Ep. 151/ Be Shameless, Be Weird: Jenny Wood’s Blueprint for Career Success and Confidence
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Have you ever felt that being weird was something to be ashamed of? Just wait till you hear what Jenny Wood has to say about that. Jenny is a former Google executive and newly-minted New York Times bestselling author of Wild Courage: Go After What You Want and Get It. As someone who’s spent years helping corporate leaders and entrepreneurs alike, Jenny brought a treasure trove of advice on everything from silencing your inner critic to reframing those so-called “negative” traits we often hide, think “shameless,” “weird,” and “reckless”, into your actual superpowers at work and in business. Her candor and humor made the conversation electric, and I was inspired (yet again!) by her bold “move, then map” approach to chasing what scares you and owning your wildest aspirations.
If you’re betting on yourself, whether you’re growing your own business or navigating the corporate ladder, you’ll find a ton to relate to in Jenny’s journey. We discussed breaking out of the perfection trap, advocating shamelessly for yourself, and getting nosy, in the best way, to build real connections and open up new opportunities. Jenny’s story reminds us that it’s not about waiting your turn or muting your personality to “fit in,” but rather about leaning into who you really are, and turning fear from an obstacle into rocket fuel. I walked away from this chat fired up and ready to keep encouraging everyone tuning in: Your wins are on the other side of speaking up, sharing your story, and being unapologetically you.
In this episode you will learn:
How to embrace fear and find success - 10:35
How to brag like a leader - 16:55
Mentoring tips to network confidently - 21:09
How to bridge perceived power gaps - 25:43
How to overcome hesitation - 43:22
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In this episode you will learn:
How to embrace fear and find success - 10:35
How to brag like a leader - 16:55
Mentoring tips to network confidently - 21:09
How to bridge perceived power gaps - 25:43
How to overcome hesitation - 43:22
Quotes from our guest:
"Shameless could be having a career development conversation with your boss every six months and titling the meeting invite career development conversation, right? Not having it be the seventh bullet out of seven in your weekly one on one every Tuesday, because you'll either never get to it or you'll spend 30 seconds on it." - 8:54
"It's pushing past that fear to the joy and success on the other side. Because everything you've ever wanted is right there waiting for you on the other side of fear. And oftentimes when we don't ask for what we want, when we don't speak up, when we don't follow up with the client or the customer or the company, it's because we think, 'Oh well, they aren't interested or you know, I'm not good enough...' But that's just that gremlin on your shoulder trying to keep you down and keep you small and keep you safe." - 10:20
"Within your so-called weirdness lie your greatest strengths. So hone every ounce of weird you've got and highlight it, right? And so it's about believing in who you are authentically." - 12:48
"Specificity is one, nosiness is two... Rather than, 'Hey, will you mentor me?' Write the three things that are, you know, on your mind and what specifically you want help with... Count how many sentences in your pitch email to a mentor or somebody you know, or your boss's boss start with the word 'I' versus the word 'you.' ...It’s about being specific about how they can help you." - 21:54
"So muster the wild courage to chase what you want in life, to ask for it, to put yourself out there, to post on social media, to do video when you muster the wild courage to do those things, you will discover a vital truth." - 38:24
BIO:
Jenny Wood, a New York Times bestselling author, speaker, former Google executive, and former Harvard Business School researcher who knows that real success isn’t about following the rules or waiting your turn. She is also the founder of Own Your Career, one of Google's largest career programs. In her new book Wild Courage: Go After What You Want and Get It, Jenny breaks down 9 bold traits that defy conventional career advice: Obsessed, Weird, Selfish, Shameless, Nosy, Manipulative, Brutal, Reckless, and Bossy. Her practical, no-nonsense approach empowers ambitious people to break the mold, be better leaders, build influence, and reach their full potential. Jenny has been featured in NBC, Bloomberg, Harvard Business Review, Forbes, and Business Insider. She lives in Boulder with her husband and two children and is in constant pursuit of the perfect zucchini bread recipe.
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JENNY’S LINKS:
Kim (00:01):
You are going to hear from Jenny Wood whose new book, Wild Courage, Go After what you Want and get it. Just hit the New York Times bestsellers list. Jenny was a Google executive who launched Own Your Career, one of Google's largest career programs. She has awesome advice on how to speak up, how to fight the negative voices and how to reframe your own traits into positive ones and then how to crush it. These lessons are great for people both in corporate or working for themselves. Jenny also gets real on the ups and downs of self-employment and the hilarious way she picked up her husband.
(00:35):
Welcome to the exit interview with Kim Rittberg. Do you work for yourself and want to supercharge your business while still having fun? Well, this is your go-to podcast, part MBA Part Cheer Squad. Every week I'll be joined by top business owners who share the secrets to their success. After I found myself working during childbirth true story, I quit my executive media job to bet on myself fighting the fear and imposter syndrome to eventually earn six awards, an in-demand speaking career and features in Fast Company and Business Insider. Now I'm here to celebrate all you rock stars betting on yourself, and I want to help you win. Tune in every Wednesday to hear from remarkable founders and don't miss our Solo Friday episodes, a treasure trove of video and podcasting mini masterclasses with me. Exit the Grind, enter success on your own terms. Don't forget to subscribe today and grab my free video tips at my website kimrittberg.com.
(01:36):
What we're talking about today is fighting fear is being yourself is getting what you want. And if you work for yourself and what you want, our clients, speaking engagements, invitations to me on podcast, I am here for you. Make sure to connect with me online at kimrittberg.com. Grab my free download, how to Be Confident On Camera, and if you're looking to take the next step, I have a May intensive for my video bootcamp, which in four days you learn to master video, you get confidant on camera, know what to make and how to make it because it's an interactive program where I teach you how to write scripts and actually teach you how to make the videos. It is super fun. I've had hundreds of people come through the class. One client got four new clients in a month, which is fantastic and doable for you as well.
