Episode 176: Three Reasons to Try Something You’ve Never Done Before with Anna Oakes
Allowing yourself to be a beginner isn’t just a phrase, it’s a life-altering freedom.
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.
In this episode, Erin and Anna discuss why it’s not just important—but essential—to try something you’ve never done before and how it acts as a catalyst for your growth as a leader and a human being.
ICYMI – Your Post-Episode Homework: What is that thing that's been on your heart but you have been too afraid to pursue it? Think about your one thing and give yourself permission to do it. Second piece of your homework: If this series blew your mind, please consider leaving us a five-star review on Apple Podcasts.
Connect with Anna Oakes:
Show Links:
Tell us about your fails and/or send a question/voice message on SpeakPipe here!
Want to book Erin to speak at your organization or large-scale event: Learn more here!
Did today’s episode resonate with you? Please leave us a review for a chance to win a self-care package from us!
Take the quiz to download your free Wellness Workbook!
Connect with Erin Diehl:
@itserindiehl on Instagram, TikTok, and Twitter
Connect with Erin Diehl:
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!
“I love this podcast and I love Erin!!”
If that sounds like you, please consider rating and reviewing this podcast! This helps Erin support more people – just like you – move toward the leader you want to be. Click here, click listen on Apple Podcasts, scroll to the bottom, tap to rate with 5 stars, and select “Write a Review.” Then be sure to let Erin know what you loved most about the episode! Also, if you haven’t done so already, subscribe to the podcast. That way you won’t miss any juicy episodes! Thanks in advance, improve it! Peeps :)
Episode 176 Transcription
Erin (00:00):
Welcome to the Improve It Podcast, Improve it peeps. Welcome to part three of our series with Anna Oakes. If you have not listened to episode 174 and episode 175 of the show, let me just have you pause, go back, give these two a gander because they are so juicy. This show, this series is mind blowing. Episode 174, we're talking about how to be an entrepreneur and reclaiming ownership of your career. And then in episode 175, we're talking about ways to add more humanity to your workplace. Today. This episode is for the people who are having difficulty stepping outside their comfort zone. If you are an entrepreneur and you want to become an entrepreneur, or you're thinking of taking on more of an preneur role within your organization, this episode is for you. I have heard from so many of you that you have entrepreneurial ideas or you want to create a side hustle or you wanna scale your career right where you are. This is for you. This episode is anecdotal, but it also gives so many tangible tips. So let's go ahead, let's get to improving it with Anna Oakes. So I wanna switch gears. This is a, this is a hard turn, hard turn because I love that you went on your own career from the, from the entrepreneurial side to the entrepreneurial side. Now you're doing a combo of both. You've really just shifted gears and you've, you've stretched yourself in ways that a lot of people are afraid to do, if I'm being honest. So why would you say that triangle role or trying a, let's just say, going from entrepreneur to entrepreneur, trying something you've never done before is crucial to personal and professional growth?
Anna (02:27):
Yes. Yes. I mean, look, I'm, I'm a real, I love strengths, but I'm also a very science-based thinker because I wanna know, I wanna understand how the human brain works and there are people, guess what, out there Who know how it works. So why don't we listen to those people? Why don't we listen to the neuroscientists or the doctors or the psychologists or the psychiatrists, these people understand how the humans, how humans work. And if all I have to make a, a, a thing at my company, or do whatever I'm trying to accomplish are these humans, then why wouldn't I wanna understand them better? Yes, we're spending all this time worrying about understanding ai. Let's, let's understand our people because then we're gonna understand how they will use ai. That's when we're gonna get the innovation, is when we tap into our people.
Erin (03:09):
Yes, yes, yes, yes. Okay. So let me ask you this. When you just personally went from entrepreneur to entrepreneur, what were some of the reasons that you told yourself? Give me, can you gimme three, three reasons why you decided to make this shift? Mm-Hmm. <Affirmative>. And then I wanna talk about that in terms of how it can relate to our audience. Cuz a lot of people listening, I hear from, we call ourselves the improve at peeps. I hear from a lot of people that they wanna make this shift. Yeah. From entrepreneur to entrepreneur. I got a lot of y'all out there and I know it. And maybe you're not ready for that shift from intra to entrepreneur yet, but maybe you are thinking, how can I become even more of an entrepreneur in my career? So I wanna just speak from Anna's experience, from your experience. Yeah. So this can help our peeps.
