Episode 174: How to Be an Intrapreneur and Reclaim Ownership of Your Career with Anna Oakes
If you’re not taking all of the candy in the candy jar, you’re exactly where you need to be.
Anna Oaks is a change agent focused on restoring humanity into both our work and workplaces. Raised by hippies, she’s always had a natural inclination to leave the world better than we found it. She brought this proclivity from her childhood into over two decades of work in small, mid-sized, and large companies focusing on strategy, growth, and culture.
She toggles between being both an intrapreneur, or working directly in companies, and also an entrepreneur, or working on solutions to make work better through her own company, Oaks Co.
In this episode, Erin and Anna discuss what it means to be an intrapreneur vs. an entrepreneur (and why you’re probably already doing both), why intention overrules your opinion, and how doing what is asked of you and nothing more is saving our workplace culture.
ICYMI – Your Post-Episode Homework: Think about your current role. Maybe you're an intrapreneur listening to this show and you don't recognize that you are an intrapreneur. Or maybe you're an entrepreneur listening to this show and you lead a team of people and that team might include some intrapreneurs. How can you get more curious? Is this the season of your life that you are going to do that? Maybe it's not your season and you want to leave the candy on the table. But if this season feels like you can dream and you want to get curious, I want you to jot down a list of three ways that you're going to get more curious at your current role.
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Email Erin: info@learntoimproveit.com
Erin Diehl is the founder and Chief “Yes, And” officer of improve it! and host of the improve it! Podcast. She’s a performer, facilitator and professional risk-taker who lives by the mantra, “get comfortable with the uncomfortable.” Through a series of unrelated dares, Erin has created improve it!, a unique professional development company that pushes others to laugh, learn and grow. Her work with clients such as United Airlines, PepsiCo, Groupon, Deloitte, Motorola, Walgreens, and The Obama Foundation earned her the 2014 Chicago RedEye Big Idea Award and has nominated her for the 2015-2019 Chicago Innovations Award.
This graduate from Clemson University is a former experiential marketing and recruiting professional as well as a veteran improviser from the top improvisational training programs in Chicago, including The Second City, i.O. Theater, and The Annoyance Theatre.
When she is not playing pretend or facilitating, she enjoys running and beach dates with her husband and son, and their eight-pound toy poodle, BIGG Diehl.
You can follow the failed it! podcast on Instagram @learntoimproveit and facebook, and you can follow Erin personally on Instagram @keepinitrealdiehl here. You can also check out improve it! and how we can help your organization at www.learntoimproveit.com. We can’t wait to connect with you online!
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Episode 174 Transcription
rin (00:01):
Okay Improve it! Peeps, let me just tell you, this week's guest is incredible. I could talk to Anna Oakes for 500 hours. Truly, if you are a people leader or if you have any desire to impact and grow in your career, which is every single person who listens to this show, get ready, get out a pen, get out a pencil. Because Anna Oakes is giving us so many juicy chicken nuggets of wisdom. Like, this show is so juicy. I can't, I wanna like dip it in ketchup. So let me just tell you about Anna. Anna Oakes is a change agent focused on restoring humanity into both our work and workplaces. She's raised by hippies, and she wants to leave the world better than we found it. She brought this energy from her childhood to her over two decades of work in small, mid-sized, and large companies focusing on strategy, growth and culture.
Erin (00:58):
Now, she toggles between being both an intrapreneur, which we are gonna talk about working directly in companies, and an entrepreneur working on solutions to make work better through her company Oakes Co. Now, Anna recently was named Head of People for the Independent Media Company courts, where they'll partner to advance the mission to make business better. Now, while Anna's work improves the companies and systems we work in, she knows that the humans who make it all happen deserve more support, resources, and encouragement. You can catch her thought leadership through her three audio and video casts, or through social, where Anna shares best practices for maximizing your impact as an entrepreneur who owns your career, talents and voice. Okay? So today's episode is all about becoming an entrepreneur and reclaiming ownership of your career. This episode is mind blowing. So there's so many fantastic stories that she tells you to help visualize what it means to be an entrepreneur, and if this is something you're thinking about doing, how to actually make it tangible and make it happen for you.
