Welcome Ashlee! Tell me about your background:
I come from the international development and nonprofit sector. I did that for about 7 years before taking my business full-time in 2019. That was my entry into the world of communications, donor relations, events. These experiences translated into marketing when I started working with small businesses and the social impact sector.
Now, it’s been over two years of running my business (plus a couple years where I was freelancing on the side) and the evolution has been constant. From my audience to my offerings, I’ve been fine-tuning and have finally gotten some clarity through all the experimentation.
I’ve figured out that I like to work with purpose-driven founders on their brand messaging strategy so they can have as much impact as possible through their business. It’s about connecting the dots from the high-level vision to the tiny details, and everything in between.
When did you know this is what you needed to do?
All these realizations took time. It took about a year for me to formally connect my personal conscious consumerism path to my business and the types of clients I wanted to work with. It took even longer than that for me to realize where I’m most helpful, which is strategic consulting, rather than being in the weeds. And that I like to work with founders because they’re visionaries and action-takers.
How did you know? How long was the gap between when you know and when you took the leap?
I can technically cover a lot of holes in people’s businesses, and I did for quite a while. But if my heart isn’t in it or if I’m only one step ahead of them, the result isn’t going to be as good as it could be. Plus, I finally realized that ideating, planning, and strategizing isn’t something everyone can do, especially not in the way I view problems and solutions.
It took some external validation—sometimes even from one-off networking calls when I said something that resonated (without even “trying”). It also took some personal reflection, which isn’t my strong-suit. I worked with a couple coaches—never anyone steady, but the same themes came up enough times that I finally connected the dots for myself.
I’m much better at seeing clear solutions for other people, but I can get lost in the possibilities when it’s my own life.
What was that time like, in the gap?
It felt like I was spinning my wheels, which is especially painful since I like tangible progress so much. Essentially, it was constant growing pains. I would see what other people were doing, or I knew I could Google my way through something, so I’d try whatever came my way. And then I’d wonder why it didn’t feel quite right.
That said, the experimenting can also feel invigorating. Variety is one of the biggest reasons I started freelancing in the first place. But as I slowly step into the entrepreneur role (replacing that freelancer mentality), I am coming to appreciate the value of systems and repeatability and sustainability. I’m gradually seeing the nuanced variety each client brings to the same tasks and offerings.
What was the catalyst event that got you to take your risk to pursue your dream?
There were two. The first was when my husband kept getting rejected for tourist visas, so we couldn’t travel to the US for holidays like we wanted to. We decided it was time to apply for his green card. That uncertain timeline is what made me start freelancing, so that at least I’d have SOMETHING to fall back on when we had to up and move.
The second was when I got a new boss at my day job. I felt underutilized, out of the loop—just not in a space where I could use my full potential. So as my side gigs continued to grow, I decided to bet on myself and have faith that I could find another job one day if I needed to.
If this hadn't happened, where do you think you would be?
On one hand, I’m not sure I would have stepped outside of the conventional. I grew up seeing 9-to-5, long-term employers as the model. In fact, the only option.
But on the other hand, I think those of us who end up running our own business have something specific in our bones.
For us, the appeal of creating something from nothing and being accountable to ourselves always wins.
What did you think of this at the time?
It was scary and frustrating. But I tend to go into problem solving mode. I couldn’t control much about the situation, but I could control seeking out alternatives. So I did.
How long were you thinking of pursuing this idea before you went full time?
It felt like I was toying with the idea for ages. But really it was probably more like five months. I was trying to calculate how many hours I’d need to work with my anchor client and what other income I’d need to make up my salary and benefits.
There was definitely a spreadsheet involved. But ultimately, I just decided to follow my gut, which was telling me to make the leap the whole time.
What held you back from doing it?
I had big monetary concerns and some confidence blocks. I’ve always been the breadwinner and leaving a “sure” position for “uncertain” freelancing seemed reckless in some ways. I’ve since learned that in a lot of ways, running your own business is more certain than relying on a single “steady” employer because you call the shots and you have the capacity to seek out the growth you’re after.
When you felt stuck, what made you feel most stuck? What did it take to get unstuck?
I like to weigh my options, look at the issue from all sides, think through all the possible outcomes. It’s what makes me a really great partner for business owners and an insightful consultant. But that same process often bites me in the butt when I need to make my own decisions.
I can mull and mull, not wanting to commit to a decision.
Even though the hesitation is agony and the decision always brings such relief.
How does it feel like now to think about the time when you were uncertain if this life pivot was the right path for you?
Sometimes I kick myself for not narrowing down my focus sooner, or just picking a direction and sticking with it for a bit. But I still think the trial by fire works for my brain and I need that little bit of pressure to thrive. I don’t think the time in between was wasted because I was still learning, trying new things, meeting new people. It all got me to where I am now and will be part of where I’m going.
What is one sentence of advice you have for people who are reading right now and afraid to pursue their true passion?
Make the leap—what’s the worst that could happen?
Was there a lightbulb moment for you before you took your leap?
It was a slow build. My brain planted the seed and my gut kept going back to it over and over until it couldn’t be ignored. I did lean into online resources, especially after quitting my job. I consumed so much business building and skill upleveling content. It was really useful to see what the possibilities were. You don’t know what you don’t know, so I prefer to get information en masse before I tease out what’s important and fits with me, and what I can ignore.
At what moment did you know your ideas had to work?
It’s so funny because when I first quit my day job, I would tell people, “I’m giving myself three months.” That turned into six months. Then at the year mark, I was convinced I could NEVER go back to working a set number of hours during a fixed period of the day doing tasks I didn’t choose. I’ve never looked back.
How did that feel?
While I’ve definitely had ebbs and flows, and plenty of stress, I’ve never doubted my path since starting on it. The alternative (working a “normal” job) never outweighed anything I was going through with my business.
Alignment feels good.
Even when I’m unsure of what’s coming next or the best way to grow, I have at least a baseline level of confidence in myself, which feels reassuring!
Did you reach a milestone or was it more a willful decision to live in that peace (or turmoil) that it's going to work?
Most of my reassurance is just intuition, pure and unquantifiable. But I think revenue is a great way to measure “success.” My first year, I was gauging myself based on the salary I left behind. I didn’t quite replace it, but it was close. My second year, I had great growth in terms of the number of clients, size of projects, and revenue.
When the numbers match the feelings, then I know I’m moving in the right direction.
Knowing what you know now on your journey, what would you tell your past self at the moment you were most afraid to change course?
Trust in yourself. You’ve never let yourself down before, so why would this be any different?
If you want it badly enough—whatever “it” is—you’ll make it work. Plus, things almost always turn out bigger and better than you imagine, so take one step at a time and get moving.
What's new or next for you?
So many things! I just beta tested my brand messaging strategy VIP Day and it was the most aligned I’ve ever felt in my business. Both the result and the intensive model really worked well. I’m excited to make that a core offering. I’ve also been taking on more consulting calls. These are not tied to any specific project—I’m there for the founder when they need outside perspective to brainstorm or create an action plan. And then to replace some of the done-for-you copywriting I do for clients, I’m thinking about a marketing strategy program that equips founders to do their own marketing or know what to look for when they hire it out.
The common thread is that I’m using words to help founders feel rooted in their values and propelled by purpose in order to use business for good. That’s pretty darn exciting to me.