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The journey to Reimagine Work:
Lessons in courage, clarity and connection
By Becky Webber
Why I chose to tell my story
I’ve spent most of my career helping others grow, but I rarely stopped to reflect on my own journey.
Each role, challenge and change has shaped how I see people, purpose and potential.
This collection of reflections traces that path—from the lessons I learned watching my dad to finding my own voice to creating Reimagine Work.
It’s about what happens when you stop chasing the next promotion and start asking, “What kind of work feels true to me?”
What my dad taught me about work
My dad is one of the most positive people I know. At 82, he’s still out helping with community events, chatting to neighbours, and generally brightening the day for anyone within a five-mile radius.
He started out at Southampton Docks as a trainee accountant. He was good with numbers but restless. One day, staring out of the office window, he saw a window cleaner outside, whistling and singing to himself.
In that moment, he realised he wanted that man’s joy more than his job title. He handed in his notice the same day and told my mum he was going to become a window cleaner. (I can only imagine her face 😲.)
From there, he cleaned windows, delivered milk, ran the local meat round, and later joined Everest Double Glazing as a salesman. Not your typical door-to-door salesman that you may have in your imagination, he even took his slippers to appointments so he wouldn’t ruin anyone’s carpet. Year after year, he became the top performer, not through slick sales tactics, but through kindness, humour, and genuine connection.
Eventually, he was promoted to manager—the natural next step for many top salespeople—but he hated it.
The spreadsheets, the meetings, the distance from customers. It took him away from what he loved: people.
So, he stepped back into sales. Not down, but back. Back to what energised him, what made him good.
He always stayed true to himself.
I think about that a lot as the world of work keeps changing — AI, hybrid models, constant reinvention. We talk so much about adapting to the future, but maybe the real skill is adapting without losing yourself.
Work will always evolve. The tools will change. The titles will shift, but the core of good work — curiosity, connection, integrity — never goes out of fashion.
My dad figured that out without a strategy deck or a leadership programme. He just listened to his gut and chose happiness over status.
Maybe that’s the most future-ready skill of all.
Those early lessons — about joy, integrity and doing work that feels like you — stayed with me. They were the quiet compass I carried into every chapter that followed.
The promotion that looked like success —
but didn’t feel like it
I didn’t climb the ladder through careful planning or ambition. I said yes when opportunities arrived, often before I felt ready.
When I transferred with Thomas Cook from the South to the Midlands, I thought it would be a short-term move. Instead, I ended up covering several branches, often ones that were struggling. I rolled up my sleeves, worked alongside the teams, and we turned things around together.
It was exhausting, but it taught me how to lead through people, not position.
Then came the big offer: my own flagship branch in Coventry. At 25, I became the youngest branch manager in the company. On paper, it was everything I’d worked for.
In truth, it was one of the hardest experiences of my life.
The culture was cold. I was young and female, constantly having to prove myself. Respect didn’t come easily. By the end, I’d earned it, but I’d also learned something crucial: achievement means nothing if it costs you your sense of self.
That realisation was a turning point. I moved back south, took a role with a training provider running its Southampton operation, and discovered that not every job—or culture—fits your values. After eight months, I left and began a new chapter in recruitment.
That’s where I finally found work that made sense, where people, performance, and purpose connected.
Sometimes the proudest moments aren’t the ones that look like success from the outside, but the ones where you quietly decide to realign with who you really are.
I debated whether to add this relic from my Thomas Cook days… then remembered confidence comes in many forms, including sharing your worst hair decisions ;-).
This experience taught me that titles mean little without meaning. It also pushed me to start looking for the kind of work where people, not politics, came first.
When I found recruitment, I found my people
Moving back south felt like a fresh start. I knew what didn’t feel right, but I wasn’t sure what would. I just knew I wanted to do work that felt more like me again.
Then I found recruitment. Or maybe it found me.
It was fast-paced, people-centred and unpredictable, everything I’d been missing. For the first time, my natural instincts to listen, problem-solve and support others weren’t seen as “soft skills”, they were strengths.
I loved helping people recognise their potential and connect with roles that felt right for them, not just on paper, but as people.
I also gave feedback to job seekers, always with permission. It’s not something everyone finds easy, but when done right, it’s usually received with real appreciation. Watching people grow from what were once blind spots was incredibly fulfilling. It reminded me that honest feedback, shared with care, can change the way someone sees themselves.
It wasn’t always easy. The pace could be relentless and the pressure high. But even on the toughest days, I knew I’d made a difference, however small, to someone’s confidence or career.
That’s when I realised something important. I cared less about the placement itself and more about helping people find their spark again.
Over time, that instinct shaped how I led teams, built relationships and created ways to help others grow.
Recruitment taught me that purpose isn’t something you stumble upon. It’s something you build through experience, reflection and staying curious about what energises you.
