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The Entrepreneur's Journey

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The *Real* Entrepreneur’s Journey

There it is.

After grinding it out for years…

After hustling every minute of every day….

After putting 100% of everything you’ve got into your journey…

You see the top and it’s within reach. It’s been a long time coming.

You take a knee to pause and reflect…

When you began, the wins were easy: beginners luck is on the side of every person starting a new adventure. Everyone supports you. You feel invincible. Even the Gatekeepers tip their hats, opening the gate for you to walk through. Some of your peers, so inspired by your enthusiasm, follow right behind you…

But once outside the ramparts of Median City, the easy wins fade; trials and challenges take their place, testing your intellect, passion and resolve.

The shock to your system reverberates down to your soul.

You want to turn back and return to the safety of the ramparts and masses you left behind. Your peers do just that (and now they’re sitting at the town tavern regaling stories of stepping outside the walls and their adventures that ended before they wanted them to, but life is life and you have to do the reasonable thing, right?).

Your heart sinks. You see the reason in your peers’ choices to turn back…but the thought doesn’t comfort you; it boils you to the core. Your feet stayed frozen, planted to the ground, not wanting to concede an inch to fear, uncertainty, or failure.

There you are, all alone once more. Scary at first, but then…freeing. For some reason, a weight has been lifted, as if you were carrying their packs all along. No longer.

You set off on your own, your burden less heavy, your mind clearer with every step.

Days, weeks, months pass…

You keep marching.

You conquer the Army of Bad Habits, navigate your way through Conundrum Forest, dodge and weave your way through Hater Swamp, and muscle your way up the testing Cliffs of Insanity…

At the top, you look around; all the progress you’ve made? A drop in the bucket compared to what lays beyond.

You keep marching.

Every day you learn something new. Each day, you become better: your skills expand, your strength (emotional and physical) improves, and your instincts become more refined. You handle your sword and shield effortlessly, as if the heavy steal is made of feathers – as if these tools are a part of you now. When the path diverges in the woods or stops dead in its tracks, you don’t wait for inspiration – your gut tells you left or right and you go – no hesitation.

But there’s a hidden side-effect to improvement: every increase in strength, intellect, and resolve brings with it a new path, a new obstacle, a new challenge that would have forced you to turn back just weeks or months ago, but now it’s within your ability to conquer.

Your skills have improved, but so have the challenges.

And with each new lesson-learned comes a painful realization: how much you still don’t know. It’s as if for every step up the jagged, rocky slope of Tribulation Mountain, another mile of perilous journey appears before your eyes.

You keep marching.

More than a few times you want to quit; to throw in the towel and head back. Yet with each renewal of commitment to stick it out no matter what, providence provides you what you need, whether a new friend who walks the path with you for a while, access to new tools and resources to help you along the way, or an easy win you didn’t expect (even the smallest win in times of desperation can change everything).

You keep marching.

Through the wastelands, deserts, and valleys, you keep marching.

After so many tests, so many obstacles, so many struggles, you’re within reach.

You rise and make your way to the top.

You grab your prize – the goal that was just an ephemeral vision so many years ago, but here it is, in your hands, made manifest. As you enjoy a few brief moments of unfiltered gratitude and pride, you look around. Behind you, on the horizon, you can see the silhouette of Median City on the water. It sure would be nice to go back now and share your stories with old friends…

But then you spot something on the horizon, opposite the way you came. A distant light that glimmers in the fading sunlight. The whisper of light vanishes as quickly as it came into view, but the vision…the vision sticks with you. You don’t know what it was, but your heart does.

You make your way down the mountain.

Do you turn back or keep moving forward?

That’s an easy one.

You answered that question a long time ago.

You keep marching.

* * *

Started, finished, and shipped on the coast of Hourcon, Chile.

Total writing time: 3:03

Total drawing time: 3:16 (harder than it looks, believe me!)

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  • Hi Tom, I absolutely loved this piece. A couple of times I thought of a couple of things to add, eg the more you learn, the more you realise you don’t know. But I read on and you covered that too. I’d like to make a constructively critical comment, but there’s nothing more to say. You said it ALL. Good work. I look forward to more stories as the journey continues.

  • This is awesome! Don’t give up your drawing gig just yet. It’s the best representation of the entrepreneur process I’ve seen so far.

  • Indeed, this grand idea of setting out on a long journey enjoys a narrative through line that has followed us forward through the ages. It’s as true now and it was then. In his poem Ulysses, Tennyson reflects on what it means “to be part of everything you have met” and what it means to make your way to the top or wherever you decided to go:
    “For my purpose holds
    To sail beyond the sunset, and the baths
    Of all the western stars, until I die.
    It may be that the gulfs will wash us down:
    It may be we shall touch the Happy Isles,
    And see the great Achilles, whom we knew.
    Tho’ much is taken, much abides; and tho’
    We are not now that strength which in old days
    Moved earth and heaven, that which we are, we are;
    One equal temper of heroic hearts,
    Made weak by time and fate, but strong in will
    To strive, to seek, to find, and not to yield.”

  • Can I get a bigger copy of the Dip Drawing somehow please Tom ? Even on the Enlarge I can’t read any of the words on it. I want to show it to my buddy who runs something called Territory Mapping as a way to show the vital importance of Territory to is humans. The different Territory Maps front line staff create compared to Comfy little drawings by Director types opens a radically different approach to developing the biz etc . Territory Mapping and our VizBiz system look like a great fit with your work.
    As per my earlier note … long list .The Qollaberative is ready !

  • Thanks for the great story and drawings. They comfort my struggling soul. The struggle is who I am and it is joy. I could not live any other way. I am “the resistance”. Thanks again.

  • What a great message and accompanying diagram. Life is just a hike through challenges both known and unforeseen. Failure isn’t a sign of defeat but rather a lesson for the next success. I’m so glad you posted this as so often do we get down on ourselves for not having the outcomes you had hoped. Instead, we need to keep matching ahead to tomorrow where the next adventure awaits. Thanks for the beautiful post!

  • Since I’ve become an entrepreneur, I’ve come up with many exciting ideas for my business — but every single time, I’m overwhelmed by how much more there is involved in executing it then I ever realized!!! I just need to accept that’s it’s always going to be that way — there were always be more things that I need to learn.

  • Life, is full of ups and downs. The 9-5 grind can feel more like a merry-go-round going around the same things day in and day out. The great thing about being an entrepreneur is it’s more like a rollercoaster – like life, there are challenges to breakthrough and learn from, plus incredible highs to celebrate. It’s challenging, but I believe it’s worth it – and it sure beats monotony. Best wishes for rising to your next entrepreneurial peak.

  • This is fantastic, Tom. I loved the visual of “The REAL Entrepreneurs Journey.” I don’t think I’ve ever seen a diagram that captures this so well. I found myself nodding in agreement with each phase of the journey. Well done. Here’s to continuing the march forward.

    • hahaha, thanks so much Michael! So glad you liked it.

      p.s. I’m planning to refine it a bit and get it suitable for a physical print…will keep you posted 🙂

  • I stumbled upon this article through someone else’s site (can’t remember who) and loved it so much that I included it in my monthly Link RoundUp! I especially loved the drawing you made. Funny, real and motivating at the same time!

    I’ll be digging through the rest of your archives this month and if there’s anything in there that was especially helpful in there I’ll definitely follow this blog and share more of it with my readers 🙂

    Much love!

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