HM Insights

Simple Tools, Hard Questions

Article provided by Gayle Mann, Co-Founder of Misadventures in Entrepreneuring 

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In the last week at Misadventures in Entrepreneuring Lucy-Rose and I have been taking a dose of our own medicine, that is, we have been picking back up tools and techniques that we use when we’re working with entrepreneurs all the time but very rarely apply to ourselves. And this week I have been reminded of why. 

We live in a world where there is a simple tool, technique, model, formula, 1 pager, canvas, video, tutorial or short course for quite literally anything you might need. Need a business model? There’s a 1 page canvas for that. Need a pitch? Try our tested formula (we actually do have one of those btw…). Need to figure out how to make culture change stick? There’s a formula for that. The trouble with these ‘simple’ tools, and one of the reasons that we see many entrepreneurs misadventure is, that they make the job of completing them sound easy. And this is where simple ends…

This week our focus was vision and more specifically creating a vision for Misadventures in Entrepreneuring beyond the podcast and the book. When we set out on this project 2 years ago we knew we wanted to talk to more relatable role models and we wanted to document their stories in a book that would help other entrepreneurs, but we had no idea where that project would take us. Now the time has come to take all of our experience and learnings and create a more concrete vision for a sustainable business and future.

I know how to create a vision, I have all the tools and I’ve spoken to entrepreneurs over and over about the importance of creating a vision and how to do it. We even included our 10 top tips for creating a vision into our book (simple right?)! Yet when I sat down to put pen to paper I drew a blank and I couldn’t understand why.

I realised that trouble with all of these simple tools is that unless you truly understand the details of where you want to go, what you want to the journey to look like and how you want to be doing it, and then what success at the end of the day means to you, then the exercise of completing them is futile. It will feel easy, but it won’t be meaningful or effective in the long run. 

Take pitching as an example. At Entrepreneurial Spark we created a tried and tested pitching formula and when we began the entrepreneurs that went through our accelerator programme stood out all over the country at events and in pitching competitions for their pitching prowess. We drilled them hard on their pitch, not just on the delivery and the carefully crafted words, but because if you don’t understand the granularity of the detail that goes into creating the perfect pitch, the level of understanding that you have to have of the mechanics of your business and how it all fits together to deliver a successful outcome, then 180 pretty words mean nothing when someone comes to unpick the detail of it. Pitching is not about the words, it’s a simple tool that communicates all of the effort and insight you have put into making your business work.

When I was approaching the vision exercise, I had confused a simple tool with an easy process. In fact, the process was anything but easy. It required introspection, soul searching, understanding what we were both looking for in life and in business. What we want every day to look and feel like? Who we want our customers to be and how we want them to feel? How we want the impact of working with us to feel and how it can enhance their life and work? This wasn’t a surface level activity. It was turning out to be a culmination of everything we’d learned or absorbed as well as asking some really challenging questions, and it was about going truly deep with our desires for the future. 

By the end of the weekend I had created a vision board for Misadventures in Entrepreneuring and boy am I proud. Not because I cut fancy words or pretty pictures out of a magazine and stuck them on a board (I did that too), but because I genuinely asked myself the hard questions and now, I own every single one of those words on that board. They reflect everything I feel about the work that we do now and the work we want to do in the future. It hangs proudly in my home office where I can look at it every day, holding us accountable to the vision we’ve set and making sure everything we do drives us in the right direction towards that. The impact this could have on us and our lives is immeasurable. Every time I look at it, I get goose bumps.

And the irony of it all is that work that we want to do – it’s a perfect reflection of this entire principle. Simple tools, hard questions. The tools you need to be the best entrepreneurial version of yourself are simple, they really are, it’s the execution of them that’s hard. And it’s meant to be! It’s the hard that makes it great, impactful, unlimiting, and true to you. 

We want to create simple tools for entrepreneurs that will change the way they think and act forever. That enhance their lives and enable them to create the kind of life and business they’ve always wanted. And if that sounds like a tall order, it should be, and I’m so excited to get started. 

So, the next time you see a tool or technique that promises you the world in 5 simple steps, remind yourself that its only easy if you know what you need to do to complete those steps, or where you want those steps to take you. Entrepreneuring is not an easy life to lead, but it can be one of the most rewarding if you’re willing to put the work into the business and more importantly yourself. Over the next few months we’ll be busy crafting those simple, yet powerful and unapologetically hard tools that will help you do the work to define where you really want to go, so that getting there feels a little easier.

If you can’t wait until then we currently offer one to one coaching where we use all of these tools to work with you on your life and business, so feel free to get in touch for more details, or head to and sign up to our newsletter for all of our latest news and views.  

Article provided by Gayle Mann, Co-Founder of Misadventures In Entrepreneuring.

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