Nothing Is Working in Your Career? Listen To This Before You Give Up

Nothing is working. 

The applications, the interviews, the effort — and still no results.

If you've ever felt stuck, behind, or like your career just isn't moving, this episode is for you.

Because what if the problem isn't you? What if this phase is actually building something you just can't see yet?

In this honest conversation, host Olajumoke Fatoki sits down with Yousra Nawara — communications professional and community organizer — to unpack what career "failure" actually looks like from the inside, and why the moments that feel like dead ends are often the ones doing the most work.

You'll discover:

• The cover letter move that turned Yousra's biggest rejection into her next job offer
• Why community involvement builds the career skills that job applications never test
• The self-awareness shift that shortens how long setbacks knock you down
• How to keep showing up authentically when the workplace doesn't make room for it

Whether you're navigating a career pivot, the Canadian job market as a newcomer, or quietly wondering if your path is taking too long — this one's for you.

This is not a "stay positive" conversation. It's an honest look at what it feels like to struggle — and how to keep going anyway.

If you're close to giving up, listen to this first.

👉 Share this with someone who needs to hear it today.

Connect with Yousra: 

LinkedIn: Yousra Nawara 

Instagram: @scuttlebutthasit
Website: scuttlebutthasit.ca
Substack: Prolifically Random — substack.com/@prolificallyrandom

Transcript

PART 1 — INTRODUCTION

OLAJUMOKE: Welcome again, Yousra, to the Thrive Careers Podcast. I'm so excited to have you and I can't wait to share this conversation with the world. Before we get into it, I'd love for you to briefly introduce yourself — tell us a little about who you are, what you've been up to, what you do now — and then we'll take it from there.

YOUSRA: I'm so excited to be here. Thank you for having me.

So — I'm Yousra. I would say I'm a very dynamic person. I'm involved in arts, community work, and social justice. I also work in communications, most recently at the YWCA.

My career has been built around marketing, psychology, and radio. I've lived in Peterborough for about ten to twelve years now, and over that time I've done a lot of community organizing — going to town halls, things like that. I've done pottery. I just love this community, and I feel like that's a big part of who I am. I've spread myself thin across a lot of different things in my life, but I think that's just how I'm wired.

PART 2 — WHEN THINGS DON'T WORK OUT

OLAJUMOKE: So, this episode is about those moments that feel like failure — like dead ends or setbacks — and how, in hindsight, some of those moments can actually come together into something we're really proud of. But when we're in the middle of them, we don't feel that way at all.

This isn't a silver linings episode. It's an honest conversation about what it actually feels like to be stuck, to feel behind, or to feel like you're starting over — and how you were able to navigate that season and turn it into something impactful. I know a lot of our listeners are in that exact place right now — navigating career pivots, different seasons of life, quietly wondering if they're on the right path.

So — take me through a specific moment when something didn't work out for you. Where were you? And how did it feel at the time?

YOUSRA: I love this question — because honestly, career-wise, I don't think I've ever had a single moment that didn't work out. It's more like a duration thing for me. How long does something work, and when does it collapse? And the duration before the collapse just sort of... extends. So it becomes more about endurance and resilience than any one dramatic moment.

But a really specific moment — the one that stands out most — is when I got a job at Trent University. I was hired as a communications officer, and I was so excited because it was the first full-time job where I was being paid really well and doing something I love — writing, researching, interviewing people.

But because it was that first job I loved so much, I felt enormous pressure to perform. And the way I presented myself to other people there wasn't as confident as I actually am in community spaces. It was a two-month contract with the possibility of extension — and I didn't get extended. It felt like it just crashed and burned.

What really didn't work out, I think, was that I didn't know how to ask for help, and I didn't know how to ask for or give feedback. That moment taught me the importance of collaboration — because you can be the most competent person in the room and have so much passion for what you do, but collaboration is everything. At the same time, it's hard to always be aligned with everyone you meet in the workplace.

PART 3 — WHAT WAS ACTUALLY WORKING

OLAJUMOKE: Looking back now — can you see some of the ways that experience was actually working for you, even while you were going through it?

YOUSRA: I love how authentic I am in the workplace. If I'm not feeling something, it shows up. My body language is very clear about how I'm feeling — but I wasn't always elaborating on it. That was something I recognized in my younger self: I wasn't putting words to what I was experiencing.

So I think what was working was that I was staying true to myself. But I didn't yet have the ability to advocate for myself. And looking back, that environment wasn't the warmest — it didn't give me what I needed to fully show up. Staying true to myself was the thing that carried me through.

PART 4 — THE SHIFT: COMMUNITY AS A CAREER TOOL

OLAJUMOKE: Was there a specific moment or shift that changed things for you? You mentioned collaboration — can you zoom in on that, and what helped you develop it?

