The Climb with Cherie Clonan – Details, episodes & analysis

Welcome to The Climb, a podcast about the messy, brilliant, relentless journey of building something meaningful.

For more than a decade at The Digital Picnic, Cherie has had the privilege of shaping other people’s climbs... helping brands, teams, and leaders grow in ways that actually last.

Now, after close to x2 decades working in marketing and leadership, she's turning the mic around to focus on the thing she's most obsessed with: real, honest stories about climb.

This podcast is where we talk honestly about the three things Cherie lives and breathes: marketing education, founderhood, and neurodivergent leadership.

As an introvert who believes in adding value, not noise, every 40-minute conversation is built to respect your time and actually teach you something useful. 

Hosted by Cherie Clonan [@cherie_thedigitalpicnic] and co-hosted and produced by Steph Clifford [@stephssocials] 

Follow us on Instagram @theclimbpod_

Check out our agency @thedigitalpicnic > we teach digital marketing, and we can manage yours, too. 

We unpack what actually helps you succeed in your first 90 days at a fast agency and why “dazzle” often backfires. We share the boring basics that build trust, how to handle culture shock, and what to do if your probation period ends with a no.

Key Takeaways:

• The first 90 days in a new job are about risk reduction, not trying to dazzle
• Reliability is the fastest way to build trust
• Strong new hires ask thoughtful questions
• In a new role, accuracy should come before speed
• The first 90 days are easier when you observe first and challenge later
• A move from brand side to agency side often comes with culture shock 
• New employees should bring past experience without constantly comparing their old workplace.
• A successful probation period is often built on boring things done brilliantly.

Hosted by Cherie Clonan [@cherie_thedigitalpicnic] and co-hosted and produced by Steph Clifford [@stephssocials] 

Follow us on Instagram @theclimbpod_

Check out our agency @thedigitalpicnic > we teach digital marketing, and we can manage yours, too. 

We pull back the curtain on what actually gets someone hired at The Digital Picnic. We share the practical steps that help you stand out, plus the mindset shifts that keep you grounded when you’re applying to a workplace you admire.

Key Takeaways: 

• To get a job at The Digital Picnic, tailor your application instead of mass applying.
• A good resume should be clear, relevant, and submitted as a PDF.
• Creative job applications only work when they are backed by real technical skill.
• If you want to work at TDP, explain exactly how your experience fits this specific role or business.
• Parasocial enthusiasm is not the same thing as job readiness or culture add.
• Strong candidates ask thoughtful interview questions and show how they would add value in the first 90 days.
• In a job interview, confidence matters.
• How you handle job rejection can shape future opportunities with that employer.

Hosted by Cherie Clonan [@cherie_thedigitalpicnic] and co-hosted and produced by Steph Clifford [@stephssocials] 

Follow us on Instagram @theclimbpod_

Check out our agency @thedigitalpicnic > we teach digital marketing, and we can manage yours, too. 

You dialled into episode 1 where Cherie talked about TDP's no-good-very-bad-year... but episode 2 is where we talk about how Cherie - quite literally - CLIMBED her way out of that no-good-very-bad-year.

This year [21/22FY] was that one point in TDP's x11 year history where even Cherie, wired for perpetual optimism, says this was the moment where she thought to herself: the only reason I'm not closing this business right now... is because I *actually* can't afford to.

And so she persisted, and TDP went on to hit its best EVER season thanks to that persistence... and we are breaking it *ALL* down in this episode.

From half a million dollars down, to
BEST YEAR IN BUSINESS > EVER

This episode was proudly sponsored by Mel Browne Money.

Key Takeaways: 

• Why a full business audit is the first step in a business turnaround 
•  How business clarity can help a founder rebuild confidence and fall back in love with their business 
•  Why cutting operational expenses can improve profitability faster than chasing more revenue 
•  The hard truth about people-pleasing leadership and the courage to be disliked in business recovery 
•  Why financial visibility and founder-friendly reporting matter when making tough business decisions 
•  Why systems, operations, and workplace culture matter more than revenue growth alone 
•  How hiring for kind genius, not just talent, can strengthen a service-based business 
•  Why business recovery happens one good decision at a time, not through hope alone 

Hosted by Cherie Clonan [@cherie_thedigitalpicnic] and co-hosted and produced by Steph Clifford [@stephssocials] 

Follow us on Instagram @theclimbpod_

Check out our agency @thedigitalpicnic > we teach digital marketing, and we can manage yours, too. 

