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The Art of The Ask
Chelsea Riffe
6 episodes
1 week ago
Ever wonder what could happen if you just… asked? Like, REALLY asked— for the raise, the date, the discount, the collaboration, the last slice of pizza, or the life you actually want? Welcome to "The Art of the Ask," the limited series podcast hosted by Podcast Host, Strategist and Professional Shot Shooter Chelsea Riffe, here to help you stop overthinking, start pitching, and finally get what you want. Each episode, Chelsea unpacks the psychology, strategy, and sheer nerve it takes to ask for what you want—and flip your "who am I to ask?" to "why not me?!"
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Entrepreneurship
Business
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All content for The Art of The Ask is the property of Chelsea Riffe and is served directly from their servers with no modification, redirects, or rehosting. The podcast is not affiliated with or endorsed by Podjoint in any way.
Ever wonder what could happen if you just… asked? Like, REALLY asked— for the raise, the date, the discount, the collaboration, the last slice of pizza, or the life you actually want? Welcome to "The Art of the Ask," the limited series podcast hosted by Podcast Host, Strategist and Professional Shot Shooter Chelsea Riffe, here to help you stop overthinking, start pitching, and finally get what you want. Each episode, Chelsea unpacks the psychology, strategy, and sheer nerve it takes to ask for what you want—and flip your "who am I to ask?" to "why not me?!"
Show more...
Entrepreneurship
Business
Episodes (6/6)
The Art of The Ask
How to Ask for What You Want if You Have Imposter Syndrome

Let's address the elephant in this visibility glow-up room: imposter syndrome.


In this episode, I'm breaking down what an imposter actually is (spoiler: unless you're actively scamming people out of their life savings or the Tinder Swindler, you're fine) and why feeling intimidated just means you're expanding. I'll walk you through the real mindset shifts and practical moves that'll help you own your expertise... no more $5K+ certifications required.


I'm pulling from my own messy AF business moments, podcasting fumbles, and what I've seen working with clients to show you why most of us feel like frauds when we're literally just... growing.


You'll learn how to build ACTUAL self-trust through prep, being completely honest about what you know (and don't), and really embodying your thing, so you can stop enrolling in 8 courses every quarter to "be ready".


What you're going to hear today:

  • Why the literal definition of "imposter" proves you're off the hook (unless you're Anna Delvey reading this...)
  • The difference between feeling intimidated and actually being unqualified (no, they're not the same)
  • How to swap "I don't know enough" for "I can figure this out or ask someone"
  • What embodiment actually looks like in real life, and how to know if you've got it
  • Why DOING the thing creates confidence way faster than THINKING / spiraling about it
  • How to use "borrowed confidence" when you're too in your head to just ask
  • Why putting people on pedestals and over-apologizing wreck good collaboration
  • The reframe that helps you trust your clients' ability to make their own decisions


My Biggest Takeaways:

  • Everyone is winging it. Yes, even them.
  • Certifications don't give you confidence. Reps do.
  • You're not an imposter, you're in a season of growth
  • Stop assuming your audience is as harsh as your inner critic. They showed up for a reason, even if it's to "be in your energy" (because YES, many people DO just want to be around you)


Episodes mentioned today:

  • Taylor Swift, Bad Bunny and Modern Day Titans
  • How To Ask for Something with No Track Record, Portfolio or Massive Social Following

If you liked this episode, you'll LOVE these:

  • ⁠The Witch Wound - Taking Down the Patriarchy Through Putting Yourself Out There⁠
  • ⁠Shoot Your Shot - Or Miss Out On Life's Biggest Opportunities⁠
  • ⁠Rejection Won't Kill You - What It Means & How to Deal With It⁠


Here's my ask for you!

  • DM me on IG ⁠@chelseariffe⁠ or email team@chelseariffe.com and tell me - what have you asked for recently, and what were the results?
  • Follow this podcast, rate, review, and ⁠tag me on socials⁠ - and following the law of reciprocity, I'll send you my handy-dandy Visibility Vault Notion doc - a list of newsletters and platforms to pitch to and get strategically placed!
Show more...
2 weeks ago
44 minutes 23 seconds

The Art of The Ask
How to Ask for Money

Your most requested episode is here: HOW TO ASK FOR MONEY!


