Guiding You Up the Online Marketing Mountain – My Digital Sherpa Approach

Update from Your Digital Sherpa: Learning to Follow My Trail, Not Theirs

Hey there, fellow adventurers! If you’ve been tracking along on my “Digital Detox” adventure, you’ll know I’m making some big shifts in the way I approach this online marketing mountain we’re all climbing. And it’s not just about changing how I do things — it’s about learning to follow my trail, not anyone else’s.

I set out with a simple goal: track where my time’s going. You know, find the rabbit holes and actually avoid them. I started with a fancy time-tracking app that sounded like it could help… until I realised it spent three days “learning” my routine — and mostly logging me sitting around at home. So, I’m going old school: pen, paper, and the simple art of keeping tabs in a notebook.

If you’re curious, I’ve even made a time-tracking sheet you can grab for yourself right here! (I have imported the worksheet into Goodnotes on my iPad, so I can write on it on there.)

But today’s update goes beyond time tracking — it’s about the mindset shift that got me here.

Discovering My Digital Sherpa Role (and Why I’m Sticking With It)

Somewhere along the way, I stumbled on the term “Digital Sherpa.” Now, it’s on all my posts, and if you’re one of my email subscribers (thanks for that!), you’ll see it at the end of each one. And I’m leaning in hard. Why? Because I love this idea of being a guide rather than some self-proclaimed expert. 

Here’s the thing: I don’t want to stand at the top of the mountain shouting down at you. I want to be right there beside you, trekking up the rocky path and saying, “Watch out for that slippery bit!” I prefer the word “adventure” to “journey” because, let’s face it, adventures aren’t perfect. Adventures are messy, sweaty, and exhausting — but they’re worth it.

So, here I am, guiding us all along this crazy adventure of building an income from home, while I carve out more time for my family (and myself). And yes, there have been some funny detours along the way — including an attempt at using that high-tech time-tracking app. Lesson learned: maybe not all shiny tools are meant to make it into the Sherpa kit.

My Big Goal (and Why It Scares Me)

So here’s the big goal I’m setting out to conquer, and it’s not just about making money online. I recently sat down with Simon Sinek’s process to figure out my "Why", and this is what I came up with:

Sean Street

My "Why" statement. Why am I in this business?

“To inspire people to recognise their worth and potential, empowering them to break negative cycles and grow with confidence. I strive to create a world where compassion, humility, and respect are the norm, helping others live more fulfilled lives while positively impacting future generations.”

Sounds pretty cool, right? But here’s the honest truth: this mission scares the living daylights out of me. Can I really live up to it? Am I inspiring, educational, even entertaining enough to make this a reality?

The answer, after a few detours and a lot of deep breaths, is yes. But only for the right people. I’m not here to inspire just anyone. I’m here to inspire those who want to learn how to create their own path, who are currently doing the 9-to-5, but looking for a way out. This adventure is for people like me, looking to sidestep the traditional ladder and create something meaningful.

Why Your Adventure (and Your Voice) Matter

I get it — putting yourself out there is daunting. What if people judge you? What if you get those keyboard warriors who swoop in with their negative comments just because they can? The thing is, there will always be people who don’t understand the adventure you’re on, and that’s okay. They’re simply not the ones who’ll join you on the trail.

Take Australia’s classic Ford vs. Holden debate. (Bear with me, international friends!) People tend to pick a side, and that’s it. You can’t convince a Holden fan to suddenly buy a Ford. They’ve made up their minds. It’s the same in business — your voice will attract the right people, and that’s who we’re here for.

If you’re creating content that isn’t connecting, it may not be about you; it may be that your voice just hasn’t reached your people yet. So, stick to what feels authentic. The right folks — the ones who see the adventure in this and are ready to trek alongside you — they’ll find you.

The Plan Moving Forward

I’m not promising you’ll find success on your first step or even your first hundred. I’m here to show you the way, point out the shortcuts (and the long ones!), and walk beside you. I’m your Digital Sherpa, not your boss. I can’t make you do the work, but I can be here for you, cheering you on every step.

Here’s the one piece of advice that’s kept me going: don’t wait until you feel “ready.” Just start. Write, post, create. Let people know who you are and what you’re about. This isn’t about convincing people to join you on your adventure; it’s about welcoming those who are already looking for the same path.

"An entrepreneur is someone who will jump off a cliff and assemble an airplane on the way down"

Reid Hoffman

Internet Entrepreneur

So, if you’re feeling inspired (or even just mildly curious), drop by this website and come along for the adventure. Because this adventure is ours, and I’m grateful to have you along for the ride.

About the author Sean Street

Sean Street is a digital marketing enthusiast with a varied background providing a well developed ability to relate to and get along with others.

Sean's ability to break complicated topics down into simple to understand language makes him an asset when it comes to his teaching.

  • Hi Sean,
    Great post filled with very important information! Our stories could probably intertwine on a few levels; I can definitely relate to having bought so many online courses, I’ve forgotten how many!
    That being said, when you’ve found your “why” and work towards it, there’s no stopping you!
    Totally love the Reid Hoffman analogy!
    All the best!

  • Hi Sean,

    I can completely relate to your journey! I’ve discovered that focusing on authenticity and learning from my own experiences, rather than trying to follow someone else’s path, has made a significant difference.

    It’s reassuring to see that we’re all on this challenging journey together. I can really relate to your perspective on taking action even when we don’t feel fully “ready.”

    Here’s to taking in this crazy adventure and supporting each other along the way!

    Meredith

  • Hi Sean – I just love this post and the attitude that you portray within its content! Being able to shift in any direction based on the needs of your business this key to understanding what needs to be done. Sounds like you’re on the right path. Thank you very much for the tracking sheet. I downloaded it and may consider going your route with the old pen and paper or maybe just add to it electronically for a digital diary. It’s a tool I’d like to consider and I appreciate you offering it as an option. Have a great week!

  • Hey Sean, I love your website and the tone you gave to it! Images are great and your tag line is spot on! Regarding this post, I really liked reading through it. It is well written and motivating. Your thoughts about negative comments are so true! People take position and that’s it, whatever arguments you could throw to them. Why caring for them if they won’t be part of your adventure. Their negative attitude would impede progress of others along your trail. People on your path will never fall, they will become entrepreneurs and learn to build that plane!
    Thanks for posting.
    Martin

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