76% of your clients vanish in a day. Your team is looking at you through a Zoom screen for reassurance. You can do the maths and you know the runway is short, but you still have to lead. That’s where we start Episode 1 of The Climb, as Cherie tells the raw story of The Digital Picnic’s darkest stretch through COVID and beyond, and why it became the “no good, very bad year” that actually lasted years.

We talk cashflow shocks, founder stress, and what it’s like to carry a pandemic in 30 different ways for a team that’s lonely, burnt out, and stretched thin. Cherie owns the leadership mistakes too: people pleasing, avoiding hard conversations, a feedback culture that turns explosive, and the slow erosion of accountability that quietly poisons company culture.

Then the numbers get real. We unpack delayed financial advice, the e-learning boom, the half-million-dollar course built from a walk-in wardrobe, and the money mindset decisions that stopped that win from becoming true stability. By 2022, Cherie is half a million dollars down, tries to close the business, realises she can’t even afford to shut it, and attempts a sale that falls apart. The turning point is brutal and empowering: nobody is coming to save you.

If you’re a founder, leader, or marketer building a business, this is a clear-eyed look at resilience, financial management, accountability, and the cost of delaying tough decisions.

This episode was proudly sponsored by Mel Browne Money.

Key Takeaways: 

• Founder honesty matters, but so does financial transparency
• People-pleasing leadership can damage business culture
• Poor financial visibility makes bad decisions worse
• Revenue growth does not fix broken operations
• Founder burnout is a business risk, not a personal weakness
• Delaying hard decisions usually makes the outcome worse
• Nobody is coming to save your business
• Values still matter, even in the worst seasons

Hosted by Cherie Clonan [@cherie_thedigitalpicnic] and co-hosted and produced by Steph Clifford [@stephssocials] 

Follow us on Instagram @theclimbpod_

Check out our agency @thedigitalpicnic > we teach digital marketing, and we can manage yours, too. 

We break down what it really means to hire people who protect a neurodivergent founder’s energy. We share the frameworks Cherie uses to spot friction early, set boundaries and build a team culture that supports performance and wellbeing. 

Key Takeaways: 

• Hiring the right team means hiring people who protect your energy, not just fill a role.
• Energy raisers reduce friction, support momentum, and make leadership feel lighter.
• Energy drainers create conflict and unnecessary mental load for founders.
• A quarterly team energy audit helps founders spot green, amber, and red dynamics early.
• Strong hiring decisions should measure friction removed, not just work produced.
• The best hires bring solutions, systems thinking, and lower executive function strain.
• Do not get seduced by charm or a polished CV while hiring.
• Brilliant jerks and chronic conflict cost more energy than their output is worth.

This episode was proudly sponsored by Graham Psychology.
Receive an ongoing discount of 20% off all appointment types [therapy and assessments].

Listeners can book directly via the website and enter ’THECLIMBPODCAST’ into the booking notes or call or email and mention the podcast. 


Mentioned in this episode: 

• The Instagram carousel Cherie shares 
• Disc profiles 
• Patrick Lencioni definition of charmers
• Shelley Johnson from Boldside 

Hosted by Cherie Clonan [@cherie_thedigitalpicnic] and co-hosted and produced by Steph Clifford [@stephssocials] 

Follow us on Instagram @theclimbpod_

Check out our agency @thedigitalpicnic > we teach digital marketing, and we can manage yours, too. 

We break down how to grow on LinkedIn in 2026 without chasing daily posts or virality, and why the platform still rewards real thinking over polished noise. We share practical ways to choose a single topic, add a true thought leadership angle, and use comments, carousels, and social SEO to get discovered. 

Key Takeaways:

• LinkedIn growth in 2026 starts with one clear thought leadership topic.
• LinkedIn rewards people of influence.
• The best LinkedIn posts teach something, not just share an update.
• One high-quality LinkedIn post a week can outperform high-volume posting.
• Human LinkedIn content stands out more than polished AI-generated content.
• LinkedIn comments can drive reach, impressions, and connection requests.
• Text posts and LinkedIn carousels usually outperform video content.
• An optimised LinkedIn personal profile supports SEO, GEO, and discoverability.

Send this to someone who needs a little push to start their own LinkedIn.
 

Follow us on LinkedIn:
Cherie Clonan
Stephanie Clifford

Stepps Framework Explained

Ryan Kelly on LinkedIn

Hosted by Cherie Clonan [@cherie_thedigitalpicnic] and co-hosted and produced by Steph Clifford [@stephssocials] 

Follow us on Instagram @theclimbpod_

Check out our agency @thedigitalpicnic > we teach digital marketing, and we can manage yours, too. 

