Episode 188: Self-Trust Before the Evidence | Maggie Olson on Big Bets

Guest: Maggie Olson — Founder of Nova Chief of Staff, the leading destination for Chief of Staff education, certification, and development.

Watch it here: YouTube or Spotify

Episode Summary

Maggie Olson built a six-figure certification business inside two years, and one of her biggest early moves was agreeing to spend $40,000 on a podcast sponsorship before she had any proof it would pay off. In this conversation, Maggie and Dawn walk through what actually made that decision a self-trust decision instead of a gamble, and why the confidence to build something new rarely shows up before the doing does. This episode is for the coach or founder who is sitting on a decision she already knows the answer to, but is still waiting to feel sure before she moves.

Key takeaways:

- Choice Before Evidence: Why Maggie's $40,000 sponsorship decision had to be made before she had proof it would work, not after — and why waiting for proof first was never actually available to her.
- The Momentum Cycle in Action: How Maggie's bias for action, repeated decision after decision, built the kind of embodied confidence that no amount of planning could have given her in advance.
- Clinical Evaluation Beyond the Outcome: Why the decision would have taught Maggie something valuable about herself even if the sponsorship had failed — because the result was never the verdict.
- Identity Lag and the Unfinished Update: Why Maggie, three years and thousands of students into building Nova, still catches herself unable to fully believe she'll be financially secure, even when the evidence already says otherwise.
- Returning to the Inner Room: The practice Maggie uses to hear her own decision underneath fear and outside noise, including literally unplugging and walking without input until she can feel the pull toward yes or no.

Guest Bio and Links

Maggie Olson is the Founder of Nova Chief of Staff, the premier destination for Chief of Staff education, certification, and development. With 20 years of experience in retail, F&B, and tech, she has held leadership roles at Nordstrom and T-Mobile. As the first Chief of Staff to the President of T-Mobile Business Group, Maggie built the Chief of Staff model, establishing a highly efficient team and executive back-office structure supporting the President, SVPs, and over 5,000 employees. Through Nova Chief of Staff, she continues to shape business leadership, equipping Chiefs of Staff with the tools needed for success.

Website: www.novachiefofstaff.com
LinkedIn: linkedin.com/in/maggie-olson-cos
Instagram / TikTok: @maggieolsoncos

Full Transcript

Dawn: What if trusting yourself doesn't begin when the doubt disappears, but when you decide the doubt no longer gets the final word? Welcome back to the Self-Trust Solution Podcast. I'm your host, Dawn Ledet, and on this podcast, we explore the moments when people are asked to trust themselves before the outcome is certain, before the evidence is complete, and sometimes, often, before they feel ready.

My guest today is Maggie Olson, founder of Nova Chief of Staff, a leading destination for chief of staff education, certification, and professional development. Before founding Nova, Maggie spent 20 years in retail, food and beverage, and technology, including leadership roles at Nordstrom and T-Mobile. As the first chief of staff to the president of T-Mobile Business Group, she built the chief of staff model and created an executive support structure serving senior leaders and more than 5,000 employees.

Today, through Nova Chief of Staff, Maggie is helping define and professionalize a role that has become increasingly more important inside growing organizations. But today's conversation is about more than the company she built. It's about making big decisions while carrying doubt, learning to hear your own voice beneath the voices you inherited, and trusting yourself before trust feels natural.

Maggie, welcome to the show.

Maggie: Thank you so much. What an introduction.

Dawn: For listeners who may be unfamiliar with the chief of staff role, I'd love to begin there. What does a great chief of staff actually do?

Maggie: Great question. So a great chief of staff is focused on leveraging their executive's time. So you can think of an executive assistant as the tactical partner and the chief of staff as a strategic partner for a business leader, and the best business leaders have both.

Leaders have long known they need that tactical support: inbox, travel, expense, logistics, scheduling. What's growing is this awareness that they also need that strategic execution-focused support. So a chief of staff supports the business leader in aligning their team, facilitating sessions, driving the rhythm of business.

What are all the meetings and sessions that the leader has to approve and move business forward? A great chief of staff runs initiatives that have nowhere else to land, and they really optimize for the leader's time to allow them to focus on what's most important, generally vision, growth, strategy, and leadership, rather than that business leader being heads down focused on execution, which we all know is a problem for leadership.

So a great chief of staff leverages that executive's time and allows them to focus on what's most important, taking strategic execution off of their plate.

