Why Crossing The Line is Better for You

Boldness: Build character with risk

Boldness is one of the greatest qualities a man can possess in his arsenal. Boldness when it comes to standing firm when needed, and moving forward when it feels most difficult. Sometimes boldness is found when there’s nothing left to lose. It’s the age-old story: a man down on his luck, pushed against the ropes, comes out of nowhere, puts it all on the line, and swings for the fences… and wins.

Think about your life for a moment. How many rules are you following without question? More importantly, how many unspoken rules have you been following since you were a teenager? I can personally attest to the volume of rules and “facts of life” I’ve collected – most of which are wrong, by the way.

We’re all dealing with a myriad of lines we’re afraid to cross. Taking the big leap of faith to start your new business venture, or having the courage to make that pretty girl your wife, or investing in yourself after years of investing in everyone else – these are lines we’ve drawn and need help, encouragement, and a good push to cross.

How do I go go boldly?

The easiest way to switch gears and bring boldness into your character, assuming that’s what you want, is to realize that everything you do – every single action you take – is a step closer or further from your ultimate goal – e.g. the man you want to be, and the life you want to live as that man. Every time you are faced with a decision that could have you taking bold action, you also have the choice to be timid and remain seated.

Stand up.

Boldness: Build character with riskActions speak louder than words, and actions are the first place to start. Boldness can sometimes be akin to saying yes to crazy opportunities. If you’re a business owner and a dare to be great situation drops into your lap, do you take it? Do you worry that you might not be equipped to handle such a potentially awesome opportunity, or do you take a deep breath and yell, “Hell yes, I’ll take it!”

A timid man would worry about practicality and probability – both valuable pieces to consider. A bold man would step up and take the opportunity, and then find a team of people to help crunch through the practicality and process.

Take Note: You can be bold without being a hero. You don’t need to be a big wig or have the weight of the world on your shoulders to be bold. More often than not, the greatest stories of boldness are from ordinary people making extraordinary choices. Rosa Parks was an ordinary person whose extraordinary choice made her boldness pivotal in the Civil Rights Movement. Bringing a homeless person a sandwich when nobody else is paying him any attention – that’s a bold and admirable move, and one we highly recommend.

The last piece to remember when on your journey to more boldness is not to become a grand storyteller. When you say you’re going to do great things, but never actually do them, you end up creating a reputation you might not like. We all have that uncle who’s an armchair politician, right? He’s constantly yelling at the talking heads on TV, but he won’t actually do anything about it. You don’t ever want to be the guy that people warn other about do you?

“That’s Ted, he talks a big game but he’s not going anywhere.” 

When you stand up and take action –even if it’s small– you turn the tides in your favor. You don’t have to save the world, you just have to save yourself from a bland flavored life. The best time to plant a tree is 20 years ago. The next best time is right now. You will regret every chance you didn’t take when your life comes to a close.

If at the end of your life, you met the person you could have been, would you regret not taking more chances?

Of course you would.

It’s better to cross the line and manage the consequences than to stare at the line for the rest of your life.

What are your thoughts? What line do you wish you had the courage to conquer? Share in the comments below.

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The Author

Blake Hammerton

Blake Hammerton

Blake Hammerton is the founder and coach at The Sharp Gentleman, and helps men earn more respect while gaining confidence in who they are. He is a certified relationship coach and loves writing about men's fashion, style, character-building, relationships, travel, adventure, and more.