I am an undefinable.

And I've lived beyond conventional labels for as long as I can remember. 

Titles like Social Entrepreneur, Endurance Athlete and Community Builder have shaped me, but none have ever told the full story. I've worn many hats, followed many threads, and often struggled to find a space where the whole of me could belong.

So I started designing one.

Over the past few years I've:

• Competed semi-professionally in endurance sports by getting sponsored and representing GB.
• Built the undefinable community, a 40+ person non-profit for those in the Age of Discovery (22-35).
• Written and refined the 3rd draft of my book on undefinable life design based on 70+ early readers. 

Along the way, I've learnt that life design isn't about rejecting structure. It's about creating your own.

This is why I founded undefinable life design. As a way to help individuals who live beyond conventional labels to design a life for their uniqueness. And for organisations to enable them to do so.


✋🏼 For Individuals

If you've ever struggled to answer "So, what do you do?" my 9.3/10 rated workshops are for you.

"Designing a Life That Doesn't Fit in a Box" is a 2.5h public workshop I host once a month. In it you'll map your many interests, draft your Golden Thread and connect with others like you.

→ Check upcoming dates: https://luma.com/undefinablelifedesign


🏢 For Organisations

Early-career talent (22-30) are the most likely to leave unless they feel aligned, engaged and invested in. 

With 51% of employees actively looking for new roles and 89% of Gen Zs saying purpose is key to job satisfaction, young professionals are hungry for meaning and alignment. If they can't it inside your company, they'll look elsewhere.

That's where I come in. 

I run interactive team workshops and off-sites that:

• Help your people discover their uniqueness.
• Connect their role with their purpose.
• Design a meaningful plan for their next 5-10 years.

The result? Greater engagement, stronger retention, and emerging leaders who bring their whole selves to work.

→ Book a call: https://calendly.com/charlie-undefinable/30min


🌱 The Movement

Beyond workshops, I'm also growing:

• The undefinable community - a non-profit London-based space home to 40+ members.
• The undefinable life design book - now in its 3rd draft.
• A newsletter read by 1,000+ subscribers each week.

If you’re an individual seeking clarity, or a leader seeking to engage your people, let’s connect.

Website: https://www.undefinablelifedesign.com/
Newsletter: https://www.undefinablelifedesign.com/

Charlie Rogers

Today was so much fun!

After helping organise last year's edition, it was great to go along to 2025's Portfolio Career Festival as a member of the community.

The team absolutely smashed it. They one upped last year with the incredible venue, speakers and topics.

I loved catching up so many faces both familiar and new. It's always such a lovely crowd.

Shout-out Fiona, Nicola and the whole The Portfolio Collective team. See you in 2026!

Helping undefinables design their life for uniqueness

In 12 days I'll have a permanent home 🥳

After living in 10 places in 2025, I cannot tell you how excited I am.

The year of living out suitcases, constant logistics, splitting my belongings between storage units, sleeping in 30+ beds and packing my bag every 3 days is finally coming to an end.

To sign a 6-month contract might not sound like a big deal. But after this year, I want nothing more than to enjoy the simple luxury of having all my belongings in one place.

Hopping around has been a necessary (if at times stressful!) step while I've built business momentum. And I'm grateful for all the hosts who've welcomed me into their homes and sorted me out with some solid sublets.

But, now it's time to reclaim my energy.

To stabilise my surroundings so they can re-energise me for all the building that's coming in the next few months. This feels like Charlie 2.0.

Let's gooooooo!

Looking forward to making a home with you Jess

When I was 17, one of my teachers questioned my choice of university in front of the entire class.

They were angry. I'd just turned down "prestigious" Russell Group offers to make Loughborough University my only choice.

I had to justify myself. I told them: "I'm not going to university for the degree. I'm going for the broader education. To join societies, do sports and meet incredible people. I know that will equip me with the entrepreneurial skills to start a business (my dream at the time)".

I didn't have the words for it then, but I was rejecting the default path of specialisation entrenched since the Industrial Revolution. 

This world my teacher valued was one that sought stamps and prestige, only to end up as a cog in the machine. 

My instincts were telling me to prepare for a different world.

Today, I call that world the Age of the undefinable, which rewards synthesisers and polymaths who connect disparate ideas.

That prestigious path wasn't wrong.
It was just built for a world that's eroding.

Now, 10 years later, I'm on business no.3, have built a truly epic community, am finalising my first book and have a career that is 100% undefinable. I'm damn clear on how I uniquely add value, precisely because I chose the broader education over the narrow, default path.

It's wild to think that my 17-year-old's 'mistake' is the foundation of everything I've built.

My book's manuscript is DONE! 🥳

Today is a great day. In fact, it hardly feels real.

18 months after starting and 4 major versions later, I have 36,000 words that I am deeply proud of. What I've created perfectly articulates how to design a unique life that sustains your energy and income. It's my perspective on paper. And it stands as the book only I could create.

