The Secret To Wandering In The Startup Wilderness & Coming Out On Top




Dreaming of one day escaping the corporate grind is fantasized by most. Whether it’s to work for yourself or acquire a staff in the thousands, most wander and dream about the possibility of living a life built on freedom.

Had you asked me five years ago about owning my own business, I’d have said, “Probably not.” I liked the idea of freedom, but my perception of those risk taking go-getters was placed high on a pedestal. Then the dream grew stronger and the disillusion of the nine-to-five took hold, and when I saw the many people creating and setting up shop – people just like me… people with an idea and a passion and a laptop in hand – I decided: THAT’S THE LIFE FOR ME.

Mine wasn’t a spur of the moment decision, but it came about rather quickly. The wanderings grew stronger, and then, as my role at work was about to change, I knew the time had come. I was:

  • Terrified
  • Excited
  • Hopeful
  • Ambitious
  • Terrified
  • Doubtful
  • Confident
  • Did I Say, Terrified

In May 2012 I left my job and set up Turndog Millionaire. I created the website, designed the business cards, and developed a plan that kind of made sense. I was my own man, an entrepreneur, a professional writer and completely and utterly naive.

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We’re All Naive Sometimes

I wanted to focus on my writing (complete my first novel and start my second) and create Non-Fiction and take my Blogging to the next level. However, my background and expertise is in marketing, and I love it when it’s done right. The problem is I see most people doing it awfully, which made me think I could consult and help them on the right path.

My world didn’t align. On the one hand I was a creative artist, on the other a marketer – and even though I approach marketing unlike most, people assume I’m just like the rest. I dreamt of an aligned world, only I had no idea how to make it so. This was the beginning of my Wandering in the Startup Wilderness.

What the F*!k is Wondering In The Startup Wilderness?

It’s the confusing period when you first start out. It can last weeks or years, and in truth you may never fully escape it. It’s when you realise you want something, but have no idea how to monetize and build a life around it.

I’ve met dozens who’ve wandered in this wilderness. In fact, it’s one of the most common subjects during my interviews for The Successful Mistake. Successful and awe inspiring individuals speak of the time when it made no sense at all. They were kind of doing, but not really. Kind of loving, but not at all.

I went through this during the summer of 2012. I wandered in the startup wilderness and was pretty darn lost. I was writing copy, consulting about social media, doing design, writing this and that, and was so far torn that my world began crumbling around me.

It’s scary as hell, but in my opinion one of the most important periods for any entrepreneur. It helps you realise what’s important, why you set up and took the risk in the first place, and what you have to offer that nobody else does. I found clarity in my wanderings, and although I didn’t come through the other side smelling of roses (the hard work has only just begun), the fear and self-doubt has taken a back seat.


The Secret to Coming Out on Top

Unless you’re one of the lucky few who know exactly what you want and knock it of the park from the offset, YOU WILL GET LOST IN THE STARTUP WILDERNESS. People often focus on the overnight success, but what they forget to mention is that overnight success was eight years in the making.

Don’t worry because this is also the period when you discover more about yourself than any other. In the beginning the pressure isn’t as high because the excitement of setting up is all around you. After a few months when the bills pile up but income doesn’t, that pressure builds and builds – not just money based pressure, but the pressure you place on yourself.

You’re forced to look within and ask important questions: 1) what is and isn’t working?    2) is what you’re doing, what you love?

Everyone wanders through this startup wilderness in their own way and escaping is different for all. Based on my own experiences and from others I’ve spoken to, here are my secret tips for Wandering In The Startup Wilderness & Coming Out On Top:


1: Devour Your Vision… OFTEN

I‘m like a broken record when it comes to crafting your vision, but it’s only because I believe in its importance. As you wander through the startup wilderness, devour your vision as often as possible. Ask yourself:

  • Is this new project helping me achieve it?
  • Is this client the right client?
  • Am I doing what I love?

Your vision not only keeps you on the right track, but wandering in the wilderness helps you develop and refine it. This is what happened to me. I realised my love for storytelling because I was approaching everything like a story all ready.


2: Don’t Be Afraid of Saying YES… A Lot!

I only realised what I did and didn’t enjoy by saying yes and remaining open to new opportunities. Luckily you’ll have to do this in the beginning because you have bills to pay. Although you should stick to the plan and your vision from the outset, wandering off course a little isn’t always a bad thing.

If nothing else it helps you realise what you love and hate. Consulting on Social Media made me realise that I couldn’t do it because people wanted a short term solution, whereas I wanted to dig deep – aka build and develop their greater story.


3: Plan for Two Launches

Within weeks I knew my first website and first plan didn’t epitomizes what I wanted. From that moment I was working toward Turndog Millionaire 2.0 – this occurred exactly one year after my initial launch.

That’s not to say I changed everything and made a huge deal about this re-launch (or even termed it that way), rather worked my socks off to learn as much as possible and refine my vision and missions and aims and objectives. I wanted to take my hazy idea and create a unified embodiment of awesomeness.

I wandered in the wilderness and didn’t worry about mistakes or working on crappy projects, I simply learned, learned, and learned some more. Toward the end of 2012 it began to make sense, and by the summer of 2013 I had an outlook I was happy with.

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Whether you’re a solopreneur, freelancers, artists, writer, small business owner, or simply thinking about becoming one at some point in the future, don’t worry about Wandering in the Startup Wilderness. I’ve lost myself in it (still are to an extent) and met many minds greater than mine who did exactly the same.

It’s scary, but you’re never alone. Although some get it right from the beginning, most don’t. Your idea at inception doesn’t have to remain the same in a year’s time…or two…or ten. Allow yourself to evolve and gain comfort in your surroundings.

As you do you’ll gain confidence in who you are, how you look, and what you do. You’ll stop conforming and instead be YOURSELF, and when this happens everything becomes lighter and brighter and the stress and worry eases to an extend where you can enjoy happiness and take advantage of the freedom you’ve built.

I Wandered in the Startup Wilderness and Came Out On Top. YOU CAN TOO.


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