Have you ever been told--as an insult--that you were "trying too hard"? Maybe you raised your hand often in class, or tried to make friends with a lot of different people. From a young age, we're conditioned to think that "trying too hard" is a bad thing. Not only is it not a bad thing, it's not a thing.

As a CEO, I want people to try hard. I want people to work to their full potential, and to keep pushing for greatness. I don't want to be surrounded by anyone who's just coasting along, riding the coattails of whatever their latest success is; it's 2018, and more is more. Here are a few times when doing more is the thing to do.

When you're trying something new.

Listen, if you're trying something new, there's probably a 50/50 chance that it's going to be successful. You can't really do anything to change those odds; it's a new thing, which means there's no way of knowing if it's going to work. And you know what won't increase your odds? Playing things safe.

Trying to innovate? Go beyond just adding an extra function, or gadget, or step in your product. Think beyond the scope of what you already know to exist--then, shoot for it.

When you've got an idea.

This is what I always say: don't ask--announce. Don't wait for someone to tell you that your idea is brilliant and wonderful and worth doing; announce your idea as though it's a known fact, and your audience (investors, customers, co-workers) will automatically think those things.

Announcing takes the self-doubt and self-sabotage out of things; there's no need for you to downplay your own great idea by asking someone else to tell you it's great. When I started Kiip, I didn't ask people if they thought that rewards-based advertising was a good idea; I told them that it was, and because I had that confidence, they believed it was, too.

When you're making a first impression.

We're often told that for a job interview, or a presentation, or even a first date, that we should find the perfect balance of confidence and humility. This applies nicely to the first-date scenario, but can hold us back in a professional environment. You only get one first impression, and while not everyone will hold you to that first impression, why not make a splash with it, anyway?

When I entered college as a 14-year-old, I had a choice to make: I could fade into the background and hope that no one noticed the literal child in their class, or I could make myself known. As you may have guessed, I chose the latter--and wound up getting elected to an office of student government.

When you're looking for media coverage.

As someone who used to work for a media company, I can assure you that journalists receive hundreds of pitch e-mails a day. If you want someone to open your pitch, you've gotta make them notice it (note: this does not mean using all caps or a "cool" font).

If you're smart about your relationships with journalists, you'll only reach out to them if you really have a scoop. And since you do have that scoop, make it known. Don't downplay your story; say it loud and say it proud. Give them the numbers, the tagline, the (necessary) details. Journalists want a big story, so if you've got one, they'll definitely be interested. You just have to let them know it's the real deal.