On Reaching For Opportunities That Are Out of Your League

When searching for the next opportunity to advance your career, or taking the next big step in your business, it’s normal to stay comfortable and reach within your capabilities.

It’s safe. You’re confident about it because you know you’re going to achieve that goal. No stress. No big deal.

But when was the last time you aimed for something that you thought was completely out of your league?

You know that job listing that requires 3-5 years of experience, but you have only 1-2 years? Why not just apply?

You know that big client you’ve been eying but you think wouldn’t hire a small-time freelancer like you? Why not just reach out and start the conversation?

The worse thing that happens is “no.”

In that case, you just end up back where you started. You didn’t lose anything, except maybe some time. But you learn to change your approach and experiment with different emails or pitches.

Imagine the best case scenario. You get a “yes” and you have to figure out how you’re going to make it work.

How are you going to handle that new job that you totally didn’t feel qualified for, but got hired for?

How are you going to meet expectations for that big client and make sure you don’t lose them?

Those are great problems to have.


I recently got hired for a content marketing position on the growth team for Sidekick by HubSpot. That means I’m moving my life from Southern California to Boston to take on the role and help build out the new product (goodbye sunny SoCal weather, hello mounds of snow).

Let me tell you why this is relevant.

I learned first hand that reaching out of your comfort zone can result in huge rewards.

HubSpot is the marketing company. The founders, Dharmesh and Brian, literally defined inbound marketing. I’m going to be working alongside people like Mike Volpe and Brian Balfour (and tons of other people). If these names don’t sound familiar, just know that they’re each a big deal.

I’ve been in the marketing scene for a little under two years. I’ll be working with these huge marketing influencers. Influencers! I’m a total newb compared to them.

Here’s the crazy part.

I wasn’t even going to apply for the job  the first place. I found the job listing on Inbound.org and thought “Whoa! HubSpot is hiring!? Cool.”

I, and millions of others, hold HubSpot in high regard. So my next thought was,

“But it’s HubSpot. I’m probably not qualified.”

I almost didn’t apply!

The next day, I found myself revisiting the job listing.

Damn it. I would really love to work for HubSpot. I’M JUST GONNA DO IT.

I’M GONNA APPLY.

And I did.

Eights days and four interviews later, I got hired.

And I wasn’t even going to apply because I thought I wasn’t qualified.


Even if you think that something (or someone) is out of your league, just give it a shot. You never know what might come out of it.

If you’re the type of person who always thinks you could be better, you’re probably like me: you don’t give yourself enough credit.

So do yourself a favor. Give yourself more credit and reach for those opportunities that are out of your league, right outside your comfort zone.

When you reach far enough, you might find that it really wasn’t that far after all.

Heyo! I’m creating a resource to make the job hunt easier. Want first dibs?

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