How to Use Your Values as a Compass to Navigate Career Transitions

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WorkLife Stories from School of WorkLife Episode: How to Use Your Values as a Compass to Navigate Career Transitions

Learning how to use your values as a compass to navigate career transitions begins with recognising that the emptiness you can't explain away is often the clearest signal you have.

Jack had built exactly the technical career everyone said he should want — exceptional engineering skills, a salary that had tripled since university, recruiters messaging him weekly. Three years in, he sat at a funding celebration and felt a profound emptiness he couldn't explain away. This is the story of the Saturday afternoon that showed him why — and the eight months that followed before he was ready to act on it.

RESOURCES MENTIONED

The Storytelling Newsletter (Free) Short, focused, and grounded in real WorkLife situations — how we communicate, lead, make decisions, and navigate challenges at work.  

Story Lesson: How to Use Your Values as a Compass to Navigate Career Transitions Learn how to use your core values as a compass for navigating career transitions — and build a working life on what genuinely matters to you.

Guided Programme: Values Alignment Career Transition Guide - How to Navigate from Success to True Significance 

Commissioned learning resources, speaking engagements, and organisational partnerships: carmel@schoolofworklife.com 

schoolofworklife.com

The stories I write are based on real WorkLife challenges, obstacles, failures and successes. Persons and companies portrayed in the stories are not based on real people or entities. Carmel O' Reilly