Dawn: What did you recognize about the role of chief of staff that made you want to build an entire company around educating and developing chiefs of staff?

Maggie: So I was a buyer at Nordstrom for years. I ended up going back to school, getting my MBA. I'd had a career that was marked by success and promotions and constantly raising my hand for the next thing. But I'd never really felt the fit, the alignment with my own skillset and what I love to do until I found the chief of staff role.

So what I loved about the chief of staff role was the fact that it's really beneficial to be highly organized, a systems thinker. You get to sit right next to a business leader and learn how they run a company. You're involved in all of the things. You're aligning people. And I have always stepped in, and this happened at Nordstrom in all my buying roles, stepped into a new business, learned it really quickly, tried to get buy-in quickly from the team, and then optimized processes and built systems and solutions and templates and tools to really make the inner workings more effective.

And in short, that's really what a chief of staff does. Chiefs of staff everywhere are focused on different day-to-day responsibilities based on the environment they're in, based on their own skillset, based on the leader's opportunities. But the core purpose of the chief of staff role is really that: building systems, tools, and processes to drive organization and efficiency and alignment, and really help that leader thrive.

And that is just what I love to do. So when I got into the role, I quickly realized that I was on an island alone. There was no training for this. There was nobody telling me how to be a chief of staff. In fact, most chiefs of staff operate under different titles than chief of staff, which makes it even more murky and confusing, like business operations manager or director of strategic development.

The titles are vast. So when I found myself in the chief of staff role and fell so in love with it so quickly, I also had a team of seven or eight people that I built over the first 11 months, and I was in this role for a couple years. I left this chief of staff role thinking, "Gosh, I wish I would've had some resources."

I remember sitting on my mom's couch in New Mexico telling her, "Isn't it crazy that there's thousands of project management certifications," at the time, this was in 2022, "and yet nothing for chiefs of staff?" And she said, "Well, honey, why don't you go build it?"

So the rest is history. That's kind of where we're at now. I launched Nova Chief of Staff in 2023, basically because there was no place that you could go and get hands-on practice doing the things chiefs of staff do every day until Nova. So that's why I ended up building Nova.

Dawn: What did you know from your own experience that gave you the confidence in the need, even before you had proof that the business would work?

Maggie: You know, I wonder if I even did. I think about it as, I've always had the confidence to take the next action, to be active in that moment to build the thing.

I love to build. When I think about long-term confidence and what is this thing gonna really be or can I do it, that's where I struggle. So I don't think there was really a plan. It was a little bit more like, "Hey, this could be interesting. This could be fun." I considered doing chief of staff consulting actually as my main responsibility after my T-Mobile role, and I built this course thinking it'd just be going on the side, and it ended up being really successful really quickly.

So we dedicated all of our resources, it was just me and now I have a team, to our chief of staff certification course. But no, it was just one step in front of the other. I've always had that kind of bias for action, and I deeply believe that action leads to confidence, and that's something that I say a lot, and I think that's been true for me.

Dawn: What did that season... You take this leap to build something that you see is missing in the world. What did it feel like from the inside?

Maggie: Oh, it felt scary. It felt unknown. Chiefs of staff do everything, but I never did marketing, and marketing's like 99% of the job as an entrepreneur, I feel like.

So very unknown, confusing. I was also navigating a very busy life change at the time. I had just met my husband a couple years prior. We were pregnant. We were moving to Nebraska from Seattle, where I was my whole life. He had quit his job. He was on the hunt for another job. And yeah, it was really just a lot of unknowns.

We didn't have a lot of financial security at the time. It was kind of like, okay, let's do this. Let's just keep trying to believe every day that this is gonna work out. And it did. My husband ended up in a news anchor job here in Lincoln, Nebraska, for the first three years we were here, and I slowly built Nova Chief of Staff.

We had our baby in January. Nova launched in June of 2023. And honestly, I don't know how the timing worked out so well, but to have the flexibility to build and parent and rest and find the joy that I need and the movement that I need kind of in this phase of life where it was the first time of all these unknowns outside of the corporate world, it did kind of work out from a timing perspective as I look back on it.

Even in the moment, it may have felt a little bit more scary and unknown.

Dawn: There was an early decision that became an important moment in the growth of Nova. Can you tell us about the opportunity that came in front of you and why it felt significant?

