Share Your Story, Build Your Brand, Own Your Pivot with Alyssa Olerud
Guest: Alyssa Olerud I Founder, Fearlyss Media
What happens when success on paper no longer fits the life you’re trying to live? For Alyssa Olerud, that realization hit hard—in the middle of a national sales conference in Las Vegas. Today, she’s the founder of Fearlyss Media and creator of the Fearlyss FLOW Framework, a system that empowers professionals to confidently share their stories and turn their personal brands into business assets.
In this inspiring episode, Alyssa shares her powerful pivot from corporate trainer to full-time entrepreneur and breaks down how storytelling, structure, and self-trust helped her build a business that works for her life—not the other way around.
Whether you’re stuck in overthinking, struggling to show up online, or trying to balance growing a business with raising a family, this conversation is packed with insights and mindset shifts that will help you move forward with clarity and confidence.
We cover:
✅ The Las Vegas moment that sparked Alyssa’s pivot
✅ Why personal branding starts with your story
✅ How the FLOW Framework helps turn content into connection
✅ Balancing motherhood, mindset, and marketing
✅ Embracing ADHD as a strength, not a setback
✅ Letting go of the “success = a number” myth
Takeaways:
Pivoting doesn’t require a perfect, linear plan, but it does require self-trust, support, and clarity on your “why”
Entrepreneurs should give themselves permission to experiment and find their niche
Your personal story isn’t just valuable—it’s vital to building a brand that converts and connects with potential customers
Alyssa’s FLOW Framework (Foundation, Lifestyle, Offer, Wisdom) helps turn your expertise into purposeful content
ADHD and imposter syndrome can be challenges—but also superpowers when you learn how to work with them
Mindset work is non-negotiable in entrepreneurship—and therapy, boundaries, and routines are key to long-term success and work-life balance
Balance isn’t a perfect equation—it’s about building smart guardrails and listening to what your body and life need
Showing up on LinkedIn as yourself (yes, even with a selfie!) outperforms curated content every time
Delegating isn’t weakness—it’s a power move that frees up energy for what you do best
Success isn’t just about numbers. It’s about personal alignment, flexibility, and building a life that actually feels good
Memorable Quotes:
Alyssa:
“We can do anything if we get out of our own way.”
“You are your brand. It’s not just what you’re selling—it’s your story…Being able to tell your story is what builds trust—and trust is what sells.”
“I had to tell myself: people invest in me, so I have to be willing to invest in others.”
“Nobody knows how to be their own boss when they start. You have to give yourself grace.”
“ADHD isn’t something that’s wrong with me. It’s just how my brain works—and I finally stopped resisting help.”
“The FLOW Framework helps you take your expertise out of your head and turn it into content that connects.”
“Balance? I don’t even know what that word means. I just put guardrails in place to protect my energy.”
“Every day is a surprise in entrepreneurship—but you might just surprise yourself with how much you can handle.”
Kristy:
“We don’t just wake up mentally strong—it’s built through baby steps, reflection, and grace.”
“Entrepreneurship turns all of us into DIYers—whether we want it to or not.”
“When you build a business that fits your life, instead of forcing your life to fit your business—that’s where the freedom is.”
“Just because it looks like success on paper doesn’t mean it feels like success in real life.”
“If you want to grow a business you love, you have to show up as yourself.”
“It’s okay to rest. Sometimes rest is what lets your next creative idea break through.”
Chapters:
00:00 Introduction to Pivotista and Alyssa Olerud's Journey
02:02 The Moment of Clarity in Las Vegas
05:53 Diving into Entrepreneurship: The Initial Steps
09:19 Finding Your Niche and the Importance of Storytelling
12:54 Building Authentic Connections in Business
16:34 Navigating Setbacks and Embracing ADHD
21:51 Mindset and Growth in Entrepreneurship
24:14 Scaling Beyond Success
28:06 Balancing Business and Family Life
33:09 Mindset Surprises in Entrepreneurship
35:47 Finding Your Why in Business
Connect with Alyssa Olerud:
🔗 Website: https://www.fearlyssmedia.com/
🔗 LinkedIn: https://www.linkedin.com/in/alyssaolerud/
🔗 YouTube: https://www.youtube.com/@AlyssaOlerud
🔗 Instagram: https://www.instagram.com/fearlyssmedia/
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Disclaimer:
A friendly reminder: the information presented in this podcast is for educational and informational purposes only. It is not intended to diagnose, treat, or cure any medical condition, nor is it intended as a substitute for professional medical advice, diagnosis, or treatment. Always consult with your doctor or a qualified healthcare professional before making any decisions related to your health and well-being or starting any new wellness practice, including mindfulness and meditation.
