101 lessons I learned before turning 28

101 Lessons I Learned by the Time I Turned 28

101 lessons I learned before turning 28

I turned 28 last month and spent a bit of time reflecting on things I learned over the course of my life. I was amazed to find out that most of the things I know to be true are things that (i) my parents taught me; (ii) I learned through experience, or; (iii) I learned through experience after reading it in a book.

The following list of 101 items are lessons I learned (sometimes painfully) and things I wholly consider to be true before my 28th birthday. The list isn’t exhaustive, and the things I consider true may not be true for others -- so take it with a grain of salt.

On money

  • 1. Nothing is free
  • 2. Talk is cheap
  • 3. Pride is expensive
  • 4. Save/invest at least 20% of your income
  • 5. Retirement planning starts when you turn 18
  • 6. Pay off your credit card bill (in full) every month
  • 7. The best investment you can make is an investment in yourself
  • 8. If you have to sweat your housing and car payment -- it's too expensive
  • 9. Treat your time as if you are literally spending money every second -- don’t forget about the opportunity cost too
  • 10. The second-best investment on earth is earth
  • 11. Whole life insurance isn’t for everyone -- max out the IRA and 401K first. If you're self-employed, get a SEP IRA on the side and deposit the yearly maximum
  • 12. Going to college is not an insurance policy (anymore) -- unless you're a STEM major
  • 13. Always keep some physical gold in case government fails
  • 14. Always pay your taxes and don’t hide money
  • 15. Cars are depreciating assets
  • 16. Money is important, but not everything
  • 17. Always carry cash
  • 18. Be a good tipper
  • 19. Who you marry is the most important financial decision you will make in your entire life

On luck

  • 20. Luck doesn’t exist, it’s a myth -- read more

On health

  • 21. You need at least 6.5 hours of sleep every night
  • 22. Choose salad over fries
  • 23. Nothing good happens after 2:45 AM
  • 24. Humor is the spice of life
  • 25. Meditation is 5,000 years old -- it has stuck around for a reason
  • 26. Don’t self-diagnose
  • 27. Don’t worry about things you can’t control
  • 28. “Buy a tuxedo before you are thirty. Stay that size” (from Business Insider)
  • 29. Driving is the most dangerous activity you do (see #91)
  • 30. Learn how to be comfortable being alone
  • 31. Drugs. Don’t do them
  • 32. If it tastes really good, it’s either too salty or too sugary
  • 33. Drink water -- go for a gallon per day
  • 34. Think of your body as the only car you will ever have in your entire life -- treat it that way (courtesy of Warren Buffett)
  • 35. Buy and use nice skin cream (without alcohol)
  • 36. Replace whiskey, vodka, and coffee with tea as much as possible
  • 37. Use melatonin instead of Ambien or other habit-forming sleep aids

On business

  • 38. Every business decision has input metrics and output metrics -- calculate both before making a decision
  • 39. Don’t be your own lawyer
  • 40. Remember people’s names -- read more
  • 41. Most business decisions come down to common sense and simple math
  • 42. One A-player is better than ten C-players
  • 43. Read at least seven books per year
  • 44. In a capitalistic economy, you should endeavor to own the means of production at all costs. As my good friend told me: “get equity or die trying”
  • 45. Marc Andreessen is still right, software IS eating the world
  • 46. You are entitled to nothing (courtesy of Frank Underwood)
  • 47. Don’t be the smartest (or loudest) person in the room
  • 48. You should have at least five mentors
  • 49. Listen a lot more than you speak
  • 50. Know exactly what your time is worth (per hour)
  • 51. Practice your elevator pitch on anyone who will listen
  • 52. Never work with (especially hire) friends
  • 53. Always keep driving hard -- don't quit
  • 54. Learn your weaknesses and surround yourself with people who fill that gap
  • 55. Don’t be a “Yes man/woman.” Learn to say NO
  • 56. Acknowledge calls/emails and reply back. If you are busy, tell the person when you will get back to them
  • 57. Make goals every year, write them down, and look at them periodically
  • 58. You have a personal brand whether you like it or not - build it accordingly
  • 59. Learn how to negotiate -- you do it every single day
  • 60. Your resume should be one page and not include acronyms you can’t understand
  • 61. Take the risk if the risk/reward ratio is in your favor (favor low risk and high reward - be wary of the opposite)
  • 62. Experience is more important than book smarts

On you

  • 63. Buy and wear clothes that fit
  • 64. Invest in a nice haircut
  • 65. Figure out your Myers Briggs personality type -- and the type for people around you (read more)
  • 66. How you treat service staff, homeless people, and those struggling IS a reflection of your character
  • 67. Always use an internal frame of reference instead of an external one
  • 68. Your word is your reputation -- guard it with your life
  • 69. Stop being afraid
  • 70. Never take advice unless you asked for it. Ask people for advice -- and then hear them out
  • 71. Never give advice unless someone asks you for it
  • 72. Use a password manager, don’t reuse passwords, and turn on two-factor authentication for every account you can
  • 73. Don’t be a “taker”
  • 74. Step out of your comfort zone -- it’s how you grow
  • 75. Learn how to drive a stick shift
  • 76. Flush the toilet
  • 77. Pick your battles carefully, and know when to walk away
  • 78. Pick core personal values -- stick to them
  • 79. Don’t compare yourself to other people, it doesn’t help you
  • 80. Have a basic understanding of important concepts: evolution, gravity, geography, and how the internet works
  • 81. If it would eat you if you died, it’s not a pet
  • 82. Give back to your community: money, time, labor, or whatever you can reasonably afford 