Maggie: So in 2023, I launched Nova Chief of Staff in June, and actually, I just launched it as a Chief of Staff certification course, without actually being called Nova Chief of Staff. There were a few things that led to me realizing that I needed to brand really early, and I'm glad that we did. So November 1st of 2023 we launched as Nova Chief of Staff. During that time period, I started connecting to different industry leaders in the executive assistant space, and there's a few in the chief of staff space, and one of them is Jeremy Burroughs.

Jeremy Burroughs has a really successful podcast for executive assistants. He's active on LinkedIn and different social media channels. Jeremy and I were talking about how we could partner, and we did a little test where he wanted an amount of money I could not afford for his newsletter to start out with, and then he came back a month or two later and said, "Okay, you can sponsor my newsletter for 3,500."

It was half of what he first quoted. And I said, "Okay, let's try this test." At the time, I hadn't really made much money through the course. We were just kind of finding our way. And the test in the newsletter was really successful. We had probably 150, 200 clicks on Nova's syllabus from this newsletter, and he had 14,000 or so subscribers at the time.

So then we started talking about how we could partner in a bigger way. He said, "Okay, well, I have this podcast. I usually try to find an annual sponsor so that I'm not finding different sponsors every month." I said, "Okay, that makes sense. What would that cost?" This is in December of 2023, and I think his first number was $50,000.

I was like, "Are you kidding me? That's about what I'm making this year. How could I even imagine doing this?" And remember, I don't have a marketing background. I don't really understand the world. This is all brand new to me. I talked to my marketing strategist, a contractor I had at the time, and we just kind of weighed the pros and cons.

What did we think 2024 would hold? What did we think from the test in Jeremy's newsletter? We brought him down a little bit on price, and I ended up sponsoring his podcast for the year of 2024 for about $40,000, and that is half of the gross revenue that Nova made in December, because we raised our price.

So that's usually when we have a little bit of an influx in registration. So yeah, I decided to spend $40,000 a few months in to sponsor his podcast, and that was a big sum of the net revenue that we even would've made. So that was super scary. Super, super scary.

Dawn: Yes. What were the competing voices that you were hearing as you tried to decide? Whether within your own mind... Actually, yes, that's what I want to hear about, in your own mind. What were the "we need to do this" thoughts, and what were the "what are you thinking" thoughts?

Maggie: Through all the milestones, I always have this one thought that's like, "I'm so proud of you. That's so cool. It's just cool that you're even having this conversation. It's just cool that you're even being approached." So that's one side. And then another side is, what if I don't make any money next year? What if we close down? What if nothing happens? What if people find out that the course is horrible?

Which, by the way, of course it's not. We've got incredible reviews. Why do I keep thinking this? I think we all have these thoughts at times. Another thought is, well, what if something else comes along? Or I'm so early, I don't know what's out there yet. What will my peers think? What will my family think? What will my friends think? As entrepreneurs, we're kind of on islands alone. There's not a lot that we can share, but the big moments we can share, and that was a big moment for me back then, but no one's gonna understand it. I don't even understand it. So confusion, scared, a lot of doubt.

Really hoping it would pay off. Yeah.

Dawn: What do you think was the ultimate thing that made you say yes? Is it faith? Is it belief? Is it just courage? Is it determination? What do you think made you say yes?

Maggie: All of the things you mentioned, and I had, I still do have, a great relationship with Jeremy. I really trusted him from the very beginning. He's continued to be a very benevolent, generous mentor in this space that I'm a lot newer to than he is. And then honestly, again, the things you mentioned and the data. Diving into the numbers, looking at the number of clicks that we got from his newsletter, realizing that, and a little bit of research, realizing that the best audience you can find, especially with sponsorship, is a niche audience.

And I built Nova's course for existing and aspiring chiefs of staff. What I did not expect is the incredible open arms that the executive assistant community have given us because they've been so hungry for development, and I'd been getting all these early signals from this executive assistant community that they wanted this course, they needed it, and enrollments were over 50% executive assistants.

So it was kind of this courage and bravery and gut, and then, okay, let's check the data. Let's see what the data's telling us, what's happened already with conversion. Let's apply that to next year. And it honestly was a good decision. We've had, I believe, over 250, probably 300 enrollments out of our 2,300 students that are directly attributed to Jeremy Burroughs, and our course price is around $2,000 now, so it was a good investment, but at the time, there's no way I could have imagined Nova having that high of registration, so there was no easing of my nerves back then.

Dawn: What do you think turns a bold move from a gamble into a self-trust decision?