Erin (02:11):
I'm gonna stop talking because Anna is so amazing. Let's get to improving it with Anna Oakes. Hi, new friend. I'm Erin Diehl, business improv Edutainer, failfluencer and keynote speaker who is ready to help you improve your it, it being the thing that makes you, you. So think of me as you are keeping it real professional development bestie, who is here to help you develop yourself into the best version of you possible, so you can develop your team and lead with intentionality, transparency, and authenticity. Oh, and did I mention we're improving your IT through play? That's right. I'm an improvisational comedy expert who uses experiential learning to help you have your aha haha moment. Those are the moments when the light bulb goes off and you're laughing at the same time. So grab your chicken hat, your notebook, and your inner child, because I'm going to take you on a journey that is both fun and transformative. Welcome to the Improve It Podcast, Anna. Oh my God. Okay. I am stoked. I feel like we're already fast friends. Welcome to the Improve It Podcast.
Anna (03:34):
Aw, thanks for having me. It's always an honor.
Erin (03:37):
Okay, now here's what I wanna do. I want to start off the show just by setting an intention. What is one word that you want to give our audience who we call the Improve it Peeps today?
Anna (03:52):
Hmm. You're gonna really test me here. Okay. So my sign off in my email and how I sign off of co conversations is wishing people peace and progress. But you know what? For this session, the prop that you and I have done, I'm gonna pick, I'm gonna pick progress. Like, that's the one thing. I want them to listen to this call, and I want them to progress a think mindset, progress process, progressive approach that they're having to their work. So I'm gonna go with progress.
Erin (04:18):
I love that so much, and I love that salutation, peace and progress. But we're gonna go progress and through progress, we're probably gonna find peace. You know what I mean? Yes. I mean, truly, I gotta tell you my word of the year is actually peace. So
Anna (04:34):
Here we go. Look at this.
Erin (04:35):
Mm-Hmm. <affirmative>. Mm-Hmm. <affirmative>. Peace, peace, love. And I've never had it before, so <laugh>. Oh, I
Anna (04:41):
Can't wait for you to get more of it. More of it, right. There's an abundance of it, we just have to fight for it.
Erin (04:46):
That's right. Yeah. It's intentional, which is why I love a good intention. And I, I'm so excited in speaking of intention because every month here on the show, we have an intention or a theme for the month. And this month's theme is all about connecting to our inner child. So things that bring us joy, things that help remind us of who we are. So let me just ask you really quick, what's something in your life that brings you joy? What do you, when you think of the word joy, what comes to mind?
Anna (05:26):
Honestly, I have to go with my family. I mean, really, they are, and they, you know, look, the past three years of this pandemic has tested us just like everybody else, and living in the same household with two twins who are now in sixth grade. So that's been a journey. And really, you know, my marriage marriages are hard, relationships are hard. So the fact that we've made it through the last three years we're so much stronger because of it. And that, that keeps me granted. That makes me joyful.
Erin (05:56):
Oh my God. I love that. And are your twins identical or fraternal?
Anna (06:01):
They're fraternal. So Asher is my son, and Juniper is my daughter.
Erin (06:06):
Best names ever. Okay. That is awesome. Congratulations. Sixth grade. Oh my God, what a time. And congrats on making it through these three years. I know. It's, it's like if you can do the past three years of 2020 to 2023, you can literally do anything. I've told myself that multiple times. <Laugh>. Ugh. It's just crazy. But I, I wanna, there's so much I could talk to you about, because when I was researching you for the show, just fascinated by the work that you've done, and you have such an interesting background, and I think, so what you've helped so many people realize is their fullest potential, their progress, if you will, with this idea of intrapreneurship. So I wanna just start right there. What, what does it mean to be an entrepreneur for somebody who's like, what does that mean?
