3 Questions You Need to Ask Yourself before Becoming an Entrepreneur

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Starting a business will always be trade-off for entrepreneurs. The key trade-off usually is leaving a secure job for an uncertain future with uncertain pay. It’s a scary step – too scary, for most. My trade-off when I started SyndicateRoom was deliberately unusual. The problem of leaving a well-paid job is the sudden lack of income. I resolved this mantra in a rather simple and neat fashion – I didn’t get a well-paid job to start off with. While my fellow colleagues were busy applying for lucrative post-MBA positions, I was busy meeting people and brainstorming business ideas.

I knew this would leave me jobless when the MBA finished, but that was the whole point – it would light a fire under me and make the decision to start a business much easier. All I had to do was answer three questions that every entrepreneur should ask themselves.

  1. What if I try and fail?

This is the question that stops most entrepreneurs-to-be, and rightly so: it’s terrifying. There are important financial consequences that entrepreneurs need to consider. Also the social pressure (intended or not) that surrounds failure can be hugely off-putting.

I didn’t particularly care about the social pressure of failure as much as I cared about my own sense of disappointment. Financially, I cut out on superfluous expenses and gave myself a deadline to get SyndicateRoom off the ground based on when I’d run out of money. Then I broke my own rule by asking for support from my wife. It paid off, but I probably shouldn’t have broken the rule, and I would still recommend others don’t. Do as I say, not as I do.

  1. What if I try and succeed?

Although this one seems easy on the outset, it can be rather intimidating and is certainly worth consideration. How do you measure your own success? When do you consider yourself to be ‘successful’? Is it the money? Is it to retire shockingly early and disappear to The Bahamas? Is it the sense of accomplishment? What success means for you will determine the what, why and how you do it.

My case was a bit of all of the above. It would be nice not having to worry about money for a change, to be able to escape on a whim and go sailing in exotic locations for a couple of weeks. But above all, it would be great to achieve the sense of accomplishment that comes from building a great business that I’m hugely proud of, and in the process lead SyndicateRoom’s excellent team – which puts up with my demanding personality every day. The sense of inspiring others, counting on their help to make SyndicateRoom a success, and repaying them by providing an opportunity of a lifetime to join and profit from such journey, is a huge driver for me.

  1. What if I don’t try?

This is the question that most entrepreneurs fail to ask themselves, yet it is the question they should be the most afraid of. Think about it: what if you stay in your cosy job, only to find out three years down the line somebody else became successful doing the same thing you had thought about three years earlier, but were too scared to chase? What if you had tried it? Would you have become equally successful?

This is a thought that can stay with you for the rest of your life – ‘what if?’ For me, this was the toughest question of them all. It was the whole reason I threw myself into becoming an entrepreneur and chased after my dream. I could cope with trying and succeeding; I could cope with trying and failing. But I would never have been able to cope with a lifetime of a doubtful ‘what if I had tried?”.

By Goncalo de Vasconcelos (Forbes)


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