Here is some stuff I wish I could have told 22-year-old me (assuming I would have listened, which is a stretch) and at the end of the day why playing it safe will probably NOT be your “best bet” after all.

1. The people who say the least have the most to say.

Bragging is a mask for insecurity. Truly confident people are quiet and unassuming. Hang around them. When they do speak, you’ll be glad you were listening.


2. Everybody wants something.

Almost everyone acts out of self-interest (especially when they claim they don’t). Often the people most eager to offer advice or help will want the most in return.

Assume all career or business assistance is part of an expected exchange, either now or in the future. Then you won’t be disappointed. But keep in mind that occasionally…

3. A few people just want to help others.

So don’t get too cynical. Occasionally you’ll meet those rare people who like to help simply because it makes them feel good. Those people are hard to find, though, because their names aren’t listed as sponsors on event programs or plastered on the sides of B-school buildings.

When you find someone truly and genuinely giving, make them a permanent part of your life.


4. Everything before “but” is bull.

“I don’t meant to be critical, but…,” “I’m not trying to tell you what to do, but…,” “Please don’t take this the wrong way, but…,” Yes you do, yes you are, and yes I will.

Disclaimers are anything but and usually indicate the true meaning behind what is said.

5. “Boring” people win.


The people who achieve the most do a lot more of the boring stuff. Routine, rigor, attention to detail, churning away day after day… that is how you will succeed. Every elite athlete, every gifted entertainer, and every successful businessperson you will someday meet put in thousands of hours of practice and effort. They are successful mostly because they are willing to do what other people won’t do.

Learn to enjoy the mundane and you can outdistance the pack — and oddly enough, then your life will be anything but boring.

6. Stop brainstorming and start borrowing.


Many people try to be original — and want to be perceived as original – simply to serve their ego.

Results are all that matter. Stop trying to think of something new. Someday you’ll spend two hours in a Coors bottling plant and bring back more great productivity and quality ideas than you can implement in a year.

Ideas you can borrow — ideas that you can see will actually work — are everywhere. Borrow freely. Borrow often.

7. The women you really want to meet don’t care about the car you drive.


So don’t buy the Mustang GT. Or the RX-7. (And maybe, just maybe, think about not wrecking every motorcycle you ever own.)

8. Training is great; advice is not.

Advice is what you ask for when you already know the answer but wish you didn’t. Ask, “Should I…” and you get opinions often colored by individual perspectives. Instead ask, “How do I…?” because “how” leads to training and knowledge.

Always ask to be shown or taught. When you know how, then you can decide for yourself whether you should.

9. Visibility is everything.

The people who get opportunities and promotions are the people who are seen and noticed. Customers, partners, media… no one will discover you on their own. You have to help them find you.

Spend the majority of your time doing great things, but spend at least 5 percent of your time getting the attention of the people who matter.

10. Always take one thing out.

Every initiative, every project, every decision… you’ll constantly be tempted to add one more thing to make it even better. Addition almost always results in subtraction. The more you eliminate, the more you can focus on what remains; what you leave out is as important as what you leave in.

11. Your parents are a lot smarter than you think.


And they only want the best for you. And they’ll always be there for you. And they won’t be around forever.

Call them.

12. Always learn on the fly.

Waiting until you’re ready means waiting forever. When you’re “preparing,” there are millions of reasons to delay a little longer.

Trust yourself. Learn a little and jump in. Make mistakes, adjust, adapt, and develop greater skill by doing and reflecting, not thinking and dreaming. You’ll save time and achieve a lot more.

13. Don’t expect to get back what you give.

Favors will not be returned. Sacrifices made for others will not be rewarded. None of the people you mentor, develop, promote, and work with are going to call you when, years from now, you’re suddenly let go.

When you give, give because you want to or because it’s the right thing to do. Then you will never be disappointed.

14. A little ego is not a bad thing.


You need a strong ego. Otherwise you’ll believe all the people who say you don’t have the talent… or that there’s too much competition… or simply that you won’t succeed.

No one will believe in you until you believe in yourself.

But keep your ego to yourself. Be humble on the outside; keep the proverbial 800-pound gorilla on the inside.

15. You will most regret what you decide not do.

You won’t regret broken bones from motorcycle racing; you will regret not taking a shot at a higher level of the sport. You won’t regret taking a crappy job; you will regret turning down what could have turned into a great job. When you look back you will only regret a few of the things youdid. (And even so, the things you do regret doing help make you the person you become.)

What you will most regret are things you decide not to do due to lack of confidence or fear of the unknown — like the businesses you should have started and the joint venture you turned down.

For you, safe will almost always equal sorry. Take intelligent business and personal risks, and trust you will be able to work through any challenges.

If nothing else, you’ll have a lot more fun.

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