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Transcript

Do you undersell yourself?

Downplaying your skills due to comfort with fitting in

Hey! Caffeine is your weekly nudge to help you craft a business and life as unique as you. Each week, I invite you to join the community conversation about creating value, purpose, and enjoyment in what you do and how you do it.


I feel uncomfortable promoting myself.

I feel equally uncomfortable (albeit in a slower, death-by-a-thousand-small-cuts way) being overlooked…

If only there were an alternative!

(I’ll share mine below, which feels way better…)

Practical Professionals / Hiding in the Crowd

One thing I see with friends who aren’t longtime entrepreneurs is the trap of being competent, practical professionals. They do things the “right” way, yet this doesn’t lead to exceptional results. Their outcomes are “ok”, and their clients and careers are "fine," but not remarkable to them in the way they want. They avoid playing politics or self-promotion, preferring to stay in the background.

You get jealous seeing photos of other people online, thinking, “Why do they get all the opportunities?” However, just copying what others are doing feels inauthentic, so you’re trapped… hiding…

One of the great pains today is not scarcity but a lack of abundance.

Life is better than 100 years ago, yet untapped potential eats away at you. Social media influencers make this worse, constantly pointing to something missing.

Your True Self, Valued by The Market

Sacrificing who you are for external approval isn't sustainable. You want to feel like you’re rising to your potential without feeling inauthentic. You want your true gifts to be seen, valued, and heard by the market.

This builds confidence and self-respect. And what we’re really wanting to feel is confidence and self-respect.

Standing up to Stand Out

I believe this isn’t a skillset gap but a leadership challenge. How you lead others affects how they perceive you. There's a risk in being a leader—it means creating more, consuming less, and presenting your own ideas to the world. It's about testing something new and enjoying the challenge of how it’s received rather than being crushed by misunderstanding.

This is the vulnerable step to master. Not selling, overselling, or underselling, but leading others by standing out and putting yourself out there.

Allowing yourself to be seen

How much are you willing to allow yourself to be seen? One of the scariest aspects of our self-development is getting to the point where we no longer can hide from ourselves, and in turn, can no longer hide from our communities. Something doesn’t feel right when you know for yourself you have a skill, experience, or idea to share but you aren’t able to allow yourself to be known and seen for that skill or experience. It’s not that you’re being fake, it’s more like you’re not fully presenting yourself how YOU know yourself to be.

Take the Next Vulnerable Step

What would you share with your community or company that speaks to more of your full experience? How can you lead others more effectively through action rather than persuasion?

Ask: What next step could I take that would move my ideas into the world through action rather than persuasion?

As always, let me know how I can help,

xx David


If today’s Caffeine resonates with you comment on this post on Substack. If you have a question you’d like me to answer via a blog post you can add it to this form.

You can also find me over at The Elevator where I curate transformational recommendations for entrepreneurs. If you’d like to support my work, you can purchase my book, Founders Flywheel here or get in touch about coaching for entrepreneurs here. See ya next week!

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Caffeine with David
Caffeine with David
Learn how your favorite creators are building a brand and community around who they are.
This podcast is hosted David Sherry, Founder of Death to Stock and Community organizer of Jacuzzi Club.