Meeting at the Crossroads podcast

This is the first episode in this two-part special, where Sarah sits down with Ciarán Casey, Director of My Learning Limited and author of Leadership in Tune.

In part one, Ciaran walks us through his career, from programming on IBM systems in the 1980s, through GE Capital, a startup venture with his brother, and back into corporate life at First Active. 

Ciaran has moved across five or six industries over a three-decade career, a pattern most people avoid, choosing instead to build deep expertise in one lane. In this conversation, he unpacks what actually drove those moves: not ambition or a grand plan, but a restlessness with stability and a constant pull toward growth and challenge.

Along the way, Ciaran shares the personal framework he uses for big decisions: weighing not which choice avoids regret, but which regret is easier to live with.

• Why Ciaran believes stability doesn't equal fulfillment, and how boredom, not crisis, has driven most of his career moves
• The "exam question" he asks himself before any move: is there an opportunity for growth here?
• His end-of-year ritual of asking, "What did I learn this year?"
• Why the real danger isn't standing at a crossroads, it's staying too long on a comfortable road
• His most defining career pivot
• Introducing regret as a decision-making tool

In part 2, Sarah and Ciarán dig deeper into his decision-making framework around regret, and the leadership model behind his book Leadership in Tune.

Meeting at the Crossroads is available on Apple Podcasts, Spotify, and wherever you get your podcasts.

If today's episode resonated with you, share it with a fellow business owner who might be standing at their own crossroads.

Connect with Sarah

LinkedIn

Website

Instagram

Connect with Ciarán

LinkedIn

Website

Hosted on Acast. See acast.com/privacy for more information.

Frank Fleming, CEO of Verifact, joins Sarah Daly to unpack the crossroads that reshaped his business: the 2015 decision to pivot from a consultancy into a full software company. 

Frank traces the mix of ambition and fear behind that leap, how his years as a commercial fisherman built his tolerance for risk and change, and the blind spots he only recognised in hindsight. He shares what he'd tell anyone facing a similar pivot today: build an MVP, get feedback early, and surround yourself with people who can show you what you can't see for yourself.

In this episode, you’ll discover:

• Why a service business can hit a scalability ceiling and how to know when it's time to build something more scalable
• How to weigh the excitement of a big pivot against the fear of leaving a known, working business behind
• Why your past career can shape how you handle risk and change
• The concept of "blind spots" in decision-making, and practical ways to reduce them
• Why thinking about your total addressable market matters from day one, not after you've already built something
• How looking back on big decisions with hindsight can clarify what to do differently next time, without dwelling in regret
• Why building a trusted network of people to bounce ideas off is one of the most valuable things you can do as a founder

Meeting at the Crossroads is available on Apple Podcasts, Spotify, and wherever you get your podcasts.

If today's episode resonated with you, share it with a fellow business owner who might be standing at their own crossroads.

Connect with Sarah

LinkedIn

Website

Instagram

Connect with Frank

LinkedIn

Website

Hosted by Sarah Daly

Edited by Amanda Fitzgerald

Hosted on Acast. See acast.com/privacy for more information.

Dawn Coupe built Equinox Consulting from a single 3-month contract into a multi-million-pound consultancy over 11 years, growing the business tenfold in just 4 years. But behind the growth was a business barely holding together: contracts overrunning by hundreds of thousands of pounds, mounting supplier debt, and a company that had scaled faster than its systems could support.

Dawn shares what it really took to walk away from a deal that looked like a lifeline, how she rebuilt trust with her leadership team, and the lesson she now carries into her coaching work with founders who've built something brilliant and lost themselves inside it.

In this episode, you’ll discover:

• Why rapid growth can be as dangerous as decline
• How to spot a "helpful" offer that isn't 
• A simple way to test any high-stakes decision 
• Why your busiest, most stressed moment is the worst time to sign anything 
• The real cost of carrying a crisis alone
• How to build a support network before you need one 
• What recovery actually looks like 
• The mindset shift that changes everything

Meeting at the Crossroads is available on Apple Podcasts, Spotify, and wherever you get your podcasts.