YOUSRA: I would say my shift happened when I started being more active in community. Interestingly, I started the Trent job right around the time I was becoming more present in community spaces — going to organizing meetings, coalitions, social justice spaces.

My career is really built on my lived experience and my experience in community, because it was those people who empowered me. Being in community with people who understand that nobody's perfect, who accept you as you are while also giving you room to grow and appreciate what you bring to the table — that's where I had exponential growth in how I communicated and collaborated. And I think that's constantly expanding.

Community builds your capacity. And one thing that's different from work is that in community, you kind of get to choose who you're organizing with. But you don't always get to choose who you work with.

I went to a conflict transformation workshop at some point, and I remember asking how you organize with people where there isn't much alignment. Something the facilitator said just stuck with me: "If I waited for everyone to be aligned, we would all be dead by now."

I carry that into my current workplace. It's not that I feel completely out of alignment with the people there — it's just that it's never perfect alignment. And I try to remember: how do I do this without waiting for perfect? It's remembering that people aren't perfect, I'm not perfect, and asking — how do we make the best of an imperfect situation?

PART 5 — COMMUNITY IN PRACTICE

OLAJUMOKE: I want to go back to community, because that sounds like it gave you your voice back in a real way. For someone listening right now who's wondering how to use community as a tool — what would you tell them? What did your involvement actually look like?

YOUSRA: It's interesting — from a very early age, I was like, I never want to volunteer. I don't want to give out free time. That's not who I am.

But around the time I started the Trent job, I remember feeling lonely. And I realized I couldn't just keep going to art events as my only way to meet people. I always had strong beliefs — I was always an environmentalist, a feminist, pro-justice — but I wasn't actively organizing until I felt lonely enough to look for something more.

So I started going to spaces where people were having real conversations: about housing affordability, what's happening in Palestine, budget cuts in the city. And those spaces were aligned with what I already believed.

My advice? Go to spaces that align with your beliefs, and you will meet some of the best people — people you actually get along with. And it won't feel like you're working for free, because you're actively building the world you want to see. I think that's more powerful than any high-paying job. When you pour your energy and soul into making the world more aligned with your values, it never feels like unpaid work.

PART 6 — PROCESSING THE LOW MOMENTS

OLAJUMOKE: For people who are in a foggy place right now — unable to connect the dots, feeling behind, like they're starting over — how do you think they can process those moments? And were there times when you had to reach out for help?

YOUSRA: I think the honest answer is that I'm the type of person who needs to go through the actual process to understand what it was for. Sometimes we think the point is to get the job — to succeed at this specific thing. But you actually don't know the full narrative while you're in it. It's the same as asking, what is my purpose? You can name what you're passionate about, but it's a much bigger story — and you don't always know the last chapter while you're still inside a particular chapter.

A really concrete example: there was a maternity leave contract I applied for — a communications role — and I didn't even get an interview, even though I had connections in that organization. I remember calling the HR person and asking why. They told me it was a mat leave contract and they needed someone who could take the reins immediately, with no time for training.

I was so bummed. But a few months later, I saw another mat leave contract. And this time, I specifically highlighted in my cover letter: this is a mat leave contract, and you need someone who can step in right away. I even created a 30-day work plan for them — because I thought, that's what someone who already has the job would do. And I got that job.

That experience is so highlighted in my memory because I used it as a direct lesson for the very next opportunity.

On reaching out for help...

YOUSRA: Yes — there was one night I was hanging out with a friend, playing video games. This was a period where I was doing so much job searching and getting no results. I was still spending time with friends, but I was kind of moving from one person to the next — games, karaoke, company — until 2 a.m., when it suddenly hit me how sad I actually was. I realized I was just escaping through other people.

And then I called the person who has inspired me most in the world, and who has always seen my potential — my cousin Nadine. I called her and I said, "I feel like such a failure. I've had all these interviews and nothing worked out. I don't even know what my place is in this world."

Her response was just: you are not a failure at all. And because I think so highly of her — and because I know she's completely honest — that was genuinely validating.

Something she said that really stuck with me was that she doesn't like to think of work in the traditional sense — this expectation that you'll work forty hours a week, or more, and that's the whole of it. There's a life beyond that. Sometimes you need a foot in the door, so you do things you don't want to do — but it's often only later in your career that you get to do exactly what you want. Until then, it's just a struggle. And she reminded me that our lives are not built around making other people money.

PART 7 — AUTHENTICITY IN PRACTICE

OLAJUMOKE: Authenticity is one of those words that gets thrown around a lot — almost a buzzword. What does it actually look like for you in practice?

YOUSRA: I love that you called it a buzzword — it kind of bothers me too, because I feel like people use it in this almost clichéd way, like standing on a mountain doing yoga. But at the heart of it, authenticity is being true to yourself and not sacrificing yourself. Because when things don't work out and you put your whole life on pause, everything gets so much worse.