Transcript:
Kristy Cook (00:02)
Welcome to Pivotista, where we help women leaders and founders turn their overwhelm into burnout-proof success. I'm Kristy Cook, your guide out of survival mode and into success that fuels your ambition and your wellbeing. If you've ever felt like you're meant for more, but life, work, or self-doubt keeps pulling you back, today's guest is proof that your path doesn't have to be linear to be powerful.
Alyssa Olerud is the founder of Fearless Media and creator of the Fearless Flow Framework, a simple yet game-changing system that helps entrepreneurs show up confidently, tell their story, and turn their personal brand into a business asset. From a career in sports to corporate sales and now to full-on founder life, Alyssa's journey is a lesson in betting on yourself and building a business that fits your life, not the other way around. We're diving into what it really takes to pivot from corporate to entrepreneurship, how to stop overthinking and start showing up, and why your brand is more than just your logo. It's your legacy. Let's dive in.
Alyssa, welcome to the Pivotista podcast. I'm so excited to have you here. I've really been looking forward to our conversation. How are you?
Alyssa Olerud (01:33)
I'm so excited. I'm good. How are you doing?
Kristy Cook (01:36)
Yeah, doing well. You know, your story really speaks to so many of the women listening. Those moments when things look successful from the outside, but on the inside, we know that something just needs to shift. From working in pro sports to sales training to then founding Fearless Media, you have navigated some pretty bold pivots.
And you've done it all while raising a young family and building a business that actually supports your life. I'd like to start today with your biggest pivot, the one that led you to becoming an entrepreneur. And it happened in Sin City of all places. ⁓ Can you set the stage for your story by taking us back to that moment in Las Vegas where you realized something had to change in your life, and what was going through your mind and how did that clarity spark the creation of fearless media?
Alyssa Olerud (02:33)
Sure, so I would say the decision to start Fearless Media happened in Las Vegas and I'll walk you through that in a moment. But if I'm being totally honest, that was a thought in my mind for years that just was kind of always on the side and I would come up with an excuse or push it away and say, I'll do it later. But when I decided that it was time for me to start a business, I didn't even have a name to be honest.
I just knew that I needed to do something different than what I was doing. So I was in Las Vegas for the national sales conference for the company I was with at the time. And traveling had always been my favorite part of my job. I got to travel pretty regularly. I got to see new places pretty regularly and I loved it. But as I started to have kids, I have two kids who are now two and four, that got a little harder. When my oldest son was born, I stopped traveling for a little bit. And then after a couple months jumped back in. And then when my second son was born, again, it got a level harder, you know, because there are two kids now. And when I was in Las Vegas, my son was sick. And my husband was on the phone kind of panicky, not really sure what to do. And I was a three hour flight away, and I felt helpless. But I also was breastfeeding at the time and started to feel like mastitis might be coming on. I was not feeling well. So physically I wasn't feeling well, mentally I wasn't feeling well. And I remember clear as day thinking to myself like if I am not happy to be in one of my favorite cities, then there is a huge problem. And through a series of events, I actually texted my therapist while I was there. And she talked me out of quitting on the spot. And we came up with a plan and shortly later I put in my notice to leave my corporate job and the planning on Fearlyss Media began.
Kristy Cook (04:24)
Wow, that's incredible. And I love that you had the foresight to reach out for support and help in that moment instead of just sort of blowing it all up at once. Well, in my last one of my last episodes talking with someone, they mentioned the importance of having this board of directors around around us that we
Alyssa Olerud (04:39)
I was this close.
Kristy Cook (04:52)
create and self-select so that when these moments come up, we actually can reach out to them and get their advice and kind of talk us off the ledge. And so I applaud you for doing that work.
Alyssa Olerud (05:06)
Yeah, that was an important
Kristy Cook (05:09)
Yeah, it's good, especially looking back now, I'm sure going into entrepreneurship with a plan instead of feeling
you know, so much pressure because you did blow up your life first, I imagine made that a little bit easier.
Alyssa Olerud (05:22)
Mm-hmm.
Yeah, I will say when I left my corporate role, I didn't have any clients. So I think a lot of people will take time over a year or so to build up their roster and then leave their job. But I knew myself well enough to know that I would make an excuse. I would say that I was too busy at work or if I was working and with the kids and building a company, would be too much. So I made the decision that if I was going to do it, I had to go all in.
And luckily my company was very gracious in supporting the way I exited. So I didn't just give a two week notice and leave. actually stayed for, I think it was another nine months and just over time lowered my number of hours, which did give me sort of that ramp up with the business, but it was a really good way for me to dive all in without putting myself into hot water too quickly.
Kristy Cook (06:16)
wow. That's amazing. And how wonderful that you were able to have that honest conversation with your employer about, you know, your next chapter. And so when you went all in, talk to me about what that looked like. I imagine initially there were some mindset challenges around fear and what did I just do kind of thing. But can you talk to me about your experience diving into entrepreneurship?
Alyssa Olerud (06:26)
For sure.
