The Entrepreneur's Journey

the entrepreneurs journey - The Entrepreneur's Journey
The Entrepreneur's Journey: a map to help you navigate the trials and tribulations of creation.

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 reaching your goal…

You see the top. It’s within reach.


You take a knee to pause and reflect…

It’s been a long time coming.

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 vanish. 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; to the masses you left behind. Your peers do just that, and now they’re sitting at the town tavern regaling stories of their heroism for stepping outside the walls, and of their adventures that ended too soon, but they had bills to pay, you see, and they didn't have time for a fanciful adventure to chase some ephemeral dream…

Your heart sinks. You see the logic and reason in their choice to turn back…but the thought doesn’t comfort you; it boils you to the core. Your feet stay frozen, planted to the ground, not wanting to concede an inch to that coward known as fear.

Yet here you are, all alone, refusing to go back. In the midst of uncertainty, you take a step forward. The fear subsides and you feel…free. A weight has been lifted. It's as if you were carrying their packs, and them, all along. No longer.

You set off on your own, your burden is less heavy, your mind more clear with every step.

Days, weeks, and months pass…

With full conviction and complete commitment, 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 lies ahead.

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 someone else to tell you where to go or what to do – instead, your heart tells you left or right and you go – no hesitation.

But there’s a 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 even days ago, but now it's within your ability to overcome, conquer, or complete.

Your skills have improved. 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 the perilous journey appears before your eyes.

Each day you think you're there but it's another false summit.

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; a new friend who walks the path with you for a while, access to new tools and resources to help you along the way, an easy win you didn’t expect (even the smallest win in times of desolation 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, you can see the foggy silhouette of Median City. 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...



I originally created this image to go along with the article:

The Entrepreneurs Journey what the real dip looks like - The Entrepreneur's Journey
The *Real* Entrepreneur's Journey

Got a lot of positive feedback on it, even though I made it in PowerPoint (I got skillz). So I decided to update the image with proper artistry, which I then printed on metal and now hang in my office. It's great when you need to ponder something deeply:

pondering the entrepreneurs journey - The Entrepreneur's Journey

Let me know what you think in the comments below.

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23 comments on “The Entrepreneur's Journey”

  1. 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.

    1. Kay, thanks so much. Glad you enjoyed it and that it resonated with you...I'll keep you posted on how the journey goes! 🙂

  2. 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.

  3. 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."

  4. 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 !

  5. 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.

  6. 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!

  7. 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.

  8. 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.

  9. 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.

    1. 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 🙂

  10. 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!