Anna (06:57):
Yes. Yes. Okay. So the easiest definition that I use for an entrepreneur is somebody who has the strengths and skillsets of an entrepreneur, but chooses, chooses to use them internal to another organization. So maybe the best example Erin, I could give you is me. Right now. I'm both an entrepreneur and an entrepreneur. I have been out on my own for over eight years, and that is the way that I use my entrepreneur skills. Mm. A little over a year ago, I chose to come on to courts, which is an online business publication, to be their head of people. And that was a big ask of me to, like, I will, I will, I'm very picky. Let's say that Erin. Yeah. Very picky about where I go join. So fast forward courts ends up getting bought. I end up getting asked to be the editor, of course at Work, which is our arm that writes and thinks about the world of work.
Anna (07:47):
And that was always a long term plan, but didn't necessarily plan for it in the past year. So now I'm an entrepreneur. I'm using very similar skill sets over here. I agree to work for somebody else and to play nicely in the sandbox with what their mission and vision is. Over here, I have complete control. Super, super scary. Sometimes super, super annoying sometimes, right? Yeah. I mean, they both, they're pluses and minuses. And so we can be both or we can be one. And I just say like, can't we all just be entrepreneur of whatever we want to do?
Erin (08:15):
Hmm. Oh my God, I love that. I, I mean, and here's the thing too. Both, like you said, are hard. I am an entrepreneur, and I have been an entrepreneur I think in my previous roles, and I think when I think of preneur, I think of somebody full of ideas, an innovator. So let me ask you this. If you identify as both now, right? With this new role, an intra and the entre with, with both things going on, which I don't, I have, I think I have done both in my life when I was first starting improving. I don't know if I did it well. But I feel like you're crushing it. And if somebody listening today is wondering, am I an entrepreneur? What might be some of the signs that they might also be an entrepreneur within their organization?
Anna (09:05):
I, I love that. You know, I think there are signs, but maybe what I'm gonna point to that, if you can stay with me, is less of signs that you are one and more of signs that you can become one. Mm-Hmm. <Affirmative>, right? Cause I don't think it's something you are or are not. I think there's probably like varying degrees on the spectrum, Aaron, where it's like, eh, I'm in a series. Maybe I'm in a season of my life where for personal professional reasons, I gotta like, go down a gear. Like I'm pushing it too hard. Maybe I don't feel so much like an entrepreneur during those winter months when I'm in that season. Whatever. That's okay. Give yourself that grace. But there will be times like I'm feeling myself entering a zone of really creative potential and that I don't know how long that's gonna last.
Anna (09:46):
Maybe it's because spring is coming. Maybe it's because summer and you really are looking at the seasonal change, but start to look for those opportunities that you can be one. So here's what I would say. Couple things about entrepreneurs. They're very curious, right? They let themselves be curious. I have talked to hundreds and thousands of people in my career, and so many are like, oh, I'm not creative, or I'm not innovative, right? That's a really scary word. Or I'm not strategic. You can be all those things. You just have to find your most honest route to be them, right? Oh, so how can you use your own strengths? For example, Erin, and we'll get back to entrepreneur, but a lot of people think I'm super high empathy. I am, I'm very empathetic, but I show my empathy through my strategic strengths. So I'm a Clifton strengths fanatic.
Anna (10:30):
If you, yes, if you're familiar with Clifton's strengths or used to be strengths finder, I'm super high strategy. So when you and I are talking about your career, let's just say I'm gonna be pouring into you, you're gonna walk away and feel like I, I, I adore you and I do. The way that I'm showing you I do, is that I'm being strategic about your career. That's how I can help you. That's how I can show empathy. So if you're trying to be strategic, find out your route to strategic. If you're trying to have more creativity, which is one of the traits, curiosity and creativity of an entrepreneur, tap into that. I think it's about being intentional. What levers can I pull? Right? Like, let's imagine this is an ant farm that we're looking at, and there's two or three paths. We have full permission to create more paths for ourselves to poke at them until we find out that we either like them or not. So I use the phrase poke until we should be poking until, right. Like poke until we prove that that's not the thing for us. Or maybe right now is not the thing for us, or that it absolutely brings us so much joy.