For me, authenticity is always finding my inner joy, and also allowing myself to feel the full range of what I'm going through.

What I've noticed in workplaces and at networking events is people masking. And it's interesting — I love all kinds of fashion — but when everyone shows up to a networking event in a suit or a pantsuit, it's almost like we've all subscribed to this streamlined definition of what professionalism looks like and how you should speak. That puts pressure on all of us to be one version of ourselves at work and a completely different version everywhere else.

Obviously, each space requires some tailoring. But there has to be a level of grounding and consistency in yourself. And I think it's really important to be critical in every space you're in — to ask, is there pressure being put on me to act a certain way? How do I find the balance of showing up as I am, while also seeing people for who they are and giving them that space too?

OLAJUMOKE: What has showing up more as yourself actually changed for you?

YOUSRA: That's a hard question — because honestly, I don't think I ever really had the ability to not show up as myself. I'm some flavor of neurodivergent where even if I try to mask, it doesn't last very long.

There was a point where I did try, and the duration just kept getting shorter until the lights went out. I just couldn't keep up the act. People can see it in my body language, in my expression. And because of that, I've made peace with it: there's no reason to let people expect something of me that I'm not going to be able to sustain. I'd rather show up as I am.

PART 8 — THE MINDSET SHIFT: SELF-AWARENESS

OLAJUMOKE: What is one mindset shift that has made the biggest difference for you — particularly at those junctions where things felt unclear or nothing was moving?

YOUSRA: Self-awareness. And I think throughout our lives, our self-awareness is constantly expanding. But for me, around the age of twenty-seven, I gained a huge amount of self-awareness all at once. And that gave me what I needed to move through challenges — because when I'm faced with conflict or failure, I'm now able to be genuinely critical of myself. Not in a way that's too hard on myself — I think that's its own trap — but in a way where I can see what I brought to the table and what I wasn't able to bring.

Even if I think someone else is ninety-nine percent in the wrong and I'm one percent in the wrong, that one percent still matters. Self-awareness means being able to see how something could have been better — and sitting with that.

And I'll say this: it takes me processing time to self-reflect. In the moment, I might not have clarity yet. But what I'm grateful for is that as I get older, the time it takes me to reach that clarity gets shorter and shorter.

PART 9 — ADVICE FOR THOSE FEELING BEHIND

OLAJUMOKE: If someone is listening right now and they feel behind — looking at their peers, people who graduated at the same time, who seem to be further ahead — what would you say to them?

YOUSRA: I would definitely say: look at what your narrative has been up until now, and how it has mattered to the people around you. Because the people who care the most, who are most active in community, who have the biggest positive impact on others' lives — they don't always get the best jobs, and they don't always get paid the most. We don't have a political or institutional system that rewards the kindest or most compassionate people. So look into that part of your life. That part matters.

And it's not easy to compare yourself to anyone, because you're only seeing their surface. A lot of people I know who make a lot of money aren't that happy. And I also know people who've moved ahead in their careers who are genuinely happy. Everyone builds their life differently.

It's kind of like a ten-thousand-piece puzzle. You get stuck because all the pieces look alike. But you're still completing the picture. Even if it's slow, it's still progress. And whoever you were a year ago wasn't in a better position than you are now. I think even failure is a vital part of that picture. It's lived experience.

PART 10 — THE HARDEST LESSON

OLAJUMOKE: Last question: what is a lesson you had to learn the hard way — one that genuinely shapes how you work and approach life today?

YOUSRA: It brings us back to one of the first things we talked about — collaboration and communication.

I often encounter people where I genuinely don't know how to collaborate or communicate with them, and that's something I'm always working on. But I'll be honest — I sometimes feel like, why do I have to be the one doing all this work? Why aren't they doing the work to understand me better?

And I think that feeling is real and valid — especially as someone who is racialized, queer, and neurodivergent. You already carry so many life experiences that set you apart, and then on top of that, you're also filling gaps that others have never had to think about.

But here's where I've landed: it's a disservice to yourself if you don't do everything you can to make a specific collaboration work. It's okay if it ultimately doesn't. But if you do everything you know how to do — that's all you could have done. At least you tried.

CLOSING

OLAJUMOKE: As we wrap up — if someone takes nothing else from this conversation, what's the one thing you want them to remember?

YOUSRA: Who you are and what you bring to the table is perfect — and exactly what we need. And where you are in life does not define where you will be.

OLAJUMOKE: I love that. And I think that's really the heart of this episode — helping people reframe some of the narratives that society puts on us, and reminding them that there is a bigger picture being painted, even when you can't see it yet. Yousra, thank you so much for sharing so honestly with us today.

To connect with Yousra, you can find her on LinkedIn under her name — Yousra Nawara — and her website is scuttlethathasit.ca. 

And to our listeners — if this episode hit home, don't keep it to yourself. Share it with someone who needs to hear it. Until next time, keep thriving.