Get Your Pitch On: Your Personal Pitching Challenge

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Y’all know I can’t go too long without talking about pitching. 😉

It’s kind of my jam. And kind of how you’ll be successful as a freelancer. Or an entrepreneur. Or in life really!

Why? Well, we’re all in sales.

Whether you want to admit it to yourself or not, it’s true.

Some of us are in sales, sales. Others of us just sell ourselves (and not like that sicko!).

We’re All in Sales

As I said, regardless if you have a product or a service to sell, we’re all in sales.

Yep, even those of you in Corporate America, sitting in your cubical way far away from the sales department. Even you had to sell your boss on landing that particular job. (Whether you like it or not isn’t the point here.) 😉

And if we’re all in sales, then we’ve all had to pitch ourselves at one point or another to land a job. Traditionally, this is called an interview.

I can hear your hamster wheel turning…

At least that’s how I think of it. And I think you should too. Especially if you’re looking to start (or grow) your own business.

Because whether we have a product, advice or a service to sell, if we don’t pitch ourselves and sell it… we’re kind of SOL. Am I right?

Pitching Is an Essential Part of Business Building

I can’t tell you how many times I’ve said:

If you don’t put yourself out there, you won’t be successful.”


Clients won’t come knocking on your door – you must do the door knocking.”

At least at first! When you’re first building a new business, outbound marketing is essential.

get-your-pitch-on_-your-personal-pitching-challengeOutbound Marketing Vs. Inbound Marketing

Inbound Marketing (per Hubspot):

Inbound marketing focuses on creating quality content that pulls people toward your company and product, where they naturally want to be. By aligning the content you publish with your customer’s interests, you naturally attract inbound traffic that you can then convert, close and delight over time.

Outbound Marketing (per Bold Think Creative):

Outbound marketing is a strategy in which a business advertises its products and services by presenting information to consumers even if they are not looking for those products or services. Because of this, outbound marketing has been commonly referred to as “interruptive marketing.” Companies do this via the use of television, print ads, direct mailers, radio and more.

Or in essence, inbound = blogging or content generation of some sort and outbound = traditional marketing methods or in our case, cold pitching.

While we’d all like to start off with inbound marketing (and we should focus on positioning ourselves to do so), it isn’t something that happens overnight. You should get started setting up a blog and online presence now, but you should also start outbound marketing now too.

Because bills need to be paid now yo! 😉

Your Personal Pitching Challenge

Now that you’ve fully bought into the idea that everyone is in sales, that you need to put yourself out there and that doing some outbound marketing aka cold pitching at first is necessary, I want to give you a little challenge.

Note: This challenge can go hand-in-hand with the 90 Day Pitching Challenge I brought to you back in May of this year. 

The premise behind this challenge is two-fold:

  1. We’re all visual people.
  2. We thrive off of external motivation.

What You’ll Need

  • 30 days (the time frame could be shorter or longer, but I like operating in one month increments)
  • A clear jar or vase
  • Coins (quarters work well), candy (think jelly beans, M&M’s or Hershey’s Kisses) or another tangible item
  • A reward for completing the challenge

How It Works

You can operate this challenge in one of two ways.

  1. You can remove an item (think candy) from the jar one at a time.
  2. You can add an item (think quarters) to the jar one at a time.

Either method works. It just depends on if you think you’ll be more motivated seeing your jar get empty or full. Dealer’s choice!

Next, you need to determine how many pitches you should send in that month. Anything less than one per business day isn’t enough. So let’s say anywhere from 20-300 (total, not per day).

Pick your start date – tomorrow sounds good to me! 😉 In all seriousness though, the sooner the better. Can you wait until the New Year? Sure.

Should you? Nope. Too much time to talk yourself out of it!

Small actions equal BIG results.

(I’m living proof!)

Then pick your reward. Maybe it’s a pedicure, a new book or something else relatively cheap, but that you actually want. You don’t need to drop a couple hundred bucks on a reward, but you should want the prize if that makes sense.

