Paving your own path with Angela Scott

Fernanda: Hi friends, welcome back to Connectedness. I'm Fernanda, your host and founder of Filled Cups. And this is the space where we explore what it means to grow, connect, trust ourselves, and show up authentically with each other.

Today's conversation is a special one for me. I'm joined by my friend Angela, someone I used to work with many, many years ago and someone whose journey has quietly but powerfully challenged the way I think about courage, identity, and choosing yourself.

Angela is a bit of a contrarian in the best way. She's American, she moved to the UK, and then made her way back to the US—each move reshaping how she saw herself in the world. She admitted to me a long time ago that she is an introvert who once struggled to find her voice at work and who intentionally put herself in uncomfortable rooms by joining Toastmasters, a decision that ended up changing everything.

A few years ago, Angela did something many of us dream about but hesitate to do: she walked away from a stable corporate job and decided to bet on herself. Today, we're talking about what that really looked like, what it taught her, and how challenging yourself can sometimes be the most loving thing you do.

If you ever felt shy, stuck, or quietly craving a braver version of your life, this is the conversation for you. Angela, thank you so much for joining me. I really appreciate it. Can you take us back to how you and I first met and what you were doing professionally at the time?

Angela Scott: Yeah. We first met when we were both working in supply chain. My recollection is that you were coming into supply chain from a different discipline, and I had come in a couple of years before you, also from a different discipline.

Right away, I noticed that you positioned yourself as someone who was there to help and listen—a servant leader. And I was like, "Yes, thank you." We had different communication styles, so we've been on a journey together, girl.

Fernanda: We definitely went through it, and once we were working together, we were just in it to collaborate and fulfill the mission. I learned a lot from you; actually, I was inspired by you to join Toastmasters.

For our listeners who don't know you, you've lived in both the US and the UK. What initially drew you to move to the UK?

Angela Scott: I can tell you, no lie, I moved for love, not the weather. I grew up in the Midwest around Chicago, and eventually fell in love and got married to a Brit. We negotiated and agreed that we would move to the UK first.

That meant I really had to put things on the line with my role in Chicago. There was no appetite within the leadership at the company for remote working. It was kind of a big deal when I gave my two weeks' notice after asking HR and escalating the issue of whether we could make some kind of deal.

I was getting a lot of pushback, but the day I was packing up my desk, a UK contract suddenly appeared: "If you sign this by the end of the day, we're square." In the end, I'm really glad that I did it, because it turns out it's quite difficult sometimes when you're an immigrant in the UK.

Fernanda: You were a trailblazer because by the time you and I started working together, it wasn't even an issue anymore. You had already proven that you were perfectly capable of doing your job.

It sounds to me like you've always trusted your instincts. Is that something you had to learn, or have you always trusted your own instincts?

Angela Scott: I do have a tendency to second-guess my instincts, and sometimes to a fault, I push myself to rationalize. If I have a gut feeling, I'm not going to trust it until I've really rationalized it.

When people would say, "Oh, you're so brave to go and lay it on the line that you're leaving," I was like, "Well, what's my alternative? Either I can try to make this work and make the grass greenest where I water it, or start from scratch."

Fernanda: I wanted my listeners to hear about your experience with Toastmasters. Who was Angela before Toastmasters, and how did it change you?

Angela Scott: I used to be the person who showed up to a status meeting where everyone sat around a big boardroom table to say their name and what was happening that week in their department. The first time I attended one of those meetings, I realized a lot of people said, "No updates, nothing special is going on." I thought, If I can get away with that, that's what I'm doing.

I was so busy trying to remember my own name and department that I couldn't even hear what other people were saying. I was so shy, and I did not want to call attention to myself in any way.

I got away with that for about three months at our company. Then in the fourth month, after a status meeting, I went to somebody and said, "Hey, I wanted to ask this question in the meeting, but I'm pretty new and worried it's a stupid question. Can I ask you?" That person said it wasn't a dumb question.

An hour after the meeting ended, I was talking to the seventh person who had been in the room. They finally sat up and said, "Angela, we had this meeting at 9:30. It's almost lunch, and you're just bringing this up now? That was a really good question, and you needed to ask it in the meeting, because there's a problem and now I have to make phone calls at lunch when I can't reach anybody."

It was the first time someone gave me really direct, constructive feedback: "No, your job is to speak up. That's why you're in the meetings. Knock it off."

Around that time, I was also listening to podcasts about speaking up in meetings because I had this sense that there was something else I should be doing. One of the podcasts mentioned Toastmasters, so I looked it up and decided that's what I needed to do.

The first couple of times I went, I wanted to die. The impromptu speaking section is the closest you get to giving a status update in a meeting. I put myself forward every time, and every time I wanted the floor to swallow me whole.

We met once a week, and it took about four months before it started to feel less threatening. Six months after I joined, I had my semiannual review. The director of my department, who I didn't think knew me from an ant on the floor, actually said, "Angela, I don't know what you started doing in the last six months, but I have noticed a dramatic increase in the impact you're making on the team."

