From politics to nonprofits to executive coach, meet Katie O'Malley of Chicago, Illinois
This week, Jenny chats with Katie O’Malley, founder of Encourage Coaching, whose career path took her from the world of politics and nonprofits to coaching individuals from underrepresented communities into leadership roles. Katie’s story is one of heart, grit, and staying deeply connected to her “why.”
Together, they dive into the emotional side of career pivots, what it takes to build a business that actually cares, and how listening, real, intentional listening, can be the most powerful tool for change.
If you’ve ever felt the nudge to do work that feels more meaningful, or if you're building something new and wondering how to stay aligned with your values, this episode will speak right to you.
What We Talk About:
Favorite Quote:
“Listening is more than a soft skill—it’s a radical act of care.”
More from Katie:
Katie 00:00:00 And even when I did it, Human Resources was like, but you're physically fine, right? Like you're here. And my response was, yeah, I'm here. But I wake up crying every day and I go to bed crying every night, and that is not normal.
Jenny 00:00:16 Hello and welcome to the Career Flipper podcast. I'm Jenny Dempsey, your host and fellow career flipper and someone who's still figuring it all out. This show started after I got laid off from my customer experience job and no one wanted to hire me. 400 job rejections later, I got scrappy. I picked up some junk furniture off the curb. I taught myself how to use power tools, and I started flipping furniture that I found on the curb in my garage and covered in paint and sawdust and existential dread. I thought, okay, wait, like, how are other people getting through this kind of career chaos? So I started asking questions and people started answering them. People who've changed their careers. They were messy, honest, and sometimes heartbreaking, but always full of hope.
Jenny 00:01:11 And this podcast is for you. If you've ever stared at your calendar thinking another zoom meeting that should have been an email, really, or felt that pit in your stomach. The is this really it kind of moment? You're not broken. You're not behind. You're not crazy. And you're definitely not alone. Every week you'll hear from real people who flipped the script on their careers. Sometimes at a choice, sometimes at a desperation. And they all live to tell the tale. There's no fluff. There's no five step formulas. Just real humans. Real pivots and proof that starting over doesn't mean starting from scratch. This week on the career flipper, We're diving into a story that's all about listening, really listening to what matters. My guest is Katie O'Malley of Chicago, Illinois, the founder of Encourage Coaching and someone who's made it her mission to amplify the voices of those who are often left out of the conversation. Katie's career started in politics and nonprofits, but along the way, she realized she wanted to make a change on a more personal level.
Jenny 00:02:25 So she pivoted big time. And now she works as a coach, helping folks from underrepresented communities step into leadership and take up space where it counts. In this episode, we talk about what it means to build a business with care, how mental health in the workplace can't be ignored anymore, and the power of taking risks that feel a little scary but a lot worth it. Katie's not afraid to get honest about the tough stuff, like the emotional roller coaster of entrepreneurship, and she reminds us that listening isn't just a skill. It's a way to change lives. She's even giving a Ted talk soon all about it. June 30th, 2025 and Andover, mass. If you're nearby. Definitely check it out. If you've ever wondered what it looks like to. Pivot with purpose. Stay rooted in your values, and still keep room for joy. This one's for you. Let's get into it. You know, Katie, I have to say what we were chatting about before we started recording. But the canine office assistants are really the absolute best.
Katie 00:03:39 And we just had Foxy who jumped up on my chair. You, Judy. Oh, my little buddy. Yes. It's so.
Jenny 00:03:48 Cute.
Katie 00:03:49 Yeah, it's his chair. Jenny. I just sit in it all day.
Jenny 00:03:53 Absolutely. Absolutely. How dare you? Oh my gosh, Katie. So good to have you here. Thank you so much for being on the career flipper with me. Tell everybody who you are, where you are, and what you're doing now.
Katie 00:04:07 Oh, for sure. So my name is Katie O'Malley. I am the founder and principal coach of Encourage Coaching. we are in Chicago, Illinois, and service the entire United States. even out to the UK and Germany. And so it's really just I like to say I'd encourage coaching. We are on a mission to elevate more women, people of color, LGBTQ folks into the rooms where decisions are being made. Because until we are represented at the top of organizations and in the rooms where decisions are made, work is never going to feel joy, joyful and just for most folks.