Yeah, hard for me to answer because I definitely had fear, but I don't think I acknowledged it for a solid nine to 12 months. I was just put on the gas and hyper focused. I think that's one of the benefits of having ADHD. I have very severe ADHD and when you're interested in something and you are passionate about you hyper focus on it. So I gave myself that permission to really just dive into every area and get questions to things that I didn't know the answers to. And I didn't know what I didn't know. So I just had to welcome it all and figure it out. And fear kind of came later when I was like, my God, if that wouldn't have worked out we would have had a problem.
Kristy Cook (07:36)
Looking back, my goodness, what did I do? Thank goodness it worked out. ⁓
Alyssa Olerud (07:40)
Yeah, exactly.
Kristy Cook (07:43)
And so what steps did you take? You you mentioned that you didn't have a name yet for the business. Does that mean that a clear idea of what the business would become? knew that you wanted it to be branding focused? Talk to me about how you found your niche.
Alyssa Olerud (08:00)
Sure. So in the beginning, I was probably like a business coach's nightmare because I didn't have a specific clientele that I wanted to work with. I knew that I wanted to work in the social media space and I didn't even know if I wanted to be on the creator side or if I wanted to be managing social media. And I gave myself the permission to figure that out as I went, which only got me so far, right? Like you have to clarify your brand message and you have to clarify your goals and all of that. But in the beginning, I let myself take on different types of clients so that I could figure out exactly who I wanted to work with. And through that is how I honed in on personal branding, because I realized that with every client that I was working with, whether they were in corporate sales, or they were in dentistry, or they were in mental health, regardless of industry, people had trouble sharing their story.
And as we talked about earlier, my story is the opposite of linear. It seems to regularly. And so I've gotten pretty good at weaving those pieces together and talking about my story, but it took me a long time to get there. So when I realized that other people had that struggle, and I mean, typically the smartest people in the room, I would be like in awe to sit next to them, right? And then they would tell me that they were having trouble talking about X, Y, and Z. So I just realized, you people need not only the confidence to tell their story, but almost like a framework that helps them take it out of their head and figure out how they can share it with people. And we have the ability to do that through social media. So it took me a while.
It took me about a year to get there, but I figured out like we use social media as a tool, not only to grow our business, but to really connect with people and tell our stories, which will in turn grow our business. So I hope that answered your question.
Kristy Cook (09:57)
Wow. Yeah, absolutely. And it had me come up with two more because of it. So the first is one, I just, love that you gave yourself permission to experiment I know when we're entering into entrepreneurship for the first time, all we're hearing about is the important of the niche, niche down, niche down, niche down. And that can be really difficult to figure out in the beginning.
It's kind of like when you come out of college, for example, and you think you're going to go into whatever career you majored in without maybe having any life experience around that career. And stepping into entrepreneurship, especially a service-based business, has the same feeling, right? You don't know until you've done the work and worked with certain types of clients who you're really going to enjoy working with, and we put so much of ourselves into growing our businesses as solopreneurs that it feels so personal. And so all of those feelings and the people we're working with, of course, we're going to carry those experiences into our day-to-day life. So really applaud you for kind of quieting that niche pressure and allowing yourself to, to really discover what felt right.
And I'm wondering, can you talk to us a little bit about why it's important as entrepreneurs that we have a story and that we share that story?
Alyssa Olerud (11:28)
Yeah, of course. So I always say you are your brand. It's not what you're selling. Some of it is the experience and the client turnaround, but especially for service based business owners, small business owners, you are the face of your brand. And you can educate, you can do all of the things that an expert would be doing. But if people aren't buying into you, they're going to go and work with the expert that they can relate to, that they can buy into, that they see some sort of credibility in. So, let's say you are a lawyer, right? That's a great example. You can be the best lawyer on the face of the planet. But if all I know about you is that you have a degree from Harvard and you've been practicing law for 10 years, that's not going to mean anything to me most of the time, right, your clients have never needed a lawyer before. So I'm looking for someone who I trust. I'm looking for someone who I believe is going to get me through to the other side and being able to tell your story helps paint that picture.
Kristy Cook (12:20)
Alright.
It makes so much sense because at the end of the day, we're humans working together. And especially in a service-based business, you just feel so much more connected to the people that you're hiring when you can relate to them on that human level.
Alyssa Olerud (12:48)
Mm-hmm. Absolutely.
Kristy Cook (12:49)
And so how do you help your clients discover their story?
Alyssa Olerud (12:54)
By listening, honestly. I know the right questions to ask. I've been told that that is my superpower is asking questions. I ask a lot of questions. And that might be going back to the ADHD thing. I just have this inquisitive mind and I want to understand the path that people took and the decisions that they made and why. So when someone is telling me their story, I've gotten really good at pulling out what would be a good content piece as it relates to their business. And part of it is also just giving them inspiration. Because if we're going back to the fact that people often don't wanna share their story, it's because one, they have some sort of imposter syndrome. Two, they don't wanna be pompous. They don't wanna seem salesy. They don't wanna be all of these things when really their story is what's going to inspire people, right?
