Sally Mildren takes us on her journey from being a burnt-out brain injury therapist to becoming the CEO of her own marketing and customer experience agency—with all the crazy twists and turns in between.
Ever thought about what making and selling granola can teach you about running a marketing agency?
In this episode, Sally Mildren takes us on her journey from being a burnt-out brain injury therapist to becoming the CEO of her own marketing and customer experience agency—with all the crazy twists and turns in between. She talks about the tough stuff, like dealing with a controlling boss and getting laid off multiple times. Sally dives into why taking risks and chasing your dreams, no matter your age and even when you're scared, is so important. She also shares tips on nurturing your creativity and not waiting for 'someday' to live your best life. Tune in to hear Sally's real-life advice on bouncing back from failures and finding your true path.
Episode Takeaways
Connect With Sally
Jenny Dempsey (00:00.078)
Well, I may have the ultimate career flip because I started as a recreation therapist working with patients with brain injury and now I am the CEO of a marketing and customer experience agency. Hey there, welcome to the Career Flipper podcast. I'm Jenny Dempsey, customer service leader, term furniture flipper and podcaster. Each week I bring you inspiring stories from people who've made career changes, whether by choice or circumstance.
through unexpected layoffs, launching businesses, or switching gears entirely. This week, I'm chatting with Sally Mildren, CEO of Boss Lady Consulting, a marketing agency specializing in human -centric marketing. Sally's journey from brain injury therapist to agency CEO is incredibly amazing. She shares valuable lessons like taking risks, pushing past self -doubt, and staying true to your values. Trust me, her story gave me goosebumps, and I can't wait for you to hear it.
Let's go. Sally, thank you so much for joining me. This is awesome to have you here. I'd love to be here. Thanks for inviting me. Yeah, so I'm going to hear all about it. I know you have had a very unique and interesting career, and I am excited to have you share it. So tell me your career flip story. Where'd you start? Where'd you end up? And all the things in between.
Well, I may have the ultimate career flip because I started as a brain injury therapist and now I am the CEO of a marketing and customer experience agency, which is like a whoo. There's no way those two connect, but I think that the biggest career flip moment happened for me after. I mean, I went from therapy into marketing just by sheer.
selling myself and the basic skill sets that I had. But I think that the real marketing flip for me came when I was working for a boss in marketing that was just not working. Super controlling, super micromanaging, and it just wasn't working and I needed out. It was crushing who I was as a human.
Jenny Dempsey (02:21.71)
And so I decided to make a shift and quit that job. And that was when I started my first side gig business, which at the time a lot of years ago was gift baskets, which is insane also. And so I made a go of it. And I, after about a year, we ended up moving. And I mean, I even had articles in the local newspaper. They sent up a...
to my house. I had lots of clients that were, we were doing really creative and unique things for businesses to get a foot in the door or as thank yous to their clients. But what was interesting was after about a year, I flipped back because it, you know, financially wasn't panning out. Gift baskets were very hard to compete against Costco.
You know, baskets started showing up everywhere from Walmart to whatever. And so I went back into the work field at that point and worked in marketing for many more years. And then at some point, I also felt like I was part of a layoff of a big system, which I know a lot of people can relate to now. And you're kind of faced with this.
Okay, I have a few weeks of unemployment. And what am I going to do with myself? And for my and for me, I was, you know, getting I was 50 at that point. So 50 in a very tech heavy state of Washington near Seattle, where Amazon and Microsoft and all that was ancient. I even had one young guy who was interviewing me at a company say,
Yeah, well people your age miss work all the time because they're sick and you know older people… So I told him I said let me give you a little advice honey Don't ever say that again, you're gonna open yourself up to a lawsuit But also, you know, I'm done with the kids age. I don't have wine flu every Monday I'm not you know, whatever but
Jenny Dempsey (04:43.374)
Anyways, it was very difficult to find a job and I began to really kind of evaluate what am I going to do? I mean, I was in probably the prime of my career and doing the best work of my career, having huge results for Fortune 50 companies and I wasn't done. So, you know, for me, I started my consultancy, Boss Lady Consulting.
to begin to help small business owners and other businesses to take advantage of my years and years and years of experience and how to really help them self grow. And I was learning that for myself at the same time, promoting my business and finding new clients. And so it was a huge jump and financially, you know, I could do it because my husband had a really secure job.
so it's not necessarily a jump that anybody can just go from zero to full time. It, a lot of folks build it up on the side, like a little side hustle thing. I didn't have that Liberty and I could not find a job. So I started out on the side. I ended up getting a job again for about a year and a half and then was a layoff during COVID cause they.