Katie 00:04:51 And so we make good on that mission in three different ways. The first way is through career coaching. so helping people navigate a career change, a career flip, a career pivot. also helping folks re-enter the workforce, who have taken a step back for a variety of reasons. typically caregiving, whether that's caring for a parent, being a parent and caring for children, or any other reason that you may have had to exit the labor market. and for folks who are not in toxic work environments and are not looking to escape or make a pivot. We offer leadership development coaching. So for folks who love what they're doing, love where they're at, but can't seem to break through to that next level. where we'll come in and do some really good work around deepening self-awareness, improved communication skills, and interpersonal effectiveness, all of which is the the root of a great leadership practice. Because until we can lead ourselves, it's it's nearly impossible to lead anybody else. And then finally, I'm sure you can appreciate this.
Katie 00:06:06 And and those who are who are listening in right now. Oftentimes the challenges of work are not an individual employee issue, but it's more of a systems or systemic issue. And that's when we'll come in and work with organizations and companies around culture, creating longer term learning journeys, around career development, professional development and leadership education.
Jenny 00:06:32 That's a lot of great stuff. I mean, you're helping so many people figure it out, whether they don't like their job or whether they do. And I'm so curious because that is a lot of important work. How did you find your way into doing that? How did you land there? Where did you begin your career?
Katie 00:06:54 Oh my gosh. So my career did not start anywhere near the well. I didn't see anywhere near it was helping profession adjacent. but I like to say I was I was a career nomad. I mean, really, until about three years ago. Three years ago this month was when I began my resignation at the University of Chicago Booth School of Business so I could go full time into my coaching practice.
Katie 00:07:20 But this was never the end goal. I'm not even sure this is what I actually I can say with certainty. I am certain this is not what I had envisioned for myself. Right. And so, if we go back to 2004, when I graduated college, I went to Miami of Ohio. So just north of Cincinnati. And for those of you who are confused by Miami being in Ohio, I like to say we were a university before Florida was a state. and while I was in college, I studied political science and the the main thread, Jenny, that pulls all the way through my career is this driver of altruism and wanting to make a difference in the world, a positive impact in the lives of others. And at 18, 19, 20 years old, I thought politics was going to be the way to do that and make good on that value of mine. And lucky for me, I graduated in an election year in 2004. was hired to work on a coordinated campaign for John Kerry, moved out to Minneapolis, Minnesota.
Katie 00:08:31 And I tell folks to this day, that is the hardest I've ever worked in my life, until I became a small business owner and 16 hours a day, seven days a week. And then, my goodness, your candidate doesn't win. And it's like, all right. no job, no health insurance, no real prospects. And while I loved the work, I didn't love the instability of it and very much new for who I am, I needed I needed more security than that and couldn't be jumping from campaign staff to campaign staff until someone brought me on full time. But then, holy cow, if they didn't get reelected where my I end up and so transitioned into the nonprofit sector, I was like, all right, not campaign work, but nonprofits make a difference. jumped. I jumped right in to living in New York City. because there are more nonprofits there per capita than anywhere else in the country, and ended up getting hired at the Innocence Project. and the Innocence Project is an organization that works to exonerate folks who have been wrongfully convicted using DNA evidence that wasn't available at the time of their conviction.
Katie 00:09:50 So these are people who went away and were put away through our justice system on their blood type false confession, false eyewitness identification. And so the the work of the organization was was threefold, truthfully, exonerate wrongfully convicted folks, get policies established at state and federal levels that would prevent these wrongful convictions from happening in the first place. And then once folks are exonerated, these are humans that went to prison at 15, 16, 17 years old coming out 46, 56, 66. And the world is different. Their community is gone. And how can we help folks reenter society in a way that is really is really supportive and that work while incredibly meaningful. also really challenging to do. I was on the fundraising and development side of things. So raising the money to support the DNA testing, the legal services, the reentry support, but living in New York City on a nonprofit salary? Holy cow. I mean, it's hard to live there on any salary, much less a nonprofit salary. I'm sure you can appreciate living in San Diego.