So sort of giving them that pep talk is a really big part of my job, but it's also fun because not only do I get to be their social media manager, their personal brand strategist, I get to help them step into that next level of themselves. And for me, that is super fulfilling. So to get back to your original question, I listen to their story, we go through their history, we talk about their future goals and things like that. And then we put it into what content can help them reach those goals via social media.
Kristy Cook (14:16)
Yeah, and I also think, know, especially, you know, lot of service based solopreneurs use LinkedIn as a major stepping stone to finding businesses and connections, network and so forth. And I feel like maybe this is shifting a little bit, but it feels like with LinkedIn in particular, there's this pressure to not show up as yourself, right? And to just kind of be buttoned up and put and, it sounds like we can actually capitalize on our story and being our natural authentic self on even platforms like LinkedIn when we're trying to promote our business.
Alyssa Olerud (14:53)
Yeah, absolutely. I have seen such a shift in the type of content shared on LinkedIn. ⁓ the stat is something like only 3 % of users on LinkedIn are posting once a week. So even if you're sharing something about your life once a week, you're light years ahead as far as brand awareness and things of that nature. So we've seen in the past year or so, LinkedIn influencers, we've seen people start to sell on LinkedIn. So to some degree, it's almost becoming more social than it has in the past. Similar to Facebook when Facebook was the most popular platform and then Instagram and then TikTok. I mean, LinkedIn has all of those components. have the video component, the newsletter component, they offer so much and people are starting to shift there. And we're seeing with our clients in particular, a post with a selfie is going to outperform any other type of content that you can put on LinkedIn. And it's kind of wild because people will push back on me when I tell them that. And almost every time I'm not surprised when I get the message like, my God, look at this. It's still getting likes weeks later. Why do people care so much about my selfie? And it's like one because you're normalizing it.
People think you can't do that on LinkedIn, but we want to see you in your element. We want a break from all of the fluff and the corporate jargon that is thrown at us and the cold messages of people trying to sell us in our inbox. Like we just want to see a real person and that type of content performs really well. And I see it getting even more social for a lack of better term in the future.
Kristy Cook (16:35)
And it really does feel, I know in my experience in building this business and in building the law firm when I had it, know, law firm can be a very stuffy experience as an entrepreneur if you let it, but it doesn't have to be. Even in situations, keep hearing about, and I've experienced it myself, the importance of building community around your business in order to grow it.
And the only way you're going to be able to grow that community is if you're showing up authentically, because we can sense when someone's not being themselves. And it's been a really fun thing to see shift because I feel like I only know how to show up as myself for good or bad. ⁓ So that's kind of been a relief because I would, I...who would go to these networking events and feel kind of overwhelmed by the network process, feeling a bit, you know, introverted, and now it's like, Oh, I'm just going to give myself permission and take, take three seconds of bravery to step into the room and shake some hands. But when we're talking, just give myself permission to be myself. And the people who connect to me then are going to be people that I'm naturally connected to as well, because I showed up as myself and shared my story.
Alyssa Olerud (17:53)
Exactly. Mic drop.
Kristy Cook (17:59)
So talk to me about, you figured out what your niche was, you're really excited about it. I can hear that it lit you up when you landed on it. You're just loving the work that you're doing right now. Along the way, did you experience any setbacks in your entrepreneurial journey? And I'm also curious, there are a lot of folks out there leading amazing businesses with ADHD or getting ready to start those businesses if you have any tips and tricks around that as well.
Alyssa Olerud (18:27)
Yeah, I'll start with setbacks because I've definitely had my fair share.
Being your own boss, I guess this does relate to ADHD, as a person with ADHD is mental hurdle that you're never necessarily prepared for. The same way I said that I knew I needed to go all in and put my focus on the business or I wouldn't do it. I knew about myself that there were certain things I would need to get under control. So as far as mental setbacks, there was a process for me in the beginning where if I wasn't producing income or I wasn't getting rave reviews from clients, or even if a client would text me, I would assume something was wrong. And I lived in this spiral of like, this business is my worth and if it fails, I fail. And that was a really scary place to be for about six months. But with my therapist, I am a huge advocate for mental health and therapy and all of that. By working with my therapist, I still continue to go through some of these things. I have a therapy appointment literally right when we get off of this call. And it's something that I work on regularly. So that mindset shift and that mindset hurdle sent me back a handful of times. And then there was the actual financial piece of it.
In any business, client flows up and down, right? I had asked my husband, can you give me six months to prove to you that this is a viable business? And then can you give me a year to match my salary from my previous job? If I could do those things, like we can do this. And that mental stress, you know, really took a toll when numbers weren't hitting the way they should be.