What changes after you survive a brutal season of founderhood? In this episode, we unpack calm leadership, the founder habits that help you protect your energy, and why reactive leadership can pull a team straight into chaos. Cherie shares the leadership boundaries, mindset shifts, and everyday decisions that help her choose calm leadership over overreaction, protect her energy, and lead more steadily when work gets messy. If you’re trying to build better founder habits, move away from reactive leadership, and create a more grounded version of calm leadership, this one’s for you.

Key takeaways:

• Calm leadership is built by choosing peace over chaos. 
• Reactive leadership creates stress, slower leadership creates better decisions. 
•  Protecting your energy is a core founder habit, not a luxury. 
•  Fake urgency trains founders to react fast instead of respond well. 
•  Healthy leadership boundaries stop other people’s chaos from running your day. 
•  Creator mode helps founders solve problems, victim mode keeps them stuck. 
•  Strong leaders ask better questions instead of rushing to fix everything. 
•  Quiet confidence in leadership comes from protecting, not proving.

This episode was proudly sponsored by PocketSmith.
Get 50% off your first two months of PocketSmith’s Foundation plan here.

Hosted by Cherie Clonan [@cherie_thedigitalpicnic] and co-hosted and produced by Steph Clifford [@stephssocials] 

Follow us on Instagram @theclimbpod_

Check out our agency @thedigitalpicnic > we teach digital marketing, and we can manage yours, too. 

Hyperfocus can look like a superpower from the outside, but living inside it is a different story. We get honest about what autistic hyperfocus actually feels like and how it helped build The Digital Picnic when the hours were long, the stakes were high, and the salary was, frankly, nothing.

Then we flip the coin to the part founders rarely admit out loud: boredom. Not the harmless kind, but the kind that creeps in when you feel underutilised, disconnected, or tempted to “fix” things that aren’t broken. We talk about why a bored founder can destabilise a business, create fake urgency, pick unnecessary fights, and chase dopamine at the team’s expense, plus what to do before that energy leaks into decisions you regret.

You’ll also hear a practical framework for separating boredom from true misalignment.

If you’re navigating neurodivergent leadership, founder identity shifts, or the messy middle of small business growth, this chat will give you the next steps.

This episode was proudly sponsored by PocketSmith.
Get 50% off your first two months of PocketSmith’s Foundation plan here.

Key Takeaways: 

• How autistic hyperfocus can drive early business growth 
•  Why founder boredom is a hidden risk in business 
•  The difference between boredom and outgrowing your role
•  How pattern recognition and deep focus create a business advantage 
•  Why underutilisation is dangerous for neurodivergent founders 
•  How bored founders create chaos, self-sabotage, and fake urgency 
•  Why updating your founder role and job description can reignite growth 
•  The bigger lesson, hyperfocus builds the business, but reinvention keeps it healthy
  
  

Hosted by Cherie Clonan [@cherie_thedigitalpicnic] and co-hosted and produced by Steph Clifford [@stephssocials] 

Follow us on Instagram @theclimbpod_

Check out our agency @thedigitalpicnic > we teach digital marketing, and we can manage yours, too. 

We unpack why you don’t need followers to build a personal brand, and why starting at zero can be the most strategic move you make. We share the content choices, boundaries, and mindset shifts that turn visibility into trust, leads, and real influence in an AI-first algorithm era.

If you’re an introvert, creative, strategist, or business owner who wants more opportunities from their social media, this one’s for you.

This episode was proudly sponsored by PocketSmith.
Get 50% off your first two months of PocketSmith’s Foundation plan here. 

Key Takeaways: 

• Why you can build a personal brand with no followers in 2026 
•  Why clear positioning matters more than follower count for personal brand growth 
•  How to use top of funnel content to grow
•  Why AI-first algorithms favour clear, repetitive content
•  How choosing 3 to 5 personal brand topics builds authority faster 
•  Why your first 100 posts are for positioning, not growth
•  How to create a personal brand that drives trust, visibility, and inbound leads
•  Why personal brand growth comes from clarity, consistency, and memorability, not vanity metrics

Hosted by Cherie Clonan [@cherie_thedigitalpicnic] and co-hosted and produced by Steph Clifford [@stephssocials] 

Follow us on Instagram @theclimbpod_

Check out our agency @thedigitalpicnic > we teach digital marketing, and we can manage yours, too.