How do you make such a big, bold, audacious ask?! In today's ep, I'm breaking down why money is such an anxiety-inducing topic, and the different ways to ask for money, including asking for a raise, a family investment into your biz, a refund from an airline and more!


PLUS, I spill the tea on the time I was in Australia and BROKE AF. I'm talking "living off a tax refund with maxed out credit cards and nannying for accommodation" broke. This experience taught me how feeling shame wasn't a luxury I could afford.


What You'll Learn:

  • Ancient anxiety: How THOUSANDS of years of money evolution hardwired financial insecurity into your DNA
  • Why It's So WEIRD to talk about money: The psychological mess of tying your net worth to your self-worth, plus cultural taboos that make salary talk feel like a federal crime
  • The trust factor: Every financial transaction is a tiny negotiation of power, status, and "will this person screw me over?" - asking for money is about trust
  • How to ACTUALLY ask: stop with the "just wondering if maybe possibly..." passive word salad and start using active language like you mean it
  • The Harvard hack: One word that increases compliance by 60%
  • My Rock Bottom Era: That time I was so broke in Australia I DM'd literally everyone I'd ever met to sell $15 yoga classes (and it worked)!


My ask for you this week? GO ASK FOR MONEY. A refund, a raise, an upgrade, an investment into your biz -- anything! DM me with your wins ;)


If you liked this episode, you'll LOVE these:

  • ⁠The Witch Wound - Taking Down the Patriarchy Through Putting Yourself Out There⁠
  • ⁠Shoot Your Shot - Or Miss Out On Life's Biggest Opportunities⁠
  • ⁠Rejection Won't Kill You - What It Means & How to Deal With It⁠
  • ⁠Selling Without Social Media⁠


Here's my ask for you!

  • DM me on IG ⁠@chelseariffe⁠ or email team@chelseariffe.com and tell me - what have you asked for recently, and what were the results?
  • Follow this podcast, rate, review, and ⁠tag me on socials⁠ - and following the law of reciprocity, I'll send you my handy-dandy Visibility Vault Notion doc - a list of newsletters and platforms to pitch to and get strategically placed!


Check out ⁠Pitch Perfect⁠ and grab your spot before we start October 13th!


Show more...
1 month ago
1 hour 2 minutes 50 seconds

The Art of The Ask
How To Ask For Something with No Track Record, Portfolio or Massive Social Following

This episode is a full on MASTERCLASS on how ask for something and position yourself when you have nothing to show for it. I'm talking no shiny analytics, no experience, no previous work... how on EARTH do you shoot your shot when it feels like you have nothing to offer?!


I break it down in the most Virgo-Moon detail possible, including:

  • how I landed podcast sponsors, brand deals and massive discounts on travel with an ugly AF Instagram, no email list, unimpressive analytics and no past sponsors
  • how to act like you're already hired
  • leading with vision and potential, not your lack of experience
  • how to show your transferable skills
  • creating proofs of concept - like a mockup design, sample copy, or outline steps to solve a problem
  • put yourself in the receivers' shows and position from there
  • research obsessively and speak their language



If you've felt insecure about pitching yourself from lack of experience, this episode is going to boost your confidence into outerspace.


And P.S. you'll learn all of this inside Pitch Perfect! We start October 13th - 3 spots left.


If you liked this episode, you'll LOVE these:

  • ⁠The Witch Wound - Taking Down the Patriarchy Through Putting Yourself Out There⁠
  • ⁠Shoot Your Shot - Or Miss Out On Life's Biggest Opportunities⁠
  • ⁠Rejection Won't Kill You - What It Means & How to Deal With It⁠
  • ⁠Selling Without Social Media⁠


Here's my ask for you!

  • DM me on IG ⁠@chelseariffe⁠ or email team@chelseariffe.com and tell me - what have you asked for recently, and what were the results?
  • Follow this podcast, rate, review, and ⁠tag me on socials⁠ - and following the law of reciprocity, I'll send you my handy-dandy Visibility Vault Notion doc - a list of newsletters and platforms to pitch to and get strategically placed!