And then when numbers did start hitting the way I wanted them to, the setbacks were how do I keep up with this? So I was always very honest and open with my husband, with even my clients on what my capacity was and where I was at. And while I would call some of those things setbacks, I will say that they were more of a learning opportunity to really just fine tune what I needed to do for my business and for my mental health.
Um pivoting into the ADHD piece, I will also say very proudly that I am medicated. Okay, um I resisted any sort of ADHD medication for a very long time because of the stigma around it. And I got to the point where I was really, really struggling. And I look back on just life in general, even before entrepreneurship and things that would have been different if I had accepted help. And the reason I decided to start medication was because the psychologist said to me, you know, if you had a heart issue, and we told you you needed medication, would you take it? And I said, yes. And she explained to me that with ADHD, it's not something that's wrong with me. It's a brain thing, the way my brain triggers and that medication would help me. And I can say pretty confidently that taking that medication and allowing myself to start that with my therapist not only changed the way I approached my business, but probably saved my life to some degree. I could go on and on about ADHD and business clearly. So I'll pause here. And if you have any specific questions, we can go in any direction you think is best.
Kristy Cook (21:56)
Yeah. well, thank you so much for sharing that because I know about that stigma. difficult, first of all, to ask for help and then to get an answer what that help might be when society around you is saying, that that outcome, you know, that tool is is looked down upon or frowned upon. And thank goodness that is finally starting to shift because people like you are willing to talk about it in, my own life, I have several people that have ADD or ADHD and their lives changed completely when they were able to get the help. And then from there could then figure out the strategies to help them stay on track in their work and, you know, focus on the things that maybe they weren't as interested in and, ⁓ you know, get things turned out that they needed to turn out. So that's incredible.
Alyssa Olerud (22:24)
Mm-hmm.
Yeah.
Kristy Cook (22:51)
And it sounds like in all of that, you've done a lot of work on mindset and as entrepreneurs, when we're starting something new, especially so entrepreneurs, if we don't have partners and there's so much self doubt that can come in, creep in and every opportunity, there's so much comparison that we do with other people and similar niches and my gosh, I'm not doing all the things they are. Should I refocus and change everything about the way that I run my business?
⁓ and, it takes a lot of mental strength and you don't just wake up one day and you're mentally strong. That doesn't happen. It comes at the baby steps, like you've been talking about, ⁓ to, build up that, that mental strength and then also have a growth mindset that every setback is a growth opportunity and a learning opportunity and an experiment really.
Alyssa Olerud (23:19)
Mm-hmm. Absolutely.
Kristy Cook (23:47)
Yeah, I think you said, we can do anything if we get out of our own way. And I'm wondering now that you overcome, you've achieved those financial goals that told you that your business was the right choice and you were on the right path for does that quote mean to you now that you can see it from this successful viewpoint?
Alyssa Olerud (24:14)
That's an interesting question because I never look at the business as, you know, it's successful and now I'm done. I don't know if this is a good thing or a bad thing, but for me, I'm always looking to scale. And when we're talking about getting in our own way, for me, it's just the things that I know have gotten in my way in the past and choosing to maybe delegate them or outsource them. I'll give you an example. I tried to be a blogger like 10 times before I started my business and I would get stuck, like I would write all the blog posts and I couldn't figure out the website. And then I would go into this spiral. Like I can't even figure out how to post this. What am I supposed to do? And so one of the first things I did when I started this business was I decided I was going to get help with my website and I was going to hire a bookkeeper because I'm a creative person, the numbers scare me and I didn't want to get stuck there. So as the business continues to grow, I and purposeful about where I asked for help and how I engage with the people around me know are certain things that are going to be tough for me mentally and I want to be performing, you know, the best that I can. So I just, don't even put myself in that situation.
Kristy Cook (25:33)
Yeah, and that's fantastic. I know when we're first starting out, it's really hard to spend money on things. But when you do that analysis, like you just said, where I know what my expertise is, and I could probably figure out how to build a website or build a X, become an accountant, whatever, I could probably figure it out. But every minute I put into learning that new skill, is less time that I have building the business that I'm actually trying to grow. And so when there is opportunity to delegate, of course, know, financials and things like that are important factor, I understand. But when there's an opportunity to delegate, it is so empowering, I find, for small businesses to kind of stand up and say, yeah, it's okay to let someone else take care of this for me because now I can focus on what I'm really good at and keep building the business instead of being hindered by my QuickBooks account.
Alyssa Olerud (26:38)
Exactly.
For me, it was sort of like a mindset thing. I had to tell myself like, you have a business because people are willing to invest in you. So you have to be willing to invest in people who have an expertise that you don't. And that was really freeing for me because when, I mean, as a small business, every dollar is important, even when you get to a point that you would consider successful, right?