If today's episode resonated with you, share it with a fellow business owner who might be standing at their own crossroads.

Connect with Sarah

LinkedIn

Website

Instagram

Connect with Dawn

LinkedIn

Website

Hosted on Acast. See acast.com/privacy for more information.

For 29 years, leadership strategist Charley Swords has asked leaders one essential question: not what are you trying to achieve, but how are you actually leading? 

But this episode isn't about the leaders she's coached, it's about her own crossroads. After years of relentless international travel, a health scare forced Charley to stop completely. A visit to her GP delivered words she'll never forget: get on a plane, and you'll come off it in a box. What followed was an 18-month recovery, the closure of her limited company, and a hard look at whether to retire, return to employment, or start again.

Charley talks candidly about resilience, the myth that stepping back is a sign of weakness, and why she believes self, family, and work must stay in balance for anyone in business.

In this episode, you’ll discover:

• How to recognise the warning signs your body sends before burnout forces a decision for you
• Why stepping back from a business is a sign of strength, not failure
• How to evaluate your real options when facing a health, career, or business crossroads
• A simple framework for keeping yourself, your family, and your work in balance
• Why closing or restructuring a business isn't the same as giving up
• How to rebuild momentum and confidence after an extended setback
• What to consider when facing more than one major life disruption in close succession
• Practical ways to adapt how you work when your usual way of operating is no longer possible

Meeting at the Crossroads is available on Apple Podcasts, Spotify, and wherever you get your podcasts.

If today's episode resonated with you, share it with a fellow business owner who might be standing at their own crossroads.

Connect with Sarah

LinkedIn

Website

Instagram

Connect with Charley

LinkedIn

Website

Hosted on Acast. See acast.com/privacy for more information.

What does it take to let go of a brand you built from scratch and merge it into something new?

In this debut episode of Meeting at the Crossroads, Sarah sits down with marketing expert Christina Clarkin to explore one of the boldest decisions of her career, merging her solo business, The Marketing Lounge, with fellow industry experts Aidan and Jim to form MX3.

• Why Christina reached a growth ceiling in her solo business and what made her reluctant to simply hire
• How she and her future partners were "matchmade" by a mutual vendor, and what made the chemistry click
• What it really felt like to consider letting go of a brand she had built entirely on her own
• Why growth alone isn't always enough, and how to recognise when you've hit a ceiling you can't break through solo
• Why fear of letting go of your brand, your control, your identity as a business owner is normal, and how to work through it
• How to use your "why" as an anchor when doubt and outside opinion start to cloud your thinking

Christina had built a profitable, well-respected business over four and a half years. But she'd hit a ceiling. When the opportunity to merge came knocking in late 2019, her gut said yes, and then COVID arrived. What followed was months of uncertainty, a house move, and a deeply personal decision about what kind of business owner she wanted to be. This is that story.

If today's episode resonated with you, share it with a fellow business owner who might be standing at their own crossroads.

Meeting at the Crossroads is available on Apple Podcasts, Spotify, and wherever you get your podcasts.

Production by Amanda Fitzgerald.

Connect with Sarah

LinkedIn

Website

Instagram

Connect with Christina

LinkedIn

Website

Hosted on Acast. See acast.com/privacy for more information.

Every business owner faces moments that stop them in their tracks. Meeting at the Crossroads is the podcast that meets you in those moments.

Hosted by Sarah Daly, a qualified accountant, transition facilitator, executive coach, and business consultant, each episode features candid, unfiltered conversations with business owners and directors who share the real stories behind their defining decisions. Short, honest, and grounded in lived experience , this podcast offers the kind of insight that's often only understood in hindsight.

Whether you're on a commute, a coffee break, or facing a crossroads right now, we're here to make sure you never have to face those moments alone.

Hosted on Acast. See acast.com/privacy for more information.