So You Want to Be an Entrepreneur - Ask Yourself these 10 Questions

November 20, 2017 / Ask Great Questions

So You Want to Be an Entrepreneur - Ask Yourself these 10 Questions

November 20, 2017

Bulldog Drummond Practicing Uncommon Sense

We’re a team of business leaders, design thinkers, writers and brand strategists committed to doing things in uncommon ways. We’re curious about the people and places around us and fascinated by the search for what’s next. 

Laurence McCahill is the co-founder of The Happy Startup School, the uncommon startup school that helps people bring their ideas to life. He spends his time helping people question their passions, their reasons for doing things, and even themselves and their abilities. He is damn good at asking damn good questions. Questions that make you think, and perhaps even consider, why your answer is what it is.

McCahill framed 10 questions most entrepreneurs are too afraid to ask themselves.

  1. Why am I actually doing this?

Entrepreneurship isn’t easy. There are undoubtedly easier ways to earn a living. But, if like Laurence, you’re a terrible employee and would rather inject your eyeballs with vodka than work for someone else, then you don’t have too many other options. Before taking your first step, really consider why you want to be your own boss. What’s driving this big idea? Whose needs will it serve? By taking time to reflect on, and define the purpose behind your idea, you’ll not only attract the right customers but you’ll also get more clarity as to what you should be working on. It will help you to know what’s in and what’s out.

  1. What can’t I do?

Constraints are your friend. At the beginning the world will be your oyster, but this can mean too many options. And one of the things that kills energy at the beginning is procrastinating over making decisions. True innovation happens when the options are limited – fewer resources breeds creativity. So, work out which constraints are your friend. Got kids? Then base your new working life around school hours. Hate office politics? Build a remote team. See these limitations as a positive, not negative and you’ll develop better ideas faster.

  1. What will I never do?

Put a stake in the ground. The HSS Home School program advised all the startups they work with to make a list of things they’ll never do. Often founders find it hard to think of their values, but find it easier to decide upfront what it is that would clash with their vision for their life and business. For instance, at The Happy Startup School they’ll never run an event in a conference center (they prefer mountains). They’ll never hire someone they wouldn’t want to go on holiday with. And they’ll never choose work over family commitments. These pledges will help to highlight what’s important to you, and ultimately lead you to the values you hold dear and clarity on what matters.

  1. Who would I love to serve?

Building your true fans. If you’re to build a successful business, you’ll need people to buy your product or service. But sometimes people end up serving audiences that they can’t relate to or even like. The HSS community is proof that if you love the people you’re working for and understand their world, then the bonds you create will be unbreakable? and will lead to loyalty unprecedented in the business world.

  1. Who will be watching my back?

Find your tribe. If there’s one thing first-time entrepreneurs underestimate it’s the loneliness you can feel when putting your heart (and money) on the line. So, it’s crucial that you have some soulmates who understand you. You can have loving friends and family but more often than not they don’t understand what it takes to go against the grain and do something different. So, surround yourself with likeminded people who will be your support in the early stages and beyond.

“I’ve found my tribe. A space to learn from beauties—teachers, buddies, mentors—that see amazingness in other people’s nuttiness.” Rula, London


  1. Do I really want this?

Resilience is key. If you really believe in your idea, then you’ll have to persevere even when everyone around you thinks you’re insane. There’s a fine line between belief and delusion, but you’ll know when the time is right to walk away. Don’t let others decide this for you. Some of the most successful businesses hit rock bottom and spent years hustling before they became an ‘overnight’ success.

  1. Would I do this for the next 10 years (aside from the money)?

All great things take time. Would you want to do this if money was no object? Is this an obsession that won’t go away? I’ve had tons of ideas for businesses, but only when I ask myself this question do I get a clearer sense of my commitment to this idea. We tested out many ideas before The Happy Startup School. But when this came to us, it had to happen. As the vision was so strong, we had firm belief the money would follow.

  1. How can I be proven wrong?

Think like a detective. Despite what many people think, entrepreneurs aren’t great risk takers. If anything, they’re more cautious than most?—?they hate failure but see it as part of the creative process. They want to make any failures small, so therefore work hard at the beginning – not to be proven right – but to be proven wrong. They know that bad news gets worse the longer you leave it. So the sooner you can find out issues with your product, the faster you can improve and reach your goals.

  1. What pain do I want to make my own?

Happiness comes from solving problems. To increase your chances of success, create a painkiller, not a vitamin – every great problem is a great opportunity. Consider which problem you want to take on. What pain do you want to own that others experience? Apurva Kothari didn’t want to start a business. He knew nothing about clothing. But he started No Nasties to play his part in addressing the cotton farmer suicide crisis affecting India, where to date 300,000 famers have lost their lives unnecessarily.

  1. How am I going to look after myself?

Put on your own life jacket first. If you’re too stick at it and have fuel for the long haul, you’ll need to look after number 1. How will you look after yourself physically and mentally? Whether it’s mindfulness, yoga, walking your dog or floating in a ton of salt, you’ll need to find your thing to get the perspective and space you need to stay calm, clear and sane.

The most important thing? Just start starting things. You never know where it will take you but it will be a fun ride. And you’ll have some stories to tell the grandkids of stuff you did, rather than didn’t do.

Read our full Interview with Laurence McCahill here


Original Post: Medium

Bulldog Drummond Practicing Uncommon Sense

We’re a team of business leaders, design thinkers, writers and brand strategists committed to doing things in uncommon ways. We’re curious about the people and places around us and fascinated by the search for what’s next. 

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