Episode 9: The Reality Behind Ambition — A Conversation with Erin Winter

What does ambition really look like when life doesn't go according to plan?

In this episode, I'm joined by Erin Winter, founder of Erin Winter Mortgages, for an honest conversation about ambition, resilience, and what success really looks like in different seasons of life.

We talk about building a business while navigating the unexpected, balancing work with family, and why success isn't always measured by the next milestone. Erin shares how she approaches serving her clients, managing the pressure that comes with entrepreneurship, and staying grounded in what matters most.

We also dive into:
• What ambition looks like beyond achievement
• Why every season of life requires a different definition of success
• The pressure of feeling like there's always more to do
• Building support systems before you need them
• Learning to appreciate the small moments along the way
• Why comparing your journey to someone else's only holds you back

If you've ever wondered how to stay ambitious while honouring the realities of life, I think you'll really enjoy this conversation.

If you enjoyed this conversation, be sure to follow the podcast so you never miss an episode. If this conversation resonated with you, I'd love it if you shared it with someone who would enjoy it too.

💫 Connect with Kate Hanson
🌐 LinkedIn: Kate Hanson/Kate Hanson Co.
🌐 www.katehanson.co
📸 Instagram: @xokatehanson
🎧 Listen to all episodes: katehanson.co/podcast
💌 Subscribe for insights on resilience, alignment, and ambition.

Transcript

SPEAKER_01 0:00

Welcome to Aligned Ambition, authentically A, where we dive into the truth behind business, mindset, and well-being. I'm Kate Hansen, and I believe it's best to feel aligned, not exhausted. So join me for inspiring stories, some actionable insights, and the confidence to build a life on your terms. Today's episode is with Aaron Winter, a Winnipeg-based mortgage broker and the founder of Aaron Winter Mortgages. In this conversation, we talked about what ambition really looks like behind the scenes, especially when you are building a business in a fast-moving, client-driven industry while also navigating real life because we know life happens without any heads up or warning. Erin shares honestly about the demands of her work, how quickly things can shift, and how she manages client expectations while still creating space for what matters most outside of work. We also get into what success looks like for her in this season of life. And it's a perspective that feels both grounding and really refreshing. If you've ever felt pulled in a lot of direction, but still want to keep moving forward in a way that actually works for your life, you're going to take something away from this episode. All right. Erin, I am so happy to be here for round two. We did try to uh do our recording yesterday with a little bit of technical difficulties. So this beautiful angel was willing to try again. And I appreciate that. Uh, I'm also really looking forward to this conversation based on some of the teasers we kind of gave each other yesterday from the conversation that came up while we were chatting. And so um, just so the listeners know, we've known each other for a couple of years now. Time really flies because I still feel like you're one of my new friends that I cherish. Um, but I've had an opportunity, lucky me, to kind of see how you approach both your work and your personal life. And one of the things that always stood out to me and resonated with me is just how much you care, the level of care that you put into everything that I saw you put your mind to. And so you come across as someone who is always willing to step up, to take things on, and definitely to support the people around you. I'm just gonna keep bragging on you, Will. You have to sit there awkwardly listen to me and pump your pump your tires. Say more, say more. Um, thank you. You've also built a business where you guide people through some really important financial decisions. And at the same time you're doing that and taking care of those clients, you're navigating your own real life, obviously, caring for children and your family, your own health, and still building something special in the meantime. So what I've come to realize about ambition is that different seasons, ambition looks different, at least as far as like how we perceive ourselves and what we're capable of, because the realities around us change. And I thought that's such an important conversation for people to have, for women to have, because I feel like if we have unrealistic expectations of how easy it should have been or how smooth it should have looked, um, it could be really crippling and it's like unnecessary baggage for us to carry around. So the whole conversation is I want people to be real and honest about what it takes and how they have to make decisions and choices. So to start it off, I just want to know how are you feeling about this conversation today?

SPEAKER_00 4:02

I feel great. I um I love, you know, talking about growth and goals, and I find it really motivating. So thanks for letting me be here.