(02:20):
So make sure to connect with me on Instagram or LinkedIn at Kim Rittberg, K-I-M-R-I-T-T-B-E-R-G. And you could check out Video Bootcamp or my other offerings or just say hi and just say you're a fan of the exit interview. I'm so excited for you to hear from Jenny Wood because I've known her for a few years and I've been following her online. We've chatted and gotten to know each other over the last few years, and I just think the advice that she shares both for people in corporate are so applicable to people betting on themselves that every nugget is so valuable. One thing I love about her book, the different chapters are about all these traits that can seem negative, but she basically teaches you how to own it and how to actually take that, make it a positive thing and go really hard on it, which obviously speaks to me and Jenny and I kind of talk about for me, owning the things about myself that I do know to be true and not feeling like, oh, I need to kind of put myself in this box because that's what I'm supposed to do in this office.
(03:16):
And the same thing is now that I'm running my own business is the more I am me, I am finding that is what is bringing me speaking engagements and clients is people being like, you're knowledgeable, but also I feel like you're real and you seem encouraging or kind or funny, which I am of course. And the words that Jenny has this weird, selfish, shameless, obsessed, nosy, manipulative, brutal, reckless, bossy. But what does that mean, right? Shameless can mean kicking imposter syndrome, promoting yourself with ease, which is of course right for me. Nosy instead of thinking of it as nosy, think of it as being curious. And I really just love the way that it's about reframing and not letting fear get in your way. So we have a great interview and Jenny actually now works for herself, so she shares the ups and downs of entrepreneurship and gets real.
(04:02):
It's like not all roses. It's kind of scary living a stable paycheck even though she hit the bestsellers list. So Jenny comes with candor, with wisdom, with humor. It's just a great interview, so make sure to listen. I am so excited to bring in Jenny Wood. She is a New York Times bestselling author. Yes, a speaker, a former Google executive, Harvard Business school researcher who knows that real success is not about following the rules or waiting your turn. She's also founder of Own Your Career, one of Google's largest career programs, and in her new book, wild Courage, go After What You Want and Get It. Jenny breaks down nine bold traits that defy conventional career advice, obsessed, weird, selfish, shameless, nosy, manipulative, brutal, reckless and bossy. Jenny's practical, no nonsense approach, empowers ambitious people to break the mold, be better leaders, build influence, and reach their full potential.
(04:53):
Jenny has been featured in NBC Bloomberg, Harvard Business Review, Forbes and Business Insider. She lives in Boulder with her husband and two children and is in constant pursuit of the perfect zucchini bread recipe. Jenny, thank you so much. I was like, I have a good banana bread recipe, but not zucchini bread. I am so excited to have you here. It's really fun to be here, Kim. So Jenny is now a bestselling author, which is super, super exciting and I have to say I love this book and I thought it was so smart. I'd love to first of all just get a little bit of backstory in you were a Google executive, you were not an hr, you were not in talent. How did you from internal end up building this massive career coaching program inside Google
Jenny (05:35):
By begging forgiveness, not permission. I love that. Basically it was a program that was for the business by the business, and Google has some of the most incredible training, learning and development programs, guidance, but it's all very official. It's all a little bit ivory tower. And I wanted to do something that frankly ruffled feathers a little bit. I wanted to give the real deal advice of how you actually get promoted, how you actually build relationships, how you actually get a raise, how you actually land that job. And it was just based on my experience growing from entry level to executive.
Kim (06:07):
Did you get pushback because obviously you have to fit that into your regular job. Did you get pushback saying, well, what about your actual work? What was your actual work and did you get pushback on that?
Jenny (06:16):
Yeah, at first, no. At the end a little, let's start with my actual job. It was running an operations team that sits between sales and engineering and it helps diagnose bugs and push engineering and making the product better based on customer feedback and customer challenges had nothing to do with HR or people operations. So Google is this incredible place where if you have an idea, you can go create it and thrive and build something amazing for the company. So like Gmail, Google Earth, these products were created out of individual contributors, brilliant ideas, and Google, they help these things thrive. They give them fuel, they give them budget and headcount and support. So at first it was like, oh my gosh, this contributed to my getting promoted to executive at Google because it was like, look at this person who's doing her day job, but also lifting as she climbs these other folks in the company.
(07:06):
So it was seen as really, really positive. Now I said no, it did not get any pushback. I did not get any pushback at first and then a little toward the end because I had to balance the portfolio of my work. And I think there were definitely times where I didn't balance it well, and I did have a core job and I definitely had some conversations with my manager where she was like, okay, so about your core job, Jenny, and obviously that's fair and natural and expected, and so I always had to make sure I was balancing it the right way. And that got hard toward the end because I did become really passionate about helping people and coaching people to be better than they think they can be. Even though I did rebalance at that point and took the feedback and pulled back and own your career and dialed up my core job, I still ultimately realized in this process my true passion was helping and coaching and giving keynotes and consulting to Fortune 500 companies. And so here I am doing that now.
Kim (07:53):
This is so exciting. What an exit you've been having.
Jenny (07:56):
Yes,
Kim (07:57):
I want to talk about the exit and your feelings around the exit after, but first I really want to dive into the things in the book. So I have to say for those of you, well Pete, this is an audio so you can't hear it, but Jenny put a little sticky note on my chapter. So each chapter, the chapters are about different traits that are seen as kind of negative, but how you actually have to own and embrace them. And so what I love, for example, Jenny pulled out the chapter for me shameless and says, shameless subheader, find your swagger. And I love this because I do think that so much of what you talk about is owning the things that are you and just not apologizing for them and in fact leaning into them. And I think that I have a big personality, I'm kind of intense, but I'm also really fun and I'm really myself and I make people feel good, so I love that. Tell me a little bit about what that means in the book for someone to be shameless. What does that mean? What are people not doing in the corporate world that they should be more shameless about and what does that mean?