Katie 00:11:13 very, very similar. And so moved home to Chicago. was born and raised in Chicago and then lived all over the Midwest and started working for the Aids Foundation of Chicago and had kind of similar feelings. while I was at home, I'm like, you know, I think I feel disengaged from this work and burnt out from this work because I'm not being compensated in a way that's going to allow me to have a stable, vibrant future for myself. And so after about three and a half years, I had a lot of friends who were working in commercial real estate and doing really well for themselves and just assumed, all of this disengagement dissatisfaction was rooted in compensation and salary. And so I made the move from non profit into commercial real estate, which is about a the biggest hundred and 80 degree pivot, that someone can make. And had I met with a career coach or career counselor, they might have said, Katie, there's a huge values discrepancy here that you might want to investigate before you make this leap.
Katie 00:12:25 I didn't do that. And Jenny, on my very first day, I knew I'm like, I have made the wrong choice. But I was 28 years old, raised to not quit. and I was like, I gotta I gotta give this a chance. And so in giving it a chance over the course of three years, it really took a toll on my mental health. Because when we are in environments that don't align with who we are, that don't allow us to bring our whole selves into the work in a psychologically safe way. Of course, it's going to take a toll. And so ended up in 2012 taking a mental health leave of absence from work. falling under FMLA and this medical leave of absence for mental health. It was really new back then and hardly anyone was doing it. I didn't even know about it until my therapist was like, this is an option. And even when I did it, Human Resources was like, but you're physically fine, right? Like you're here. And my response was, yeah, I'm here.
Katie 00:13:31 But I wake up crying every day and I go to bed crying every night. And that is not normal. And so during, during that leave of absence, when we were hardly talking about mental health at all, but definitely not mental health in the workplace. I realize this is not just a Katy O'Malley specific issue, right? This is this is something that's far more endemic, I think, in our society because we're told do well in elementary school, do well in high school, get into the good college, check all these boxes, do all these things, and you will have the career and the life that you want. And we're all kind of sold that bill of goods that very few people can make good on, through no fault of their own. Right. We're not really set up for success in those ways. And so I made the decision while I was on leave that I was going to go back to school and help people at the intersection of career and mental health as a therapist. And so at 30, went back to school, got my master's degree in counseling, and learned pretty early on in the degree program.
Katie 00:14:41 Insurance companies are not keen to cover conversations about career because career is not a mental health diagnosis. Even though our careers lead to burnout and the symptoms of burnout are identical to those of depression, anxiety, and post-traumatic stress. And so I completed the degree, but ended up not getting licensed as a therapist and instead pivoted into coaching and started working in higher education. And so my thought was, let me cut all of this off at the pass and help students figure out their strengths, their values, what types of companies and roles might align with that, the types of leaders that they want to work for and with. and so I spent ten years working at institutions like DePaul University, the University of Texas at Austin, the University of Chicago Booth School of Business. And it was incredible. And it was incredibly rewarding for me to be able to work with the students, but also to be surrounded by brilliant minds where I was getting access to information that often takes ten years to trickle out into society. And so I loved that.
Katie 00:15:52 What I didn't love was that it's a very small segment of the population that gets to access an educational experience like that, much less all of the bells and whistles with career and leadership development that come along with it. So again, going back to that driver, that value of altruism, I thought to myself, well, I have this skill set. and I'm really scrappy from all of my years working in nonprofit and wearing a bunch of different hats. What if I start a business? What if I built something? Would would anybody come? I didn't do any market research, didn't do any of the things that a lot of folks do before starting a business. And for me, I had my full time job and this was going to be more of a passion project or something that I got to do that really let me use my full spectrum of skills and strengths instead of just one part. And wouldn't you know, if you do what you say you're going to do for clients and you build credibility and trust, not only will they come back, but they're going to refer you to other folks.
