Have you ever met someone who just seems to be living life on their own terms, not following the expected path and unapologetically pursuing what they want? Amanda Jackson is the perfect example of that person. Not only is she running her own original research report writing and strategy business, Mandaroo Marketing, but she brings a creative and experimental mindset to nearly every facet of her personal and professional life.
Amanda and I first connected through the Superpath community and after our initial conversation, I started noticing all the different ways Amanda was showing up in the world, from getting Noodles & Company to sponsor her anniversary dinner and hosting virtual crafting sessions to publishing a newsletter and interview series on Substack.
While I couldn’t necessarily connect all these dots on my own, each of them sparked my curiosity. Why was Amanda doing so many cool things, and what lessons might I be able to glean from a more in-depth conversation with her?
Luckily Amanda was kind enough to sit down with me and share both the logistics and benefits of living life with an impressive amount of intentionality.
Let’s start with an overview of your freelancing career to date—when did you start, what are some typical types of work you do, and is there anything else you’d like to highlight?
I spent the first six years of my marketing career in house as a generalist on a small teams. And then in spring of 2022, I left my role and started building up a network of clients, specializing in long-form content for B2B software as a service. I had a wide variety of clients, including a few agencies.
A few years ago, one of the agencies I was working with started offering original research reports alongside their other services. They had me write a research report, and that went really well, so that became a lot of the work I did with that agency, and I looked for opportunities to do it in other places.
About a year ago, I launched a custom service offering that is really meant to be from start to finish—data analysis to writing to the distribution of the final created asset report. I offer the package all in one, and I also have engagements that are focused on just one of those elements. So I might be doing just the narrative development and the outline structure. Or I might be doing a distribution plan for a company that’s already worked with a firm to develop their report and want some support in scaffolding what they could do with that data across a number of different channels.
That’s my specialty and my signature offer. And as solopreneurs do, I’m always refining my positioning and messaging to make sure it matches what content teams need.
Are there any examples of original research that you find particularly inspiring?
The Storyblok Content Debt report that came out this summer had a really strong headline stat that they led with, which is that the total value of content debt is $4.63 trillion.
And then they went above and beyond! To represent that stat, they printed out these six-foot receipts that itemize the report findings and sent them to some B2B influencers.
Those are the kinds of things that I get excited about and love nerding out about.
You took a little dip into influencer marketing with Noodles & Company and Descript earlier this year. I’d love to hear more about this whole experience. What inspired it? How did you decide which companies to approach?
I decided coming into 2026 that this was going to be a year that I experimented a lot. That’s shown up as me starting a Substack and spending a lot of energy on building a platform there.
It’s looked like making videos for LinkedIn and trying different methods of sending pitches.
Naturally over the course of things, those two influencer opportunities came about in their own ways.
I had become a paid Descript customer this year because, as part of my Substack, I was doing interviews, not too dissimilar from the conversation we’re having. The series is called Healthy Jealous. I decided to repurpose envious energy into conversations and what can I learn from them and what is worth actually doing.
I knew I wanted to record those conversations and share clips both on LinkedIn and on Substack, so I became a paid Descript customer. I really liked the platform. They were pioneers in the space of video editing where you can edit the script and then that edits the clip itself, which always felt like magic to me.
I had used Descript for transcription for a while, but this is when I really started to use the whole platform for what it’s made for. I had used the product enough that I felt comfortable with it and could be an advocate for it.
So I found the right contact on LinkedIn, sent a connection request, and asked if they work with influencers with this number of followers. I recognize that I’m still growing my audience, so I wanted to be transparent about that upfront, while letting them know that I’m a customer and a happy one, and I would love to partner with them if they were up for it.
We corresponded back and forth, worked on a script for me to make a video that would be a sponsored post for them, and I published that and got some good chatter in the comments. A lot of other happy customers commented to say, “I love this platform.” And then a few other people wrote that they’ve been wanting to try it and they feel like now they should.
That was a positive experience.
Noodles & Company came about through a very different kind of thought process. My fifth wedding anniversary was coming up and my husband and I had been talking about the idea that it never hurts to ask—the worst that they can say is no.
We know people who are naturally inclined to ask for what they want and take bold swings. They do get a lot of nos, but they’re really resilient to keep showing up in that way, and every once in a while, they get a yes.
So my husband and I decided that we should reach out to some companies around our anniversary. I think I probably reached out to five or six and I heard back from two. We met on Bumble and I had submitted our story in their “success story form” and they sent us this really lovely Bumble-branded game box, which was sweet as well.
In addition, I had sent emails to a few different companies that had played some part in our story, large or small, and just said, “Hey, our anniversary is coming up, you were present to our story in this way. Would you be willing to be a part of our anniversary and sponsor or donate something?” Or I just asked if they’d be a part of it.
My husband and I went on our first date to Noodles & Company. I actually have a macaroni noodle tattoo on my forearm. And so that has always had a very special place in our hearts.
