Reflection, Experience and Ownership: Adrian Whitcombe’s Midlife Story

This is the story of how a corporate sales and marketing executive pivoted at midlife, drawing on decades of experience to design a new chapter.

Adrian Whitcombe’s career traces the last great shift from analogue to digital across industries, countries and decades. He built his foundation in the first wave of UK telecoms, travelled across continents, and rose to lead European marketing for Expedia’s business travel arm. Then the world stopped.

When the pandemic grounded travel, Adrian found himself with a rare chance to pause. For the first time in years, there was space to reflect and question what he wanted the next chapter to look like. That pause guided his midlife pivot.

The early years: Building a foundation in a changing world

Adrian starts his timeline in the year 2000 in the early days of tech. He joined Cabletel, which later became Virgin Media, selling connectivity to businesses at the very moment the UK’s telecoms market deregulated.

“It was the early days,” he remembers. “Nokia brick phones and Blackberries with QWERTY keyboards felt like magic. Fax numbers still sat on letterheads. The economy was thriving, rents were affordable, going out was the norm. If you worked hard and showed up, doors opened.”

Those years brought early lessons in sales and resilience. But they also brought appetite for something different and that was curiosity. Adrian took time out to travel across North America, Central America and Europe. He later settled in Madrid, teaching conversational English to banking executives. “At thirty, not twenty-two, I could sit with a fifty-year-old client and talk business,” he says. “It was a different kind of credibility.”

These early adventures gave him adaptability, cultural fluency, and the confidence to speak across generations. Qualities that would matter later in corporate and entrepreneurial life.

Corporate leadership: Expedia Group

Returning to the UK, Adrian joined Expedia Group who then had over twelve thousand employees across 60 countries, multiple brands, and big budgets.

He brought a rare edge - sales instincts in a marketing role. “I’d succeeded in sales. I could translate. We won awards. We filled pipelines.”

He was there for a decade and had reached a quiet clarity. He had a budget, a team, responsibility, and recognition. But he knew what the next rung meant: more time zones, more stress, more sacrifice. “I was happy with what I was doing. I didn’t want the extra layer,” he says.

During his time, Adrian loved that Expedia put genuine weight on culture. They trained early on unconscious bias, including around age. They saw the value older staff brought. “They spotted mistakes younger colleagues missed. They weren’t climbing ladders. They had knowledge and experience. They saved the business money and stress. They were worth their weight in gold.”

The pause only came when the world stopped.

A golden opportunity to pause and rethink

The pandemic grounded planes, closed hotels, and shut conference halls. For the first time in years, Adrian had space.

Homeschooling and gardening sat alongside reading, journaling, and revisiting health principles he had studied years before. He reopened old notes from Anthony Robbins’ programmes, flicked through photo albums, looked back over his journals, and started blogging again.

The question emerged: did he want to go back into the corporate world, or did he want to design something different?

He was in midlife and chose to treat the impending fiftieth birthday as a ten-year arc to design the next stage with intention.

Immersed in tech: A different kind of corporate

When the world opened up again, Adrian didn’t return to a corporate rival. Instead, he joined three others to launch TechInformed, a new tech publication. The CEO provided vision and funding, an editor handled content, a commercial lead handled sales, and Adrian built the brand and go-to-market from scratch.

It was an immersion into technology at the disruptive edge of cloud and AI. He applied two decades of lessons. “You can waste so much money in marketing and GTM if you don’t know what works,” he says. “I’d already learnt those lessons. We stripped that away.”

The results came quickly. Experience turned into fewer missteps. “The CEO said the business was in a safe pair of hands. That wasn’t just me. That was experience doing its work.”

Three years on, as the company expanded into the US, Adrian stepped aside. He had taken it from zero to an annual recurring revenue engine, hired his replacement, and chosen his next inflection.

Beyond business: A confidence crisis that doesn’t need to be

Adrian also sees a wider story that matters to people in their 50s and beyond. He notices peers losing confidence as technology, especially AI, accelerates. “I see people nervous, overlooked for promotions, thinking they can’t keep up,” he says.

But he insists the fear is misplaced. “You’re not starting again. You’re starting from everything you’ve lived and learned. The ability to spot mistakes, the wisdom to pace yourself, the judgment that comes with experience — that doesn’t disappear. It becomes more valuable.”

His message is clear: don’t let tech turn into an excuse to diminish yourself.

Confidence at midlife comes from remembering you have already navigated revolutions from fax machines to mobile phones, from analogue to digital. This is just the next one.

The three challenges that stop a midlife pivot

Adrian names the three hurdles that stall many midlife pivots before they start and confirms that each challenge is real and survivable.

• The Unknown
  Stepping into the fog can paralyse. Shrink it by choosing a space where you already have instincts and history.
• Self-Doubt
  Moments of change can shake confidence. But experience doesn’t disappear with a job title.
• The Admin
  The least glamorous truth is that there’s always admin in business and in transition — and it has to be built into the day-to-day.

Editor’s reflection

Adrian’s story is not about chasing executive titles or chasing exits. It is about building a career across chapters, and using midlife not as a cliff edge but as a deliberate reframe.

He shows how a pause can become opportunity. How networks built in earlier decades can still open doors. How the three challenges of the unknown, self-doubt and admin can be recognised and managed into confident knowing.

For employers, Adrian’s journey is a reminder to value the cohort who may not chase promotions but keep businesses steady, accurate and safe. For individuals, it’s encouragement to design the next decade with intention.

Adrian reframed success at midlife by combining adventure, corporate leadership and entrepreneurship. The result is a business that feels both purposeful and sustainable. His message to others is that midlife isn’t the end of growth — it’s when real clarity begins.

You can connect with Adrian on LinkedIn or via his business website Boost.

Me/Redefined

Adrian’s reflections highlight a wider truth for employers about their midlife workforce. Many midlife workers hit this stage with huge reserves of knowledge and loyalty but feel vulnerable in the face of change, particularly when technology accelerates. Without support, they may exit too soon or doubt their value when in fact, their judgement and steadiness are most needed.

By offering Me/Redefined, an online career coaching programme, organisations can turn moments of doubt into opportunity for employers. The result is stronger confidence, extended careers, and businesses that continue to benefit from decades of skill and insight. Find out more https://work-redefined.co/work/me-redefined

Explore more at: https://work-redefined.co/work/me-redefined