Anna (04:07):
Yeah. Ok. So lemme give like those cliff notes version, Erin, of how this, how this sort of, how I got there. And by the way, I didn't think of the entrepreneur idea, and it's not my word. I didn't make it up, but I didn't even think about that I was an entrepreneur until I had already been outside. So here's how the story art goes. As I look back, I'm in higher up and higher up roles and I'm like, oh my gosh, this is really fun because I love to lead. I really do love to lead Erin. But what also happened is that I realized I wasn't doing a lot of producing. I was like yessing things and giving feedback, but I am a really creative person and I need to see that I did that. Yes. Like I wanna be a part and I want, I have high impact, right?
Anna (04:46):
I wanna make an impact. So I did everything I could as an entrepreneur. I'm, I'm the yes girl. Like we got an after, after work group that's gonna talk about it and how to make it better. I wanna be in like, I made an it, but I wanna be part of the conversation because again, raised my hippies in a community. It's up to all of us, right? So if I only stayed in my little HR lane or supply chain or operations lane, then I don't know other people. I don't know what matters to them. And therefore I don't know what matters to the company. Cause these are the people that are making the company run, right? So I started to ask questions. I started a photography business. So here in its simplicity, these are all side hustles. So you, you're, if you're intimidated by the word entrepreneur, just think about this as a, a small hobby, a side hustle, a part-time job.
Anna (05:33):
However you wanna think about it. I started a photography business called Ash after my Children. So yes. And I loved it. I loved it. I was doing wedding photography. I did a little bit of family photography. Boo, too much stress. So it was up for me, Erin, to go, this is my company. I'm gonna say yes to the things I want to, cause I'm doing this first to bring me joy. Second. It was a nice little added income, right? So it started with the photography business. From there, since I've been out on my own, I also like started my own company. And by the way, when I quit, well, I don't wanna miss this moment. I agonized <laugh>. I wanna be honest here. I agonized for over two years because I was up, I was being groomed to be the chief human capital officer.
Anna (06:16):
And I was like, all of a sudden I thought, I don't know if I really want that. I dunno if this is what I wanna do. And it's natural for us to ask that question, Erin. But that season that I was asking that question ended up being very long. So I was super honest with my boss. I went and sought out other people. Should I go do this? Should I go run that company? Should I start a nonprofit? Should I do these things? When I left, I was so loyal to the company, I hadn't put a lot of work into my business plan, but I took a six month sabbatical and I got real quiet and I detoxed because I've been working since I was 14. Mm-Hmm. 11 sitting, 14. Taco Bell, let's go. Let's go, let's go, let's go. Mm-Hmm. <Affirmative>, and I'm a lets go person.
Anna (06:54):
That cortisol, my stress levels were high. Mm-Hmm. <Affirmative>, I needed to honor that. I was now in a season where I needed to downshift a little bit. Yeah. So from me wanting more curiosity or more creativity, adding in a part-time job on the side, that side hustle, then I burn out and I leave because I realize that I don't wanna do all those other things. I think I just need to be on my own for a while, especially in an HR role. Erin, I'll be honest, we are just the sin eaters. We are the givers. Like, man, that stuff can really wear on you. I needed a break. I didn't wanna leave people for a while, so I went, it was just me for over a year. I didn't even wanna add in any support because honestly the thought of giving more of myself to somebody else I knew I wasn't ready for.
Anna (07:36):
Yeah, I get it. So fast forward, those like little storylines of the entrepreneur and the entrepreneur still go, because I was open, I always said I will was open for the right company to be their head of people. And I was absolutely the right decision to say yes to courts and to be their head of people, even if it was only for a short time. Because it led me to this editor role. When on earth would I be getting, this is where I'm talking about the candy people, because I doubled down because I was honest, because I had really good conversations with my leader. And before I was even hired, we were envisioning me being the general manager, of course at work someday it was right. Right now we have a newsletter and we write daily bylines. We had this vision to turn it into consulting business and to sort of combine my strengths.
