most important life lessons you can learn. Consider that every item you paid for you paid for with a piece of your life. You used up your time (i.e. your life) to earn money for that purchase. Was it worth a piece of your life?

10. Goals Are THE Secret To Success. By now everyone knows that I am passionate about having a plan for your life. I have done this for myself since I was fifteen-years-old. My goal-setting system has evolved from a list of things I want to do to a series of powerful statements, images and feelings about the future I want to create along with a plan to make it happen.

11. See The World When You Have The Chance. Traveling is such a worthwhile thing. I rank it right up there with success of any kind. The ability to take off and get away is one of the most exciting, fulfilling and fun things I have done.

12. Keep Track Of Your Victories. Many people dwell on the things they didn’t do (but wish they did) or things they did (but wish they hadn’t). When you look back at your life, chances are you have done more than you thought you did and made many good decisions. Post your proudest accomplishments in a place where you will see them.

13. Commit To A Lifetime Of Learning. A library card is more valuable than a Mastercard or American Express card in my opinion. It isn’t because I have written eleven books that I believe this. It is a result of all the books I read as I researched my books that I recommend a daily dose of reading-or listening to tapes in your car.

14. A Mentor Can Work Magic. The secret to my success was to find someone who knew all the right moves, all the right people and all the right things and was willing to share. I have had some wonderful mentors who made a huge difference in my life-providing a shortcut on the road to success.

15. Get Your Mid-Life Crisis Over Early. First and foremost, there is no need for one when you are living the life you want to. If you do feel like your life has been a series of compromises and you want to make up for lost time, try to do it early and get it over with quickly.

16. Wait For The Right One. When I hear things like, “Marriage is a lot of hard work” and “Relationships requires constant compromise” I often wonder if these people simply married the wrong person. When you find your soul mate (Read: Best friend and love-of-your-life all rolled into one) being together is simple, satisfying and super easy.

17. Take Care Of Your Stuff. I have always been the guy who did the preventative and required maintenance at the right time-before things broke. Hanging onto items that work well without having to spend money on new ones is one of the ways I have been able to save, travel and take time off.

18. Money Saved Is Money Earned. The secret to “having it all” is to live large on less. Many of the most affluent people I know are very frugal. (Not cheap, but cost-conscious.) They have the best of everything, but they wheeled and dealed to get it for less than full price. Being able to buy what you want without paying full price for it is an art. It’s also a mindset-and one worth working on. It’s not how much you make, it’s how much you keep that counts.

19. Simplify. I was raised by pack rats and I was becoming one, too. I awoke one day (during a move) and starting selling off some of the things that didn’t serve my life any longer. Now that I live in a beach house (with a baby), I have to keep things moving or else they start to stack up and there’s no room for my surfboards. (Wink.)

20. You Need An Outlet For Your Creativity. Playing drums in a cover band was not what I dreamed about when I was a kid. It is, however, the perfect outlet for my creative (and musical) aspirations today. I may never be a rock star, but I can still have a small (very small) sampling of what it’s like. Find some way to express your creativity.

21. Early To Bed (2:00 AM) And Early To Rise. . . I have found that many prolific writers work well into the night. I have also used the early morning hours to get things done. I guess it’s my need to be different (I’m up while the world sleeps) and the need to eliminate distractions that makes 10:00 PM to 2:00 AM the perfect time to work. Find your own prime time and don’t waste it on trivial tasks.

22. Don’t Sweat The Small Stuff. I realized recently that many of the things I have stressed and obsessed about over the years were not worth the time and energy-they simply didn’t matter. It’s easy to get upset and to feel slighted over silly things, it’s far better to just let them go if they won’t matter in a month.

23. Make a Difference. Charity does begin at home and the place to give back first is to your family and friends. There are also a lot of opportunities to make a difference in other areas-whether you give your time, money or share your expertise-this is one of the most rewarding things to do.

24. Brand Yourself Before Someone Else Does. When people hear your name what three things do you want them to think of? I have worked so hard to develop a reputation that I am proud of. I did this by acting as if I were the person I wanted to be and then when I achieved it, I continued to make the tough (right) choices.

