99 Lessons For Living A Life You Won’t Regret


A year ago on my birthday I wrote a post called: 32 Years, 32 Lessons. Now almost a year has passed and I thought it was time for another reflective post. This time I’m going bigger in numbers but shorter in description. This list – and the 32:32 post – might be combined and broken down deeper in an upcoming book. I as thinking of writing it in the spirit of Rework but call it Relive or Relife.

But that’s another story.

Before we get into it, know that I wrestled with this title forever because this list is a combination of lessons, tips and truths about life, business and travel learned through research, listening, or the hard way. So you see, no one title really fits it neatly so I went with what I went with to keep it short and sweet.

Without further ado, here’s my list of 99 Lessons For Living A Life You Won’t Regret. 

  1. No adult ever mentally feels grown up
  2. You will always doubt yourself, get used to it
  3. Permission has already been granted to you. You just have to take it
  4. The timing will never be as perfect as you want it to be
  5. You won’t know what you’re doing when you start doing what you think you want to do
  6. So choose to make every decision the right decision, even if something doesn’t go your way
  7. Because success is a mindset
  8. But success is also dangerous. The more you have, the less support people think you need
  9. There’s no such thing as making it, only making it further than where you were yesterday
  10. Starting a business means you’ll have less free time, not more. A lot less.
  11. If you can’t figure out how to market yourself in this world, you’ll always be paddling upstream
  12. Everything is selling. But now we’re selling ideas and opinions not only gadgets
  13. Older does not equal smarter
  14. Not everyone has experience, but everyone can have initiative
  15. The best skill to have is one that is rare and useful
  16. If you knew how much work it would take to get your dream job, most of you would run for the hills
  17. And anyway, it’s only a “dream” job until you get it. Then it’s reality. And reality has its ups and downs
  18. You choose what kind of mood you want to be in when you wake up
  19. Don’t hang up the phone angry with your mother
  20. Foster the relationship with your siblings. You’ll live with them a lot longer than any other family member
  21. A strong handshake and solid eye contact will change your life for the better
  22. Image is everything, at first. Don’t pretend that it’s not. Being well-dressed and decently-groomed is a form of politeness
  23. There are no re-deals in life. The faster you accept that, the sooner you can excel at playing whatever hand you have
  24. So often what we say inspires us also makes us feel inferior and paralyzed. The trick is to find the inspiration that stirs action. Otherwise it’s not inspiration, it’s comparison
  25. Aspirations are wants based heavily on outside factors. Goals are wants based solely on your efforts
  26. For all those instances you think you just can’t do it, maybe you just should do it
  27. You live up to your own expectations
  28. Ignorance is bliss but it’s not allowed to vote. If you don’t want to be informed, don’t complain
  29. Speaking of complaining, it’s easier than succeeding. Be careful what you whine about
  30. Owning memories beats owning “things” every time
  31. Except maybe if that thing reminds you of that memory every time you look at it
  32. Don’t be afraid to be broke. Be afraid to stay broke
  33. Helping others is noble, but be sure to take care of yourself too. It’s not selfish if it’s growth
  34. Embrace the suck. Your story is in the grit beneath your fingernails
  35. Because in the end, it’ll be the stories you tell and the people you tell them to
  36. Great days = (luck) x (a bunch of average days). Let the great days take care of themselves
  37. Stress = reality not matching your expectations. It’s harder to change reality than your expectations
  38. Fear is a choice, not a mathematical constant
  39. We often don’t want to accomplish our goals, we just want to be liked by our friends
  40. Independence isn’t free. The more you have of it, the more you’re paralyzed by it
  41. We do care what people think
  42. Don’t change the world, change the moment
  43. Don’t strive to be the best. Strive to be your best. “The best” is insanity
  44. Death by research is no way to die. Start already
  45. In 5 years you’ll be wrong. Start already
  46. Successful people finish shit. Finish already
  47. Don’t go the extra mile until you go the last mile. Finish already
  48. If you can put yourself in the shoes of an outsider, you win
  49. Passions are your selfish desires. Purpose creates value for other people. Do something for other people and figure out how to tie your passions into it
  50. Because how you treat people is more important than what you do
  51. In fact, don’t treat others how you want to be treated, treat others how THEY want to be treated
  52. While you’re at it, you’ll need to figure out how to pay your vulnerability tax
  53. Surround yourself with people who are smarter than you. If you’re the smartest person in the room, you’ll always be that dumb
  54. Exercise. No seriously, get off your ass
  55. But if you’re only going to the gym because your friend is going, it’s not going to work for you
  56. You are not right just because you speak. Give people a choice and a chance
  57. Follow up or die
  58. Know when to let go
  59. Keep your digital self fed, but don’t let him/her rule the show
  60. Create more
  61. Tweet less
  62. Craft first, community second
  63. It’s not who you know. It’s who you know once you know what you need to know
  64. Emotions are contagious. You are in control of what you are spreading and what you are susceptible to
  65. Stop apologizing for not knowing. Everyone was a rookie once
  66. All that evil needs to flourish is for good people to see nothing—and get paid for it
  67. What makes people happier is: other people
  68. Have longer dinners with friends
  69. Happiness isn’t reached, it’s tended to
  70. Take that trip you’ve been thinking about. (See #4 above)
  71. If you only have a backpack, board the plane last. No sense in standing in line or sitting on a cramped plane for longer than you have to
  72. Perspective is one simple thing that can make you more likable
  73. If tuk tuk drivers speak English too well, don’t trust them
  74. Partying is worth it while you’re in it, tragic when you miss it, regrettable the morning after, epic the day after that
  75. Party your ass off every now and then, but wake up sober on Saturday more often than not
  76. There is no such thing as “the one.” You don’t have time to meet all the candidates
  77. Marriage and commitment is not about riding off into the sunset together, it’s about jumping in a foxhole together
  78. Ladies, you hold all the cards. Own that
  79. Guys, less gawking at ladies, more hellos
  80. No one is thinking of creative ways to give you money
  81. A service business is convincing someone you know more than them about something they value and getting them to pay you for that knowledge
  82. Know the answer to “What are you working on and how can I help?”
  83. When it comes to a potential new customer, nothing is nothing until it’s something
  84. No one’s going to steal your idea
  85. You’re not stuck in traffic. You ARE traffic
  86. When you give someone change, don’t put the coins on top of the bills. This drives people crazy.
  87. You have to enjoy the process somehow
  88. Sadly, we spend most of our time worrying about what the people who don’t ever think about us, think about us
  89. Do something you hate. It’ll make you appreciate the things you love more
  90. Build something you can point at
  91. Efficiency runs businesses; inefficiency starts them
  92. You don’t make money from a blog, you make money from a business
  93. Piss someone off. You can’t market to everyone
  94. You can’t outmuscle being tired. Go to sleep
  95. You can’t outlogic your goals. You have to understand emotion
  96. Having no social awareness will be catastrophic for your career
  97. Rinse the sponge out after you use it. People don’t like smelling mold on their hands
  98. Have a hobby that entails you actually learning something new
  99. The world owes you nothing. It gave you life. Let’s consider that “paid in full”

What would you add to the list?

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