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Entrepreneur Smarts: 30 Lessons I Learned in 30 Years

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Editor’s Note: A version of this article previously appeared at LewisHowes.com.

It was a warm night outside Caffe Dante, my favorite Gelato spot in New York’s Greenwich Village. I usually go there alone. I walk through Washington Square Park, people watch and get my two scoops of gelato: one scoop of stracciatella, one of tiramisu. This particular time I sat outside at a table next to an older Italian woman and her little French Bull dog. I struck up a conversation.

We chatted about things like Italian culture, her grandkids and how her husband is an artist who has a gallery in the city. I was 29, about to turn 30, so I asked the woman if she could go back in time and tell her 30-year-old self anything, what would it be? Her response: “Don’t worry so much. We create drama from nothing so often, but the things we think are major issues always pass, and we forget about them usually within a few months at most.”

It’s good advice. As I look back at my 30 years of life so far, I’ve come up with 30 simple yet important lessons I’ve learned — about being a better entrepreneur and a better person in general.

1. Don’t worry so much.
She was right, there’s been so much stress and drama I’ve allowed in the past that really doesn’t matter. There are ways to handle situations and instances in your life, but worrying about them never does much.

2. Be extremely grateful for what you have.
I was a pain most of my childhood, always mad at the things I didn’t have. Things shifted drastically in my 20s when I started putting an emphasis on gratitude. Focus on the good you do have, not the things you lack.

3. Strive to be a better version of yourself every day.
Each day we have the opportunity to learn something new, apologize for our mistakes and become better.

4. Drop your ego.
It’s something I continue to work on because having an ego never did anything positive for me and usually doesn’t accomplish much for anyone.

5. Eat clean.
I used to eat whatever I wanted and it didn’t matter as much when I worked out six hours a day. I still love my gelato from time to time, but I’m all about eating as much organic foods, experimenting with cleanse, and drinking green juice as possible. Focus on what works for you, but educate yourself on what you put in your body.

6. Sweat daily.
Movement is important, especially when so many people sit at a desk for 10 or more hours a day. Not moving can have ill effects on one’s body. Doing the conditioning program CrossFit, playing team handball for the U.S. national team and playing street basketball are my weekly activities. Do something you’ll have fun with and focus on moving every day.

7. Give back.
I wouldn’t be where I am today without the help of countless people. The support I’ve received from family, friends, teachers, coaches and mentors is overwhelming. Find a way to help others and give back as it’s the best form of gratitude.

8. Frame your goals.
I was in my 20s when I started writing my goals down, assigning each a date that I would achieve them by. I was amazed when I started reaching these goals by the date I had listed on them. It was a daily visualization exercise, and it almost always works. I believe the things you put your energy toward the most will most likely come true over everything else.

9. Don’t let others dictate to you.
If you don’t want to live a life where you go to a job every day just so you can enjoy your weekends and get two weeks of vacation every year, then don’t do it. Read Entrepreneur, read The Four Hour Work Week by Tim Ferriss, or other inspirational blogs about creating a lifestyle around a business you want to live.

No excuses, just do it already.

10. Follow your passion.
We only have one chance in this life. If you aren’t following what you love then what are you doing? Why show up every day to live a life that doesn’t inspire you?

11. Be enthusiastic about what you do.
Former football player and coach Vince Lombardi said, “If you aren’t fired with enthusiasm, you’ll be fired with enthusiasm.” It’s the truth.

12. Focus on relationships.
You can accomplish anything with the right relationships both personally and professionally. People don’t care as much about what you know as they do on how much you care about them.

13. Be open to trying new things.
I’ve been an extremely picky eater my entire life, but the more I try the more I learn and become a better version of myself.

14. Feel your fears but embrace them.
My friend and sports psychologist Dr. Jeff Spencer told me this once and it stuck with me. Elite athletes feel fear just like everyone else, but they channel that fear to fuel their spirit and passion for competition.

15. Your childhood matters, but don’t let it control your adulthood.
Don’t let the things that happened to you as a kid control the rest of your life. Shit happens to all of us. Use it to your advantage, learn from it, and focus on gratitude and giving.

For lessons 16 – 30, click Next.


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