Should you swap the jailers and choose self employment?

Self employment is coated in unicorns, myth and a healthy dose of cynicism. But sometimes, it can seem like the more appealing option.

Under the weighty crush of life in a busy workplace, many of us look at the world outside and wonder – “is there something better than this?”

From the customers you can’t fire to the snarky, mean spirited cow in the corner who appears to take a perverse joy in ruining your day, here you are. You are doing stuff you don’t like while having the same conversations over and over again.

Perhaps your mind is permanently aching for stimulation, or perhaps it could do with a little respite. Waking up to face another day of a commute, crap and under appreciation sits like a gargoyle on your Sunday night shoulders.

Your mind is always prodding and poking at you, quietly affirming “there has to be something better than this!”

Is it time to make a leap and try self employment? It’s not all beer and skittles- so grab your hat and read on.

The tug, the pull and the call of freedom’s ring

No grass is greener than the lawn on which the flowers of your ideas sprout. When we spend our time dreaming of a better tomorrow, our lens is often coated in Vaseline and our grass vividly filtered to impossibly bright.

It can be ridiculously hard to work out if what we have as a business idea is indeed lightly toasted in appeal and centred with rich, chewy, sustainable goodness. Sometimes we fall in love with the idea of freedom so much that all the doubts, all the fears and all the problems can be ignored.

But beyond the siren’s seductive call of freedom, how can we tell if our treasured idea and warm Sunday night sleeping comfort can be a reality? How do we cut through the desire for freedom and uncover the nugget of good idea within?

Self employment takes a lot of guts. You have to be brave enough to back yourself. Forget delegating- everything is up to you. At least for the first while. The buck stops with you, too. So you have to be comfortable with accountability, even when you’ve done all you can and the clients still demand more.

If you think it’s civilised wagging, have we got news for you. Self employment means working longer and harder than traditional workplaces. Plus, there is increased risk and responsibility.

This isn’t holiday camp, champ!

Sharpen the focus. Study the cracks and lines

If you are serious about self employment, you need to sharpen the focus. You need to shift your gaze away from the centre of the happy grassy green and seek answers in the less fertile edges. Look for the crags and the cracks. Spend time amongst the dried leaves and hidden, dirty edges.

Find the patches of less than perfect soil where innovation can grow.

Kick the tyres and ask yourself the hard questions:

  • Is your idea nice to have or does it solve a problem?
  • Can you capture the story in the time it takes you to take 3 sips of a good wine?
  • Are the audience waiting, itching and in pain, for your idea to come and cure them of their ills?

These are the questions you need to ask yourself.

Honestly. Truthfully. In the nude before your harshest self criticism voice and it’s thorny tongue. The planning of your self employment adventure depends on it.

You need to study the cracks and imperfections of your idea and dedicate time to thinking if they will hold you back or propel you forward.


Write it down to get it right and down-pat

Hurrah for the coffee conversation and the wine flavoured pitch! You have arrived on the shores of an idea that other humans admire. From here, it is time to pull out your pencils and sketch your own map towards the freedom you desire.

Things to include in the topography:

  • How will you afford to kick off in self employment as you grow your audience?
  • Who do you need along for the ride?
  • Can this be done in squeaks and bubbles of usually lost time?
  • What does it look like on paper?
  • Is that sentence of description watertight?

You, your pen and a thousand pieces of little paper have a date, my friend. A date that is so important that the conception of your future idea depends on it.

Self employment is about picking out the pieces of your idea and flattening them against the less romantic cousin of conversation, a plan. This plan gives you background, bones and shape with which to move. It is both drearily challenging and delightfully comforting at the same time.

And it bites and it tears at that original Sunday night session of ceiling appreciation. It knocks the delicate, lacy and lovely tendrils of your idea off. Snipping, snapping and contorting it.

You will at times feel as though your idea is being whisked from your hands and turned into something entirely. If someone is brave enough to do it for you, you will probably resent them. But it will be the same sort of angst we reserve for the loving parent, mentor, lover or fitness trainer who cares enough not to lie. It will be the hard news we shrink from, we bottom lip out on, but that will ultimately see us picking up our kit bag and march up the mountain because we know we can nail it.

Swapping the jailer

Make no bones about it, self employment is hard. That jammed printer, angry customer, screwed up roster and every skerrick of joy-poisoning admin is yours. When the supply chain melts, when the product cracks and the tax man comes calling it’s all you, sunshine.

This is in essence, swapping one jailer for another.

We swap the steady income, set hours and the ability to turn our heads off for chasing money, chasing the work and the never ceasing hum of a business that lives in your living room and head 24/7.

But we also swap it for the opportunity to be on the right side of a decision. We carry it through to carving out a work process that we like. At a certain point, we pick the hours and the people we interact with. We accrue customers we value while leaving the less desirable behind. And things begin to make far more sense as we do things not because someone else holds a grand vision in their hand, but because it makes sense and gives light to us.

We happily swap the jailer knowing that the worse that could possibly happen is we may need to swap them back.

Welcome to the exercise yard

Welcome to the yards before a self propelled career. The air is a little chilly out here sometimes, we must admit, but we wouldn’t change this for maximum security.

We’ve learnt to adapt and to thrive. Part of the journey has indeed been working out the system. But it is a system we now know how to use to our advantage.

This is why we are inviting you (who is clearly curious considering you are dancing at the 1000 word mark) to join us in swapping your jailer, too.

Call on me if you want to start your freelance and self employment journey the right way.

If you are serious about self employment, come along and join the fun of the Freelance jungle. 

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