Katie 00:17:04 And the very first piece of advice that I got was, don't go searching for other clients right away. Don't market yourself. Just focus on the clients that you have. Treat them like gold and more clients will come. And for me, as someone who never saw themselves as a business owner, or someone who was trying to sell things or get people to buy things. It felt so good to just say, I'm going to do the very best I can for this person, and then let's see what happens after that. And so very much treated the business. you know, like, how do I want to say this? I pretended that the money I was earning wasn't there. It was, the accountant would tell me how much I needed to pay in taxes, recommendations for how much to reinvest in the business, and just let the rest of it sit in that business account. And over the course of, over the course of the next two and a half years, really built up a nice little nest egg.
Katie 00:18:12 So when it came time in, 2022 to make the decision, do I want to bet on myself? Do I want to see what I can achieve? If I were to go all in on encourage coaching, what would happen? And 2022 was the year that I turned 40 and basically said, If I'm not going to bet on myself now, what am I going to do it? And worst case scenario, I go back to working for someone else in 2023. And for me, what made that possible was seeing that in the business account after taxes, after reinvesting, there was enough money in there to pay my mortgage and my health insurance for a full year if I never brought on another client. And so that also, when we're operating from a place of freedom and not fear, also can drive success a bunch because we're not worried or hedging, we're just saying the thing, doing the thing and and taking the next best step that we can. And Jenny, wouldn't you know what you can do for a business when you can invest 40 to 50 hours a week in it, instead of just accepting clients that are referred to you or come your way.
Katie 00:19:25 So my first year in 2022, going all in on the business. Doubled my salary from the university. Second year out tripled it and now I'm in the process of merging encourage coaching with another woman owned business called the Collective Academy, run by Emily Drake. I'm also a mental health clinician, so very much aligned on this idea that we are humans that happen to work, not workers who happen to be human and helping individuals, teams and companies in that way. but we are getting ready to merge our companies. And the new venture is called In Good Company. with the taglines being getting good company for career development. Be in good company for team and leadership development, and then stay a good company at the organizational levels. And like I said, where I started about 7 or 8 minutes ago as I was sharing all of this with you and your listeners. This was never the plan. However, I just kept taking the next best step. And this is where I landed, and it has been the most professionally and financially satisfying and successful three years of my career, operating from that place of just take the next best step.
Jenny 00:20:44 Wow, Katie, I am blown away at your resilience and your determination to make things work, even when you're not quite sure what that next step is and make an impact. Like a lot of you know that you mentioned, the thread that's woven through everything was that you wanted to make an impact from the start. And, I just, you know, the calculated risks that you took. I want to also touch on that, too, because I think that's really important when people are thinking about flipping their careers, especially those that might be in jobs and they're like, I can't stand it here. This is a toxic environment. This is, you know, not where I want to be anymore. and sometimes, like, it is hard to leave because of financial stuff, it can feel really impossible. And the way that you kind of shared how, you know, there were things that you were able to build up kind of on this on the side and to get to the point where it's like, okay, it is this calculated risk that I can now take.
Jenny 00:21:49 And, but always keeping your mind open to accepting things and, and making little pivots when you, you see an opportunity and knowing when things aren't the right fit, the burnouts that you experience working, you know, with the the campaigns and in nonprofits. And I mean, a lot of people just settle. A lot of people are like, okay, it's a job. It's supposed to be this way. I've talked with other career flippers who also had those feelings early on in their careers or like, I don't know, it's just what I was told. Jobs suck and you just deal with it. And it's like, what if that's not the option? Because I honestly used to believe that too. I've had anxiety attacks at work in the past, like there are things that I was just like, oh, that's just what happens. It's stressful, but it doesn't have to be that. And you're doing work now to help people. So thank you for sharing your story in such depth and with such heart.
Jenny 00:22:44 It's just I think, and then the merge, I don't know, I just have so many, so many things to kind of comment on and, and questions to ask. But I guess I wanted to start talking first about and if it's okay to pick your brain on this, because the thing about making an impact, this is something that you said was the thread that's woven through, and I'm going to go out on a limb and guess that it didn't just start in college. Maybe there were things that you did when you were younger where you're like, I want to make an impact. Or maybe you learned from people in your life of like, what? What does it mean to make an impact? Because there are kind of two types of people that I know in my life where you, you work to live, and then there are people who the quote is, you know, what does it live to work? But it's like more along the lines of, like, you want to make an impact and some people don't care about making that impact.
