10 questions budding entrepreneurs are too afraid to ask themselves (but damn well should)…

It’s all too easy to startup without questioning, but a bit of time soul searching early on just might save you some heartache later

“We are each of us a wise guru... in charge of a mental patient.” 
Jamie Catto, Happy Startup Summercamp

The new year is traditionally a time when people assess their life and career goals. And for an increasing number of disillusioned workers this means thinking outside the boss — taking the much-threatened leap into the unknown that is entrepreneurship, flicking the Vs to the dudes in suits.

Often this can be because the thought of going back to the 9–5 is too much to bear, plus those pangs of regret get stronger when looking back over the last 12 months. Another year gone with lots of dreaming, but little action.

But if you think starting your own business is all daisies and rainbows, think again. You’ll be building your wings on the way down.

“Entrepreneurs – the only people that are willing to work 80 hours a week, to avoid working 40 hours a week for someone else.” Lori Greiner

When working for yourself you’ll find, at the beginning at least, you’ll probably work harder, for less reward and question your very existence. But, as Daniel Pink highlighted in his book Drive, it’s this autonomy, mastery and purpose that motivates us to keep going.

So don’t be put off. There are incredible rewards to be had from stepping out on your own. You’ll learn to love the rollercoaster and experience life on the edge, where the highs and lows are all part of the ride. And creating something new that makes people’s lives better makes us feel good.

So back to those questions. Spending a little time on these should smooth your journey in those early days and boost your chances of getting the freedom/fame/time/riches/meaning* you crave. 
*delete as appropriate

1. Why I am *actually* doing this?

Entrepreneurship ain’t easy. There are undoubtedly easier ways to earn a living. But, if like me, 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 your own boss. What’s driving this big idea? Who’s 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, 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.

2. 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 begining 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.

3. What will I never do?

Put a stake in the ground. On our Home School program we advise all the startups we 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 up front what it is that would clash with their vision for their life and business. For instance at The Happy Startup School we’ll never run an event in a conference centre (we prefer mountains). We’ll never hire someone we wouldn’t want to go on holiday with. We’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.

4. 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. Our 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 it will lead to loyalty unprecedented in the business world.

5. 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 soul mates that get 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 that 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

6. 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.

7. 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.

8. How can I be proven wrong?

Think like a detective. Despite what may 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.

9. 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. So consider which problem do you want to take on? What pain that others experience do you want to own? 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.

10. How am I going to look after myself?

Put on your own life jacket first. If you’re to 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.


At The Happy Startup School we help budding entrepreneurs get on the right path. Our next startup course starts this coming Monday.


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Image by Sean Wes