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Ask yourself these 9 questions before you quit your dayjob

Do you spend your Sunday evening dreading Monday morning? Do you feel like you would prefer to clean the toilet than go to work, or what about stabbing yourself with a pencil instead, as it means you can call in sick tomorrow?

Does your dream of climbing the corporate ladder snow feel kinda empty?  And do you instead dream of breaking this cycle by working for yourself?

If you are nodding at the computer screen like an idiot then you are probably one small step away from throwing in the towel and telling your boss to stick it.

This is all well and good but before you tell your boss his breath really stinks and you cannot put up with it for one second longer, dig deep and ask yourself these following questions with the honesty of a tourette sufferer.  They will help you work out whether becoming an entrepreneur is something you are really cut out for.

 1.     How comfortable are you with uncertainty?

Working for yourself is never going to be a sure thing.  It will never come with a guarantee that you will make it, you will never have enough information, you will never have an up to date sat nav map, and you will never generally know from month to month how much money you will be able to take home (if any at all during those first few months).

Although any job is not guaranteed (certainly not in this market) you will have a much better idea of how much money you will receive each month.  You will also most likely have a corporate structure which will provide guidance for you rather than you having to be comfortable with “making it up as you go” as an entrepreneur.

Don’t get me wrong you can plan for the uncertainty, in fact it is something I highly recommend (for instance I had a 12 month cash reserve under my mattress just incase I made zilch in my first year. It provided me with peace of mind and meant I could always afford baked beans for dinner!) but you need to become comfortable with the uncertainty entrepreneurship will bring.

 2.     Are you a diehard perfectionist?

Ever heard a friend wax on about how everybody at their work are idiots and it never seems like said friend takes one wrong step? Well guess what, running your own business strips you bare and you become quite aware of your strengths and weaknesses. If you are a diehard perfectionist and are not willing to accept that you will make mistakes and that getting it done is infinitely better than making it perfect then you will have a long hard journey ahead of you.  Even worse your competitors who have a much crappier version of what you have will be whipping your butt because they have launched and are generating real revenue and you are still tinkering with draft 64!

Are you prepared for the change in yourself as a person that the path of entrepreneurship will force upon you?

3.     How quickly can you make decisions, accept losses and move on?

Following on from the last point, you WILL make mistakes. It took me much longer than it should have to accept that I had bet 10k on the wrong software horse for my business. Lured by all the bells and whistles I thought it was the right solution. Sadly it wasn’t even close. I spent months kicking myself metaphorically in the arse for this bad decision, rather than cutting my losses and walking away from the lame horse.

You need to be able to cut your losses and get out fast, whether this be a wrong hire, a business plan which in the cold hard light of day just isn’t working or a product you just can’t sell.

You will recover from bad decisions, this is a certainty, but you need to be willing to do this fast.

If you struggle to accept your losses and move on, you won’t cut it in business and will rack up a huge counselling debt!

4.     Are you an active learner?

Do you love trivial pursuit? Ok so that technically is not a true prerequisite for becoming a successful entrepreneur, however you must be willing to continually learn and actually love this fact.

Entrepreneurs are a curious bunch. They are also willing to self educate and do whatever it takes to learn and therefore succeed.  Are you an active learner, or do you believe it is your current bosses job to educate you?

 5.     Do you love to travel?

Running your own business is often like travelling.  You used to drive everywhere now you need to navigate the subway.  You wish you could clear customs in 20 mins when in fact it takes 3 times as long as you predicted.  See the similarities?

When you first start you will be dropped into a city you have never been (solo town) and you will have no map, nor a clear idea of exactly where you are actually going.  You need to make sure you do not get overwhelmed when people speak a different language and you didn’t even know you needed to bring your lonely planet guidebook.

Your surroundings will change as well. Your plush corner office may become the living room, cafe or even garden shed.  You need to be ok with slumming it for a while.

You will need to learn how to immerse yourself completely and just go with the flow, even if that means accepting that offer from a German backpacker when you really wanted to land a Greek Adonis.

