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3 | Impostor syndrome, self-worth, & building soft skills with Kaitlin Maud (Part 1)

The Art of Speaking Up

Release Date: 10/09/2018

99 | A warm hug of gratitude (special Thanksgiving episode) show art 99 | A warm hug of gratitude (special Thanksgiving episode)

The Art of Speaking Up

Today’s episode is a very special gratitude themed episode in honor of the holiday.  If you want to shift into an energy of gratitude and feel warm and fuzzy, then this one will be perfect for you.   You’re going to hear some of my season 4 guests open up about what they’re grateful for in their careers.  The women you’re hearing from are:   Amelia Anderson (Episode 71) Kara Diane (Episode 79) Erin Foley (Episodes 73 and 74) Meg Duffy (Episode 90) Jeanette Jordan (Episode 80) Ashlee Leppert (Episode 84) Margot Leitman (Episode 93) Leonela Vaccaro Padron (Episode 86)...

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98 | How to project confidence when you’re not feeling confident at all show art 98 | How to project confidence when you’re not feeling confident at all

The Art of Speaking Up

Today’s episode is for anyone who wants to project confidence at work, but struggles to feel confident deep down inside.  In today’s episode, I share my struggle with this topic and one of my greatest learnings that took me way too long to figure out.  I also share a framework you can use to move from feeling unconfident, to feeling confident.   To download the worksheet that goes with today’s episode, click here: To learn about working with me 1:1, go to:   And, check out these amazing resources I’ve created:   Ebook: The Smart Ambitious Woman’s Guide to...

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97 | A powerful tip to elevate your communication to an executive level show art 97 | A powerful tip to elevate your communication to an executive level

The Art of Speaking Up

Today’s episode is perfect for anyone who wants to communicate with greater impact and authority at work. Sometimes we think that speaking up with credibility is difficult – but in this episode, I’m showing you that it’s actually really easy.   Get ready to use your imagination in this episode!  I hope you love it.   I’m now offering 1:1 private career and life coaching!  If you’re interested, you can learn more here:   And check out these free resources!   Ebook: The Smart Ambitious Woman’s Guide to Assertiveness in the Workplace:   Private...

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96 | How mindset can make you unstoppable with Bryn Drescher  show art 96 | How mindset can make you unstoppable with Bryn Drescher

The Art of Speaking Up

Today’s interview is SO good.  If you like mindset, you will love this conversation.  Today’s guest Bryn is a mindset coach and she is sharing her best advice for leveraging your inner world to achieve your peak performance.  This conversation will not only motivate you to show up way bigger at work, it’ll also give you a gentle and loving reminder that struggle is part of the process, and not a sign that anything has gone wrong.   Remember – you can do this!   To connect with Bryn:   Instagram: Facebook: Twitter:     Connect with Jess:...

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95 | A letter to my inner critic show art 95 | A letter to my inner critic

The Art of Speaking Up

Welcome to the show!  This week, I’m sharing a letter I wrote to my inner critic.  If you struggle with impostor syndrome and that voice inside your head that tells you that you aren’t good enough, then this episode was made for you.   I also share an exciting new announcement at the end of the episode.   If you’re interested in working with me 1:1, you can learn more here:       And below – you’ll find some awesome free resources:   Ebook: The Smart Ambitious Woman’s Guide to Assertiveness in the Workplace:   Private Facebook Group: ...

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94 | Let’s talk about money show art 94 | Let’s talk about money

The Art of Speaking Up

Today’s episode is all about MONEY! It’s time for some raw, unfiltered dialogue about getting past the fears that prevent you from owning your desire for more money and asking for more money in your career. If you have a hard time admitting to yourself you want more money, or you feel unworthy of negotiating your salary, this episode is a must-listen.   Let me know what you think by messaging me on Instagram! (@theartofspeakingup)   And of course, be sure to check out these free resources:   Ebook: The Smart Ambitious Woman’s Guide to Assertiveness in the Workplace: ...