Erin (11:32):
Oh my God, the ant farm analogy is going to stick with me forever. I literally pictured that green little ant farm that you get when you're in, in elementary at school, and you're poking, you're poking. They're trying to dig a new hole. And I hear that so loud and clear. Curiosity and creativity, major signs. You
Anna (11:49):
Know, I'll, I'll say something else that is more, I, I think it's more of a mindset, but I'd like to say it's also a skillset which is permission. Mm. Giving ourselves permission to fail, to try new things. To ask, you know, questions, to be something at work or in the world of work that maybe we weren't there yesterday, but that doesn't mean we can't be there today. Think so many of us get jiggy like, oh, I don't want them to think I'm getting too big for my britches, or that, you know, I think I'm better than them now. It's not about that. It's about us constantly seeking opportunities to do better or differently when it's aligned for us. Right? There's that seasonal thing. It's not always line. I'm not asking for a hustle culture and people hear me say like, I have these two jobs and Oh, she must be working these hundred hour work weeks. No, no, I'm not. I just got really smart at how I do my work and I'm really with applying those skills and I look for opportunities. Here's another visualization for you, Erin.
Erin (12:47):
I'm here for it. Do
Anna (12:48):
You remember Willy Chocolate Factory?
Erin (12:50):
Oh. Said Ver Salt Alte Long. Yep. Okay.
Anna (12:55):
Yes. Okay. So before Charlie gets the golden ticket, the real golden ticket, he's goes into the candy shop and the guy starts singing. You can grabbing all the candy. That's how we should be in our career. There is candy on the table and we should feel free to take it when we're hungry and leave it when we're not.
Erin (13:16):
Anna
Anna (13:17):
<Laugh>
Erin (13:18):
First. Okay. <Laugh> these visualizations, you are painting some pictures and I'm here for it. And now I want an everlasting gobstopper. Okay? I want it so bad. Yes. And maybe some days I don't want it. Maybe I just wanna leave it on the table cuz I'm tired and maybe it's not the right, maybe I got a lot going on in my personal life. So I don't need that gobstopper today. But I am super here for these analogies, and you're painting the most beautiful picture because there's so many people listening to this show right now. I know so many people who come and tell me how this show has impacted them in so many different ways. And I can think of individuals right now listening who this will resonate with. Because I'll tell you what, they're some of the most curious people on the planet and they care about the work and they want to seek out answers. But sometimes things get in the way, and it's okay to not have to, to not pick up the candy.
Anna (14:16):
Yes. To leave it on the table. This is why I love that we started naming things like quiet, quitting. Yeah. Cause I, I feel like we should celebrate that. First of all, the definition of quiet quitters are doing what is asked of them and nothing more. I feel like that's a pretty good baseline for work, right? <Laugh>, you asked me to do these 10 things and I do those 10 things, and you're talking to somebody who probably normally does 12 or 15, Erin. Yes. Right? But sometimes as I'm getting older and maybe a little bit more wise in my age, maybe I won't do all 10. Maybe I'll do five and I'll do five really, really well. Right? That's it. We've gotta make that decision about how we're pushing into these things and giving ourselves permission. That giving what you ask of me is pretty darn good. If I don't have the energy to go at above and beyond for the next two weeks, two days or two months, we should be talking about that and making sure that the energy I do have to put into my work, Erin, is put on the right things. That's the leader's job to help us do that. But that's where the gap is.