got rid of about 80 % of their staff. And that's when I said, okay, forget it. I'm not gonna put my future in the hands of anybody else. I'm gonna be the boss of me. And I went all in on the consulting and it will be four years this fall. Wow, that's a lot of flips in there. That's a lot of flips. Can you talk a couple things pop into my mind, Sally, like these, you know, moving from one industry to another.
imposter syndrome can sometimes come up. Like that could be really like there's imposter syndrome, but there's also like fear. And so I'm wondering, like, did those ever get in your way? Like, were there times where you're like, no, I'm not going to do this. I'm just going to, I don't know. It would, did anything come up for you on this and how'd you work through them? You know, what's interesting is a little flip I skipped, which ironically I was a gymnast for years and years. So there's a lot of flipping in here.
Jenny Dempsey (07:09.87)
During that layoff period where I couldn't find a job, I set up a little commerce business called the Polka dot farmer. And I sold food farm and for fruit. I made, we lived on a little farm that had blueberries. So I made blueberry hand pies and homemade granola and popcorn. And I made crafts and framed things and.
all wreaths and all kinds of things and I sold them at the farmers market every Thursday to just make ends meet, but also to keep alive the creative need in me. Because it's very easy to, yes, fear, yes, imposter syndrome, but also yes, just really profound discouragement to not, when you go through a layoff, it's hard to not take that personal.
And to start then second guessing all the talents and all of the richness that you bring to the table. And so I think for me, the keeping any kind of activity that kept the gifts and the talents I had alive was essential. And this setting up a polka dot farmer, I had goats and chickens and blueberry farm and I
I did my thing with branding and I had people driving from all over the Seattle area to come get my granola. It was the best they've ever had. And so, you know, it in a very small way, it kept my skills sharp while I was finding my next it. And it showed me that I'm really good at this because I could set up a business from scratch. I had an e -commerce business. I had an in -person business.
And so it was really fun to do. So I think that for me, dealing with the fear and kind of that self doubt, one of the things that was vital was just to prove with evidence, review the evidence from the past, but prove with evidence now that I have what it takes to make this work. Okay. I have a brand new Facebook page. I've got 50 followers. That's not nothing. You know,
Jenny Dempsey (09:32.398)
It's like just find the things that you can do that demonstrate to yourself that yes, you are good at this and yes, you do know and know you're not crazy. And then in the terms of the fear of flipping or going for it, I have a business coach that said something to me that has changed my life. She said, okay, when you start doing that what if game and you're like, my God,
What if, what if, what if? She said, play that all the way out. Okay. So what if it doesn't work out? You'll get another job. Okay. What if you can't find a job that you love? Okay. You could work at Target for a little while. What if you lose money at it? Okay. You will sell something or, you know, get a side gig or start writing. And she, she had me begin to...
play out all of those what if scenarios and when you chased it all the way to the end, it wasn't like, my gosh, I'm gonna die and have to be buried. It was, I might lose a little bit of money or maybe I will embarrass myself or maybe I will, you know, whatever, but the consequences of chasing those what ifs all the way out.
were rarely something so tragic and dramatic as I was afraid of. And it made it go, okay, I could jump. I could do this and I'll try it and I'll give myself six months. And if I need to go get a side gig waiting tables on the weekend to make tips for a minute, I will, or I could, you know, take a different job. And so I think that that's the thing for me that really helped with the fear of this situation.
And kind of self, I think I struggled at that time with self doubt more than imposter syndrome. As a CEO of a marketing company, imposter syndrome comes in waves. That makes sense. And I think something else that really stood out was that, you know, all the things that you've tried, especially, you know, making granola and people coming from all over and knowing that you can try different things and it doesn't necessarily have to be what you do for.
Jenny Dempsey (11:55.63)
ever and ever. I think I talk to people and even myself included. I'm like, well, this is what I've done for X amount of years. So that's all I'm going to do forever. And it's like, we don't know. Like, it's okay to try these things and creative, you know, pursuits and like, enjoy it. Like, it sounds like that was something so I don't realize that's so cool. And I actually, you know, I didn't know that about you. And that is such a creative, fun pursuit. And you've made people's breakfast so much better. And like,
How do you fit in the creative time now, you know, as you are, you know, running the agency, like, how do you, how do you find time to still be that creative side of yourself? Well, for me, it comes down to just being very intentional about my commitments. And I think particularly when we go off on our own thing, it's too easy to put yourself behind the business.
