Storytelling is a muscle. The first rep feels awkward. You overthink every sentence. You post something and then resist the urge to throw your phone out of the closest window and watch it crumble on the sidewalk.
Whether I’m working with a team in the early stages of brand storytelling — or need the reminder, myself — these words from Theodore Roosevelt’s The Man in The Arena, remind me of why it’s so important to push through that resistance:
“It is not the critic who counts.
The credit belongs to the man who is actually in the arena.”
Getting into the arena – and pushing away any thoughts of critics holding you back – is the only way to build your storytelling muscle.
For a lot of smart, capable, wildly competent professionals, that’s the sticking point. Not the strategy. Not the messaging framework.
It’s putting themselves out there that’s the scary part.
The first rep is the hardest. But by the tenth rep? The fiftieth? I promise you, you’ll begin to find your groove. Here’s how.
How to Get Comfortable Stepping into the Storytelling Arena
The key to getting comfortable with brand storytelling is starting small.
Keep these tips in mind before you take your first storytelling step, whether it be on social media, in a sales meeting, a newsletter, or as a guest on a podcast.
Stepping Into the Arena on Social Media
- Lead with a Moment, Not an Announcement
Start by sharing a lesson you learned, a mistake you made, or a client challenge you solved. - Speak Like You Would in Real Life
If you wouldn’t say “leveraging streamlined systems” over coffee, don’t say it on video or in writing. - Pick One Storytelling Medium to Start – and Stay Consistent
If you’re comfortable writing, then start with a written story. If talking into your phone is less intimidating, start with a short video. The goal isn’t perfection – it’s showing up with consistency.
Stepping Into the Arena in a Sales Meeting
- Replace Credentials with Proof
Instead of listing experience, tell a short story: “We worked with a business owner last year who was struggling with…” - Obstacle → Tension → Solution
Share the obstacle you faced, the tension you had to overcome, and how you ultimately solved the challenge. This storytelling structure makes you relatable and memorable
Stepping Into the Arena in a Newsletter
- Open with a Specific Moment
This could be a conversation, a question, or a realization you had from some past experience. - Widen the Lens
Bring that opening point full circle with insight your reader can apply to their own professional or personal lives. - Think Publication, Not Promotion
Tell your story like an editor-in-chief. Welcome the reader in, to experience the story you have to share, setting them up to get to know you and your brand on your terms – without a sales pitch.
Stepping Into the Arena on a Podcast
- Prepare Three Stories in Advance
Don’t wing it! Put in the work to prepare a few stories in advance, so your storytelling is strategic rather than reactionary. - Practice Your Stories Outloud
Write out your talking points. Stand in your office, kitchen, bathroom – wherever – and say your story outloud. Building that muscle memory helps ensure you’re not searching for something to say when it comes time to share your story with the audience,
If You’re Working With a Storytelling Agency, Lean On Them to Make Your Job Easier
There are several ways we work with our clients to get the raw story content and turn it into ready-to-share stories.
We often start with voice notes. The client will record a five-minute audio reflection after a meeting, while driving in the car, or on a walk. We transcribe it, shape it, and turn that one raw recording into a number of social stories, newsletter pieces, short articles – you name it.
For video, we help them gather flattering raw footage that we can edit into polished clips.
For example, we’ll ask them to stand near natural light and use a ring light if they need the boost. Propping a phone at eye level and wearing something they feel good in are musts. When you’re not distracted by how you look, you can focus on what you’re saying.
Ask your storytelling agency to script lightly – bullet points, not teleprompters – so delivery stays human.
Getting Into the Arena is Step One. Consistency is How You Win the Match.
If you’re willing to try, learn, adjust, and keep going, even when it feels mildly uncomfortable, you will find your voice. And when you do, you won’t just be ‘putting yourself out there.’
You’ll be helping someone else feel less alone in the arena.
And that’s where the real work—and the real impact—happens.