Jenny (08:54):
Yeah, I mean, shameless could be having a career development conversation with your boss every six months and titling the meeting invite career development conversation, not having it be the seventh bullet out of seven in your weekly one-on-one every Tuesday because you'll either never get to it or you'll spend 30 seconds on it. So shameless is being proactive and asking for the promotion, asking for the raise, asking for the big project. If you're not a leader and you're an individual contributor and you're one of five people on the team, someone's got to raise their hand to present to the client. Someone's got to raise their hand to write the comms each week to the internal team. And the reality is the person who writes the comms gets the lion's share of the credit. So even that is shameless. Now, what does it mean as an entrepreneur?
(09:32):
This is what I think about frankly as much as my 18 years in corporate. Now, shameless, when I was putting this book out was emailing 300 people and saying, are you interested in buying one to 300 copies in a bulk sale of wild courage? And could I come in and help out for a little bit with your team by way of keynote or fireside chat or workshop Ed Kim having been at Google, which gave me a ton of confidence and Google's just rich with resources and support and budget, I just expected out of those 300 emails, by the end of the day, I'd have at least three checks in my mailbox and 295 of them would've said yes, and only the other five hadn't read the email yet, right? Not exactly what happened, but Shameless is sending out another follow-up email after that saying, still excited to partner with you.
(10:20):
If 300 books isn't in your budget, maybe 50 books ISN in your budget. And just like shamelessly following up, right shamelessly asking for what would help support this work because I believe in this work and I know that it can help inspire wild courage in millions of people. So that's a flavor of shameless as well. It's about, like you said, finding your swagger. It's the audacity or the shamelessness that can be a survival skill because there are people who feel too insecure or too much imposter syndrome. And by the way, I feel this all the time, especially as an entrepreneur, but it's pushing past that fear to the joy and success on the other side because everything you've ever wanted is right there waiting for you on the other side of fear. And oftentimes when we don't ask for what we want, when we don't speak up, when we don't follow up with the client or the customer or the company, it's because we think, oh, well, they aren't interested, or I'm not good enough, or This book's been written a thousand times before, but that's just that gremlin on your shoulder trying to keep you down and keep you small and keep you safe.
(11:12):
And when you push past that fear, incredible things can happen.
Kim (11:15):
And I love how much you talk about fear and I think about, I'm a fairly confident person. I don't think people think I'm some wallflower, but I think fear has kept me playing small for a long time in my corporate career. It took me a long time to stop saying, oh, I'm sure that person just isn't interested. And now I'm just like, who knows? Maybe they didn't read the email. I'll follow up with a friendly note. You have to remember that people are busy and doing their own thing and maybe it's a no, but maybe it's a yes, maybe it's they haven't seen it. So a stop creating narratives that aren't true, but also stop being afraid. I remember in my corporate career, there are lots of opportunities that I wanted but was worried that somebody would perceive me in some way to even ask for it. For example, I was in TV for about I think eight years as a producer. Great doing great writing, producing, very well respected. I didn't even have the confidence to ask if I could do some on-camera work for the companies that I was already at because I thought that they would think I was, I don't know what narcissistic or
Jenny (12:12):
Whatever, let's label it. Maybe they think you were shameless or maybe opportunistic or maybe obsessed or maybe too ambitious or maybe it wasn't your time yet. These are all the things that we don't take action because we think people are going to label us these things. And that is exactly why I'm so passionate about putting this work into the world. I want people to be aware of the fear of judgment of others to name it and then reclaim it. I love that.
Kim (12:35):
Weird. I have to ask you about this. There's a chapter that says, be weird and own your weirdness. What does weirdness mean both in the corporate setting and in the self-employment setting that we should be owning?
Jenny (12:44):
Yeah, so weird is the courage to stand out, right? Because within your so-called weirdness lie, your greatest strength, so hone every ounce of weird you've got and highlight it, right? And so it's about believing in who you are authentically. I'm actually going to use a personal example here that is neither corporate nor the entrepreneurial because I just think that it's a good example of life in general, and I have this wonderful husband, but before I found the right guy, I spent many years chasing the wrong guy. And there was this guy, we'll call him Brian, and for six years we were in this kind of InBetween friendship relationship, something gray, and Brian wanted a wall flower, someone blonde, someone petite, someone who his words is beautiful but doesn't think that she's right. Exactly. And I'm out there, I'm bold, I'm a little bit much, I dance down the sidewalk listening to acapella show tunes right in my earbuds.
(13:38):
And so I was never going to be his flavor of weird, I was going to be my own flavor of weird, it's just who I'm, but for so long I tried to squeeze my round peg into a square hole and I really did end up bent out of shape as a result of that. It's like, I'm not going to be his person. I'm never going to be his person, but it took me a long time to figure that out. So in a professional environment, your weird could be what are your superpowers? What are your special things that you bring to the table? Do you know the three things that you offer as a consultant, as a business partner, as an employee, right? For me, for example, it's people, leadership, stakeholder influence, and building things from startup to scale. Those are my three, what I call power assets that make up my power portfolio.
(14:19):
And I've got a couple business ones in there. I've got a couple people skills in there. It's good to have a mix of both. You'd want your financial portfolio to have both stocks and bonds. And so sitting down and thinking about what is it that makes you unique, what are your skills and talents that you bring to the table? It sounds so obvious, but a lot of people, if I were to ask them right now, walking down the street, what are your three strengths that you bring to your clients, your customers, your partners, or to your boss, your company, your team? I think a lot of people would say, huh, good question. I don't know if I could name them on the spot, but putting some time, 15 minutes. That's it. To sit down and write out what did you love to do as a kid? What did you love to do in college? What do you love to do in your job? And then asking some mentors, colleagues, bosses, friends of what they think you're good at, that helps you define your weird, and then you need to leverage that. Then you need to go to your mentors, to your boss, to your partners and say, Hey, this is what I bring to the table. And be really explicit shamelessly, so know you're weird and share it shamelessly.