And yet when we don't nurture and honor our own physical biology first, water, you've got to move, you need to eat well, you need to get some sleep. When we put all of that on the back burner, which I did working for corporate, you know, so busy, so much to do, so I quit going to the gym in the morning at five. You know, that was the beginning of the end. It's like this downhill slide of stress.
I wasn't taking care of my body. I was working earlier and longer. And you know, it's like, there comes a point where I realized if I can't keep the promises to myself, I can't expect anybody else to. And so, you know, it became this commitment to myself to say, I have to be very intentional about making time to be creative. Last week, for instance, on Tuesday, I took
a little block of time off of my schedule and I told the team I wasn't available and I made candles, which is something I learned for that polka dot farmer. But I love, I can't find candles that I love more than my black oak and current candles. So that's the ones I will make and use around my house or give to friends or family. And so it's just, it doesn't have to be, you know, weeks of vacation. Some this weekend or in the long weekend, I told Tim, I said,
Jenny Dempsey (14:23.374)
I need to read for a little bit this weekend. And he's like, okay. But then I got something and inspired me. I sat down, I've been working on a book and I wrote the whole introduction out in one setting and I love it. That's incredible. And just by being intentional and it sounds like communicating that to those around you. I think you mentioned that is.
To have that supportive network of people who are like going to be in on what you're doing and like cheering you on and giving you the space you need is also incredibly important as you're going through it. Right. I read a quote yesterday actually that said, put yourself around people who think your next big idea is a guaranteed success story.
You need those kind of people in your corner when you when you're doing a flip. I mean, there are a lot of people who will be happy to give you advice that this isn't a good idea or won't make money or what are you thinking or but you have to know in your own gut. I'm going to give this a go. And if it doesn't work, no harm, no foul. My polka dot farmer didn't sustain. We moved away from the farm ultimately. But,
You know, it's you have to know there's something in you that is saying, yes, do this thing. And you know the difference between a whim kind of and a, my gosh, this is something I need to do this podcast for you. You need to do this. It came to you profoundly, personally, specifically, and you know, you got to make this happen. And so.
You have to have people around you that are going to say, you know what? I might not understand it, but I am in your corner and cheering for you. Yeah. Yeah. Yeah. It's so true. It's so true. It came to me in a dream and I felt like, am I like going delusional at this point? I think it gets to that moment where you're like, maybe there is a little bit of that delusion in there, but in order to like dream bigger and actually make things come to life, you need a little bit of that.
Jenny Dempsey (16:43.342)
because it hasn't necessarily come to fruition yet, but it is on the way and it's happening. Like new actions are making it. And I was talking to someone recently too, and they were mentioning like, I think every entrepreneur is a little delusional because dreaming about something that or building something that hasn't happened yet, but believing in it so fiercely and knowing that like, this is gonna be something and not letting...
society or you know, whatever it is, whether it's about age or experience or you know, things that we have, you know, dreamed about in the past and never made happen. But like now suddenly we are and like, just comparing ourselves to others and letting that go. And the self doubt which you brought up like, whoo, that is it's hard to navigate through, especially in those moments when you're like, I got no money in my bank account.
I'm trying to figure this out. I have this big dream and I believe in it. But yet every society is saying like, you need to just get a job and it doesn't matter if you like it or not. But I love how you kind of weave in like sometimes, you know, go work at Target, go work at the restaurant, go do this for a little bit, pop around and do it because it's going to lead you to the next step of what you've been envisioning for yourself and not settling for the cringey boss who's...
you know, destroying your soul and not feeling you have to be stuck in that and complaining and turning into a very grumpy, sad person and living a life that's not fulfilling. Yeah. And I think there's just nothing sadder to me. I've seen it in my own family. And certainly the boomer generation, the older generations lived like this where they did work. They hated for us someday.
And I frankly am just not willing to trade happiness today for a someday. And so for me, I've made some jumps that people think we're stupid. They think we're crazy. Some people in my family call me a vagabond or something because when it hasn't worked out in a certain location, we have, you know, collectively looked and decided and prayed and found out what our next it was.
Jenny Dempsey (19:04.206)
And we have not been afraid to make a change, but that came after years and years and years and years of being afraid and being stuck in an environment that was oppressive to us. And so for me, I think it's the seeing the freedom of owning your own agency, meaning your own choice. You have agency over your life. And if.