Interested in getting more visible and collaborating with people you admire, WHILE converting at rates that will make your eyes pop out of your head??! Check out ⁠Pitch Perfect⁠ and grab your spot before we start October 13th! Only 3 left

Show more...
1 month ago
37 minutes 12 seconds

The Art of The Ask
A Case for Asking: The Visibility (& Revenue) Glow-up with Antonia Dolhaine

Remember when every coach told you to "post consistently", "show up" and "provide value" on social media? Somatic Depth Coach Antonia Dolhaine did that for YEARS. She created insane viral graphics, wrote endless carousels, and dealt with the classic entrepreneur nightmare: hours spent on Canva graphics leading to tons of inquiries from people who weren't actually a good fit for her work. Wasted time, energy and effort. Sound familiar?


Antonia ditched the content grind and worked with me to get her featured on podcasts instead. Something wild happened: Her applications dropped, but her revenue spiked!


Turns out, getting 30 knee-jerk reactions from a viral post isn't as valuable as getting 3 people who've already heard your voice for an hour and know exactly what you're about (and are ready to make a high-ticket investment).


In this conversation, we break down why she made the switch, and the incredible visibility glow-up that's happened since.


Direct quotes from the convo:

  • "80% of those people who are writing in weren't the right fit for my containers because they were just coming through this very simplified graphic that had mass appeal, but like I'm not a mass appeal coach."
  • "I find it so much easier to explain what I do when it's in a conversational format... I'm very much someone who needs something to respond to."
  • "My client work has doubled... I get a third fewer applications that come through, but those applications are 90% aligned, whereas the applications I was getting before were like 15% aligned."
  • "It feels like at this point, any marketing efforts that I'm making are like the bare minimum with the maximum impact."
  • "It doesn't feel like work every time I've recorded a podcast. And I have just gotten into this routine of going for this very jaunty walk after every podcast episode, just like letting all of that enthusiasm kind of spring through my steps."


This could be you! You'll learn everything about pitching yourself for aligned opportunities like we did for Antonia inside Pitch Perfect. Space is limited - only 4 spots left! Enroll right HERE.


Connect with Antonia:

  • https://www.antoniadolhaine.com/
  • https://www.antoniadolhaine.com/substack-community
  • https://www.instagram.com/antoniadolhaine/?hl=en

  • Here's my ask for you!

    • DM me on IG ⁠@chelseariffe⁠ or email team@chelseariffe.com and tell me - what have you asked for recently, and what were the results?
    • Follow this podcast, rate, review, and ⁠tag me on socials⁠ - and following the law of reciprocity, I'll send you my handy-dandy Visibility Vault Notion doc - a list of newsletters and platforms to pitch to and get strategically placed!
    • Check out ⁠Pitch Perfect⁠ and grab your spot before we start October 13th!


    If you liked this episode, you'll LOVE these:

    • ⁠⁠The Witch Wound - Taking Down the Patriarchy Through Putting Yourself Out There⁠⁠
    • ⁠⁠Shoot Your Shot - Or Miss Out On Life's Biggest Opportunities⁠⁠
    • ⁠⁠Rejection Won't Kill You - What It Means & How to Deal With It⁠⁠
    • ⁠⁠Selling Without Social Media⁠⁠
    Show more...
    1 month ago
    41 minutes 35 seconds

    The Art of The Ask
    How to Handle Rejection When Asking for What You Want
  • This week, I get into the number one thing that holds people back from asking for what they want: fear of rejection.


    I'll share the psychology around the fear of rejection and why building up a tolerance to get rejected is the fastest way to build meaningful connections, ironically!