SPEAKER_01 4:14

Yeah, awesome. Um, so I always find this fascinating because everybody answers this differently. But do you see yourself as ambitious? And why or why not?

SPEAKER_00 4:25

So I do see myself that way. I always have, ever since I was young. Like it's just always been something about me. I had a drive. And um and yeah, it's just always been that way.

SPEAKER_01 4:44

Interesting. Yeah, I know um from some of our conversation the other day that um, and just from knowing you, the amount of things that you take on the variety, I'm I could definitely, you can feel when somebody's ambitious. Like you could just feel that they have this like hope or desire to learn, grow, try something new.

SPEAKER_00 5:03

It's a fun energy to be around. Like when, you know, when I'm around people that are, you know, really interested in something or, you know, ambitious, it's just exciting.

SPEAKER_01 5:14

It is even to watch them, actually, because might not be what you want to do, but it's fascinating to watch. Yeah. Um, so I want to also talk about industry because I feel like even um there's so many different professions out there, and everyone has to be handled differently, obviously. So I want to have a variety of people, but when you look at your personal industry right now that you're in, what does success actually take? Like, does it what does it require for you to be successful in your industry as far as how much time, how much you have to be available, like for showing up for your clients? That's kind of my first question. I'm gonna save the second one because last time they kind of blended.

SPEAKER_00 5:52

Yeah. So great question. And I think that, you know, it there's a season for everything. And my role is no different than that. Like there are days that, you know, I'm up early, I'm working before I send my son to school, I'm in the office all day, and then I'm often working till midnight, you know. But with that being said, you know, it's not all of the time. And but there is a season for it. And so I think that I've never lost sight of what I'm really thankful for that my career gives me, and that's a lot of flexibility to, you know, to be there for my family, you know, to be a good friend and to to do things in other areas of my life. And so it's never a trade-off that that I am not thankful to have the opportunity to have, if that makes sense. So it does take a lot of hours and and a lot of work and and effort, but I'm thankful for the the life that it gives me and the flexibility that it gives me as well.

SPEAKER_01 7:11

Yeah, I found that like um a lot of new business owners or solo printers, it's getting used to that instead of a nine to five that like is specifically in your industry. I'm just thinking about when my husband and I have been looking at houses and all of a sudden we find something how it's like boom, boom, boom, things happen so fast. Like you have to have your approval and you have to have all the paperwork in a line. And I'm just thinking about you guys getting that call of like, hey, I need these things right now or right away. But then you could go probably days without people like knocking down your door to get it. And it's like, it's an interesting where business kind of comes like that, and you get used to that.

SPEAKER_00 7:46

Mm-hmm. Absolutely. And, you know, so for someone, you know, that would be, you know, set up and they do have the pre-approval, et cetera, like they, I'm gonna have a relationship with them and we're gonna have an agreement that they're gonna keep me informed. And so it's not necessarily all of a sudden. Like my clients are often really communicative. They're like, just you know, we're going house hunting, just you know, we're gonna offer on this house. And so, you know, I will be ready. But there are other instances that, you know, you do get that call all of a sudden because maybe it's someone that is in a stressful situation that does have a really tight timeline that I've never heard from before. And it's like a please, can you help fix this? You know, and that's what I'm here for. That's why I do what I do, is because I love helping people and trying to alleviate stress and you know, find solutions to problems, but it can really erupt and and change my schedule all of a sudden, for sure.

SPEAKER_01 8:56

As you're describing that beautiful process between you and your clients and realizing we are the problem because we look for nine years. So then it's like things change over the time, and um, I'm realizing we're the ones that keep starting fires. So that's an interesting thought to be prepared ahead of time.

unknown 9:13

Yeah.

SPEAKER_01 9:14

It can all go smoothly. What a beautiful thought. Okay, so that can understanding that success in your industry um kind of looks like that, that it could be different times, but that you get flexibility, right? There's like that trade-off. How would you um say that success in your industry looks like for you specifically? Like what would a successful career profession look like to you?