Kim (15:10):
I love that. What are the top things that people are doing that are hurting their career?
Jenny (15:16):
Well, I think the biggest lie people are told is your work will just speak for itself. Keep your head down, do good work, and I love that you just laughed so quickly at that because 50% of your job is doing your job, 50% of your job is communicating up, down, and across. I recommend something called a shameless Monday email really on this shameless thing here today, by the way. This is a great one for introverts. I oftentimes get the question, but what if I'm not an extrovert? You seem really bold and confident. And I've also spent, I spend many chunks of my day very insecure, right, for imposter syndrome, so feeling very introverted or very nervous to reach out to somebody. But the Shameless Monday email is a great one because it helps you highlight your work. It's basically four bullets that you send every Monday to your boss.
(15:59):
It should take you no more than 15 minutes to write two things you're proud of from last week, two things you're working on this week, simple as that. It's not a productivity report. It's basically just highlighting a couple things so they're in the loop of what you're working on. It's something great that they can then forward to their boss. You can cc your boss's boss if you've got a good relationship with them, if you're a leader or if you're running a team or a company, you can share it with your customers or your clients just saying like, Hey, just want to keep you in the loop. Here are two awesome things that happened at Jenny Wood Enterprises last week, and here are two things that are coming up this week. We forget how much just communicating simple wins, simple highlights, simple customer successes can really have an impact on future customers, clients, or your team in a company.
Kim (16:39):
How do you recommend, I think the reason why people don't do that is because they worry that it's going to make them seem braggy. And how do you recommend sharing the positive things you're doing that in the end benefit your company,
Jenny (16:50):
But
Kim (16:50):
Obviously make you look good? How do you recommend sharing those things in a way that don't sound braggy?
Jenny (16:55):
So I think it's less of the language choice and more of the mindset shift. So having been an executive at Google with leaders who report reported to me and indirect reports below them and people everywhere from entry level to leaders under me on my team, I will just tell you, Kim, that I want people to brag. I am judged by my boss on how I'm running the business. So if someone comes to me and says, I got this glowing feedback from a partner on our athleisure line launch for the in-store marketing campaign and throws a number in there, even better, we were tracking 112% to goal. I'm like, thank you for giving me something I can talk about in my meeting with my boss. Thank you for giving me something I can highlight in the newsletter that goes out every week to our broader team.
(17:44):
It's a total gift to me. When you show me that you're moving the business, that's what moves your career because we are all here to solve business problems. So show me that you're solving the business problems. I think just think of it as sharing information, sharing data as opposed to bragging or if you're a leader, a great tactic. I love it. I call it thank down cheer up. So I would thank my team so it didn't feel braggy. I'm like, Hey, team, incredible job increasing customer satisfaction by 4% quarter over quarter. Mary, I love that you did this, Brian, you crushed on that and Sam, you were a rockstar and X, Y, z other thing. And then I would CC my boss and maybe some other leaders in the organization and so they could see the great work the team did. Obviously as the leader, I get a hundred percent credit for everything the team has done, and if you're an entrepreneur, you could do the same thing.
(18:28):
If you have a small team, you could thank your team. Well, this one maybe doesn't work as well as an entrepreneur. So maybe this one's a little bit more if you have any kind of hierarchy, but you're basically thinking down to the team below you or the team that works on you and you're cheering up, you are CCing the right people or even just your boss and let them take care of sharing it with others. Have a really intentional subject line that basically says something like huge win alert, increased customer satisfaction, 4% quarter over quarter. People want to read that stuff.
Kim (18:55):
One thing that I want to flag for listeners that I really love is this idea of really thinking about how it's going to help the end person. So earlier you were talking about asking people to buy your books to bring you in, but again, without you thinking about this is about buying my books, you actually were saying, I know this book will help a lot of people. So I think the mindset shift around how I am actually providing something that's going to help people and really believing that. And the same with sharing wins. So I am helping my boss maybe make the case for more resources, maybe look better. And then the same way if you're sharing something online, I think a good example of the brag, I recently did a keynote and I was like, I shared a picture of me with the people, but I shared what the people were excited about and then I thanked the person who booked me.
(19:42):
So again, it's the same thing, but I'm like, thank these people for processing what I had to say because I'm helping them and that makes me feel good. But I do love the angle of for both in incorporate and working on your own, it's a reframe of all these things you're doing. Instead of saying, I don't want to look braggy or narcissistic, I don't want to look full of myself. Actually just frame it as this is going to help someone else. How does this email, how does this note, how does this social media post help somebody else?
Jenny (20:08):
Yeah, and from your leader's perspective, from your client's perspective, it just doesn't come across braggy or narcissistic. It comes across as helpful. It is really hard to find good talent, whether that's hiring a partner or hiring a consultant or hiring an employee at a big company like Google. The last time I was hiring 20 people from my team in one batch, I got hundreds of resumes, and Kim, let me tell you, it was not easy to find 20 outstanding people. What would have made it easier if people sent me emails that said, I accomplished X metric in my last job, I was nominated to be a top 5% salesperson or whatever the department was that they were coming from, that would help me sift through a more quickly separate the wheat from the chaff because it's not easy to find good talent. It's not easy to find a good keynote speaker. Think about all the mediocre speakers out there. So if you share wins, if you share clips of your speaking, if you share samples of your content or you share client testimonials as a consultant, whatever your industry is, you are helping people find good talent. IE you.
