What Would You Tell a 20-Year Younger You?

If I were to run into the 20-year younger me in a Starbucks on my way to work (because there is something poetically ironic about this coincidence happening while racing to work) and I had only ten minutes to share what would ostensibly be guideposts for this treacherous and (at times) intoxicating journey called life, I would let my overheated coffee cool and tell him this:

  1. Be bold: you'll be surprised how many people let timidity hold them back.
  2. There will be a massive gap between those willing to try and those willing to watch others try. Don't let the watchers keep you from trying.
  3. You're going to screw up, a lot. Don't let it keep you from screwing up again. (You heard me).
  4. Don't let fear of what others think get in the way of doing what you want to do.
  5. Don't let fear of what others think get in the way of doing what you want to do.
  6. Don't let fear of what others think get in the way of doing what you want to do.
  7. Your work will be as fulfilling as you make it. You can't always do what you want but you can learn to enjoy what you do. Seek fulfillment wherever you land. Related: Peer pressure doesn't end after high school. Don't let your colleagues determine your work ethic (unless they are working harder than you).
  8. I can barely enjoy this cup of coffee, proof that my ambition supersedes my ability to savor important moments. (No one teaches you how to savor in school). Life is a gift. Don’t lose yourself in haste. Live while you're living.
  9. I know face-to-face networking scares you witless but here’s a secret: virtually everyone you will meet is intimidated by the mere thought of networking. You walk among mortals as frightened as you, find strength in that and you’ll make friends (so, go shake more hands).
  10. Revolt against the tyrannical abuse of self-loathing, daily.
  11. I know you hate bumper sticker wisdom but mean people really do suck. Try not to be mean. To anyone. Ever. Sometimes, it will be very (very) hard. But, try. Related: Stick to discussing ideas, not people.
  12. Vulnerability is your built-in indicator for decision making. Feeling vulnerable? You should probably say 'yes'. 
  13. Pursuant to point #8: Keep reading poetry, let the cool kids make fun of you. Poetry will teach you the art of the purposed pause. Don't piss away your life in perpetual noise.
  14. This will help you sleep: ‘Complete mastery of life is mere illusion, the real secret of the game is to make life swing.’ - Ralph Ellison
  15. I won't lie to you: you are going to experience excruciating pain. It will change you. Don't let it destroy you.
  16. Overwhelming joy will come to you. It will arrive when you least expect it.
  17. The boring parts of life are best.
  18. Money (the lack of) need not inhibit travel. Your imagination is illimitable. When unable to journey physically, pilgrim through your senses: Read deeply but widely (with a meager intake of news), explore other countries via art, photography, music, food; a vicarious adventure is superior to wallowing in excuses that you have no money. 
  19. Spend less time consuming; spend more time creating. The future belongs to creators. 
  20. Speaking of: You enjoy writing, speaking, creating, do more of that early on. Don't wait until you're forty. For courage, review points #4, #5, and #6.
  21. You’ll be shocked to discover that one of life’s greatest pleasures is learning. Never, NEVER consider yourself e-d-u-c-a-t-e-d (past tense). Be relentlessly autodidactic. Maintain a voracious curiosity. Oh, and related: buy a camera and keep a journal, they will teach you how to see. 
  22. Most important point, last: The verve of your messy life -deadlines, bosses, clients, familial commitments- this is where your true passions will play out. Not in imagined vacuity but in the interstices of life, the tiny (sometimes infinitesimal) moments available to you, the slivers of time, the momentary pauses between. Don’t buy the illusion that ‘someday’ you’ll have time to accomplish your dreams. You won’t. Eschew extremism. Someday is now.

I'm only here at Starbucks because it's close to the office. In twenty years, for our next doppelganger appointment, meet me at McDonald’s. It's where the old people hang because they are smarter than us: the coffee's cheaper and they have free WiFi. Oh, and, if I'm still on WiFi and you're on something much faster, hook a brother up. But be patient. I'm sixty.