Maggie: I do believe it's a combination of all the things you just said, and there was a turning point for me back in, I could probably name the year, 2018. I'd realized that I was doing all of this work and trying to achieve and be successful for someone else, like for my mother, for the pressure of being an external achiever.

And I had this moment click where I realized that I need to figure out, am I doing this for myself or not? And in that same time frame, I also acquired this confidence that was like, I may not know how to do everything, but I do know that I will figure it out. And I hadn't had that before. I hadn't had the "you will figure it out" confidence until really this click happened, when I think it was this transition of, "I'm doing this for myself, and I do believe that I can figure this out," whatever this is at the time.

And I think there was a little bit of that. I don't have all the resources, but I sure do have a great marketing strategist that I contract with, and I sure do have a great partner that's found me. And I've got a team that I'm building, and I can trust myself and what my gut is. And I do think there was a moment around the gut there, where it's like, "Okay, what do you really want to do? What's your gut telling you? Do you lean in? Do you lean out? Where's the energy? Where's the feeling going?" And I could feel that decision was a yes before I knew it was a yes.

Dawn: What did the result teach you? So you made the investment. It ended up being a great decision. What did it teach you about business?

Maggie: That whole period of time, those early, early days taught me a lot about having a strong brand, the powerful nature of partnerships, and just, your podcast title, right? Like having that self-belief, knowing that you can do it, and I struggle with that.

I think I said a few minutes ago, ask me if I feel like I'll be safe and good and financially secure for the rest of my life. I'm still struggling with saying yes to that, even though the logical part of me knows that answer is yes, I can build a new thing. I can create. I can continue to do what I'm doing.

But in the moment, that bias for action leading to the confidence, that is, I think, the biggest connector for me to that.

Dawn: What do you believe the decision would have revealed about you even if the sponsorship hadn't produced the outcome you hoped for?

Maggie: I go back to the feeling of pride in being approached, pride in having that conversation. Wow, I'm only six months old in this business, and I'm having a conversation about a $40,000 podcast. Feeling that pride, I think, would remain. I do take the losses hard. I think it would've been hard for me to, quote, fail in that way. But I've always said as a leader, and especially in the retail world, you learn so much more when business is hard.

You learn so much more when you make a wrong decision, 'cause you're analyzing it. You're asking yourself questions. You're way more in the details, and you're going through the harder emotions, which is the point, right? We're learning so much. So looking back, I think that's what the growth, there would've been so much growth and learning there.

In the moment, I think it would've been hard.

Dawn: Yeah, of course. A good result can confirm only that a strategy worked. It can't retroactively make you more or less worthy, more or less capable, more or less authorized, right? Those things had to be available when you made the decision, and they were.

That's what fueled your decision, was being in connection with that belief in what you were doing, the partnership that you were working with, and in yourself knowing that no matter what, you're gonna figure it out. I think that's so important and so powerful to recognize. Your relationship with yourself, you just mentioned, didn't begin, the sort of internal paying attention didn't begin with this one business decision. What first led you to begin looking more deeply at your internal life?

Maggie: You know, my whole life blew up when I was about 29 or so. I found out my first husband was having this massive affair. I'd put him through law school. I was working full time. He was in law school full time. I went back to get my MBA when he was done, and the first quarter of my three-year MBA program I found out he was having an affair with someone at his law firm.

And I was gutted. I never imagined this could happen to me. A similar situation happened with my dad and my mom when I was younger, so I just knew I'd never marry someone that could do that to me. So it was just extremely shocking. And I immediately went into really, really intense psychoanalysis, therapy.

So yeah, I found a therapist who I still see today. I'm very much more connected to my feelings, my emotions, what I want, how to communicate it. And that was 11 years ago now, and I would honestly go through all of that difficulty again to get to the place where I got to, probably about five, five or six years ago, where I felt so much more connected to myself, my emotions, how I'm feeling, and how to communicate all of that, and to know what I'm looking for and how to trust myself and have that confidence. And all of those things remain an ongoing, of course, ongoing work that I'm doing. But yeah, that's when it really shifted for me, and I'm so grateful to have that time.

I felt like, oh my gosh, I'm in my 30s and I'm just now figuring this out? And I remember someone, it might have been my therapist, saying, "Hey, that's early for some people. Some people don't feel like they have this moment until they're in their 60s or 70s." So it's never too late. I'm such a big fan of therapy, the kind where you just talk, and psychoanalysis, Freudian therapy. And it's been completely life-changing.