I actually reached out to two different people on their team. Somebody didn’t get back to me. And then the second person I reached out to replied within 10 minutes. They said, “This is such a great story; I love it. It’s actually timely because we are running a wedding-themed campaign right now and sweepstakes. And we’d love to have you share about that.” That story goes to show, one, be persistent, and two, when you find the right person, good things can happen really quickly.
I had the opportunity on both LinkedIn and Substack to share that part of our story and just mention that they were sponsoring our wedding anniversary dinner.
My biggest takeaway from both of those would be: If you’re thinking of dabbling or getting a little bit more serious in any sort of influencer space—start with the products that you already use or are a fan of. If you are starting out or if you have any level of hesitancy about whether it’s going to come across as inauthentic or “selling out,” start with the brands that you actually have some sort of connection to or are excited about. Then you can build from a more connected, real place.
How did you even know who to look for or reach out to?
My marketing background was helpful. My first stop was looking for if they had somebody with “influencer marketing” in their job title. Sometimes it might be like “creator program” or “affiliate program manager.” Those are the first places that I would look.
You might also reach out to a social media manager as a next step.
And then if none of those really surface anything, then I would reach out to whoever is on the marketing team. Since you’re being upfront and clear about what you’re after, say, “Hey, I’m not sure if you’re the right person to reach out to. If there is an influencer or marketing manager, would you send me their way?”
Another approach would be looking for influencer content for the brands that you want to work with. That can be a clue and a confirmation of what you’re asking for when you reach out.
You mentioned earlier that you’ve been taking a very experimental mindset to a lot of things this year and I think that’s so interesting. Did you set any specific goals around that?
Not a ton; I just wanted to see what would happen!
It’s sometimes hard when you’re a business owner or solopreneur because you start to put this premium on your time and think about how much an hour of your time is worth.
And it can get really easy to be zeroed in on those things. But there are a lot of serendipitous opportunities that can come when you set that aside and aren’t so focused on what 15 minutes of your time is worth. I think there’s a little bit of magic and sparkle when we separate ourselves from some of those hard, tangible metrics.
For me, the reach-outs specifically around our anniversary, I knew most of them were long shots. I knew that I wasn’t going to hear anything back.
And so the goal was just to see what happened. The fact that I heard back from two of those brands honestly felt really special. So I was grateful for that.
One of the things that’s really resonating with me is that I think like a lot of us freelancers got into this type of work because we’re creative. And we wanted to build our lives around that.
But once you’re doing it for a while, you kind of develop your routines and your habits. And then it’s so easy to get locked into thinking, ‘This is the way that I get new clients. This is the way that new opportunities come to me.’
So coming up with a completely different way of thinking about things is really powerful—your story shows that we can apply our creativity, not just to the words we put on the page, but to the way we find potential opportunities and things like that.
I think there’s something really inspiring about that.
You’re also very intentional about finding balance in your life. You carve out time every summer to take time off from work. Can you share more about how you decided that this was something you were going to prioritize and how you logistically made that happen for yourself?
Balance is not something that is innate for me. It’s not a default mechanism for sure. I closely identify with my work. I tend to put my worth in that part of my life. When work is not going well or when I feel like I didn’t perform to the best of my abilities, I can quickly feel like I’m worthless at the extreme, but also just feel kind of grumpy and frustrated and drained.
And so left to my own devices, I probably would work nonstop and be online nonstop.
My husband has helped me start to build some more rest rhythms and to be more aware of what I need. He’s a teacher. And while he doesn’t have the summer fully off, he was modeling what that extended time off might look like for me.
My first year of working for myself, the timing worked out that I could take an entire month off. And when I did that, I realized a few things: One, it felt really good. Two, it went so very fast.
I think we mold our perception of time to the environment that we’re in. So in the States, the idea of taking a month off is just unfathomable. In other places, that’s a lot more normal. A lot of people will actually say to me, “That’s very European of you.”
For in-house people in the US, I know taking that much time off might not be feasible, but if you’re a freelancer, it’s not out of the question. It just takes a lot of forethought and follow-through and boundaries.
Okay, so let’s talk about that a little more—what have you learned from doing this for several years and what advice do you have for other people to actually make this happen?
For those of us that work for ourselves, no one is going to make you take time off. It’s why I see so many folks say, “I haven’t taken time off in years!” It doesn’t happen by accident or by default.
Especially if you’re somebody with dependents, if you have kiddos or a parent you’re caring for, there’s never going to be a good time to take that time off.
But that means that there’s also never a bad time—even if you’re just going to start with a couple of days, draw that line in the sand, and you will be amazed by how much you need it when you didn’t realize that you did.
For folks that regularly take a week or two off and are thinking, how do I take a month off, I wrote a Substack essay about my recommendations and the process. But here’s one tip: Advanced communication is so important.
Ideally, let your clients know two to three months ahead of time, especially if you have retainer relationships that aren’t just one-off. You can say, “I’m going to do everything that I can to set you up for success, whether that means working ahead, having you work with somebody in my absence, or just not having that work happen during that time.” I’ve never had a client say, “This is a deal-breaker. I’m not going to work with you anymore.” Folks tend to be understanding.