That lesson has stayed with me ever since: lead with empathy, listen for potential, and never underestimate the difference it makes when you help someone believe in themselves again ❤️.
Recruitment taught me empathy, patience, and perspective. But to keep growing, I needed to learn how to lead differently, and that meant letting go of what had always worked before.
Learning to lead without the manual
As the company grew, so did the opportunities, and before long, I found myself leading a team again. Some years later, I was offered a Regional Director position. It wasn’t a step I’d been chasing, but my Managing Director saw potential in me, and I decided to take the leap.
What I didn’t realise at the time was that it came with no instruction manual.
This wasn’t about managing a bigger team; I already had managers doing that. It was about something different: context. Seeing the bigger picture, joining the dots across offices, and learning that no two teams, people, or markets are ever the same.
It was an eye-opening experience. I quickly realised how easy it is, when you’re managing side by side with others, to make comparisons. To think, “Why can’t this team perform like that one?” But you soon learn you’re not comparing apples with apples. Every team has its own mix of personalities, experience, challenges, and customers.
The step up was uncomfortable. I was used to being hands-on, fixing problems, and getting things done. Now I needed to lead through others, to empower, to trust, and to let go of the reins.
I was lucky to find an accidental mentor along the way — a business leader I met at a networking event who shared one piece of advice I’ll never forget:
“Make yourself redundant.”
It took me a moment to understand what he meant, but it was simple: empower your people so they don’t need you.
It wasn’t easy, but it changed everything. Over time, the team became more confident, decisions happened faster, and I found space to think differently about leadership.
That experience taught me that leadership isn’t about being in control. It’s about creating the conditions for others to thrive.
As I’d soon find out, it was also the start of learning to use my own voice differently.
Finding my voice (and why it wasn’t natural)
Coming from the travel industry, I was used to people walking into the branch excited to book their holiday. Happy customers, relaxed conversations, familiar territory. Recruitment was a different world entirely. Suddenly, I was the one knocking on doors, presenting to clients, pitching to decision-makers, and representing my candidates with confidence I didn’t always feel. It stretched every communication muscle I had.
I was comfortable listening, advising, and connecting one-to-one, but standing in front of a decision-maker to win business was another story. I’d overprepare, overthink, and walk away convinced I hadn’t said enough (or said too much).
For context, I once dropped out of an A-level in Business Studies because I couldn’t face giving a presentation. I wasn’t a natural speaker; I was the quiet kid who preferred to observe rather than perform.
So, presenting didn’t come easily. However, what I learned, step by step, is something I now remind the people I coach: Confidence isn’t a personality trait; it’s a skill you practise.
Every client meeting, pitch, and presentation became a rehearsal for courage.
I learned to stop chasing “perfect delivery” and focus instead on real connection.
Fast-forward to today: I’ve delivered hundreds of webinars, spoken at company events, hosted panels, and shared my story on podcasts. All things I once thought were for “other people.”
So, when someone says, “You’re such a natural,” I smile, because I know I’m not.
I built it. Bit by bit.
Through shaky starts, deep breaths, and choosing to keep showing up.
Finding my voice changed everything. Not just how I speak, but how I lead, coach, and connect.
It reminds me that the most powerful voices in the room aren’t always the loudest; they’re the ones that speak with meaning.
Finding my voice changed everything, not just how I led, but how I connected, and that shift opened the door to something unexpected.
Why I started Positive Career Advice
(and what it taught me)
Before COVID, I set up a side project called Positive Career Advice. It wasn’t a business; it was just a way to give back.
After years in recruitment, I couldn’t ignore what I was seeing: great people missing out on great jobs, and great companies missing out on great people.
It frustrated me then, and it still does today.
Just because someone’s exceptional in their field doesn’t mean they know how to present their value on paper.
I’d meet incredible professionals underselling themselves because they didn’t know how to translate their experience into words.
At the same time, I’d watch employers filter through hundreds of CVs, making assumptions based on a few lines of text or a LinkedIn profile that didn’t tell the full story.
It felt wrong, like a waste of potential on both sides.
Then COVID hit, and what started as a side project became a mission.
Over the next two years, I delivered more than 300 webinars to job seekers globally from all walks of life, helping people create CVs, improve LinkedIn profiles, and build confidence in a world that suddenly felt uncertain.
Once terrified of presentations, I found my voice in those sessions.
Speaking with purpose changed everything.
But the biggest lesson came from the people on the other side of the screen. During every Q&A, the same questions kept coming up about confidence, self-worth, and how hard it is to see your own value.
That realisation changed how I wrote, taught, and led. I stopped speaking as a recruiter and started speaking for the job seeker.
It taught me that empathy isn’t just a value, it’s a strategy, and it left me thinking about how often we underestimate ourselves.
➡️ We see talent in everyone else but miss it in the mirror.
➡️ We talk about achievements, but not the effort behind them.