Dawn: What do you think therapy helped you see that achievement or professional success could not?

Maggie: So many things. I think probably the first thing that comes to mind is, where is the pressure coming from? Why do you feel this pressure to achieve and to build and to go nonstop, and why does it have to be so big and so bold when you're so content and happy in your current lifestyle?

Where's that pressure coming from? What does it really mean? What do you actually want? Not what you think you should be doing, because you're used to a life of being busy and efficient and productive. What do you actually want to do, not what are you good at, because there's a lot of us who are good at a lot of different things.

It doesn't mean that we should be doing them or doing them all at the same time. So I think it's about that pressure. And then the other piece is I didn't have the upbringing in my youth where I knew what I was feeling, and a lot of kids don't if their parents aren't helping them tend to their emotions in the way of, "You're sad. You're upset that Jimmy took your bike. You're angry that your food fell on the floor." We need adults to give us that language as children to understand our emotions, and I didn't have that. I learned that in my 30s. So this sounds so simple, but to have this empowerment now of, how am I feeling? How do I articulate that? It makes me a better boss, partner, caregiver, mom, daughter, sibling because I understand myself. Now I can understand the world in such a better way.

Dawn: Absolutely. We can get so caught up when we don't have the names for it. Excitement can vibrate in our bodies the same as fear sometimes, or irritation can vibrate the same as anger. And if we're not tuned in and connected, we can try to escape things that we don't really want to escape or miss out on some things that we really don't want to miss out on.

Maggie: Yeah, so that's why. And I think there's this slowness that you bring into your life when you're a little more intentional about trying to understand yourself. And I think that can come through meditation and yoga and a number of different places. But slowing down to really realize, what are you thinking and feeling, and what does bring you joy, and what do you want your everyday life to look like? I did an exercise that I called my level 10 life.

It was like a year after meeting my husband now, and I just wrote down all the things that I wanted to do. And it didn't look too different, right? But then I was able to work towards what is that simple life that I want, and how do I make that happen, and why can't we do that?

Dawn: Of course. Yes, because so often we're comparing our lives to this vague, nondescript version. But if we actually take the time to define it, you'll find that you have a lot of what you want, and then what you want is so within reach. But when we don't define it, it's hard to access or get to.

Maggie: Yeah. Or appreciate. And I felt like I had to just keep raising my hand for that promotion. I should have a bigger job. I should make more. I should get the next thing. It feels good to win that next job, right?

Dawn: Yeah.

Maggie: So you just keep doing it, and then wait a minute, why? Is this aligned with my level 10 life? Is this what I want?

Dawn: Right.

Maggie: Maybe it's not, and I have so much power over that because it's my life.

Dawn: It ties to what you said a minute ago, that just because we can do a lot of things, everyone listening to this podcast can do a lot of things. You're amazing humans. But it doesn't mean you have to or that you should. If it doesn't align with your level 10 life, your what I call my ultimate vision, whatever that is, then why do it? You could be using your energy and saving a lot of energy for the things that really matter, right?

Maggie: Yeah. Wouldn't that be nice?

Dawn: How do you return to your own knowing, that inner truth, when maybe fear, pressure, or other people's opinions become loud?

Maggie: I've realized that I need movement every day. I want to be connected to nature every day. I am a busy, on-the-go person who is always doing a lot of things, and so I know that I need to slow down and unplug at times.

So I had a big decision I wanted to digest and process last week or a couple weeks ago, and I intentionally took the headphone with my audiobook out of my ear and walked around our town's little lake without listening to anything. And just sort of saw what came up and how I was feeling and how I was processing.

That's been the most important for me. And I'm an older mom. I just turned 40, and I have a three-and-a-half year old. And I really feel like being a little bit older and starting to have kids has allowed me to be a bit more selfish without the guilt because I know that what is most important to my little one is that maternal happiness is the biggest indicator of your child's happiness.

And I know that I need that time alone. I need that time outside. I need that movement most days in order to be the best mom that I can be, and I am generally not too apologetic for taking it. And I've got a great partner, and we figure that out. But of course, battle with the mom guilt, battle with all the things. But at the end of the day, I am taking action to ensure that I am slowing down when I need to and, to your question, processing in the way that I need to for the big things.