I really felt like I had to keep all these dollars for myself. I have to spend as little as possible. But when I had the connection of, no, you're asking people to invest in you, why would you not do the same? Like I said, it was so freeing and sort of fun then to figure out like, okay, well, what do I want to invest in? Where do I want to spend my money? Which again, that's why we have a bookkeeper and an accountant to keep us on track.
Kristy Cook (27:29)
Yeah, yeah, it's great. And the other thing too, you know, I'm not practicing law, but I always have my lawyer hat on, you know, can't permanently take it off, it's just there now, ⁓ but when you hire experts to do things for you, like accounting, your lawyer, you know, these people that can really come in and help your business. Not only are they saving you time, but they are also probably saving you a lot of mistakes, a lot of headaches,
that could cost more on the back end to try and unscramble. And so it's really, think, important from that perspective too.
Alyssa Olerud (28:01)
Mm-hmm.
Yeah, for sure.
Kristy Cook (28:06)
And so as you're starting your business, growing your business, sounds like your husband was a great support with you as you were getting things off the ground and you have your two small kiddos. How did you balance? Because running a business, starting a business can be all encompassing. Not only is it a ton of work, but your mind is just always kind of focused on it, even when you're not sitting in front of your computer doing the work. So how did you balance that with your family life?
Alyssa Olerud (28:34)
I don't know that I can fully answer that question because I don't know what word balance means. I did, I gave myself some, let's call them like guardrails That's what we call them in sales, right? Like the, this is the lowest I can go. This is the highest I can go. So when I found myself working until like 11 PM, then being tired when my kids woke up and then being cranky and then
Kristy Cook (28:36)
Right? Could you define that?
Alyssa Olerud (29:01)
wondering why I'm not feeling connected with my husband. I'm like, okay, we got to, we got to rein this in. So I would make rules for myself. Like you don't work past nine PM, you dedicate X number of days or whatever to a date night or phone free. Like I started putting my phone on silent mode from 7 PM to 9 AM, which is a very long time. But for me, it was like, I'm still going to check my phone, right? But I'm not gonna get a notification on my Apple watch while I'm trying to put my son to bed and then start to spiral. I've been talking about spiraling a lot, but that happens. That happens in my brain. So I have to put all of these protections in place because again, like if I see this Apple watch notification and I see a client's name, I'm not actually reading the text. I'm just seeing their name. And I'm like, my gosh, it's 8 p.m. They got hacked. Something's burning down. Like everything's wrong. And it's really just, I'm like, hey, I have this idea.
So to protect myself and my interactions with my family, I started silencing my phone just so that I'm not getting triggered by those notifications. And that was super, super powerful for me and my presence with my family. And the other thing I would say I do to balance is take care of my mindset first thing in the morning. I have this routine that I do that is very short and to the point because the whole wake up at 5 a.m. and get your workout in, like that doesn't work for the way I scheduled my day. So what I do is I do my gratitude journal, which takes about two minutes. I read for 10 minutes and it's always a personal development or business development books. So that's how I'm constantly exploring the growth mindset and things that I could be doing to protect myself mentally. And then I'll spend like five to 10 minutes just cleaning up.
Like if the kids left and their toys are still out or there's laundry all over or whatever, I take a couple of minutes to clean up my space because as anyone who works from home knows, like if your space is cluttered, it can affect you. So my routine takes maybe 20 to 30 minutes and I feel really good about it when I'm done and starting my day.
Kristy Cook (31:07)
So it sounds like you found this amazing combination of mindset work plus listening to those internal cues. You you mentioned feeling, you know, when you're feeling stressed or cranky or, you know, just tight that it's an indicator that something might be off a little bit and then developing some structure, not so rigid, but some structure around the way your day starts, which I imagine then carries through for the rest of the day, even as the chaos of work and life pops up around you, you're entering the day in that right head space because you've taken 20, 30 minutes to ground yourself. The best thing I ever did too was to, my phone just now lives in do not disturb mode. I have identified people, you know, like my husband, my mom, mother-in-law, father-in-law, that they can still get through to me if some emergency pops up but otherwise now nothing comes through and it puts me back in control of I can look at things when I'm ready to. Because like you mentioned, when these things are going off, whether it's your client calling you in the evening or anything else, it just takes us out of that present moment that we're in. Those moments are often so precious to come by, especially as entrepreneurs running the show for our businesses.
Alyssa Olerud (32:33)
I'm going to steal that. Constant do not disturb.
Kristy Cook (32:34)
Yeah.
Yeah, just leave it in there. It's great. And then you're always in control. And it feels so hard these days to feel in control. know, we're kind of addicted to our phones. And then even when we're not feeling the pull of our phone, other people are constantly chiming in through the 20 different ways people can message you. ⁓ yeah, that constant do not disturb is pretty awesome.
Alyssa Olerud (32:40)
Yeah. huh. Love that.
Kristy Cook (33:02)
Thanks. ⁓ So any surprises along the way during your entrepreneurial journey?