Kim (21:09):
It's just so funny. Yes, I disagree with this so much in terms of how much it's completely a mindset shift in terms of what you're putting out there. I also wanted to ask you about, I'm like, I have so many questions for you. I'm like looking at my list, I'm like, one of the things I would love to ask you, because I think this applies so much both in the corporate sector and outside, what are the nuts and bolts tips for both connecting with your boss's boss or finding a mentor? I think that power dynamic people struggle with in corporate, but also in entrepreneurship. I want to be on that person's podcast, but they seem really big and successful or I want to partner with that person, but they seem out of my reach, so I want a mentor, but I'm too intimidated. What's your advice for reaching for relationships with people that you perceive to have more power than you?
Jenny (21:54):
Okay, so I have a lot to say here. So let see what I want to highlight. Specificity is one, nosiness is two, just one of the nine traits and follow up is three. So specificity rather than, Hey, will you mentor me? Write the three things that are on your mind and what specifically you want help with. I get maybe, I don't know the book's doing well, it's all very exciting. Maybe I get 10 to 30 requests a week for someone to mentor me, which is a very high volume. I think most people are not getting that, but the ones that are general that say, Hey, Jenny, I'm doing this, I'm doing that, I'm doing the other thing. Can you be my mentor? That's not specific. It's also not focused on me. By the way, let throw in a bonus tool here. It's called Woo with you count how many sentences in your pitch email to a mentor or somebody or your boss's boss.
(22:51):
How many of your sentences start with the word I versus the word you? I am interested in this. I think you could help me with that versus you have inspired me with X, Y, Z, specific thing from your book. You would be the perfect fit for me because I love your energy, your enthusiasm, and your experience. So think about A, specificity, and B, how much you focus on the other person versus yourself. We all have egos, right? I just caught up with Marshall Goldsmith the other day, famous author, legend wrote, what Got you Here Won't get you there? And I told him I love his work. He's like, some people say they don't like fan girls. He's like, I'm all about the fan girl. Tell me that all the work that I've done in the last 40 years impacted you. I'm exactly the same way, and I think a lot of people are okay, but really my point here is specificity.
(23:33):
Be specific about how they can help you say, I want you to help me go from an individual contributor to a manager role at Facebook or whatever, or I want you to help me land my first three clients at $20,000 each. That is something a mentor can sink their teeth into that specificity. Nosy is the second one. So nosy is one of the nine traits. It's the courage to dig deeper. It's about getting insatiably curious because curiosity drowns out fear and pulls you toward what is most exciting to you. So use it as a compass. Just two hours ago, my PR person, Pam, sent me an email from this 17-year-old who had just simply gotten nosy. She said, I've got this podcast, I do it with my sister. Here are all the reasons we think Jenny would be a great fit. And she simply had the courage to ask a question.
(24:17):
Now, I typically have a rubric these days because I get a lot of podcasts, inquiries of 500 Apple podcast reviews or more. I need to have some kind of, unless it's like a friend who I'm really excited to do the show it or it's like great content, I just need to have some kind of bar of what I say yes to and what I say no to. So I look up her podcast and I definitely will do some that have fewer than 500 Apple podcast reviews. Do you want to guess how many she had? Four zero.
(24:43):
Okay, zero. And I was like, but oh my gosh, a 17-year-old girl who does a podcast with her sister who has written such a thoughtful email to my PR person because I read it and she's simply getting insatiably curious and reaching out to me. And also she'd had these other big names on the show. So I think other people felt the same way I did, and I was like, heck yes. I wrote back today. I was like, I cannot say yes to this fast enough. She simply got nosy and asked the question when 99% of 17 year olds would not ask. So here we have this big imbalance of power or success or prestige or age or whatever it is, because these things always get in the way. This creates the gap of you asking for something. But she just simply had the courage to ask the question, unlike all of her other 17-year-old buddies. So it was an easy yes for me,
Kim (25:25):
I have heard recommended kind of show them that something's in it for them, how you can help them. I think I see this a lot in self-employment for myself and for my peers. It's especially salient in corporate, but also entrepreneurship. So how do you present why this can help you? How this person being supportive of you can help them?
Jenny (25:43):
And here's the thing is the bar is so low for that and people don't realize it. I think because you see that imbalance of power or prestige or age or title or acronyms after their name, PhD, vp, New York Times bestseller, whatever, it's, but the bar is so incredibly low. Let me tell you, if someone were to read my book and tell me three things that stood out to them, that is incredible value to me. It helps me know what to hone in on podcasts. It tells me what standing out. It tells me what liners I should say more, what I should maybe write a social media post about. It's like that is available to anybody to do, but people perceive, when I was a Google exec, people thought, well, how could I possibly give you anything? Because you're here up here and I'm more entry level and it just could not be further than the truth.
(26:27):
You can give me your perspective as a Gen Xer. Wait, gen Z as A Gen Z, right? You could tell me what the customers are saying. You could tell me what DEI really feels like on this team. You could tell me what the dynamics are. You could tell me what you did over the weekend. You could bring your energy, which is already exciting to me and of value. So there's so much that you could give. In fact, to lower the bar, I would set up weekly office hours every Tuesday for people who reported to me. 10 to 11:00 AM always the highlight of my week, three 20 minute slots. And in the calendar invite that was on all of my direct and indirect reports calendars, it would list out seven things that they could bring just to lower the bar. And I would say, bring me a problem.