    Episode snippets:

    • Most people aren't sitting around dissecting your asks in group chats (that's your insecurity talking)
    • When someone says "not right now" or doesn't respond, they're usually just busy living their own complicated life
    • You're making it about you when it's probably about their capacity, timing, or circumstances
    • How to gamify rejection and learn to use it as data
    • The importance of having safety nets when shooting your shot
    • "Not right now" isn't "never"
    • My hot take on why thinking everyone is talking about you is arrogant
    • Start small and slowly build the heat with your asks to get comfy with hearing "no" and why it's usually redirection
    • My own personal experience with rejection, including recently in Lisbon!


  • If you liked this episode, you'll LOVE these (seriously):

    • ⁠The Witch Wound - Taking Down the Patriarchy Through Putting Yourself Out There⁠
    • ⁠Shoot Your Shot - Or Miss Out On Life's Biggest Opportunities⁠
    • ⁠Rejection Won't Kill You - What It Means & How to Deal With It⁠
    • ⁠Selling Without Social Media⁠


    Here's my ask for you!

    • DM me on IG ⁠@chelseariffe⁠ or email team@chelseariffe.com and tell me - what have you asked for recently, and what were the results?
    • Follow this podcast, rate, review, and ⁠tag me on socials⁠ - and following the law of reciprocity, I'll send you my handy-dandy Visibility Vault Notion doc - a list of newsletters and platforms to pitch to and get strategically placed!

    Want to get REALLY good at asking for what you want Check out ⁠Pitch Perfect⁠ for early bird pricing ($300 off til Sept 15th!!!) and grab your spot before we start October 13th!

    Show more...
    1 month ago
    40 minutes 18 seconds

    The Art of The Ask
    How To Ask for What You Want

    In this kickoff episode of "The Art of the Ask," a limited series podcast all about the power of asking for what you ACTUALLY want—whether in business, life, or relationships, I share how I've SHOT MY SHOT and gotten exactly what I wanted (and of course, how you can too)!


    This episode starts with a definition of what "asking" actually means (you know my Virgo Moon/Rising loves a Latin root or definition), and how I built my "ask" muscle, first with landlord negotiations, and then with a massive wellness influencer...


    What else to expect this episode:

    - Why asking for what you want is often seen as "cringe" or selfish, and how to overcome this limiting mindset

    - Real-life example of how I negotiated with my landlord and the ripple effects of those asks

    - The importance of creating a win-win situation when making requests

    - How asking led to unexpected DRAMATIC business growth, including landing podcast guest spots and new clients (like, LOTS of new clients)

    - The law of reciprocity and why timing and empathy matter when making an ask

    - The value of orbit-jumping: getting out of your echo chamber to reach new audiences and opportunities

    - Actionable tips for pitching yourself, negotiating, and building collaborative relationships


    If you liked this episode, you'll LOVE these (seriously):

    • The Witch Wound - Taking Down the Patriarchy Through Putting Yourself Out There
    • Shoot Your Shot - Or Miss Out On Life's Biggest Opportunities
    • Rejection Won't Kill You - What It Means & How to Deal With It
    • Selling Without Social Media


    Here's my ask for you!

    - DM me on IG @chelseariffe or email team@chelseariffe.com and tell me - what have you asked for recently, and what were the results?

    - Follow this podcast, rate, review, and tag me on socials - and following the law of reciprocity, I'll send you my handy-dandy Visibility Vault Notion doc - a list of newsletters and platforms to pitch to and get strategically placed!


    Interested in getting more visible and collaborating with people you admire, WHILE converting at rates that would send tech bros into a tailspin??! Check out Pitch Perfect for early bird pricing ($300 off til Sept 15th!!!) and grab your spot before we start October 13th!

    Show more...
    2 months ago
    30 minutes 54 seconds

    The Art of The Ask
    Ever wonder what could happen if you just… asked? Like, REALLY asked— for the raise, the date, the discount, the collaboration, the last slice of pizza, or the life you actually want? Welcome to "The Art of the Ask," the limited series podcast hosted by Podcast Host, Strategist and Professional Shot Shooter Chelsea Riffe, here to help you stop overthinking, start pitching, and finally get what you want. Each episode, Chelsea unpacks the psychology, strategy, and sheer nerve it takes to ask for what you want—and flip your "who am I to ask?" to "why not me?!"