SPEAKER_00 9:38

Oh, you know what? That's tough to answer because I think it changes frequently for me. You know, I set, you know, yearly goals and and you know, five-year goals, that kind of thing. But the industry changes so quickly. And, you know, different opportunities present themselves as, you know, technology changes, relationships grow and evolve. And, you know, I think that I do not know the answer to that. I don't know if I will ever feel like I've reached it because I think that is a natural thing that drives a lot of us solopreneurs. Um it is nice to be able to have a way to measure success. And so for me, that's where my yearly goals come in. Like, so I can kind of have that measurement um tool. But to actually, you know, reach that success, I don't know. I don't know what that looks like.

SPEAKER_01 10:46

The other thing I think is interesting is when I talk to all kinds of business owners about goals, it often goes to financials. We have to go to something, like you said, that you can track, like that that's actually tangible, like that makes it easier to see your progress. But like so interesting to me, and maybe as you get older, success is also about like time freedom or time like to have that autonomy. Like sometimes it's like uh I worked with someone and their their idea of success was so fascinating to me, and it made you feel something because it was so personal as far as how much they wanted to travel, how much they wanted to be supported by a team. So they had such a clear understanding of like, I'm building towards it, but I know what things I want to put in place. And I feel like this next generation coming up is doing that because I've been hearing a lot, specifically in the med field, where they're starting out working three days a week or four days a week because they are hearing about the burnout and they're hearing about the backlogs and the wait list, and it they don't want to sacrifice their own mental health and wellness. Are they learning from the last generation's mistakes? Maybe, right? But I just think it can't just be the medical field. It's gotta be feels like the next generation is just at least considering like what is the trade-off if you give everything to your goal or your profession and you sacrifice like the the well-roundedness of everything that you care about. So it's just success is really interesting. And I think in different industries, it's like a success showing up consistently, is success like being like following through when that might be something that someone struggles with. But I know what you're saying too, and that's something that I considered your industry has to change with like politics and with the like all kinds of outside factors. Yeah. So that's another interesting aspect. You kind of got a bless and release. Like, here's what I'm gonna do.

SPEAKER_00 12:37

But COVID was a big jump or a big industry change too. It just moved a lot online. I was already doing a lot online with e-signing and and that kind of thing, but it really pushed the entire industry, you know, to evolve more quickly. And so I think it's improved efficiencies in many ways, which means time can be allocated in a thoughtful way. However, on you know, we just we need to be just as aware that we're finding ways still to interact with our clients in a meaningful way so that we can really hear them out and understand their needs in a way that I don't think you can just with a questionnaire technology. And so, you know, I think it's increased efficiencies in many ways, but we still need to be thoughtful as to, you know, our touch points, if you will, and the relationships that and intention we put behind relationship building. And so, yeah, so it's changed a lot and in in exciting ways, and we'll continue to do so, but always still needs to be weighed out and balanced how that change is playing out.

SPEAKER_01 14:02

Yeah, and it is interesting how much relationships play a role, like for people to know like and trust you, but like with big financial decisions, you really have to trust that someone it's like dating because they've got to have your best interests at heart and like be able to help you navigate stuff that you're not familiar with. Um so then, okay, what comes up for me a lot is like when real life happens and it's often a challenge or something that could happen, say with family members, with your kids, maybe it's something with your own health. Right now, in your mind, how do you manage that alongside your current professional expectations, like your client support and the level of care you expect from yourself to give? How do you manage that when life happens? Because it doesn't usually give you warning, it just happens.