If this thing is something that you want to try and you're too afraid to quit your job, then start it on the side. That's fine. If you, if you think this is it and you can make it work, then try it. Why not? I mean, what do you have to lose? Usually a little bit of pride, but you know, it's, it's not, it's rarely as big of a deal as of a hairy monster that we make it because of fear. But I also,
I'm feisty enough after living a lot of life to not allow the constructs and the expectation of cultural norms decide what I can and can't do because I don't care what you think. It took me a while to get there, but I don't care what you think. There's people in my life, my twin brother included, that I'm like, some stuff I just don't tell them.
Because he's not, he's so structured and so safe and so about the someday that he doesn't get it. So I don't have the conversation with him. I have the conversation with my friends who are like, my God, that's amazing. I think you're so brave. I would love to do that, but I'm afraid. And I hear that all the time. And those are the kinds of people that you just need to be smart about who you tell what.
It's not that this person's bad. I love my twin brother, but his, his safety is found in a different thing that is not life for me. A giant IRA account, which will be nice when he's retired, is not my hundred percent focus. I don't need to know that I can live to 130 with the lifestyle I've got. I don't care. I'm going to go out in a cloud of dust. But for me,
Jenny Dempsey (21:30.286)
Being in tune with my creative and alive self is way more important than making more money. Yeah. I hear that. I hear that so loudly. I think I might have told you the story of my dad. He worked so hard his whole life. I didn't really get to know him. And he was always working so hard to save for that retirement, save for it. And then he retires. And a year after he retires, he's...
falls down, breaks his neck and then eventually passes away. But right before he passed away, he told me on his deathbed, I wish that I wouldn't have worked so much because I would have, like there was so much more and I'm like, my gosh, to work your life away. And that's, you know, like you said, if that is where someone's at, that is great. Like that's there, that's great. Not going to try to change that. But then to hear someone say that on their deathbed, it was very, it was heartbreaking.
It's like this was the chance and here you realized it and it was very profound and it really has stuck with me about these types of decisions. And it's just, yeah, it's a journey. That story is so common. I mean, honestly, I can't tell you the number of people I know who had a heart attack two weeks after retiring, you know, or whatever. It's so common. And I think,
for listeners or people who are want to jump or flip. I just feel like life is now. We don't, we, there's no guarantee that doesn't mean be foolish and don't plan anything, but it means don't put off your life. Don't wait on something else to really live or follow your dreams or do the thing you want. I feel like.
Life is today and this is all we have guaranteed. So I know that I have made a lot of flips in my life and I have not regretted a single one of them. They've all in one way steered me or helped me refine or grew me or changed me as a human or taught me new things. Even when I went back into the workforce, the things that I learned from a go at entrepreneurship.
Jenny Dempsey (23:52.686)
made me a better marketer. And so I feel like there's just no reason not to. I know I'm bold because I've been there, done that, but I really feel like it's just no reason not to. If it's in your heart to try, then find a way. Do one day a week farmer's market on Saturday when you're not at work. Test the market, find out how your product is, what people say. It's not...
It's not a dead end road and it's not for nothing. Yeah. That was, that's a, like gave me goosebumps right there. Like, and I think just hearing you say that and, you know, giving it a go and trying it and it doesn't have to be perfect. I think that's another thing. Some of these things, you know, yeah, maybe there's no, you don't have certification or you didn't go to school for this or you haven't worked in the industry for over 10 years. You know, like maybe there's something there that you're comparing yourself to that's.
completely irrelevant, but you're holding yourself to these standards that aren't real. And it's like, Kathy Heller always says, take the messy action. And I actually have a post -it note on my computer with that, because it's like, it doesn't have to be perfect to give it a try and just see. Like, you can always do better the next day and just do it. Just try. Yeah. My very first gift basket job I did was
250 baskets for a convention at a Weston. And it was in Arizona. So I thought, I'll be cute. And the basket was a straw cowboy hat. And I put in the Arizona ice teas and a bandana and a little, I thought, I'll be super cute. And I had little baby saguaros that I put in there and, you know, all the things. Well, when it came to having to deliver the host,
Baskets? Yeah. You can't like stack them into boxes. So I had to rent a huge truck and there were 250 individual baskets. It was a nightmare for the hotel. They had to fill a whole meeting room with them. And the saguaro dirt dumped all over. It was a nightmare. But I learned a lot from that lesson. And okay, no life plan. So it's not a good idea.
