"I hated marketing. I hated sales. Then I found agencies" - Rob Sherwood, The Digital Maze
Episode 17 - THAT MOMENT
What happens when you go from hating marketing to becoming a Growth Director by accident? Rob Sherwood from The Digital Maze knows the answer - and it's nothing like what career advisors tell you.
Most people think successful careers are planned. Rob's wasn't. He studied business management and marketing at Nottingham Trent because the psychological element interested him. His placement year? Tasks so simple he spent six months watching the clock, using his mum's "motivational mountain" - a family tool passed down from his diplomat grandfather - just to survive until it ended. He graduated convinced marketing wasn't for him.
So he pivoted to sales. Got into telecoms bid management at a massive Japanese tech company. Cultural clash between slow-paced lifers and an ambitious 20-something who wanted to travel. He left, spent five and a half months in Southeast Asia (strategic timing - long enough for the experience, short enough not to hurt his CV), came back to another telecoms role. Younger company, boozy Friday lunches, but a bloated sales team where every prospect had already been contacted. Then Covid hit. April 2020. Redundancy.
That's when Rob tried his own thing. Amazon FBA. He followed tutorials to the letter, found a gap in weighted fitness hula hoops - good demand, poor listings, decent pricing. Ordered 1,000 units. Sold out in two months without paid ads. Ordered 4,000 more with better branding. The factory shut for Christmas. His competitors made tens of thousands whilst he sat out of stock. When his shipment finally arrived, every single hoop was broken. The factory had lied about QA. He lost everything.
A friend had offered Rob an agency role before - back when he returned from traveling. He'd turned it down because he wanted London life, not Nottingham. But after the hula hoop disaster, after Covid redundancies, after discovering marketing placements and telecoms sales both felt wrong, Rob reached out again. The timing was perfect. The agency had just bounced back from Covid cuts. And suddenly, working with ambitious brands on PPC, SEO, and web development - it all clicked.
Now as Growth Director at The Digital Maze, Rob heads up sales, oversees brand marketing strategy, and supports teams and clients to identify new opportunities - whilst remembering exactly what it felt like to be completely lost.
This episode tackles the uncomfortable truth about careers: sometimes the answer isn't planning better. It's being brave enough to admit what isn't working and staying open to what might.
The Messy Reality of Finding Your Path:
The Placement Year Paradox: Universities sell you on careers, then companies give placement students overly simple tasks because "how much do you want to give someone leaving within a year?"
The Motivational Mountain: Rob's mum taught him her father's tool for surviving challenging periods - visualise the halfway point, map milestones between, and downhill feels easier than uphill. He still uses it today for difficult courses and tough stretches.
The Cultural Mismatch Problem: A massive Japanese tech company taught Rob resilience and cold calling confidence, but slow-paced culture and people seeing out final career years didn't match ambitious 20-something energy.
The Self-Belief Anchor: Losing his job hurt Rob's pride, but he wasn't worried about his career trajectory. "I have a lot of self-belief. I felt like I need to find the next thing."
The Amazon FBA Lesson: Everyone watches videos of people making loads of money. Rob followed best practices, found a weighted hula hoop gap, sold 1,000 in two months - then learned that perfect product research can't protect you from broken supply chains and dishonest factories.
The Timing Paradox: His friend offered him an agency role twice. First time, wrong moment (wanted London, not Nottingham). Second time, post-disaster, post-redundancy - perfect timing made all the difference.
Key Insights Uncovered:
Why telecoms sales taught resilience but never passion - Rob found it too dry to learn about indoor units, outdoor units and lease lines in his own time, a signal the work didn't fit.
How traveling for exactly five and a half months was strategic - Rob wanted the experience but didn't want a year-long gap potentially hampering his career, conscious planning even in exploration.
The hidden cost of bloated sales teams - when every business in the country has already been contacted by someone, building accounts requires extreme resilience rather than smart strategy.
Why his Amazon FBA product choice was textbook perfect on paper - weighted fitness hula hoops had great demand, good pricing, plenty of suppliers, and poorly serviced listings, yet perfect research couldn't save broken execution.
The factory betrayal that taught expensive lessons - Rob went through QA and quality checks, the factory confirmed they'd fix issues, 4,000 broken hoops arrived anyway, and sometimes you lose money learning what you can't control.
How agency life clicked immediately after years of false starts - working with ambitious brands on PPC, SEO, and web development finally felt right in ways marketing placements and telecoms sales never did.
The advice Rob would give his 22-year-old self: "Continue trusting your instincts and keep going. It's a long journey, a career, and you've got plenty of time to make it right."
From Rob's perspective as someone who studied marketing but hated his placement, pivoted to sales but found it dry, lost his job to Covid, failed at entrepreneurship, then finally found his fit in agencies - witness how winding paths aren't failures, they're education. Every wrong turn taught him what he didn't want until a friend's second offer revealed what he did.
Rob shares what matters most: self-belief that carries you through redundancy and broken shipments, strategic thinking even when exploring (five and a half months traveling, not a full year), and staying open to opportunities you've already turned down once because timing changes everything.
This episode addresses the question every ambitious professional wrestling with career doubts needs to hear: what if your winding path isn't evidence you're lost? What if it's teaching you exactly what you need to know - and your calling finds you when you finally stop forcing the wrong direction?
About Supo:
Supo provides people-first intelligence software for professional services firms, helping businesses maximise profit and motivate their people through powerful, AI-enabled business intelligence dashboards. By connecting over 500+ platforms and providing real-time data analysis, Supo helps firms make better data-driven decisions about their profit, projects, and people.
For more information about Supo: www.supo.co.uk
About The Digital Maze:
The Digital Maze is a performance marketing agency based in Derby, supporting ambitious brands nationwide. Specialising in PPC, SEO, and web design & development, the agency works across sectors from Home & Garden and Food & Beverage to professional services. The Digital Maze focuses on delivering exceptional agency experience through strategic marketing that increases leads, sales, and business growth. The agency also runs Marketing Mastered - quarterly events, monthly newsletters, and a community for Derby's marketing scene to meet, learn, and level up.
For more information about The Digital Maze: thedigitalmaze.com
Ready to discover why winding careers aren't failures, they're education? This episode isn't about planning better - it's about the self-belief required to admit what isn't working and stay open to what might finally click.