Anna (08:21):
But guess why we had that vision? Because I was bold in the interview and I spoke into what I thought we could do now and next. I wanted to be planting those ideas. So I was gonna get that candy. And now we have this whole big company that owned the Onion and Gizmoto in these really good journalistic brands, right? There's candy on this table, Erin, for me to grab. Like, if I wasn't paying attention, I would've never got this editor role. And I'm growing and I'm learning, and I hope I'm contributing to my mission of restoring new in new ways. This is a total new way to poke at my mission to restore that humanity. And I hope by telling that story, there's a lot of luck involved. There's a lot of persistence involved, but, but if I'm honest, 80% of that is just opening the door of the window and making sure that we're staying open to what's right in front of us.
Erin (09:11):
Yes, you're poking holes in that amp farm. You're picking up that candy. I'm so here for it. And by the way, like I have to just share this with our audience. You're not just with this editorial role. You're not just like interviewing anybody. I've saw some things. You've interviewed Ariana Huffington, okay? There have been some people that you have talked to. And it is, it is quite impressive. And literally this is because you said, I'm not gonna stay to, I'm not going to just stay in this box. I'm not gonna stay. I'm gonna keep on this farm analogy, <laugh>. I'm not gonna stay on this path. I'm gonna poke a hole. I'm gonna be brave enough to come to the table in this interview process, in this conversation with leaders and say, here's what I'm thinking. Here's some ideas. Let me poke more holes, let me poke more holes. And that, I hope anyone listening today can take this away. And, and you know, we're gonna, this is gonna be part three of, of these episodes of part one. We talked about this ant farm analogy and poking holes and I'm just so here for it because Anna, literally what you have done by getting outside of your comfort zone is you have created a life and a role for yourself that you probably never could have dreamed could ever be in exist for you. It's so cool.
Anna (10:34):
Every time, you know, we start, we're starting a new video cast called Reworking Work. In fact, I was with Ariana yesterday recording her episode and nobody told me, nobody asked me to start a new video cast. I was like, you know what, this editor role, like I get to talk to these amazing people. We should make this a show. Yeah. Like we're writing and doing these interviews, but why aren't we making this a show? So like, let's have those conversations. I'll still write a byline, but now we have this video or this audio content that we can share with people who are picking up what we're throwing down in different ways. And nobody asked me to do it. In fact, I got turn a little bit at the beginning, oh, do we really need it? And maybe we'll only do it if it's sponsored. Like that took gumption. That took courage. That took curiosity from me saying like, well, couldn't we just try it and see what happens? If it fails, we'll call it a short term project. If it's great, we'll do it for years.
Erin (11:23):
I am so here for that. Okay, and so we've got this new video cast. Are there any other fun things that your poking holes at coming up? Are there things but maybe you can't share and if you can, but tell us. No, like I want, this is what I want. Improve it Peeps to walk away with. Today I want you to poke holes in every single aspect of your life, career, personal life. I want, I want you to walk away from this show with so many holes poked. And I am, I'm inspired by this conversation. So what's, where are you poking a hole? What else is going on?
Anna (11:57):
Yes, I love that. Hashtag Poke and Till. That's what I want us to be talking about. Poke
Erin (12:01):
And Till. Ok. Alright. Yes, there we go. So
Anna (12:03):
This is a great example with this show because I have, when I've been on my own, I had a podcast and a video cast and I went after big dogs like Ben and Jerry's. My podcast was called Borrow From the Best. Essentially it's doing a lot of what WeWork work is doing. But now I'm under a brand, pay attention to people as an entrepreneur. Now I'm under a brand who can help me get what I need to do. So Ben and Jerry's two before was like, never heard of ya. Don't have big enough numbers. See ya later. Now we're paying attention. Now they wanna have conversations. Now we can pull back the curtain on why they chose to support gun control, for example. And what did that do for their business and how did they talk to their shareholders about it? Right? We're talking to Levi's about a similar thing, talking to Vayner Media about how they've used competencies. So Claude Silver, who's their chief hard officer, I know y'all know her and lover,
Erin (12:52):
She's been on this show. Yep, yep. Good,
Anna (12:55):
Good, good company. And then I wanna do smaller companies, maybe the ones you've never heard of, you know, Deloitte's on there. But let's go a smaller company like Ultras, Erin, who is a tech company. But what they've done is they've built a extremely diverse workforce and not just persons of color and all of those things. Also neuro divergence. I think it's something like 75% of their company as neuro divergent. And there's even some nonverbal people. How do you lead a nonverbal person? Let's talk about that. Their episode was great. I can't wait to share it, but like we're pulling back the curtain. In fact, if any of your listeners have ideas, like I want the little known company that's got that good process or that good mindset. You know, Ariana, we talked about how they use resets, 62nd resets within their company. What the goal of the talk is, Erin, is that we're trying to pull back on one process, one program, one mindset, one approach that they use internally eating their own dog food or whatever to make it better. How are we increasing humanity and operations internally? So we're gonna be pulling back the curtain on that and I can't wait to share more. Yeah, I think we're gonna, we'll, we'll probably be out by the end of May, end of April, early May.