Fernanda: By the time I met you, I would have never guessed you were someone who had issues speaking up in meetings, because you were so vocal and present.

You touched upon something important that I've experienced in the past: when you're nervous or overthinking what you're going to say, you might not actually be listening to anyone else. Toastmasters helps with active listening too, wouldn't you agree?

Angela Scott: Definitely. The other thing I noticed is how powerful it is to give concrete, constructive feedback that doesn't tear someone down, but actually gives them a tool to take the next step up.

Fernanda: When we were working together, there came a pivotal moment where you decided to resign—not to go to another company, but to start your own thing. Can you tell us a little bit about that?

Angela Scott: This was at the end of COVID, and we had all been through a lot of stress. I really wanted to be on a global team, but even though I moved to the UK and was excited to work with the European business, I couldn't quite break into those teams because they were much leaner.

I thought, I have been helping McDonald's shave a quarter of a percent off their supply chain costs for so long, and I really want to understand how other businesses operate. I had been saving up and knew this was on the horizon; it was not a snap decision, but more of a feeling that the dam was about to break.

What was really interesting was that as soon as I let people know I was leaving to do consultancy work, people came back and said, "We have work on our team, but we don't have approval to hire full-time. A consultant hits a different budget line."

Suddenly, I started getting project requests from the exact teams I had wanted to work with. It was actually easier for me to get that experience as a consultant than as a full-time employee. I was able to do that for 18 months continuously and exceed my salary expectations.

Fernanda: That took becoming comfortable with some level of uncertainty, would you agree?

Angela Scott: Yes, and I perceive uncertainty in static situations that other people might see as stable. Other people would have said my situation was stable, and leadership was telling me it was stable indefinitely, but something in me sensed that wasn't entirely true.

I was ready to grow and was getting signals to stay put. For me, the risk was that if I stayed put, when I was eventually forced to take a next step, it wouldn't be on my own terms.

I wanted to be in charge of what happened next in my career, not waiting around for permission from my boss. If the door was shut, I needed to find a window.

Fernanda: A lot of us who have worked in corporate environments know the pitfalls of middle management, politics, and the lack of clear career pathing. Those phenomena seem unfortunately very common.

Angela Scott: It's not a bug; it's a feature. You can call it a design flaw if you want, but it's very difficult to engineer out of an organization.

Fernanda: You recognized that and took what some would call a risk, though in your eyes the real risk was staying the same. What have you learned since taking that leap, and do you have any regrets?

Angela Scott: The first thing I learned is how much I didn't know. I learned more by just going out and doing it than I did during my MBA.

Even though I had gone to Toastmasters to become a better speaker, I hit my limit with the level of networking required. That's why my consulting business ended up being a lifestyle business rather than something where I hired people to grow with me.

I relied heavily on my existing network and never quite cracked prospecting for new work. Going out to do the legwork to get a cold sale just did not click for me; it wasn't natural.

If I had to do it again, the first person I would hire is a salesperson, and the second would be an accountant on retainer. I spent so much time chasing down UK small business accounting rules when that wasn't why I was there.

Fernanda: When you set out on your own, you have your zone of genius—the core thing you are there to do—and then all the other tasks of running a business. If you can outsource those, it saves you so much energy.

Angela Scott: The opposite of your zone of genius is your quicksand. You can dedicate time to shoring up weak points, but everything you say yes to is something else you're saying no to.

The opportunity cost of fumbling around for six months to learn something yourself is so much higher than hiring someone who can bring in results right away.

You turned me on to Jordan Harbinger's networking course years ago. It's supposed to be a simple process, but reaching out in that way felt so unnatural to me that I kept stalling at step three.

Fernanda: Looking back, what advice would you give to people who are trying to carve their own career path?

Angela Scott: There is a hard truth I learned when I went for a promotion and received feedback that I needed to create my own opportunities. At the time, that was very unwelcome feedback, and I raged against it because I felt I was ready and didn't know how I was supposed to carve out opportunities in a corporate setting.

Once I stopped to really take it to heart, it became a clear signal: staying where I was was the actual risk. Relying on somebody else to create the experience I needed was the risk.

From then on, whether it was starting my own company or taking on volunteer leadership roles, I deliberately put myself in uncomfortable situations. Some of those experiences brought me to tears, but they gave me the self-trust and confidence to later say, "Of course I can start a business, and of course I can do this." Putting myself in lower-stakes risks prepared me to take on the higher-stakes ones.

Fernanda: That is such great advice. Angela, thank you for sharing your story so honestly. Your journey reminds us that confidence isn't something you're born with; it's built by showing up, especially when it feels uncomfortable.

To everyone listening, I hope this encourages you to challenge the quiet limits you may have placed on yourself and to trust that small, brave steps can completely change the trajectory of your life. If this resonated, please share it with someone who might need a nudge to bet on themselves.

Until next time, take care of yourselves and keep filling your cups!