Jenny Dempsey (26:16.078)
Not a good idea. But I also learned something about different shrink wrap. And I also learned about, okay, now it's not just about designing an adorable basket. It's about portability of it, the ability to deliver, all that kind of stuff. And so, you know, at the end of the day, I had to redo a few baskets, which big deal, you know, have a 250 basket order first was great. But, you know,
That messy action taught me a whole lot about future orders and I was able to change my process just like you would on a marketing campaign that fell flat or something. Like, yeah, we need to go back and make some adjustments. It didn't mean the entire team got fired after one bad campaign, but somehow when it's our thing, we put such monstrous expectations on it that,
This means I'm a total loser and I'll never make success, but it's no different than making course adjustments in whatever professional field you're in. Great. That's such a good rule of thumb. I'm just picturing that. Picture those baskets, like it's so cute. And then you're like, wait, this is going to follow this. Then that's, yeah, you would never have known how to make those improvements had you not done that. Right.
It's so valuable. All of these things are so incredibly valuable. What do you, I'm curious, I know there's a lot of things, but what are some things that you're most proud of? As we kind of wrap this up today, what are you most proud of about your career journey? Tell me. I think I'm most proud of the fact that each step was a lesson for me.
There's a lot of people that have a layoff or a firing or a quit, whatever, that can remember only the offense of it, if you will. And, you know, certainly there's an emotional trauma to any sudden abruption of, you know, work, but I feel like I'm really proud of the fact that I can look at those things.
Jenny Dempsey (28:37.902)
The good and bad leaders I've been under and have drawn inspiration to be a better human and a better leader myself. And I feel like that that ultimately is what makes our agency and the work we do so powerful for the clients we serve is because we haven't severed our humanity from the work we do. It's not just going through the motions. My agency is very core.
value centric and very human centric by design and by the lessons I've brought through life. And so for me, I think I'm really proud of that. That one of the things that stands out the most about my business is our core values and people see it. It's not just a words, they feel it and they experience it when they work with us or for our clients. And so that's, that's pride for me.
That's amazing. You and I can speak to that like having worked with you like those values shine through in everything and It's incredibly it's just very motivating It's like I want to continue to work together because this feels like I can do my best work with you there's and so I just and everything that you've said like makes sense about how you shaped up where the values are today and
You do amazing work and I'm continuously inspired by you. I know I sound like a broken record. I feel like every time we talk, I'm like, my gosh, I'm so inspired. And I am like just all the time. And you continue just to support and uplift and just be an amazing, amazing person. And, thank you so much. I, I, you know, tell people find you at people can connect with you. They might want to reach out and ask questions or work with you. How can they find you? Well, my.
Personal profile, Sally Mildred, I'm on LinkedIn. Boss Lady Consulting is my agency. We're on LinkedIn, Instagram, Facebook, all the things. And yeah, do connect out there, because I have a book about all the things I've been talking about coming out very soon. So it's about being a human -centric leader and really taking the lessons of life to help mentor younger leaders.
Jenny Dempsey (31:01.582)
I'm so, so excited for your book. Congratulations on getting that written and for momentum on that. I'm stoked. So excited. Thank you. Thank you. Thank you. Thanks for having me. Did you feel those goosebumps too?
Thanks for tuning into this episode of the Career Flipper. I really hope Sally's journey has inspired you in one way or another to keep going no matter what anyone else says.
You can connect with Sally using the links in the show notes. The transcription will be there too. If you liked this episode, it would mean so much if you'd share it with a friend. Hit subscribe and leave a rating and review. Your support helps me reach more listeners to offer more support to others. And honestly, some serious validation that we're not delusional. Maybe it's just me that needs that. But really, you're not alone on your career flipping journey. This is just one step.
among many, many, many other steps that you've taken and personally, I'd love to hear all about it. You can connect with me on Instagram, the Career Flipper pod, or join the LinkedIn group, the Career Flipper community to be a part of these conversations, stay inspired, feel supported, and really support others. If you or someone you know would like to feature your Career Flipper story on the podcast, email me directly to hello at thecareerflipper .com. Remember, you got this.
Thanks for tuning in to this episode of The Career Flipper. Make sure to connect with Sally using the links in the show notes.
If you enjoyed this episode, I hope you'll share it with a friend who could use some inspiration. Leave a review and hit the subscribe button for more flippin' stories like Sally’s every Thursday. Your support helps me reach more career flippers and future flippers -to -be, spreading the love, support, and motivation we all need on this journey. To connect with me, just head over to thecareerflipper .com. Keep on your path, my friend. What's the best that could happen? Talk to you next week.