Dawn: At some point, like you've mentioned a few times, action creates confidence. You believe that, you're a doer. You're obviously an action taker. And at some point you began recognizing that your experience and the way you work is genuinely different, unique. What brought you to that realization, and what helped you stop treating your capabilities as ordinary just because they were natural to you?

Maggie: You know, are you familiar with StrengthsFinders?

Dawn: Mm-hmm.

Maggie: I'm very much leading with execution, achiever, maximizer, activator, competition, arranger. Those are my top five. I did a StrengthsFinders exercise a year or two ago and deeply learned what mine were, and I was like, oh my gosh, that makes so much sense.

And I did my team's as well and noticed our differences a little bit. And then I continued to listen to people's feedback that basically brought me to the point of, you are an executor beyond most people's executing skills. I can crank things out very quickly in a quality way, pass it off, and just continue to repeat and produce.

Now, for my own mental health, I want to take a slower approach, but also I think the biggest indicator to your question is that my team couldn't keep up. So tactically, I would pass the work off and my team's at capacity. We're working on this one and this one, and you just sent us this one.

So there's part of me that's like, okay, but that's how we're learning and we're growing, and I'm still gonna pass the work. That is your role. You need to figure out how to get it done. And then there's the other part that's like, okay, but what's really reasonable here? And where are we different, and what is kind of that max that I can send and expect and myself produce?

And then I had a business coach and a few other folks tell me, you are really strong in these ways and let's think about how this affects your team, and let's think about what you want to spend your time on. Feedback, lived experience. All of the above.

Dawn: Yes. At some point... Because Nova develops people who often operate very close to power and have to be pretty effective in the action they take, productive in their productivity and their efficiency and effectiveness, I'm curious how you see self-trust showing up in that chief of staff role.

Maggie: It's such a good question and something to sit with, because the chief of staff, I describe the chief of staff, I say the word support. Chief of staff is a support for a human. It's not a support role where it's fully administrative, but you're supporting another human, and generally that human is incredibly powerful.

They're high ranking in a company. There's probably this huge wealth disparity between you and them. They may have decades of more lived experience in the industry or role that you're both in, and yet the chief of staff needs to be this truth teller. They need to be the one to come to the leader and say, "Hey, I'm hearing a lot about X, Y, and Z, and I want to bubble this up because this one's worth your time."

And that leader might not quite grasp it at first, and you may have to be the squeaky wheel, and you may have to present that information in another way or get buy-in from another partner or a direct report on that leader's team to help you tell that story. That's incredibly, like, self-trust that you have to have to present over and over to a business leader who really doesn't have time for you.

Let's be honest. They're busy doing other things all day long, and you're gonna feel annoying as a chief of staff a lot of the time because you are seeing the things that other people don't, and you're raising the most important things up to leadership when you need to. So yeah, it's all about trusting yourself and considering when do I bring something forward, when don't I, when do I bring in peers? It's a high EQ position, high emotional intelligence role, for sure.

Dawn: Absolutely. What has founding Nova required from you that your previous leadership roles did not?

Maggie: Entrepreneurship in general is just such a beast. I've heard a term, it's an awful one, but it's like, entrepreneurship is like getting kicked when you're laying on the ground and choosing it every single day over and over and over. Which is awful, but it's true. It's not always awful and laying on the ground or anything like that, but I will continue to choose it every single day, and I think the reason why is the same thing that I didn't have to or couldn't even consider in the corporate world, which is you are the end-all, be-all for every single decision, and you have this incredible freedom in your time and in what you're building that you're building completely on your own, and I just love that, and it's the hardest part.

AI has come at a better time for me because I'm saving quite a bit of money on legal contracts and things by starting them myself and then obviously using an attorney once I would need to. Marketing, thought, just kind of figuring things out that I didn't previously know. Tech support, it couldn't have come at a better time. But truly, I have had to figure everything out, and this is one of the reasons they say buy a business, don't start a business, 'cause at least you have a starting point rather than building every word brick by brick, every person, every process.

I'm finally at the point three years in where I feel like we've switched from build to maintenance. And that's a nice big shift. It feels a little bit more akin to the corporate world.

Dawn: What are you still learning about yourself?

Maggie: Oh, I mean, the biggest thing I'm focused on right now is being grateful for the freedom and lifestyle that Nova is offering me, and being content in what it is.