Transcript

Speaker 0:08

Jack had built exactly the technical career everyone said he should want. Exceptional engineering skills. A salary that had tripled since university. Recruiters messaging him weekly with even more lucrative offers. Three years into building algorithms for high-frequency trading, he sat amongst a champagne celebration of a £10 million funding round — and felt a profound emptiness he couldn't explain away. Welcome to WorkLife Stories from School of WorkLife. I'm Carmel O' Reilly. And today's episode is How to Use Your Values as a Compass to Navigate Career Transitions — what becomes possible when you stop treating your values as something you fit into weekends and start recognising them as the foundation of work that genuinely sustains you. This story is about Jack. And about the moment he realised that the emptiness he couldn't explain away wasn't a signal that something was missing from his life — it was a signal that something was missing from his work. The Pattern Jack Had Never Questioned His professional logic had always worked like this: Solve the hardest problems. Build the most elegant code. Let the purpose take care of itself. Technically brilliant. Financially rewarded. And completely disconnected from the reason he'd started building things in the first place. He'd grown up in the neighbourhood he volunteered at. Where a second-hand laptop at twelve had changed his life. And somewhere between that boy and this corner of Silicon Valley, something fundamental had shifted. He had never stopped to ask what his core values were telling him.  Or what it cost to keep ignoring them. The Saturday That Changed the Question At a community centre, helping a fourteen-year-old debug her first programme, Jack used the same technical thinking he brought to microsecond trading optimisations. But something felt entirely different. Not the skills.  Not the complexity.  Not the effort. The purpose. Amara was building an app to help her grandmother navigate NHS services. The project was technically simple compared to Jack's day job. But the human need behind it made it feel infinitely more real. Jack drove home that evening understanding something he hadn't had language for before. His expertise hadn't changed. But when it served educational equity rather than financial extraction, it felt like an expression of who he actually was — not just professional competence. The Moment He Tried to Dismiss It Jack wasn't ready to walk away from what he'd built. He had financial commitments. His mother depended on him. And leaving without a clear alternative felt irresponsible. He told himself it was restlessness. That the technical challenges at TechVelocity were simply too narrow. That what he needed was a more complex problem to solve — not a different reason to solve it. He stayed. He delivered. He sat in team meetings discussing features that would save traders milliseconds — and thought about teenagers without computers at home. The emptiness didn't lift. It deepened. The Professional Reckoning Jack began to sit with what the community centre was showing him. Not just that the work felt different. But why. The same technical skills. Two entirely different relationships to what they served. One extracted value from those who already had it. One created access for those who didn't. He had always told himself that what mattered was the quality of the engineering. What he was discovering was that quality alone had never been enough — not for him. His values hadn't been absent from his professional life. They'd been present the whole time, unexamined, pointing somewhere he hadn't yet been willing to look. What He Discovered When He Stopped Dismissing It Jack began keeping a values journal. Not to reach a conclusion. Just to pay attention to what was already showing itself. He documented the work that energised him. The work that depleted him. The patterns emerged faster than he expected. He wasn't drained by difficulty. He wasn't energised by technical complexity alone. He was energised by work that created pathways — for learners, for communities, for people whose access to opportunity looked like his own once had. He was depleted by work that optimised systems that had no interest in any of that. The contrast was stark.  His technical abilities hadn't changed.  But when they served educational equity rather than financial extraction, they felt like expressions of who he actually was. Jack had been treating his values as the backstory of his career. What he was discovering was that they were the map. And he'd been navigating without it. What Happened Next Jack tested the pattern — methodically, over months. The same expertise. Two entirely different kinds of purpose. He volunteered weekly. He took on pro bono projects. He attended conferences at the intersection of technology and education — and felt the same intellectual excitement he'd experienced at TechVelocity, with something added that he hadn't felt there in years. He built the bridge carefully, practically, without abandoning what he'd already built. At an EdTech conference he met a former Google engineer who now led technology for underfunded schools. "The constraints in educational technology force you to be far more creative than when money's no object," she told him. Jack leaned forward. For the first time he understood that the salary reduction wasn't a compromise.  It was a technical upgrade — harder problems, more creative solutions, serving people who genuinely needed what he could build. And when Amara's NHS navigation app launched for her grandmother, he understood something else.  His values compass hadn't been pointing away from his expertise.  It had been pointing toward what his expertise was actually for. When the role leading educational platform architecture for under-resourced schools emerged, he recognised it immediately. Not as a sacrifice. As the destination his values had been pointing toward all along. What Jack Came to Understand But here's what Jack understood only in retrospect: He had spent years treating social impact as something he served on Saturdays. A supplement to professional life. Something to balance against the real work. His experience showed him something different. The values that had shaped him — equity, access, contribution — weren't supplementary to his expertise. They were the framework that made his expertise mean something. The emptiness he'd felt wasn't a signal that something was missing from his life. It was a signal that something was missing from his work. And that distinction changed everything. The Teaching Insight One shift changed everything. From: What is the hardest problem I can solve? To: Who does it actually serve? When that question changed, the work changed. And so did the professional life he was building. A lower salary. Deeper satisfaction. Work that finally felt like the reason he'd learned to build things in the first place. Because the values he'd been living around — rather than from — weren't a distraction from his professional life. They were its foundation. Why This Matters Professionals can believe that purpose is something you earn the right to pursue — once the career is established, once the financial commitments ease, once the timing is finally right. But Jack's experience shows something different. The most important question in any professional life often isn't whether your expertise is exceptional by conventional measures — it's whether the purpose it serves aligns with what you actually stand for. Are you directing remarkable skills toward work that extracts — while the contribution that would genuinely sustain you remains something you fit into weekends? When you stop treating your values as supplementary, so does what becomes possible. The working life that feels like yours begins the moment you stop building the one that could belong to anyone. But the impact reaches further than one career decision. When you name your core values honestly — not as ideals but as the practical foundation of what sustains you — something shifts.  Not just in the work you choose. In how you understand the work you already do. And when you share that clarity with others, something else becomes possible.  They begin to examine what their own expertise has been pointing toward all along. CLOSING That's today's story — How to Use Your Values as a Compass to Navigate Career Transitions. The complete lesson follows Jack's full journey — including the values journal that revealed the pattern he had been too busy to see, the conversation with a former Google engineer that reframed the salary reduction as a technical upgrade rather than a compromise, the eight months of parallel professional lives that tested the direction before he committed to it, and what Amara's app launch confirmed — and shows how recognising your core values can transform not just the career you're building but the expertise you already have. And if you want to go deeper, the companion Guided Programme — Values Alignment Career Transition Guide: How to Navigate from Success to True Significance — is there when you're ready. All the details and links are in the show notes, or you can find everything at www.schoolofworklife.com. Subscribe to the podcast for weekly audio stories, or visit The Storytelling Newsletter for the written versions. Or both. Next time, we'll be exploring How Research-Based Reading Strengthens Connection and Develops Collaborative Intelligence — a story about how Phoebe had been leading digital transformation for years with projects delivered on time and every procedural barrier removed, until the final chapter of a book read in an office car park showed her that the silence in her team meetings wasn't about lack of ideas at all. Until then, remember: the working life that feels like yours begins the moment you stop building the one that could belong to anyone. Thank you for listening.