Erin (14:03):
That is awesome. And I love, it's one simple, not simple. I'm sure they're complex, but one thing like I love this concept of one thing. Yeah. That you can, that you can pull out. I'm so here for this. Oh my God, okay. This time has flowed. I could talk to you for 500 hours. Let me ask you this. This is the question we always ask our guests. Yes. And improve it. We say that it is the improve of the it of improve it is the thing that it is the thing you are put here to do. It is your purpose. It goes back to this concept of peace. It goes back to this concept of progress. What is your it? What is Anna's it?
Anna (14:49):
Hmm. I really do feel like, and it came probably two or so years into it, thanks to my good friend Jennifer Barla, who was pushing me. Like, I was feeling disengaged with being out on my own. And I knew, I know it's hard, so I was thinking, gosh, I gotta be doing something wrong. But when I got real quiet, it came really clear. Like I meant I wanna see humanity into the world of work. So many of your listeners have seen the pain that systems can cause without proper attention or that one person can cause without proper attention. And we can't fix all of that, but we can be good tools for that, right? So as a practitioner, I'm doing it and I'm doing it in so many different ways by just being open. Like how am I doing it as an editor versus how am I doing it as the owner over here for Oakes Co doing that differently. And could I have done it with the vintage shop I was running for a little while maybe, but that quickly ran its course to say like, Hmm, didn't really do it for me. Didn't feel like I was getting to poke at enough things. Mm. So that's all. That's it. I think it, it's the, it's the push
Erin (15:51):
Hashtag poke and till. I'm super here for that. This is awesome Anna. I have loved chatting with you. If the Improvement Peeps wanna know where to find you, give us all the things, how can they find out more?
Anna (16:04):
Yay. Okay. So big on LinkedIn. So Anna Oakes, it's got an E in there, so it's O A K E S. So look me up, let's get connected, follow along on the journey. I'm not as good at social as I used to be, but man, I'm trying. You know, so that's a great place. Or a website, the oakesco.com. And please check us out at Courts at Work, we're writing for the companies, for the leaders, for the employees. So qsi.com/work is where you can find me as the editor.
Erin (16:31):
Love it so much. We're gonna put all in the show notes. Anna, you are a delight. I feel so impacted by this conversation. I know our listeners are gonna get so much out of it. Thank you so much for being here.
Anna (16:42):
Of course, my honor. And wishing everybody peace and progress. Yeah. <laugh>.
Erin (16:55):
Okay. Improve a peeps. I am dead. This is my ghost. Anna Oakes, you are a light. You are a delight. This series is so powerful. Go back, listen to it. Time and time and again, if you were struggling, struggling <laugh>, you're struggling to use words if you are struggling with your career, here's what I want you to do today. This is coming out of episode 1 76, which we're talking all about triangle role you've never done before. What is something that you want to do? What is that thing that's been on your heart but you have been too afraid to pursue it? I want you to think about that one thing and I want you to do it. What is the one thing that you have been putting off but you know is calling you to do? That's your homework. Second piece of your homework. If this series blew your mind, cuz my mind is blown, please consider leaving us a five star review.
Erin (18:05):
I cannot tell you how much that helps bring new people and guests to this show. Specifically people like Anna. The more reviews we get, guests see and they say, oh, this is an audience I wanna chat with. Give us these people. We need more. Annas on this show. I mean, goodness, this was so jam packed. I'm so grateful for this conversation and I'm so grateful for you because you're taking that time to invest in yourself. You're bringing humanity to you, and you are becoming more self-aware through the progress that you are putting in, by giving yourself the time and investing in yourself in this show. I am honored to be with you on this journey. I truly believe in you and I'm so here for the next level of your career. And I'm gonna be cheering you on the entire way. You know what I'm gonna say? I want you to keep failing. I want you to keep improving because this world needs that. Very, very special it that only you can bring. I will see you here next week. Until then, bye friends. 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.