Alyssa Olerud (33:09)
I like I've spent a lot of time talking about mindset. And I wish I had something else to offer, but the mindset was the biggest surprise for me. Like when I would come up on these hurdles and have to make rules for myself and have to figure out things like, you know, a sales structure and a marketing plan and all of the things that you're not really thinking about. Like as a business owner, you know, you have to do them.
But you're doing them because you want to stay in your zone of genius. So the surprise is always like, what do you mean I have to do estimated taxes every quarter? Like, what do you what are you talking all of these things that you don't know about as a business owner? Were always surprising to me, but I would feel like a badass afterwards like I remember one time malware, got malware on my computer and I was like, okay, gotta lock everything down and gotta get this off. And I spent five hours figuring out how to code the malware out of my computer. And after that, I was pissed because I lost five hours of my day. But I was also like, I just did that somehow, right? Like every day is a surprise, I would say in the first couple years of entrepreneurship, because so many things are gonna happen and you're gonna...not have any idea how to handle them and just have to figure it out. So then you might be surprised at your reaction. It's a constant surprise.
Kristy Cook (34:33)
It is, it's a constant surprise. That is exactly the best way to describe it. ⁓ And I love that you're celebrating those wins because it's so important. Entrepreneurship turns us all into DIYers, even if we weren't to begin with, because sometimes you just have to figure it out. And it also points to the importance of having those experts around you that can even let you know that estimated quarterly taxes are a thing. Or that you need a privacy policy for your website or whatever the things are. But when those things pop up randomly throughout the day, like the malware and whatever, it's like, thank goodness there's Google. I can hop on, figure this out, at least get myself started, and understand when I hit that wall where I do need to find an expert to help me out.
So any advice then for others who are considering stepping in entrepreneurship either as a side hustle to begin or just, you know, like you did going all in any advice on helping make that decision and maybe the first six months of that journey.
Alyssa Olerud (35:47)
I would say know exactly why you're doing it. A lot of people will say what your goal is or who your niche is, kind of like we discussed earlier. And I don't think you have to have all of that figured out, but you do have to know why. Because there are going to be times when you don't land a client or you're seeing a decline in sales numbers over a period of time, you're gonna have to know big picture why you're doing it because it's so easy to get into the mindset of maybe I should just go back to a nine to five or maybe I'm not meant to be my own boss. Nobody when they start entrepreneurship knows how to be their own boss because they've never done it before. So there is grace that you have to give yourself. I'd say start there, start with grace and be open to learning from the people around you and really diving into your community, both locally and in the online space. There are so many places that you can connect with people and people that you can meet. And one thing I've found so amazing about owning a business is that people who also own a business want to help each other. It's so encouraging to see.
And I remember feeling weird about it, like going into networking groups, like, what do mean you want to help me? Like, this feels weird. It's, it's not something you're used to, especially if you come from like a fast paced corporate where everybody's just trying to get promoted or, you know, hit their number or go home at five o'clock. It's really just rewiring your brain and how you look at things, which is going to be the bulk of what you need to do in the first six months to eternity.
Kristy Cook (37:29)
Yeah, and that community when things get rough are so great to lean on and help problem solve through and and yeah, identifying your why is so important to staying focused during the difficult times or you know, a lot of us as entrepreneurs have what I think we all call shiny object syndrome too, right and where some opportunity pops up and it may not actually align with your vision for your business, especially in those early days when you're first starting to make money, but you're not quite where you wanna be, it's so easy to jump at opportunities that may be completely outside of why you initially went into business to begin with. And some of those great, it's awesome, but at least if you understand your why and your core values, when those things pop up at you, you can weigh them against your why, your core values and your vision for the future of your business. And just make sure they align before you allow something to derail you because it's hard. Once derailed, it's hard to kind of bring it back. ⁓ Yeah. Or, you know, because you're doing such a great job, some company comes out and tries to recruit you and they're am I willing to walk away from my business that I put all this energy into? So I love that you mentioned the focusing on the why because it really is something even like put it on a post-it note on your computer so that it's always there to help bring you back to reality when when these shiny objects pop up or when the tough days occur.
Alyssa Olerud (39:01)
Yeah, it sounds so simple, but it's so powerful.
Kristy Cook (39:05)
Yeah, it is. And I'm wondering now where you're at with your business and kind of looking back and looking at all the pivots that came before stepping into entrepreneurship. I'm curious, has your definition of success and what success means to you personally, has it evolved or changed at all?
Alyssa Olerud (39:26)
100%. Yes. I used to think that success was just a number. I remember setting my first year goals. I was like, I want to do a hundred K in revenue. Why? Like, because that's the number everybody else says. What is, like, what is a hundred K really mean to you? Why is that the number for me? With having clients on the trainer, typically I see a standard number month to month, but sometimes you lose a client and that dips or you get an extra client and that bumps up. So I've stopped looking at the number as the success metric. The number has a goal. have an amount that I need to pay my bills, right? But if I am paying my bills and I'm still able to do a call with you at 11 o'clock on Thursday because I want to, that's great.