(27:06):
Bring me something you're proud of. Tell me what you did over the weekend. Tell me what your passions are. Tell me what your superpowers are. Just because I recognize that people do create this barrier and think there's nothing I could possibly offer you. Here's the thing, you can offer someone senior or a mentor, you can offer them the fact that you took their feedback. Literally, if I give you advice and you go out and do that thing, if I say reach out to this person, I think they'll help you. Most people don't do the advice because people get busy or take the advice or do the action. And then even if they do, I never hear from them again. Guess who I want to meet with? Again, the person who says, you told me to do these three things. Here's a follow-up email a week later that tells you, Jenny, that I did things one, two, and three. Exceptionally rare, not hard to do, nobody does it. Common sense, rarely
Kim (27:48):
Common practice. I love that. Of all of these titles, these are the traits that we should all own more embrace and not think of as negative, obsessed, weird, selfish, shameless, nosy, manipulative, brutal, reckless and bossy. Which of those have been or are showing most valuable to you now that you're in self-employment land?
Jenny (28:09):
Probably reckless, but it's also the hardest for me. So reckless is the courage to take intelligent risks to err on the side of action because better to learn from your mistakes than waste time predicting the consequences of every decision. So think fast, fearless. If you're on the fence, do it. And as an entrepreneur, you have to move quickly. You can't plan out your entire strategy and perfect your website before you go ask for your first dollar, right? This is Noah Kagan's work who wrote the book Million Dollar Weekend, which is all about becoming an entrepreneur and he just has such a great body of work. It's really about just, I guess it's maybe a combination of that and then back to nosy or shameless or selfish asking for it, going out and just pitching yourself, sending more of those emails that say, are you interested in having me in as a keynote speaker, connecting with the people?
(28:55):
You start with the people. Well ask a friend who you used to work with in corporate who you know is now at Target or Meta or Airbnb and they're a buddy of yours, ask if they can connect you to the organization that has budget to bring in consultants or speakers or whatever it is that you do. And what we do is we get caught in perfecting the window dressing, right? Oh, well, I'm not ready to go out there and ask for the business yet because I haven't quite perfected the paragraph on my website that talks about speaking or, well, how am I going to integrate AI into my keynote? I haven't landed that yet, so I probably should stop pitching until I've landed that get reckless. I say in wild courage, move, then map. It's based on a time that I was hiking in Montana with two friends and I was asking this park ranger at this fork in the road, which path is muddier?
(29:41):
Which one has the better view? Which one has a lake view versus a mountain view? Which one is out and back, which one has more construction? Blah, blah, blah, blah, blah. And then from 50 feet ahead, my friend Marsha calls Jenny, it's all gorgeous. Just start walking. Just start walking and walking in. Entrepreneurship is asking for the business is building relationships is following up with people. It's having a good customer relationship manager system, even if it's a spreadsheet, so you can continue to reach out back out to the people who you maybe had a conversation with. You don't need a fancy website. You don't need perfect business cards with the perfect paper weight and embossing and font size. You need to start asking for the business. And I think that's, we want to do last because it's the scariest and it takes the most wild courage
Kim (30:21):
That resonates a lot. I have a lot of clients and I say, done is better than perfect. You have to just move forward. And it was something that we all have to grow through it. I remember in media, I would basically, I worked in news for a long time. If you put up a typo on air more than one or two times, you're probably going to get fired. So I came from a world that it's not just, oh, perfection, you actually couldn't make a mistake because it mattered.
Jenny (30:46):
But
Kim (30:46):
Then you start to realize over time, A, you can't start delegating. You can't start growing if you don't delegate out some of the duties. But if you start to perfect the window dressing, as you were saying too much, you're losing that time. So I see that so much with my clients. I'm getting them on camera, I'm helping them make these videos, and they're really, I see they're wasting 30 minutes, an hour, an hour and a half. I'm like, that video looks just fine. You sound fine. Your message is fine. Just get it done is better than perfect. That resonates a lot. And one thing you said earlier that I couldn't remember, and now I wrote it down, super important I think for people in corporate, but also in self-employment is ask for the numbers. I liked how you were saying show somebody how what you did was helpful to them, how it's moving the business, but it's the same for self-employment.
(31:32):
You have to show someone the transformation, but until you start asking past clients for wins and asking for numbers, I didn't do that for a while, and then eventually I started saying, Hey Jessica, can I ask you? You've been saying that video's really working for you. How many clients have you gotten, would you say from video in the last year? What would you say the numbers on that were? We are all from a world of like, don't ask someone your salary. Don't tell anyone your salary. Be private about that stuff. You have to start getting nosy to your point, you have to start being nosy and asking better questions and then being shameless about using that into your new sphere. So your idea of using the numbers is great, and not enough of us even have the numbers to use.
Jenny (32:11):
Yeah, I'm going to, yes. And this here because I got really great feedback from a colleague of mine named Jen, who when I was running own your career, because even internally I wanted to prove the value of the program so Google would keep supporting it, and she said, we brainstormed different types of impact that I could show. And so she gave me this brilliant idea, and any entrepreneur could do this before I would do an own your career session. I would ask people, I would actually do it live in the session. It was a live poll and it said, how confident are you in your ability to own your career? I asked within the first five minutes of the session, I asked again at the end of the session, now that we've gone through all of these tools, all of these strategies, all of these stories, all of this research, how confident are you in your ability to own your career now?
(32:51):
And there's some bias in there because the way I'm obviously putting it at the beginning, putting it at the end, but there's bias in a lot of data that people share all over the world. And so it doesn't matter because the sentiment was still spot on. I mean, the numbers were significantly higher at the end of the session, obviously, and whether there was bias in there or not, no data is perfect, and I still could leverage this. It was like 36%, I'm making these up. It was something like this. I think it was a 56 percentage point differential of people. It was like in the thirties when I would ask at the beginning of the session and then in the eighties, I think at the end of the session, that is a massive differential. And I also asked questions, how happy are you in your ability to own? How happy are you? Things like that was happy, effective, and confident I think were the three questions I asked at the beginning of your training, ask at the end of your training. It doesn't have to be live. It could be in a survey, do an intake form, then do a follow-up form after the training or the course. I mean, that stuff is gold to be able to say as a result of this course or as a result of this video, people experience X percent more confidence or whatever. So that's huge.