SPEAKER_00 14:51

Well, you know, I that's a good question. I think that I try to, you know, within my business in those moments, set expectations, you know. So if it's a quick message, you know, to a client that is expecting me, etc., you know, just giving them a quick update as to when they can, you know, expect the delivery of the email or whatever it is. And so setting expectations is a big thing. Um, you know, one thing that I've learned from you, Kate, is, you know, to have others that we can rely on. And so that's something that I've implemented. I do have have some others that work alongside me now. And that has been huge because even the the emotional weight that it takes off, knowing that if you have to take a beat and just do something else for a minute, that things are still getting done in the background, like just the weight that takes off is honestly really for me, for me, it's a really big deal. And so, you know, I would say just trying to have the the proper support in place and ensure that communication is strong and um and hope that the problem resolves itself quickly.

SPEAKER_01 16:23

We can always have faith in that too. I I always like to talk to people about like prepare for impact. So if we know life can happen, look at your life right now and what is barely holding on by a thread that you know you need to back up or change or delegate because you don't want to wait until you're at your maybe lowest moment to have to figure out and make those decisions. So yeah, I love that you said that. And so have you kind of set you just said you kind of put some things in place so that you're prepared or protected if something were to happen. That's amazing. And don't you feel like just knowing that that peace of mind? Like I imagine, even on your nervous system, knowing you're taking care of yourself, that that's gotta help.

SPEAKER_00 17:07

Yeah, absolutely. Absolutely. And like I think all the time, like, this is maybe morbid of me. But I think like, what if something happened to me? Who would pick up my clients' files? Like they're in the middle of doing big things, and what if suddenly I'm just not answering, you know? And so I get really um like specific about like if I'm going away somewhere or if that's like everything needs to be like perfectly done. So it's like super, you know, organized and well laid out, should someone have to pick it up. And I probably shouldn't think that way, but also kind of irresponsible of me not to, you know, and so just trying to set up processes and procedures so that, you know, I can be at peace knowing that absolutely everything is done and and properly completed has been one of the things that that I've really worked on that has has given me that added assurance. I don't know if that really answers your question, but it's what came to mind.

SPEAKER_01 18:22

No, it does. And I I would like it's interesting because we had a little bit of a conversation yesterday, so they're kind of blending in my mind, but we talked a little bit about that whole how you do some things is how you do everything and your reputation, how your reputation precedes you. And we think about that um like reactively, but like how we respond intentionally when things are good. But I don't think enough people and we say, like, oh, it might be morbid. I think that's the problem is that we're not preparing. It's not you're expecting the worst outcome, but you preparing for is making it less likely it'll happen. And I used to think people like that, like, oh, are they ever tight or like my God, they're what a control freak or a detail obsessed person. And now as I've gotten older and more mature, and I've seen businesses and things that have happened to them, I'm like, they're so lucky they did take the time to get ahead of that because it helps so many people not feel stressed and like kind of go down a spiral. So the ripple effect is worth the effort, I think. I think that's a great way to behave. Okay, well, thank you. Yeah, you're doing so great. But like, you know, you think about different businesses. Like uh my grandparents owned a ladiesware and menswear. I wonder if my grandma, like if she all of a sudden couldn't work or was sick, like what would she have done? She probably had people in place. A couple of people worked at the store. But I just think, how many business owners have that coverage if something happens? Like, you gotta go turn on the lights, open the store. Like, what happens if you can't and you need that revenue? Um, but that's a whole other area. So then you're supporting people with big financial decisions, so like purchasing of a house, lending, all of those things, which can feel overwhelming, definitely to the people if they're not doing it often, like this is your industry, but it might be something they do a couple times in their life. How has supporting those people shaped your own resilience both in business and in life? Like, what have you learned from that that you took on so that you're more like prepared?