➡️ We edit ourselves down to fit what we think people want to see.
If any of that sounds familiar, stop for a moment.
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Think about the strengths people come to you for. That’s often where your real value hides. You don’t need to become someone new to stand out. You just need to start recognising the person you already are.
The lessons I learned through Positive Career Advice weren’t confined to that moment; they became part of how I lead. Over the years, I’ve learned that uncertainty takes many forms, and the principles of empathy, honesty and communication matter just as much in business as they do in coaching. Those lessons have guided me through every change since, and continue to do so today.
Leading through change (when the ground keeps moving)
The truth is, those same lessons became essential in my own leadership journey. Because if there’s one thing I’ve learned, it’s that uncertainty doesn’t only exist in job searches, it lives inside organisations too.
Throughout my career, I’ve led through one merger and two acquisitions, including a shift from PLC to private equity ownership. And, of course, COVID.
More recently, change has taken a different shape, with tougher market conditions, structural shifts, and the reality of good people moving on. When colleagues you’ve worked alongside for years leave, it’s not just a business change; it’s a personal one. You feel it too.
This is where leadership happens in the grey, when clear answers are rare and every decision comes with trade-offs.
In those moments, you’re balancing two realities. One is the leadership's view of progress and long-term goals. The other is your team’s day-to-day experience: the reality of shifting workloads, changing priorities, and uncertainty about what it all means for them.
What I’ve learned is simple. Communication is everything. Silence is deafening. Change can’t be done to people; it has to be done with them.
I haven’t always got it right. There were times I tried to protect people by saying less, only to realise that silence breeds anxiety, not comfort. The best thing you can do is be honest, even when you don’t have all the answers.
During those times, I made it a priority to stay visible and connected, holding regular calls to share updates, answer questions, and keep people part of the journey, not passengers on it.
We talked about market conditions, performance, and what it all meant for the team. Sometimes it was uncomfortable, but those conversations built trust. They reminded people that they weren’t being left in the dark and that their voices mattered.
One thing that really helped was finding ways for people to recognise and support each other. Simple gestures of appreciation went a long way in keeping morale strong, even when things were uncertain.
What I’ve learned through all of it is that leadership in uncertain times isn’t about having the right answers. It’s about staying human, listening with empathy, protecting psychological safety, and admitting when you’ve got it wrong.
Change will always keep coming. The future of work will always evolve. What matters most is how we lead through it with clarity, courage, and connection.
The lessons I learned while leading through constant change stayed with me. They reminded me that clarity, confidence and connection aren’t just business needs — they’re human ones. Those insights became the spark that would eventually grow into Reimagine Work.
From Positive Career Advice to Reimagine Work — coming full circle
Through Positive Career Advice, I learned how powerful it can be to give people space to think — to help them see their strengths and value more clearly. At the same time, leading through constant change taught me that those same needs for clarity, confidence, and connection exist inside organisations too.
The more conversations I had, the clearer it became that people weren’t just navigating restructures, new systems, or shifting priorities — they were searching for meaning and direction in work that no longer felt the same.
That realisation became the spark for Reimagine Work.
After COVID, the world of work didn’t go “back to normal.” It shifted — quietly but completely.
People began questioning what they wanted from work, how they defined success, and where they found meaning. I saw it every week — talented people at crossroads, leaders trying to adapt, and teams rediscovering what mattered most.
The pattern was unmistakable: people needed more than career advice — they needed space to think, clarity to decide, and confidence to move forward.
That’s how Reimagine Work began.
Alongside my full-time leadership role, I started shaping it as a space to help others find their spark again. To make sense of change and move forward with purpose. It wasn’t a pivot; it was a progression.
As part of that, I began studying for my ILM Level 7 in Executive Coaching and Mentoring. It's strengthened what I’ve always believed: that change doesn’t start with a new plan, it starts with a new perspective.
Now, my coaching focuses on empowering and partnering with people to find clarity and a way forward.
Helping them spot patterns they can’t always see in themselves, and supporting them to rebuild confidence, momentum, and belief.
In many ways, that takes me back to my dad. The man who once left a safe job on Southampton Docks because he saw someone outside whistling while cleaning windows and thought, I want that kind of joy in my work.
Dad taught me that fulfilment isn’t found in the title, the company, or the pay slip; it’s found in the feeling.
So yes, this might look like a new chapter, but really, it’s a continuation of everything he taught me. That work should make you feel alive.
Thanks, Dad xx
Epilogue – what comes next
These reflections are more than memories, they’re reminders that growth is rarely loud or linear. It happens in moments of honesty, discomfort and courage.
Reimagine Work was never about reinvention for its own sake; it’s about rediscovering what makes us come alive at work, and that’s the conversation I’ll keep having — with leaders, teams, and individuals ready to evolve.
Because the goal isn’t to reimagine my work anymore. It’s to help others reimagine theirs.