Kim (33:55):
So good. Okay, I need you to share the story about how you met your husband.
Jenny (34:00):
Yes, happy to. It's 2011, I'm riding the sea train home from work in New York City and about 20 feet away from me sent this really good looking guy, gorgeous blue eyes, thick brown, wavy hair, the whole works. Even though I want to talk to him, something holds me back. Well, I mean natural questions like what if he's a convicted felon? What if he's married? What if a hundred people stare at me on this packed train? Okay. So I later came to realize that underneath those questions were the same fears that hold so many people back and the same fears that held me back so much of my life, fear of uncertainty, fear of failure, fear of judgment of others, which we've kind of already referenced in this conversation. So I sit there, I do nothing, but I make a deal with the universe. I say, if he gets off at my stop, then maybe I'll try to strike up a conversation with him, and if not, then that's the universe telling me it wasn't meant to be.
(34:45):
So he gets off unfortunately at the next stop as I slump down in my seat, super sad. But then all of a sudden, Kim, this wave of wild courage washes over me and practically pushes me out of my subway seat as I run off the train. No joke, prying the doors open because I hesitated enough that new people had gotten on the train, the other people had gotten off, the train doors are about to close. I pry them open. I chase after him. I tap him on the shoulder, I say, excuse me, I'm sorry to bother you. You're wearing gloves, so I can't tell if you're wearing a wedding ring, but in the event that you're not married, you were on my subway and I thought you were cute. At any chance I could give you my business card. And then I wait for it feels like forever thinking this was a terrible idea. But then eventually he takes the card, I think after he gets over the shock of like, wait, what's happening here? We go out a week later on a date, three years later we get married. We've now been married happily for 11 years with two great. And he does not want a blonde wallflower who is pretty, but doesn't think she is. He wants my bold, boisterous, over the top zany self.
Kim (35:45):
I love that story so much. I also talked to my husband first. He like to say, I picked him up at a bar. I'm like, I knew we were both at the same party, but okay. I did pick him up though. I started talking to him. And one thing that really resonates with me from everything you do, but also this book, I've been doing a lot about fear because one thing I realized over time was fear inhibited me both in launching my business, in launching my podcast, and that's actually what I see underlies a lot of reasons why people want to be on video, want to be a thought leader, but aren't taking the steps. Talk to me about where you see fear hiding and really being damaging to people.
Jenny (36:21):
Oh, well, I've got a great example. It's actually since we're already talking about my husband, John. When John and I were newlyweds, we stayed with my grandma Lila in New York City for a couple months while we were apartment hunting. And he had this very fear-based situation where we sit down at the table, the three of us one night, and he shared that he's been laid off. And so that's just a terrible experience that can put you right into a fear cycle. And Grandma Lila was not only a bridesmaid in my wedding at the age of 88, but she was the CEO of her own financial services company, no sorry, until 92. And she was not just shameless and fearless, she was unstoppable. She had this mantra which was, no, it's just an opening offer. So John shares that he's gotten laid off. I'm super bummed, doesn't newlywed, I'm crushed.
(37:05):
I look across the table, grandma Lila has that gleam in her eye and she says, no, it's just an opening offer her classic line, don't sign the paperwork. And John's like, don't sign the paperwork. What do you mean? I think a layoff is like a one-sided thing. They say, you don't work here anymore. And I say, okay. And that's when grandma Lila says, and she's like, well, sure it would be more comfortable. It would be easier. It would make you live in less fear to take no for an answer, but that fear will pass. And she said, you both want something. They want to get stuff done even though they can't afford to pay you, you want a job because it's easier to get a job when you have a job. So finally, John relent the next day, he goes to his VP and he offers to stay on for 10% time and pay while he job hunts.
(37:49):
Surprisingly Kim, they actually say yes, and I'm not sharing this as some influence tactic per se. The point is Grandma Lila's lesson about fear and being shameless. I think the point is don't let fear shape your decisions, but how often do we do that? How often do you not do video in fear of what someone might think or how you might look? How often do you not ask a customer for the business? How often do you not ask a boss for something that you need that will help you be successful? How often do you not ask your romantic partner for what you want? Right. Chances are when we don't do it, it's because of fear, and that's actually such great news because fear you can work with. So muster the wild courage to chase what you want in life, to ask for it, to put yourself out there to post on social media, to do video. When you muster the wild courage to do those things, you will discover a vital truth no matter whether you succeed or fail in any one endeavor, client request video or work project, you will never feel as alive as purposeful and as powerful as when you're pushing past that fear to the joy and success on the other side because everything you've ever wanted is right there waiting for you on the other side of fear.
Kim (38:55):
So reach for it. When I first did one of my keynotes, speaking of fear, I had a few years ago told my brother, he was the only person I said, I want to be speaking, I want to be on stages. He's like, do it. But I hadn't told anybody else because I was afraid of what do I have to do to get there? Is everyone going to judge me? Can I make this happen? I can't even put my finger on the exact fears. It was just was so much negativity in my head around it. But I'm like, I am actually going to start speaking. I'm going to ask people to bring me in for seminars. I am going to just be guests on podcasts. I'm just going to manifest this. But in a very productive way. Two years ago when I did my first big keynote, I had probably not spoken to more than 20 people, and suddenly I was speaking in front of 300 and being paid good money, I get on the plane, on the flight back, I'm just sitting on the plane and I start crying. I was so proud of myself because of what you said is once you actually say, I did have this fear and I accepted the fear, and I said, I'm not going to let that block my goals and I'm going to go through it, you're like, actually, I'm kind of unstoppable. There's actually all these things I can do now. Now that I could do this thing, I could actually do that other thing. Now that I'm not afraid to ask my boss for that, I can ask my boss's boss for that.