Jenny 00:23:38 And so I'm curious if you could kind of speak on that for your, your life. Like, what does making an impact mean? How did that start for you? Where did you learn that? And and if you have talked with people who are not interested in making impact and just want to work, what does what does that look like for a career path? Just throwing all the questions at you.
Katie 00:24:02 Yeah. And it's oh my gosh, I think we could take this in a lot of different directions and probably have a whole nother conversation, unfortunately, that you just threw out Jenny. But the as you were like saying this didn't just start in college, it came from somewhere. And truthfully, it came from me observing and watching how my mom moved through the world. And, her name, Diane Goodman O'Malley. She passed away when I was 12 and so had very limited time with her. last year, you know, we celebrated 30 years with without her. And I've lived more of my life without Diane than I've.
Katie 00:24:44 I've lived with her. However, I have this really lovely story of her that I did not think was lovely when I was 11 years old, maybe maybe 10 or 11, but had gotten home from either dance class or swim practice. We had dinner. Mom had cleaned up the dishes and cleared off the kitchen table. She's sitting, reading like the TV guide or whatever magazine, like Women's Day or whatever the big women's magazine was at the time. Drinking a crystal Pepsi. Do you remember Crystal Pepsi?
Jenny 00:25:22 So I so remember that. Yes. That's funny.
Katie 00:25:25 And, I was on the phone with my best friend at the time, her name also Jenny. So I love that nice connection. So probably on the phone for about an hour. And I hung up the phone and my mom took a sip of her crystal Pepsi didn't even look up from her magazine and she goes, you're grounded for two weeks. And yeah, you're making your listeners Jenny's face like Jon Hamm. And I'm I'm racking my brain at ten and a half, 11 years old, thinking, did I say a curse? Word was, I mean, to Jenny, but what did I do? And I'm like, mom, I don't understand.
Katie 00:26:08 What are you punishing me for? I was just having a nice conversation with my with my best friend Jenny. And she goes, you weren't having a conversation. You were talking at her and you talked at her for a full hour all about your day in class. What happened at recess? What happened at your swim lesson? You did not ask Jenny a single question. And that's not how we treat people in this house. So you're grounded for two weeks? yeah. Yeah. And at first, of course, really angsty and angry about it and stomp up to my room and she joins me, you know, 20, 30 minutes later after I've cooled down and stopped crying. And all of the pre-teen adolescent stuff that we do, and we had a we had a really good conversation about it, and it became so apparent to me in that moment that listening is an essential part of the communications equation. Right? And as my mom was sharing this with me, I was just thinking about all the times I've observed her being in more of that, that listening stance instead of the talking or telling stance.
Katie 00:27:28 And, For the moms out there who are like, do my kids hear me? Are any of my messages getting through? I'm here to tell you that they do, because now I listen for a living. That is what I do. because I recognized in that moment, while my mom didn't say much. The space that she held for other people was transformative. and now I get to do that for others through. Through my career and at the end of June. This is something that was a goal of mine that I just said out loud a couple of years ago, because if we don't say it out loud and we don't write it down, it doesn't exist. And I, I've always wanted to do a Ted talk. Which is ironic because I listened for a living and. Holy cow. You want to do a Ted talk and be on a stage? I am doing a Ted talk June 30th. in Andover, Massachusetts, right outside of Boston. And it's all about what I'm calling a deficit of listening in our world.
Katie 00:28:35 we're in an age of. I mean, we're doing it right now. You and I are in conversation, but in age of broadcast, right? We put out posts. we don't necessarily even respond to the comments to that post, and we'll delete comments. Or if we respond, it's something that is not rooted in dialogue and truthfully, not even in debate. It's coming from a place of defense and attack, because we have become intolerant to any idea that is different than ours, because we've forgotten how to listen, and that listening doesn't mean we are accepting what the other person is saying as our truth. but that we are treating them with the dignity and respect that they deserve as a human. And so really excited about that. But realizing and this is this is what took me so long. Right. So I was like, no, I'm going to make a difference in the world because mom made a difference in the world, and she did it that way. But I'm going to do it in these big macro ways through campaign and nonprofit work.