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93 | Stage fright, small talk, awkwardness, & how to speak so people listen with Margot Leitman show art 93 | Stage fright, small talk, awkwardness, & how to speak so people listen with Margot Leitman

The Art of Speaking Up

Welcome to the show!  Today’s episode is perfect for those of you who want to improve your communication skills and become a more confident & compelling communicator at work.  Today’s guest Margot is a professional storyteller, a Moth Grandslam champion, and travels the world teaching others how to tell stories.    In this interview, you’ll hear us chat about:   The struggle to show your true self at work Feeling awkward in the workplace How to get better at small talk (even when it feels annoying or hard) How to manage stage fright How to communicate in a...

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92 | Finding your voice at work show art 92 | Finding your voice at work

The Art of Speaking Up

Today’s episode is a mini episode with some advice on how to get past your fear and speak more freely in meetings.  This took me a long time to do, and I’m hoping the advice in the episode can help you as you continue your journey of finding your voice at work.   If you would like to sign up for the newsletter, you can sign up here:   And here’s the private Facebook Group:   Thank you so much for tuning in this week!  I’ll catch you next week.    -Jess

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91 | Building the confidence to speak up at work – even when you doubt yourself show art 91 | Building the confidence to speak up at work – even when you doubt yourself

The Art of Speaking Up

Today’s episode is about two of my favorite topics: feeling confident and speaking up at work.  If you are wanting to feel more bold and powerful, and less afraid of speaking up, then this episode was created for you.  It is intended to inspire to you believe that you have EVERYTHING it takes to find and share your voice at work.   In this episode you’ll hear about:   -The unexpected thing that helped me build confidence over the past year -Why speaking up is about more than just sharing your voice -My best advice to you around the importance of speaking up -How to...

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90 | Managing your inner critic and getting out of the self-doubt spiral with Meg Duffy show art 90 | Managing your inner critic and getting out of the self-doubt spiral with Meg Duffy

The Art of Speaking Up

Welcome to the show!  Today I am chatting with Meg Duffy, who specializes in helping women build careers in tech.  Meg’s insights and work run deep, and in this conversation she shares so much deep wisdom and encouragement on the topic of self-doubt.  This is the second time I’ve had Meg on the show – the first time we chatted (episode 19), and I enjoyed this conversation even more than the first one.   To get in touch with Meg and learn about her book, go to and you can also reach out to her on twitter and Instagram (@futureproofmeg) To get in touch with Jess:...

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More Episodes

This show was designed to do two things: share real stories about personal growth from real working women, and give young women honest, helpful career advice.

 

Kaitlin Maud, digital brand strategist, seriously over delivered on both of these goals.  I was blown away by her honesty, eloquence, and her intense passion for supporting the inner growth of other women.

 

In this two-part conversation, I talk with Kaitlin about what it was like to navigate her early career days and push through impostor syndrome.  At the time, she didn’t even realize that she was battling issues of self-worth.  Like myself, she thought it was normal to be questioning her ability to contribute and finding ways to overcompensate for a perceived lack of competence.

 

If someone as smart, gifted, and talented as Kaitlin felt this way – I think it’s safe to say that this struggle can be pretty universal for women. 

 

Kaitlin also talks about the challenges she faced working in the male-dominated advertising vertical.  Her stories are funny yet haunting, and they serve as a powerful reminder of the privilege that men hold in the workplace and the ways in which men can cause harm without intending it or realizing it. 

 

My conversation with Kaitlin made me feel energized, excited, and empowered.  Kaitlin’s strong presence inspired me to become even stronger in my own presence.  Her honesty made me see that speaking up and owning our experiences is an act of courage. 

 

I truly hope that she does the same for you. 

 

Here are links to the books and resources that Kaitlin mentioned in our discussion:

 

Crucial Conversations book:

https://amzn.to/2DnaaYm

 

Google study on team dynamics:

https://www.nytimes.com/2016/02/28/magazine/what-google-learned-from-its-quest-to-build-the-perfect-team.html

 

HBR article on women being less likely to get raises:

https://hbr.org/2018/06/research-women-ask-for-raises-as-often-as-men-but-are-less-likely-to-get-them

 

Only 11% of creative directors are women:

https://www.adweek.com/digital/pinterest-right-the-ratio/

 

FREE RESOURCES

Free Ebook: https://www.assertivenessebook.com/

Facebook group: https://www.facebook.com/groups/theartofspeakingup/

Art of Speaking Up email newsletter signup: https://mailchi.mp/e7735b5f8f83/aosu