Jenny (40:09):
Now
Kim (40:09):
That I'm not afraid to actually sell to clients, I'm going to sell to three times more clients and my business is going great. I also think I've just accepted don't ask, don't get. If I do calls with people and I don't tell them that I have a coaching program, they're not going to know how to work with me. Maybe it's the perfect fit for them leading with the how can I help you? How can this be good for you and good for me? And so really just shifting the mindset,
Jenny (40:33):
Definitely. And it's still really hard. I have never lived in more fear than I have this past year as an entrepreneur. I felt very confident at Google. People knew who I was, they knew what I had to offer. And now, despite this book been out four weeks now today, and despite it hitting the New York Times, which is an incredible life goal, I'm still living in massive amounts of fear and imposter syndrome. And I'm up at 2:00 AM in the morning thinking, how is this business going to work? Are people going to hire me? And we really have to actively work past it every day. And so I appreciate what you're saying that once you overcome that, you're like, I can do anything. Again, I'm going to bring it back to this conversation I just had with legend Marshall Goldsmith who has sold 4 million books and he's almost 80 years old, and he's so wise and he's like, Jenny, do you know why I'm famous?
(41:17):
Do you know why I'm famous? And I thought he was going to say he got some lucky break or I don't know, something that was out of his control. And he's like, I'm famous because 40 years ago I said, I'm going to be famous. And then I just went and made it happen. And it's exactly like I think what you said to your brother, you're like, I want to be a speaker. I want to be on stages. I want to be up there. And then you just went and made it happen. Not manifesting in like a woo woo kind of way, but in a very practical, I'm going to tell people what I offer. I'm going to keep going. When people tell me no, like grandma Lila style, I'm going to refine my offerings as they need to be refined so that it finds the right product market fit.
(41:49):
I'm going to learn from other people and see what their pricing strategy is, see what their offerings are, see if I can offer something even better at a lower price or a higher price point if it's luxury pricing, whatever, it's, and I'm just going to keep working day by day, step by step to make it happen. Which by the way is what I call obsessed. That is the courage to set your own standard. And it's about pushing, persisting, performing, because none of these traits will serve you well if you don't have the energy and the enthusiasm to move your ideas forward. And that's what I think you have, and that's what I hope a lot of people listening to this, I trust that they have too, and that they can push past that fear to create great things for the world. Because a lot of people have tremendous things they can offer, but they're too scared to put it out there.
Kim (42:26):
And thank you for your candor. I think a lot of people are not honest about the fact that when you go out on a limb, you work for yourself. There's a lot of fear and heaviness in there, and you're like, oh, I feel this all the time. So thank you for being honest about that as a feeling that we have.
Jenny (42:43):
Yeah, I really miss Google. I'm very excited that I'm doing this new thing. I think that this book has a pretty significant tailwind behind it. And over the next 1, 3, 5, 10 years, this will be very successful. But I was back at Google for a keynote in New York, a keynote in Dublin, a keynote in London. And let me tell you, Kim, I walked in there and I was jealous, and I was like, every dollar I make feels so hard. It's totally eat what you kill. Sure. There's the ghosting of people not writing back to those 300 pitch emails. But then I got the occasional rough hand slap, which is another element of wild courage where one author who would be in the top five most famous authors in the world, and if I said the name, everybody would know it, is basically cut off his friendship with me because, and mentorship relationship, because I asked for them to support the book launch and this rubbed this person the wrong way, and then that put me in a tailspin for a week, and that made me lose sleep.
(43:32):
So these things are hard. And the reason I was jealous of Google, I'm like, oh my gosh, a paycheck that is massive every two weeks. I thought it was the hardest job I've ever had. It was the easiest job I've ever had. It is really hard to be an entrepreneur. It's hard to put yourself out there. It's hard to refine your offerings. It's hard to be ghosted. It's really hard to get your wrist slapped, which I have a couple of times, and I've made massive mistakes and learned from them and pissed people off. But it's all part of learning, refining, treating failure as data, and just continuing to keep going.
Kim (44:00):
If you're not making someone mad, you're doing something wrong. And one thing I loved that you owned in your book that I feel like we have in common is we are both intense and focused. And that's okay. It took me a really long time to not take that as an insult until I saw intensity in my children and I was like, actually, they are intense. And actually it's kind of awesome, but it takes a mirror to see that Jenny, everybody should run and buy wild courage. Go after what you want and get it. But Jenny would, you could buy it on Amazon. How else can people connect with you?
Jenny (44:28):
My website is the best place to reach out to me for speaking or consulting or one-on-one coaching. Itsjennywood.com. I-T-S-J-E-N-N-Y-W-O-O d.com.
Kim (44:38):
Amazing. Thank you so much, Jenny.
(44:43):
Thanks for listening to the exit interview with Kim Rittberg. Make sure to follow the show so you never miss an episode as you exit the grind and want to grow your business. Make sure to connect with me. I love teaching self-employed folks how to take control of their career and business by crushing it with their marketing. I help you get visible. I coach you how to show up confidently, both on camera and on stage, and then I help you make amazing video. Also, that you can connect with your ideal clients, be hired to speak and overall be seen as a thought leader. My clients are making hundreds of thousands of dollars in additional revenue, landing speaking gigs across the country, and getting invitations to appear on well-known podcasts. Let's connect so I can help you get wins like that. And I have a free download called 10 Tips to Make Awesome Videos. Plus how to go from camera shy to camera shy, all free, right at kimrittberg.com. Make sure to connect with me, Instagram and LinkedIn at Kim Rittberg, R-I-T-T-B-E-R-G, and on YouTube at Kim Rittberg content. So exit the Grind and enter success on your own terms.