25. Things Are Never As Bad As They Seem. Bad things happen to good people. It is the person that is able to put things into the proper perspective that prosper. When you have been through a tough time or two you start to realize that you are more resilient than you thought and no matter what happens, you can, and will, go on.

26. Sometimes You Have To Give Up Good For Great. My mentor used a baseball analogy to make this point. He said I needed to hit more home runs (think big and take some chances). At the time I was just hitting singles (thinking small and staying safe). It wasn’t until I was willing to give up good for great that things really took off.

27. Give People More Than They Expect. More advice from a mentor. Most people just do enough to get by. It is the person who goes the extra mile and does more than others expected that gets ahead in business and in life.

28. Thank Yous. I have learned that following up and following through is rare. Most people don’t know how to do it, nor do they want to. Sending thank you notes is the perfect follow-up. It is also a classy, thoughtful and appreciated thing to do.

29. Don’t Lend Money-Ever. Enough said.

30. The Best Things In Life Are Free. Sunsets, picnics in the park, walks on the beach and are all priced right-they’re free. The same is true about special occasions and gifts. Sometimes it IS the thought that counts more than the cost.

31. Take Time For Yourself. I was once the kind of person who would create things-to-do lists that were a mile long. It would have taken me months to complete the things on my list. Now I build white space into my list of tasks. It’s almost like I plan for spontaneity. Try leaving some room in your busy life for unexpected things to come your way and take time for yourself.

32. Make Memorable Moments. Some people call me the life of the party, the fun uncle and the person to call when you are feeling down. What I want to create is memorable moments in other people’s lives. It is the same in my own life. I am always trying something new, never allowing myself to get into a rut. I will also stop and take a mental snapshot to burn a particularly pleasant experience deeper into my memory.

33. Take It One Pitch At A Time. I read an article about pitcher Al Leiter who said that the secret to his success was to take it one pitch at a time. He couldn’t change the last pitch or predict what would happen three picthes from now. All he could control, and thus concentrate on, was the pitch he was about to throw. I have used this philosophy for my writing, promoting and presentations. By being present I am able to focus on what’s right in front of me. That kind of clarity is key to overcoming procrastination and fear.

34. Pursue Your Passion. I have had flashes of “everything is right in my world” but many times what I am passionate about is not profitable. I know that I need to “do what I love and the money will follow” but for some reason this is an area I need to work on. Don’t get me wrong, there is a lot right with my life, but what I really want to do (open a retreat center on Kauai) remains out there.

35. Appreciate The Small Things In Life. Many times we wait for the big moments in life to celebrate. There are so many simple things we do daily that are special moments. Some people keep a dairy, others meditate and still others tell their significant other about their day. Try to take note of the small things that make you smile during the day.

36. Don’t Fight Change. I’m old school and was fearful of change-especially new technology. I felt like I was being left behind. Then I figured out I needed to focus not on the technology itself, but on how it could help me reach my goals. This simplified things. Now I go with new developments that serve my goals and not worry about the rest.

37. Don’t Compare Yourself To Others. As a competitive person it’s hard to resist the temptation to see how I stack up against those around me. This is a losing game because some people will consistently have more and trying to catch up to them can leave you deep in debt and cause you to do desperate things. It’s good to strive to be, do and have more but don’t forget to appreciate who you are and what you have.

38. Empathy Is Everything. Seeing (and feeling) things from another person’s perspective is one of the most vital skills you can learn.

39. Find Work You Love So Much You’d (Almost) Do It For Free. Most of my fan mail comes from creative people who hate their day jobs. They are also trapped in those same dreaded jobs because they must make a certain amount to survive. I have found that the freedom of finding work you love-and being able to pursue it-can come from cutting back and living on less. Not having to make as much money means you may be able to do what you truly desire, even if it doesn’t pay top dollar.

40. Figure Out Your Uniqueness And Celebrate It. When I was an Economics major in college I was living a lie. I am, and always will be, an artist. I fought the fact that writing, performing, presenting and creating were my strengths. I would beat myself up because I was bad at math and struggled in science. Now I celebrate my creative self.