Because that is what fits into my life right now, and building and growing and finding more people, and launching the next thing and the next category of our business. That's not it, and yet part of me still is drawn to that producing and building and driving and pushing. But this phase of life and what I'm most focused on from a mental health perspective is accepting, this is, and being grateful of the lifestyle that I'm living right now, and that it's enough.

Dawn: And knowing that none of that goes away. It's there for you whenever you're ready.

Maggie: Totally. That's so hard for my brain.

Dawn: Really?

Maggie: Yes. It is.

Dawn: Why do you think that is?

Maggie: I think I'm a very much in-the-moment person. Okay, now it is, now's the time. Build it fast. Build it quickly. Let's launch it. Let's move on. I have a hard time holding the future, planning and holding what could be, what could be next.

Dawn: Maybe that's your invitation for this period of time.

Maggie: I think so.

Dawn: If you could sit beside the version of you who was about to spend half of the company's revenue on that sponsorship, what would you say to her now?

Maggie: I would say, "You're incredible. Believe in yourself. You have done great things already. You will continue to. Just have the confidence, slow down, think through things, and plan. Write down what you want. Be a little bit more thoughtful in kind of how you get there and what you want," kind of coming back to the, not pushing as hard. And yeah, you can do it.

Dawn: Yes. So for someone listening who knows what they want to choose, but is still waiting for it to feel like the natural thing, like they should be doing it or they're ready, what would you want them to know?

Maggie: Can you rephrase that?

Dawn: Sure. For someone listening who knows what they want to choose, but they're waiting for it to feel natural, like, yes, go for it. They're waiting for this internal, "Yes, you're ready." What would you want them to know?

Maggie: I would say take a deep breath, close your eyes, ask yourself the question at hand, and be aware of what first comes up for you and what second comes up for you and what third comes up for you. Sit with it and see if there's a pull in either direction. And if there is, that's probably what the right move is. And if there's not, do it again in a week.

Dawn: Do it again in a week. I love that. That's so great 'cause it also introduces, it's not a rush. It doesn't make it wrong if you don't jump on it right away, right? It just means it needs maybe a little more time to, I call it marinating, when it sits with me for a minute. Now tell everyone here how they can find you, how they can learn more about what you offer. Tell us a little bit about what's happening at Nova Chief of Staff right now.

Maggie: Yeah. So Nova Chief of Staff, we have a certification course, and it started as an online course, 50, 60 hour self-paced online course. That is an option. It's the most accessibly priced option that you can enroll in any time. And then we also have two other formats, which is in-person three-day and virtual three-day. So really there's an option for whatever your life can fit right now. And you can learn more all about the different Nova formats and what we do and a ton of free resources and blogs and events on novachiefofstaff.com.

And you can find me writing every single day on LinkedIn and talking to camera on TikTok and Instagram. So MaggieOlsonCOS is generally the handle that you'll be able to find me under.

Dawn: Awesome. Maggie, thank you. One of the things that has stayed with me from this conversation is that self-trust does not always arrive as this strong, certain voice, right? Sometimes it's this quieter voice beneath the fear saying, "I know enough to choose this," or, "I know enough to follow this want." And sometimes it's a decision to move while the old voices are still asking whether you're sure. Trusting yourself doesn't mean knowing that every decision will work. It means refusing to make certainty the price of your own authority, and it means knowing that the result can teach you, inform you, and help you adjust without being allowed to determine who you are or whether you are entitled to choose.

If today's conversation resonated with you, you'll find links to connect with Maggie and learn more about Nova Chief of Staff in the show notes. And if this conversation surfaced a thought you've been arguing with, pushing away, or trying to solve, I'd love to meet you in the lobby. It's a free tool based on my book, The Inner Room. There's no email required. You bring one thought, and the tool offers you two invitations, designed to help you stop making an enemy of that thought and begin using it to create more connection with yourself and a little more inner unity, if you will. You'll find the link in the show notes. And if you enjoyed this episode, please subscribe, leave a review, and share it with someone who may need the reminder that they don't have to wait until trust feels natural to choose themselves.

Until next time, remember, results inform the how. They never get to decide the who or the whether. I'll see you next time.

Ready to know where your identity is actually operating from right now?

Take the free Self-Trust Identity Map. It takes three minutes and gives you a precise read on exactly where to focus next.
https://www.theselftrustcoach.com/identity-assessment-page

Want to go deeper? The Floor: Your Build is available now. Self-paced, structured, and built around the same framework.
https://www.theselftrustcoach.com/the-floor-your-build