Erin (15:17):
Oh my God, that is it. And going back to the candy metaphor, because I'm like, yes, we're grabbing the candy. It's like, okay, so you've gotten the candy allotment for the day, you've picked up the candy allotment for the day. Good. You are getting a standing ovation. Right? But maybe you wanna try something new and maybe you want, you know, maybe tomorrow is the day that you try that. But the fact that you're constantly grabbing just that one piece of candy on the table, you're taking it. You're doing exactly what you're supposed to do. You have your allotment for the day, and now you're not going above and beyond. I think first and foremost, I think as people, leaders, sometimes we think, and I'm gonna speak for myself, sometimes I think that people, I'm so used to the people who grab the extra candy that when they don't grab the extra candy, I'm like, all right, what's going on?
Erin (16:08):
Yeah. And I, I know, you know, I was a, I'm as a leader, I know my team super well. Leaders listening here know their team super well. Generally, you know why they're not grabbing the extra candy. And it's generally has nothing to do with work. It has, it has things that happen to them as human beings in the real world. Correct. And we need to just be cognizant of that because I do think as an entrepreneur that comes, that comes with a little weight, right? Like I think the people who consider themselves entrepreneurs show up. They're gonna do those 12 to 15 things like you, they're not gonna do the 10. They're gonna go above and beyond. But sometimes we, it's okay to leave that candy. It's okay to come back another time. I think that's a beautiful message.
Anna (16:49):
Yeah. Just be really smart. And this is where another trade of the entrepreneur is powerful storytelling. If you could build your curiosity and be a better storyteller, I've been practicing it for many, many years because I realized early on in my career that I wasn't a great storyteller. Mm-Hmm. <Affirmative>, because of my strategic thinking. I was always like, I was already, already at the end when they were still back here and I had to learn how to paint the picture of what our strategy was gonna be to bring them along. Right? If that's all I did for the team and didn't do those four or five extra things, that's still pretty powerful. So let's look at the things that we can make an impact for. Be proud of them and do a good job of communicating those up, down, and across.
Erin (17:29):
Okay. And lemme tell you something, whatever. Whenever you got that feedback, you really took heat because you have painted some pictures today. Would the Aunt Farm with my Willie Walk a moment like I'm, I'm here with you. Like you have really crushed that and nailed that. And you're right. Because if you can help somebody understand how essentially what you're doing is helping them understand and take ownership and strategize with them to get to the next level that they want to be. Right? Yes.
Erin (18:06):
Okay. Improve it! Peeps. I am. I am. I'm like whispering with my hand right now into the microphone because I'm so excited. I can't wait to bring you more of Anna. This conversation left me jazzed. I'm doing jazz hands. So you know, I like to leave you with a tangible, I want you to think about your current role. Now. Maybe you're an entrepreneur listening to this show and you don't recognize that you are an entrepreneur. Or maybe you're an entrepreneur listening to this show and you lead a team of people and that team might include some intrapreneurs. How can you get more curious? Is this the season of your life that you are going to do that? And maybe it's not your season. Maybe you wanna leave the candy on the table, but if this season feels like you can't dream and you want to get curious, I want you to jot down a list of three ways that you're going to get more curious at your current role.
Erin (19:12):
Three ways. What are three things that you're going to do to get more curious? If today's episode sparked joy for you, if you're feeling like it's giving you some progress, please consider leaving us a five star iTunes review. I have to tell you, these reviews truly matter. I say it all the time like a broken record, but they help us bring guests like Anna on the show. So if you want more amazing goodness like Anna Oakes, please consider leaving us a review after today's show. You know what I'm gonna say? Keep failing, keep improving because improve it peeps. This world needs that very special it that only you can bring. I'll see you for our next show, part two with Anna Oakes. Hey friend, did you enjoy today's show? If so, head on over to iTunes to rate and subscribe. So you never miss an episode. Now, did I mention that when you leave a five star review of the Improve It podcast, an actual team of humans does a happy dance? Mm-Hmm. <affirmative>. That's right. So leave a review for us on iTunes, screenshot it, and send me an email at info learn to improve it.com. I'll send you a personalized video back as a thank you. Thanks so much for listening. Improve It Peeps. I'll see you next Wednesday.