Katie 00:29:40 and this whole time in, in high school and in college and even after I entered the workforce, people are like, you would make such a great counselor. Like, why don't why aren't you doing that? And I'm like, because it's not it doesn't matter enough. working with one person at a time, it just it's not meaningful enough. And I say those words now that I said 20 years ago, and I'm like, what was I thinking? Listening to people changes lives and those changed lives have the capacity to change the world. And so when I think about impact now, I think about changing organizational culture, one employee at a time. I think about helping a family system or family community improve, one member at a time. and planting those seeds and knowing they're going to sprout someday and create without getting too metaphorical about it, but really create a beautiful garden where there was just a dearth of dirt.
Jenny 00:30:44 Yeah. Who knew that getting grounded from that situation would lead to such such change and, and movement throughout your whole life.
Jenny 00:30:53 Like gosh I mean congratulations on the upcoming Ted talk. That is I mean that's amazing. And thank goodness that you are doing that because we do need to all listen more. I even know for myself sometimes. I get so many thoughts in my head as I am chatting with other career flippers, and I have so many questions to ask. And and then I'm like, wait, I just need to listen more. It's a good rule. This podcast has been a good reminder to myself that I. I do have a lot of questions, but sometimes it's nice to just listen and, because it really the ripple effect of that. Like you mentioned, planting the seeds, I always just picture the ripple effect to like one little pebble drop in the water and all the rings off of that. You can make an impact in little ways that goes out beyond anything you could ever expect. And it is funny also. Well, funny I say, but also just kind of these things that we say when we're younger or even just, you know, a few days ago that we say we're never going to do and we end up doing them and they change us.
Jenny 00:32:04 They teach us to be bigger and better and wiser and stronger than we ever could have imagined. And having the open mindedness to just try, even when we're not sure, or to allow ourselves to evolve and then be open to those things even though we said no, never. it's pretty amazing what it can lead to. And Katie, thank you so much for sharing such an incredible journey that you've had, and I am so excited to follow along on all the amazing things that you're going to continue to do. I cannot wait to watch your TEDx talk and I'm so, so excited for you, Katie. How can people connect with you? How can they find you? How could they work with you?
Katie 00:32:49 For sure, for sure. So I think the the two best ways to see what I'm all about is to give us a follow on LinkedIn or Instagram. I like to say LinkedIn is where I put all of the great research evidence based practices is occasionally a giggle or two, but if you want to find me there, it's just at Kate O'Malley.
Katie 00:33:11 Backslash. Kate O'Malley. You can find me. Hit the connect button. and I'd love to. To meet you. Or on Instagram. And that's where we put constant giggles. Some helpful tips and tricks. but it's more about levity than anything else there. Because, like you said, work for a lot of folks is a slog. And helping people to see they're not the only ones experiencing it. And there can be a different way. And that's at encourage coach Chicago website is encourage coaching. you can book a discovery call. You can find all of the free resources we have. I host a free workshop every month. Those are all listed on the resources page. And I would I would hope to see you there, that you would join in.
Jenny 00:34:00 Amazing. Thank you. Katie. this has been such a gift, I appreciate you. Thanks for being here.
Katie 00:34:07 Thanks for the invitation, Jenny.
Jenny 00:34:11 Thanks for hanging out for this episode of the Career Flipper podcast. If you want to connect with Katie.
Jenny 00:34:17 All the good stuff is waiting for you in the show notes. And hey, if this convo made you feel seen or you know someone else who's knee deep in the what am I doing with my life spiral, send this episode to them. You never know, it might be exactly what they need to hear right now. If you've got a career flip story of your own, or you know someone else who's made a wild, wonderful pivot and they want to share it, head to the Career flipper.com and say hi. I'm always looking for new guests to share the messy magic. Okay, and remember, even if it doesn't look like much today, that tiny, tiny step forward Counts. Even the step backward counts. It's a step. You've got this. What's the best that could happen?