SPEAKER_00 20:23

Um, so you know, I think that my life has prepared me for this role. Um, and so I I almost think it's the other way around. And, you know, I am a very resilient person and I love planning and I love problem solving, you know, and you know, my life has had many ups and downs of its of its own, you know, and everybody has, you know, challenges. So I don't think I'm unique in that. But I do think that I, you know, I really never gave up. Like I always tackle things really intentionally. And so I bring that um, I don't want to say success, but it's not wrong. But you know, when when I've had challenges, like I just never gave up and I I figured out, you know, a way forward that had a good result. And I think that I take that same approach to what I do, you know, is I um I received a kind of a joking award at work once for like the being the person that never gives up on my clients. And if you look at my Google reviews and stuff online, like people will will make lovely comments like that, like without Aaron, I don't know where I'd be. And like that's because I just am so stubborn about it. And I and I will look at every single different angle until I can find the best solution. And So, you know, I think that that's what's prepared me to excel at this. And I I hope, I think and I hope that that people understand that that's the kind of, you know, and energy and an intention that I'm bringing to each and every one of them. And, you know, I I want the absolute best, you know, solution and scenario for them. And I I hope and I think that they understand that I'm very genuine in that. And so I think that that's what has prepared me for this.

SPEAKER_01 22:38

Yeah. And that does make sense that it would be the flip of like how you show up and the lens that you look at your business with and how you support them. Um, this is kind of out of order, but it was an interesting part of our conversation yesterday that I didn't want to miss. But we talked a little bit about knowing when you've done enough. Like when you work for yourself, the list is endless of what you should do or could do. And then it's like, how at the end of the day, to me, this goes back to ambition because I feel like ambitious people want to conquer the world in a very short time. How do you personally manage the unending list of things you could do, should do, versus like, here's what I really got done. And oh, I got the flu. So that list of things now just got pushed. Like, how do you handle that internal like thought and pressure that we could put on ourselves to am I doing enough? When do I know I've done enough?

SPEAKER_00 23:34

So I don't know if I will ever feel that I've done enough because there's so much that I want to do. However, I have implemented a practice probably about you know a year ago now, and it's choosing the three things every day that move the needle for my goals as far forward as possible. And if I do those things, that feels great. And I know that I have methodically selected them. You know, I feel great about getting them done, whatever they are. And everything else that gets done, I'm a big list person. So everything else that gets done, you know, I love checking things off. That feels great. But I know that I've, you know, been intentional with my bigger, bigger to-dos. And so that is how I try to control that.

SPEAKER_01 24:46

I love that because that what you say, it gives you a sense of control. Like so for that part of our brain that needs control, it's like, okay, you're in control. There's my three priorities. And then I think more is three. Yeah, you know what? I've a little thing that I've picked up, but I've been doing this for like, oh my gosh, 15 years, is that I I've always kept a general schedule of like, here's what I have to get done, meetings or whatever. But I learned this from I can't remember who, I wish I could thank them, but I take a done list. So whenever I finish a task, I write about it. And so, like we talked about for a minute yesterday, is that I could have one box that says like create landing page of a website when that's not my background, my job, or anything. But as a solopreneur, you figure it out. That might take me eight hours and it looks like I checked one box. So now it's more like I put down what did I actually do? Checked the wording, got nice images, figured out how to edit, figured out how to do back end AI work. And then I'm like, then when I write it, it's for myself at the end of the day acknowledgement of like, you did a lot, like great job.

SPEAKER_00 25:56

That's a good practice.

SPEAKER_01 25:57

Even subconsciously, I've always done it. So I don't maybe reflect as much as I should, but I know when if I ever feel like, what have I done? I can look and be like, okay, all right, you did you've done a lot. You're good.

SPEAKER_00 26:09

Yeah, I really like that.

unknown 26:11

Yeah.

SPEAKER_01 26:11

And it's fun too. It's kind of like a journal. You can look back and remember everything. Um, so the last question I have for you are two last ones. The last one is so in this season of life that you're in right now, not doesn't have to just be professionally, it could be also personally. What does success feel like to you as an ambitious individual at the stage of life that you're in right now as a mom, working, building a business?

SPEAKER_00 26:38

So I think that in the first part of my my adult life, I have always felt like I couldn't ever relax. Like I needed to work so hard. And, you know, I don't regret that because it's one of the things that I love about myself. But, you know, even this morning, um, my daughter's Anya, she's 21. She's amazing. And we were outside just enjoying the sun. It's like what the second nice day in our year. We had coffee outside, and our cat was like running around outside and just like enjoying being outside too. And I said to Anya, I said, This is gonna be the best part of my day. And and that might sound silly based on the scene I set, but like I'm there with her, the sun is shining, you know, like, and so being able to like take those small moments and and soak them in for a second and realize how lucky I am in those moments. To me, that feels really successful because I'm not thinking of the next things I have to do, and I can be in in those moments for a few minutes.

