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    Why I send a selfie at the bottom of every email

    By Kieran Drew
    This is an edition of my old newsletter Digital Freedom.

    It's lightly edited but otherwise untouched. I've kept them on the site to show how the journey has evolved.

    Welcome to this week’s Creator’s Corner. I take your burning questions and use them as an opportunity to plug my products help you ace your online journey.

    What we’ve got cooking today:

    • The brutal truth about content and how to overcome perfectionism
    • My trick for making great decisions (and avoiding sucky ones)
    • Why I send a photo at the bottom of every email

    Let’s dive in.


    Mystery person (I forgot to save the name - go easy on me) asked:

    I'm trying to improve my writing, but I feel like "perfecting" something is a curse that will lead to unproductiveness - it's a hard balance to find since you obviously don't wanna half-ass it either.

    Do you have any tips on this?

    ​It’s an easy trap to fall into, but the pursuit of perfection will stop you from making progress. So I’ll give you two tips that help me immensely.

    First, the truth:

    When you post online, you feel like everyone's watching, but they’re not. Few people see your work and fewer people give a shit. I don’t mean that in a bad way. It’s just human nature. We're the hero of our story and everyone else is a character.

    The downside is this also makes us our own worse critics - so give yourself a break.

    Second, set tight deadlines.

    You need enough time to create but not enough time to overthink. Even now I’m writing a new welcome sequence. And because there’s no end, I’m having a terrible time. In fact, thank you for reminding me.

    I’ll finish it by the end of the week.

    This leads nicely to a bonus point:

    Make public commitments.

    Especially for the shit that scares you. Action is always the answer.

    You may notice I mention my upcoming product in most emails too.

    I’m not just trying to build hype. I’m making sure it happens.


    It doesn’t need to be perfect. It needs to be published.


    Jay Yang asked:

    How do you think about judging opportunities? When do you say yes? When do you say no?

    ​Decision-making is one of my favourite topics. I used to suck at it. But we spend our lives dealing with the consequences of our choices, so studying how to make better ones can have a crazy compounding effect.

    Few things will change your trajectory in life or business as much as learning to make effective decisions.”

    - Shane Parrish, Farnam Street

    One of the hardest skills to learn is saying no to good opportunities to wait for the great. Especially online. There’re lots of things you can do, but only a few things you should.

    The secret is constraints.

    You need to know what you're optimizing for.

    Society defaults to status and money.

    I made that mistake as a young whippersnapper. I thought dentistry would be great because dentists are rich. But for the most part, they’re also fucking miserable.

    When you realize success is subjective, everything changes. You get what you want when you define what that is. Here’re the 3 questions I ask for any business opportunity:

    1. Does this make me better at writing? (the pursuit of mastery)
    2. Does this help my audience win? (the desire to make an impact)
    3. Does this build more leverage? (the pursuit of freedom)

    I then follow Derek Siver’s framework:

    If it’s not a hell yes, it’s a no.

    Sure you miss out on a few opportunities.

    And yeah, you’ll go against your rules. But don’t underestimate how far singular focus will take you over time.

    Another great exercise is reflecting on core values. I've lined you up a great resource at the bottom of this email.


    Aldo asked:

    Can you explain the why behind your photo in every email? I expect to see it already.

    ​I’ll be honest with you my friend, I hate selfies. When I see a man post one on Instagram I immediately lose respect for them. But these little pictures go far, and that’s by design. Let me explain.

    One of the best things you can do as a creator is pay attention to what gets your attention.

    Justin Goff is one of my favourite email writers, and he sends a picture every mail. I noticed I’d actually look forward to seeing his face at the bottom. I was curious about what he’d write.

    So now I do it too.

    Does it work? I bloody well hope so.

    My open rates are now at a 57% average. I started at 32%. I’m not suggesting my cheesy grin is the only factor (I’m not Brad Pitt), but people follow people. It’s nice to put a face to the writing.

    Just don’t look too close.

    There’s pain behind those eyes.

    (Modelling your mentors is a framework I swear by and a topic of a previous email. You can read it here.)

    Kieran's Killer Resource of the Week

    Core values are one of the most life-changing exercises you can do.

    ​When you know what you stand for, you have a framework for decisions. Better choices, better consequences. I keep my values on my whiteboard to make sure I stay on the path. And this article from Taylor Pearson is one of the best breakdowns I've found.

    Take a read here.

    A Question for You...

    What’s stopping you from creating an e-book and selling it to your audience?

    Nothing will accelerate your progress more than taking action. If you build something to sell, you have skin in the game. This means more authority. More of a reason to create compelling content. And more self-belief when you realize internet money is real.

    ​Pick a burning problem for your audience. Package it into an actionable e-book. Slap on a price tag. Learn how to market yourself.

    ​I guarantee you won’t regret it.


    Kieran Drew

    About Kieran

    Ex dentist, current writer, future Onlyfans star · Sharing what I learn about writing well, thinking clearly, and building an online business