I’m also a huge advocate for deciding before you’re in that time off what your boundaries will actually be, because I’m sure that there are folks that even if they’re taking a month off might check their email once a week to make sure nothing’s on fire. They might have agreements with certain clients that they’re going to check Slack at least at the midpoint of a trip or something like that.
The key thing is building the rhythms around what works for you, deciding it ahead of time, and then sticking to it. Don’t fold halfway through and say, “Oh no, I am just going to check my email all the time.”
Substack is a personal example that for me exists in sort of a gray space between my work and my play. I did realize that I was still checking my notifications and still overstressing myself to make sure that I write an essay every week.
A few days into the month, I said, “Even though I really like this platform, I’m also going to step away from this for the rest of the month.” Because I was committed to a weekly rhythm of sending my newsletter, I queued up a few and then just closed the laptop and was not in there anymore.
So I’m just a really big advocate for noticing what your brain needs out of your time off and trying to give that to yourself as much as possible and sticking with those boundaries.
I’m glad that you mentioned Substack because I wanted to talk about that. I’d love to hear more about the inspiration for it as well as how you manage it along with all of your other obligations.
For quite a while now, I’ve sensed slowly just that I’m in a little bit of a liminal space with my career.
Last fall, I had this epiphany moment where I was catching up with some friends and they asked me how work was and I said, “It’s honestly kind of miserable right now.” So in 2025, I ended up going down all of these different paths in my mind, like, Do I go back to school? Do I consider pivoting to a completely different field? I have enjoyed marketing and have this huge skill set in it, a huge body of work, but I started to wonder if I should do something else. But what?
I wrote this essay, “I need a career change, I just don’t know what it is.” I knew I really wanted it to exist in the world because I think other people would resonate with it, and I had also been thinking for a while that Substack seemed cool and probably was a place that I would like to create.
A couple weeks into this new year in January, I launched my Substack with that essay. It just created a really solid foundation for my newsletter and connected me to this initial base of subscribers. On both Substack and LinkedIn, folks were like, “Hey, I hear you and I’m in that same place. I feel like I’m in a liminal part of my career. I don’t know what to do next. Pivoting seems really hard.” So I was really grateful for just the empathy and the connections that came from that.
And then I had some sparks of ideas of essays that I could write. But over time, I came to build this bucket that is the title and the niche for my newsletter. I call it “Like Your Life.” And it’s really three prongs. It’s about career direction, creative purpose, and everyday delights to build a life that you enjoy living.
I write a lot about career uncertainty and what that feels like and how we build resilience through that. I really care about creative purpose: I’m passionate about everyone having a creative practice, whether they know that they’re creative or not.
And some of my essays and also a lot of my notes that I share on Substack are really just about wonder, curiosity, and building habits and rhythms that make your life one that you really enjoy.
It’s related to my work in some ways, but it’s largely a passion project. So I’m willing to flex on some of the boundaries that I have for my work. My newsletter goes out on Wednesdays and I usually end up using some of my evening time to write that essay for the week.
I also have always just operated well with tangible urgency; I work a little bit better when I know that a deadline is coming up.
One of the themes I’m noticing is how intentional you’ve been about all of these different aspects of your personal and professional life and the places where they intersect. Do you have any final thoughts you want to share?
There’s really no bad time to change your life. If you’re feeling any sort of dissatisfaction or that growing nudge that something about your career, the place that you live, or a relationship. If you are wanting more community or feel like you’re not living in line with your values, there’s no bad time to make a different choice to become the person that you want to be and make your life feel more the way that you want it to.
And you don’t have to wait for those mile markers, the big social ones like New Year’s. Literally on any day, you can decide to wake up and change your life. Maybe that’s sending an email message to somebody that feels really scary, who you think you’d like to work with or learn from—there’s no bad time to do that.
There’s no bad time to say, I want to change my music taste. I’ve been listening very slowly through the Rolling Stone’s Top 100 Albums of all time—and I don’t particularly agree with the taste of the person that made that list. (There’s not enough women on it, and a lot of the albums I’m sort of gritting my teeth through.) But that came from a place of me realizing I was sort of set in my ways about my music taste and wanted to be a little bit more familiar with this classic album by James Brown or AC/DC. That also came from a place of feeling like I was in a rut and asking what different choices I could make and commit to and make a mini challenge or initiative for myself, just to shake things up.
Those are the kinds of things that can make a life feel really novel and really exciting and meaningful. It doesn’t have to be huge things, and it doesn’t have to be costly. You don’t have to move halfway across the world to change the way that your life feels.
And in an age where the headlines are really scary and it can feel like a lot of things are out of our control, I have found it to be particularly delightful to remember, “Oh, I can choose what I put in my coffee in the morning or what I play on my Spotify or who I send a text or make a phone call to.”
All of those things are within my control. And it is amazing how those things can add up even when life is uncertain to help you feel more like yourself and more like the person that you want to become.
Learn more about Amanda and her work on her website, LinkedIn, and Substack.