I now have a coherent metaphor for the entire book (more on this soon). The stories are relevant, diverse and engaging. And the frameworks have been practically lived by myself, my clients and other undefinables I've met.

I think this is the best thing I've ever created. 

Actually, I know it is. The 110+ early readers who offered their feedback, criticism and support has transformed my initial collection of ideas into the polished manuscript that I know absolutely resonates.

I can't wait to put it in your hands.

Now to put aside my Writer hat and put on my Publisher hat. It's time to add in the final imagery, lock-in the cover design and turn my Google Doc into a physical book you can actually hold, touch and feel.

Exciting times! Let's goooooo.

Recently, I've been trying to live and not just exist.

When life gets busy, my default is to get grinding. I like to lock-in and keep the main thing in my sights until I can come up for air (Christmas this time!).

But, I realised I was ignoring the best part about life:

Actually living.

So, I intentionally set out to add some unnecessary 'distractions' that have nothing to do with being my most productive self.

1) I joined an improv programme. Which is turns out is basically 6 weeks of playing kids games with adults. As a group of complete strangers it's hilarious. We laugh. We play. We have fun. And we grab a pint after.

2) I bought a 400 minute Lime bike pass. It's so much better than the loud overcrowded tube. And I now get to play "What's in my basket?". So far I've found a still-warm burrito, an unopened Rummikub, and some leftover takeaway. I'll let you know when I find the lottery ticket.

3) I hosted a smoothies and spontaneity meet-up for the undefinable community. We grabbed a drink in Elephant & Castle, ventured into a flea market (where I got a new coat!) and explored an arts museum. All on one warm Autumnal afternoon.

A month later, here's what I've learnt:

These 'unnecessary' activities aren't a distraction. They're what give me the energy to keep showing up with a smile on my face.

They aren't draining me. They're energising me.

Penfriend

Penfriend is the best goddamn AI content generation tool out there. Built from my last 10 years of content advising that's resulted in $30.6m in revenue for clients from organic traffic.

We're building Penfriend to be the toolbox for your content team to win in 2024.

Co-Founder and CMO

The Penny Drop

Head Writer

fivethreeoh

Creating SEO sprints to take your SaaS's content team to the first page. Turning 12 months of SEO into 12 weeks.

Founder

Explor Digital

GrowthMinds

Head of SEO

Content Hacker and SEO Strategist at GrowthMinds

Growth Hacker

Walsh - Structural and Civil Engineers

4D visualisation

⚡£23M revenue from Organic Growth for SaaS with Content Marketing Sprints | Storytelling, SEO and Content Marketing ⚡️

Your AI content sucks.
Your competitors' AI content sucks.
Everyone's AI content sucks.

And you know what's worse? You're all paying through the nose for it.

While you're sitting there wrestling with prompts like a cat trying to open a doorknob, we've built something that actually works. Because unlike every other "revolutionary AI tool" (looking at you, [REDACTED]), we know it takes more than 10 prompts and a prayer to write content that doesn't sound like it was outsourced to a drunk toddler.

We use 450+ prompts. Overkill? Maybe. But at least our stuff doesn't read like it was written by an AI having an existential crisis.

Some receipts for the skeptics:
↳ Slapped 400 blogs on our site = 10x traffic in 3 months
↳ Halved content budgets while 5x-ing output (yeah, your Content Manager's been lying about costs)
↳ Helped tiny startups pimp-slap Fortune 500s right off page 1

After a decade watching the B2B content circus, I've seen every "game-changing" tool and "revolutionary" AI writer. Most of them belong in the same trash bin as your last strategic plan.

Here's the uncomfortable truth: Your investors aren't buying your "we're playing the long game" BS anymore. They want to see organic traction, and your three LinkedIn posts from 2023 aren't cutting it.

You need Penfriend.ai if:
✓ Your competitors are living rent-free at the top of Google while you're still "building awareness"
✓ VCs are ghosting you because your "organic presence" looks like a digital ghost town
✓ You're burning cash on content that reads like it was plagiarized from a terms of service agreement
✓ You're ready to stop being the industry's wallflower and start being its problem child

Sound familiar? Then you're exactly who we're looking for.

The hard truth? You suck at AI. But it's not your fault. You've been sold a lie by companies who think "AI writing" means letting GPT go wild after a two-prompt foreplay.

We fixed it. Because someone had to.

DM me "PAGE ONE" and I'll show you how we're helping companies terrorize their competition online.

P.S. If you're happy with generic, soulless AI content that sounds like everyone else's, this probably isn't for you. And that's okay. Someone has to keep the internet boring.

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The Battle

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The Battle

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Performance Score.css-goub6s{font-size:var(--chakra-fontSizes-md);font-weight:500;color:var(--chakra-colors-gray-600);display:block;margin-top:var(--chakra-space-1);}Charlie Rogers's LinkedIn Performance

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