Note: If you choose candy (most of you won’t, because like me, you probably have a New Year’s resolution to drop a few lbs), that can totally be your one and only reward. Because you’re kind of cashing in each time you send a pitch… Make it your absolute favorite candy though. And DON’T let yourself eat any UNLESS you’ve actually sent a pitch.

To Recap

You find a jar –> you choose to fill it or to empty it –> you figure out what to fill it with –> you choose your pitching goal/time frame –> each time you send a pitch, you either remove something from the jar or add something to it (depending on if you want to fill it or empty it) –> at the end if you’ve hit your goal, you cash in your quarters (pebbles, seashells or whatever) for your grand prize.

You can also do a little happy dance if you’d like. 🙂

The Real Prize

The real prize isn’t a pedicure, a book or some candy.

The real prize is getting new clients. And getting new clients again takes putting yourself out there and pitching for work.

And we all know that it doesn’t happen right away (I’ve had students tell me that prospects replied to a pitch TWO YEARS after they sent it!). So get started. Now. And don’t stop when your challenge ends.

And don’t forget to FOLLOW UP – it’s kind of important too! 😉

Are YOU going to take the personalized pitching challenge? If so, comment “I’m in” down below!

23 thoughts on “Get Your Pitch On: Your Personal Pitching Challenge”

  1. Well Gina, you have done it again. You are making me step out of my comfort zone… but for my own good. I keep saying I need to be ‘doing’ instead of learning how to ‘do’. I am getting out my list of article ideas. I am getting out my pitching template. I am preparing a list of those to initially pitch to. And most importantly, I’m getting a really BIG jar. I am starting Monday, December 19, 2017 and I wish for everyone to keep me accountable.

    • Boom Lois – <3 this! Are you going to fill it or empty it? I'm curious to hear what people will be using and would LOVE to do a round up post in a month or two sharing your results!!

      • Gina, I am going to over-fill it. I am going to put a quarter in EVERY time I pitch and $1 every time it turns into a gig. I will take a picture of it in the beginning and send pics throughout the journey. Another ‘Gina just kicked me in the backside’ moment 😉

  2. Hi Gina! I am SO in! I’ve been freelancing for about 6 months now, and I feel like I’ve finally found my niche and business is starting to pick up – this is just the motivation I need to push myself into the New Year! Thank you!

  3. I’m in! Thanks Gina 🙂 I’ve been cold emailing already, but with little luck. Hopefully, it will all pay off soon. I think it’s common to lose steam after so much silence or at least it becomes dreaded instead of an adventure. Thanks for breathing new life into pitching!

    • Whoop! I totally get that – don’t give up! And the pitching challenge can include cold pitches, answering job boards, asking for referrals, etc. The whole goal is to take lots of small actions and put yourself out there. 🙂

  4. I’m in! I’m thinking I’ll either put quarters in and then buy something in 30 days OR I’m taking Sweet Tarts out. Because sweet tarts are fabulous.

    I really need this motivation to cold pitch. I’m super excited about it but I feel so unprepared to pitch myself! Time to stop saying I want too and start actually doing.

  5. I am all in. I have been saying that January is going to be a balls to the wall sales month. Thanks for this idea!

  6. I’m in! I also think I’m going to cheat a bit and add two candies for every follow-up I send, because I am terrible at sending follow-ups. I’m going to go with M&Ms, because I think that will be a lovely colorful visual 🙂 I’m going to start today as it marks exactly one month until my husband and I go on our honeymoon to Mexico. My reward will be a pedicure right before the trip 🙂

    Thanks for the motivation, Gina!

  7. Perfect timing!
    Just spent the last hour doing math — no work in the pipeline, Visa and tuition on the horizon, sick feeling in my gut. This challenge is the tonic and push I need. So, yes, I’ll be playing, starting on Monday, Dec. 19, and taking a quarter out for every pitch sent.

  8. I’m in Gina. You always do such a great job motivating people to get out of their comfort zone and strive to live the writer’s life. Thanks for all you do.
    Instead of a jar and candy, I am going to reward myself with 5 minutes of fishing time (when it warms up) for each pitch.

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