Like if I want to go have coffee with a friend, if I want to skip work and take my kids out of daycare and go to the zoo like I did on Monday, like I still feel like I'm breaking the rules because I'm like, I'm not supposed to do this. But that success to me is to be able to be present and provide for my children at the same time. And yes, money makes that happen.
But if I can just look at what do I need to feel happy, it's not the money number. So pushing to hit a certain number just because it's a number that sounds good actually made me less effective. For me, it's just like, how can I continue to serve my clients, make sure they're happy, make sure they stay with me because now I'm hitting goals and I'm paying my bills and I'm having fun with the family.
Kristy Cook (41:05)
Such a beautiful sentiment. And that gets back to really understanding your why, right? And your core values and what got you into this business to begin with. And I think your why can change over time. You know, as your business evolves, that's absolutely a thing and totally okay. But just staying in touch with that allows you, allows us all to give ourselves permission. I did the same thing last week. like, you know,
Alyssa Olerud (41:18)
For sure, yeah.
Kristy Cook (41:31)
Feeling tired, I'm feeling stressed. I've been working 10 hour days. I'm just going to take two days off and be okay with it. And I, all of a sudden it opened up. I could think again and I was getting, you know, the creativity was flowing. And, and I was so glad that I had that. And I do understand that's a luxury and a privilege. And, just, just to know that all this hard work for me is paying off because I can do things like that.
Alyssa Olerud (41:39)
Yeah.
Kristy Cook (42:00)
And it's really shaping my why as well. Well, it's been so fun chatting. And I know that our audience has just fallen in love with you like I did when we first met. ⁓ So how can they get in touch with you?
Alyssa Olerud (42:01)
Yeah.
So, social media is where I spend a lot of my time as a social media manager. I'm mostly active on LinkedIn, just under my name, Alyssa Olerud, or on Instagram under Fearlyss Media. Fearlyss is spelled with a Y instead of an E, so a pun on my name. ⁓ Either there or my website, which is FearlyssMedia.com.
Kristy Cook (42:40)
Great, and we'll be sure to put those in the show notes. And I know that you have just put out an amazing workbook to help people with their stories and their branding, and I would love for you to be able to share some more about that.
Alyssa Olerud (42:54)
Sure. So as I mentioned earlier, when I was working with clients and realizing that people were having trouble telling their stories, my corporate sales trainer brain kicked in and was like, okay, we can teach this, we can help people with this. And it took me a really long time to come up with the framework itself, because it was something I was doing regularly with clients, but I didn't know like, how to put a name on it or how to define it down. So I spent a lot of time really building the structure of, okay, if you wanna build a personal brand, you need to start with your foundation. And then you need to figure out how your lifestyle, your offer and your knowledge, your overall wisdom fit into your story. And FLOW is an acronym, stands for Foundation, Lifestyle, Offer, and Wisdom.
Through the workbook, I take you through the exercises of figuring out what your expertise and your story is, like taking it out of your head and figuring out how to turn it into a story. I teach you how to build each of these pillars into content that also fills your sales pipeline. So there's a sales component to the workbook as well. And the goal is that by the end of it, you've mapped out, know, here's everything that I have to offer. Here's how I can put it into content. And now here's my calendar and it's purposeful, it makes sense.
And it feels good to me, but it's also meant to help grow my business. So, it's in-depth exercise. I break it out into a couple of weeks so that people can do it in a way that is intentional. But like you said, it's a self-paced workbook. So take as little or as much time as you need. But it has been really powerful for the people who have used it so far. And I've been really grateful to be able to help people on that level without having to commit to any sort of high ticket item or membership or anything like that. So it's felt really good and aligned all around.
Kristy Cook (44:49)
Yeah, that's great. Well, congratulations on putting that together. I know and what you've shared about it, it's an amazing resource for people, especially as we talked about the ones who are just starting and may not have the means for some ticket service, but this can get them started and then they have you and can reach out to you if they need a little extra help.
Alyssa Olerud (44:53)
Thank you.
Yeah, yeah, it's been really fun.
Kristy Cook (45:15)
I love it. Alyssa's journey is such a powerful reminder that your path doesn't have to be linear to be successful. Whether it's pivoting industries, building a business from scratch, or finding the courage to show up and be seen, her story shows what's possible when you stop waiting for permission and start betting on yourself. And if you're ready to pivot out of overwhelm in your business or career, and into a version of success that fuels your ambition and your wellbeing, I'd love to support you. Visit pivotista.com or my LinkedIn, which you can find in the show notes to connect with me and explore how we can build your burnout-proof success together. Until next time, remember, your pivot out of overwhelm isn't a sign of defeat, it's a power move.