On relationships

  • 83. It’s better to do right than it is to be right
  • 84. Some things cannot be taken, they can only be given
  • 85. You are the average of the five people you spend the most time with
  • 86. Chances are, no person will ever love you more than your mother
  • 87. You have less true friends than you think (turn your Facebook privacy settings to hide your birthday for one year -- see what happens)
  • 88. When arguing with someone, avoid “kitchen sinking” and work through issues individually
  • 89. When communicating you are upset at someone, use an XYZ statement: “When you did X at time Y, it made me feel Z”
  • 90. Don’t try to date (or sleep with) your friend’s ex
  • 91. Put your phone down
  • 92. Write people letters and mail it to them
  • 93. Keep a contact book with addresses -- update it every year
  • 94. Use your calendar
  • 95. Loyalty
  • 96. Move on
  • 97. Respect your elders (especially your relatives)
  • 98. At all costs, avoid making enemies
  • 99. The golf course isn’t for doing business, it’s for clearing your head

On blogging

  • 100. Always use an Oxford comma
  • 101. “Brevity is the soul of wit” - William Shakespeare

Bonus round - on entrepreneurship

  • 102. If you need a contract longer than one page, you don’t really “trust” them
  • 103. Nobody really cares about stealing your “idea” and your NDA request is silly
  • 104. Don’t go around calling yourself a CEO unless your company does more than 500K in revenue per year -- even then, don’t boast your title
  • 105. The first seven people you hire at your company will determine its fate (courtesy of Steve Jobs)
  • 106. Don’t try to be Steve Jobs or Bill Gates -- learn from them and be you
  • 107. Learn the difference between an A-player, B-player, and C-player -- hire/fire accordingly
  • 108. Your company culture is who you hire, who you fire, and who you promote
  • 109. Have a simple mission statement (what you do every day)
  • 110. The world probably doesn’t need another social photo sharing app
  • 111. You are a million times more likely to build a million-dollar company than you are to build a billion-dollar company
  • 112. Competition is for losers, avoid it at all costs -- read more
  • 113. Don’t try to raise money until you have demand and sales
  • 114. Read this book
  • 115. Know the difference between being an entrepreneur and an executive -- they’re not the same
  • 116. Understand that as your startup grows, everyone’s job description changes every month
  • 117. When you fire people you should only take away their job, not their dignity
  • 118. If they lie during the interview, don’t hire them
  • 119. Poor profitability will hurt your business, poor cashflow will kill your business
  • 120. Don’t call yourself these things: guru, rockstar, or ninja
  • 121. When traveling, find a room using AirBnB instead of a hotel -- you’ll meet more people

If you liked this post and would like other useful ones, .


Businessreflectionlife-hacksentrepreneurshipTurning 28


Stephanie Aug. 16, 2017 9:12 AM
Hey Bobby,

I was just catching up with you on Facebook like the weirdest stalker in the world, and I was pleasantly surprised by the number of things I agreed with and appreciated the places where we differ (flush the toilet? Not sure how important that is, could use more explanation there). I like to consider these things you list as part of my "basic operating policy" more than a list of lessons, since, as you said, this is what worked for you. I may just write my own operating policy now. Thanks for the motivation. Hope all is well!

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Boban Dedovic Aug. 18, 2017 5:09 PM
Hey Stephanie, thanks for reading! The "flush the toilet" item makes a lot more sense if you ever lived in a house with four other males.

The list is surely my 'operating policy' and I try my best to follow it. I think it's a great thing for everyone to have for their own life goals and circumstances. If you do end up writing your own I hope you will share it with me!

All is well with me and I hope the same for you.

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Roger Scott Craig Sep. 18, 2017 6:05 AM
Dave is obviously much smarter and more successful than you are, Boban. Would be interesting to have him come up with his '101lessons' so we can tell him what an asshole he is as well! And this is the problem with the Internet - malicious and insulting comments from people who always seem to know more than you do. Most of them are probably still living at home with their parents, unemployed and on welfare, LOL! From my perspective I found your lessons to be extremely interesting and informative and look forward to future comments on your life from you - somebody who excels in so many ways and sets the pace for a new generation of brilliant young men! Way to go my friend!

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Boban Dedovic Oct. 10, 2017 12:03 AM
Thanks very much for the kind words Roger. As always, I appreciate your support.

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Will Powers Jan. 27, 2018 7:53 AM
Happy New Year Boban!

Please allow me to introduce myself.

My name is Will Powers and I noticed you were pretty scant on the relationship advice so thought I'd share a few of mine.

1. Ask the most important people (family, peers, friends) in your life to honestly grade you (A+, B, C-, etc), then average it. That's your life grade. It reflects who you really are.

2. Love is a verb. Stop telling people you love them, show them.

3. Don't listen to LOVE songs - the lyrics are by people who often fail at relationships.


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Boban Dedovic Feb. 1, 2018 1:46 PM
Thanks for sharing Will!

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Corey Avis Jun. 4, 2018 11:53 PM
I like this post, especially number 105. I think I fall in that list, for the better I hope. I didn't even know you had this website until you sent out the email change email. But I'll definitely keep checking back and reading more posts.

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Boban Dedovic Jun. 12, 2018 8:14 AM
Thanks a lot for reading Corey, it's nice to hear from you again. Yes, I have been working on this site for some time.

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