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“If you were 20 years old again today, what’s one piece of advice you’d give yourself?”
DW #108 🟡

When you are young the world is a great big mystery.
I think one of the greatest ‘hacks’ in life is finding mentorship to help guide you and shape your perspective on the world. There’s no such thing as a self-made man.
I’m lucky to have many great mentors, advisors and role models in this respect. I’ve written about this a few times before.
Recently I decided to reach out to a few who’ve made a substantial positive impact on my life and career, and see if they’d be willing to share some words of wisdom for other young people, which I’ve documented below.
I asked a simple question: “If you were 20 years old again today, what’s one piece of advice you’d give yourself?”
I was a bit taken back by the responses - common themes of hope and encouragement, some universal, some more tactical. All of them were quick and happily willing to share their insights (there is something to be said about this).
Here’s what they said, I think you’ll enjoy:
Advice from 15 Great Mentors & Role Models
“Slow down, meet as many people as you can, find mentors and “north stars,” and be humble enough to learn and grow from it all. Lean into your passions but also (maybe more so) your proficiencies. What are you best at? Master a skill and become world-class at it. Build your personal “moat” to stand out as you begin to interface with the real world beyond college and the bubble of youth.”
"Everything great takes longer than you think, but it's still worth doing. Staying humble and enjoying the process will help you navigate the ups and downs that inevitably arise. Find friends who challenge your thinking and cheer for your wins—ditch the rest because life is too short for critics and assholes."
“Set goals. Not only set them, but write them down with a roadmap. Set a reminder in your calendar every six months to review, evaluate, and modify. Everyone has dreams, very few achieve them without setting goals.”
“Keep close family ties & live each day to the fullest!👌
Live, Love & Be Happy!”
“Our time is our most precious asset and finite asset. We would be wise to staying focused and spending our time on what matters most. I would ask my 20 year old self these three starter questions: 1) How might you help your present self reach your future self? 2) What is the journey you are currently on and is this path going to get you where you want? 3) How might we avoid the distractions of fomo, imposter syndrome and being stretched too thin that are constantly pulling us away from being our best self?”
“Don’t settle for the allure of a ‘stable job’, which doesn’t really exist. Take more risk by following your instinct, do your homework, trust yourself, then jump into the world of entrepreneurialism and don’t look back.”
“Take chances, don’t be afraid to fail“
“I’d encourage a 20 something to invest in your network. Meeting new people, building relationships, and providing value over time will pay incredible dividends later in your career.”
“Start with the basics—complete your generals affordably at a community or technical college, and get a job with a company whose mission genuinely inspires you. Let them invest in your development as you discover where your talents, values, and passions align. Each experience, even the missteps, will shape your character and clarify your purpose. Trust the process, and let every role become a teacher.”
“I'd say start doing something that requires managing money. Buy some small business, or a rent house, or something that makes you really look at cash flow and gives you an opportunity to establish processes as well as get inventive.”
"You're going to figure it out as long as you keep investing in yourself. Don't stress it."
“Read more, make reading part of your every day.”
"Don't take everything personally. It's not always about you."
“Be curious - about what your spouse is doing in his/her life. Be engaged in conversations and really listen and be present. This helps me focus on the important things in life -people that bring me joy and not focusing on accumulating (buying) things. Less is more in that case.”
Documenting these as much for myself as I am for any other young person making their own way. It makes me wonder a bit what advice I’d give to my own self.. I’m still working on that.
There are some great books that document insights like this as well from Tim Ferriss (Tribe of Mentors) and Sahil Bloom (The 5 Types of Wealth) which inspired me in part to write this post.
If you’re reading this I’d encourage you to consider the same - what would you tell your 20-year-old self?
Peace,
Ramsey