Everyone has dreamed this dream at least once.

Usually, it’s a ‘Monday-morning-where-did-the-weekend-go-why-do-I-have-to-go-to-work-what-am-I-doing-with-my-life’ kind of dream.

You think to yourself, “My friend XYZ is self-employed and she makes her own hours; she doesn’t even work on Mondays!”

You remember that skill or hobby that you just haven’t had the time to do lately…

You wonder if that could be the path for you…

Fortunately, you usually get over it, get dressed and go to work… but the dream can be a tenacious one.

So how do you know if you really have what it takes to work for yourself?

Here are some key questions you should ask;

1 – Do you know how to be poor?

Not that your business won’t succeed but, at first, you’ll struggle. The best way to weather the storms ahead is to live WELL BELOW your means while your business gets on its feet.

Also, you will have months of abundance and then slow months. It’s important to be disciplined, because the fact that the money is there doesn’t mean that you can spend it.

Can you stick to a budget? Can you be frugal even when there’s money in the bank? If you can, you may be a good candidate for self-employment.

2 – Are you self-motivated?

Many self-employed people will tell you that they are their own toughest critic. They live with their boss and their boss is an absolute micro-managing, control-freak who’s never satisfied. This is why they succeed. If you allow yourself to slack off, your business will go nowhere.

Think of it like this; the last time you made a promise to yourself, like “I will not call that loser” or “I will only have one cup of coffee a day”, did you keep that promise?

To be self-employed you have to know how to prevent yourself from screwing up and how to be accountable to yourself if you do. So, with no-one else there to crack the whip, will you still perform?

3 – Are you passionate about your business idea?

Of course, you probably like whatever it is you’re thinking of doing, but liking it isn’t enough. Could you work on it all night and have no regrets when you have to wake up at 6am on Saturday to go on working?

Are you so passionate about it that you would do it for free? In the early days, you might have to offer freebies just to get your name out there.

Do you love your idea enough to do hours and hours of unpaid research? You probably have to do a few humdrum administrative tasks at your current job; filing, invoicing, writing emails, fact-finding… The thing is, your current employer pays you for your time. Even the guy who secretly spends all day on Facebook will get paid – until the boss finds out what he’s been up to.

When you work for yourself, you are only paid for the actual product or service that you deliver to a client. Everything else is only rewarding if you feel passionate about what you do.

4 – Can you SELL?

No matter what you do, if you’re an entrepreneur, you have to be a good salesperson. For the most part, my activity involves trading services rather than a physical product, but people buy my services because I SELL them.

Now, I am my product so, in a totally non-creepy way, I am selling myself. That takes a lot of energy and creativity and sometimes you have to swallow your pride if you want to make the sale.

Ask yourself; are you willing to do that?

5 – Are you willing to sacrifice your social life?


When you work in your pyjamas every day, you actually start to miss dressing up! Everyone enjoys stepping out in some cute pumps, rocking a nice handbag and having a reason to wear that new lipstick… right?

Seriously, though – working for yourself and making a success of it takes dedication. You never fully understand that dedication until you’ve spent two months without seeing a soul and your friends have stopped inviting you out.

Particularly if you’re thinking of working from home, remember that there will be no idle conversation at the coffee machine, no group retreats, no lunch-room jokes, no staff Christmas party, no team-building activities, no cute new guy in the PR department… True, there’s also nobody at work who you absolutely cannot stand – but it can be a very lonely life.

6 – Have you done the research?

This shouldn’t be a pie-in-the-sky dream based on a vague fantasy and supported by a poorly researched business plan. You need a solid foundation!

You need to be prepared to do your own taxes… Do you know how? You need to know your profit and loss projections… you should have a way to track business-related expenses which might earn you a tax write-off…

Will you have to register for VAT? Who are your main competitors? What’s your unique value proposition? How fast do similar businesses grow? Have you done a SWOT analysis? Will you need insurance? Legal representation? What is the industry standard in equipment in your field? Speaking of standards, is there some ISO Standard or legal requirement which you are bound to respect?

Don’t just assume that you know; FIND OUT.

If you’re getting a headache just thinking about this, it may mean that you are human.

If you haven’t already made a list of all the things you need to research, it may mean that you aren’t cut out for self employment…

If you already ARE self-employed and know of some other key skills or questions we need to ask, leave a comment below!

I always love hearing from you!



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