You will however wake up one day and realise you can read that train timetable in Mongolian, and that you can trade your juggling skills for a pack of pencils in your sleep.  It just takes time and persistence.

It’s ok if you weep softly at the realisation that you are standing naked in the shower and cannot work out how to turn on the shower taps (as I actually did).  Allow yourself to do this once then learn how to turn the bloody taps on next time!

6.     Do you really, honestly think you will be able to work a 4 hour work week?

If so forget it, at least for the first couple of years. You will be like that old cat lady who lives by herself around the corner.  She has to cook, clean and shop for herself. She even has to take out her own rubbish and change her own light globes as no one else is going to do it for her.

Working for yourself is not the walk in the park you think it might be. Sure you no longer need to put up with all that banal banter at work about which X Factor judge is the meanest, but you will wish you had the time to even let that worry you.

You will be switched on for longer than a stenographer at a Lance Armstrong hearing. There will be very little zoning our every night. Your every waking moment will be spent thinking, planning, deciding which way to move, and then again doing the same thing the next day and coming up with a different answer.

Being an entrepreneur is so rewarding, I wouldn’t have it any other way but it is the hardest job I know of.

 7.     Do you love those H&R Block Ads?

You need to be turned on by your business, just like those accountants at H&R block at tax time.  You may not be cool anymore, in fact old friends may not want to sit with you at lunch because you talk on and on and on about how cool Xero is, or what your conversion rate target is, or how a white background is better than black when building a website. But do you know what? If your high school reunion was anything like mine the nerdy kid who played chess ended up becoming super hot 10 years later (damn me for not noticing that one!).

New entrepreneurial friends will turn up, you will start to collect them, and who knows maybe like neon things will come around 360, and your cool friends will be asking you for advice on how to start their own business?

 8.     Would you be a telemarketer for a day?

“What the” I hear you say? No I am not talking about moving to India or the Philippines. The point I am trying to make is, are you willing to sell? Are you willing to pick up that phone again after being rejected on your last call? I hate to break it to you but being an entrepreneur involves selling.  Starting Sterling and Hyde, my handbag and accessory business, this was pretty obvious, but for other businesses it may not seem so. A personal trainer gets people fit, a dentist fixes peoples teeth – No, no no.  A dentist needs to get somebody in their chair in the first place and do a good enough job so at least they come back once a year.  A personal trainer needs to sell that vision of a fitter you, otherwise you may just go back to the couch with that packet of Tim Tams or even worse defect to your competitor.

Every successful business person sells.  Sure you may not be comfortable selling, but you need to be willing to sell to put money on the table for your family.  I do not advocate the rote telemarketer approach, and I certainly don’t advocate calling people when they are watching Masterchef The Professionals, but you need to be willing to at least pick up the phone and try, and try and try again.

9.     Would you consider base jumping?

Yes I know we talked earlier about uncertainty and risks, but this final step goes one step further. Starting your own business is one of the biggest leaps of faith you take. People will think you are crazy but you do it anyway.

If this path is truly for you, you will get addicted.  My backup plan was that if it did not work I would just go back and get a day job.  Seems logical enough, except that I have changed and am no longer that same person I was 3 years ago.  If my business Sterling and Hyde fails I simply cannot bear the thought of going back to work for “the man” long term.  I concede that may have to happen, but I know it would be temporary, until I was able to start my entrepreneurial journey all again.

Like base jumping, entrepreneurship becomes addictive. Like jumping off a cliff, building, whatever, you get my drift, there is very little turning back. You don’t know where you will land, or if you even will but you are doing what you love and that is the main thing!

If your dream of doing something different with your life and trying your hand at entrepreneurship, if this dream is like that annoying Monorail episode of the Simpsons (on all the bloody time) then prepare for your first base jump, be as safe as you can be and go for it.  Yes most people think base jumpers as lunatics but they are willing to risk dying whilst living their dream, instead of wishing what had been.

And for the record, no I haven’t been base jumping, but I have been skydiving 3 times!





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