SPEAKER_01 28:05

The best part of my day. Um, I there's this video that's out there, you've probably seen it. And the guy says, If I gave you a million bucks, would you be happy? Would you be excited? Can anybody get your mood down that day? And the guy's like, No, no, have you seen it? No. And he goes, Okay, well, how about what if I gave you 10 million? The guy's like, oh my goodness. And he said, But the the trade-off would be you can't wake up in the morning. And the guy said, No. He said, So waking up is worth more than $10 million. And we cried to give it. And I just thought, so those moments like that you have, I had them with my girls driving into school, or if we're talking and laughing at a joke together, and I just try to like savor it for a moment, just like marinate in it.

SPEAKER_00 28:43

You try to like lock like lock it into your memory, you know? You're like, I need this feeling to be here forever.

SPEAKER_01 28:49

Yes, because it's priceless, you can't even put a dollar amount on it. So, oh, it's such a beautiful example of what success looks like in the season of your life, Erin. Thank you for sharing that. The last question, this is the last one, is if somebody's listening to this and they're trying to figure out like what does ambition look like for me in this season of life, whether they're starting out or maybe they're in the same situation. They've got kids who are a little bit older and they're working on their profession and they're thinking the future, like what would you tell them? What would you want them to remember as they're trying to figure out how to still be an ambitious person, but they've got realities of life kind of weighing on them a bit?

SPEAKER_00 29:27

Well, you know, I think that the the first thing to remember that is easier said than done, but should be a focus nonetheless, is not to compare because we're all on our own journey and no one is living the same life as someone next to them. And so, you know, never compare and and think about, you know, what feels really intentional and and good for you as a person. But I also think like set those big goals. Don't be afraid to set the big goals and then set the goal and literally just work backwards to what I need to do to accomplish it. You know, I think it's easy to feel overwhelmed by by our lives because a lot of things in them can be really overwhelming if that's what you focus on. But decide what you want and and set it and then just go for that and and just find, you know, solutions ambitiously. And so don't compare and and don't be afraid to set big goals, would be my advice.

SPEAKER_01 30:46

That's beautiful advice. And I'm totally, I totally back you. That's a a beautiful thing to leave off on, um, because there's still hope. People, no matter what season you're in, it's a season. And so I love it. Still aim high, and that could be kind of your life raft if you have something outside to focus on.

SPEAKER_00 31:06

Well, if you think about it, like what we can accomplish in a day, a week, a month, it's not like sometimes it it can feel bigger than others, but not necessarily a ton. But then when you look back on like a full 12 months, your world can be entirely different. And so, you know, I think people should go for it.

SPEAKER_01 31:30

Yeah.

SPEAKER_00 31:31

Oh, love it.

SPEAKER_01 31:32

Go for it. Okay, we're gonna leave it there, Erin. I am so grateful for your time. And uh, I hope you'll stay on for a minute after I shut this down so that I can just say goodbye to you. But um, for anybody listening, if any part of this message resonated or you know there's someone in your life who needs to hear it, please share and leave a review. Let us know what you think or what you want to learn about um when it comes to building up your resilience and and staying ambitious through the challenging times. Um, Erin is a beautiful example of that. Someone who's still smiling and savoring coffee in the sun with her daughter when she's experienced challenges in her past that people would think, how do you survive those things? Like there's so many things that we can overcome. So just don't give up. And thank you so much for listening today. Bye. Thank you so much for being here and for sharing this podcast with those who need to hear it. It truly makes a world of difference in getting this message out there. And I would love to connect with you. So go check out my website at gate.co. And remember, that is the best point online.