The Silent Suffering of The Self Employed

Have you noticed how there are some people in the world, who take the view that being paid to work is only really a means to an end?

I’m talking about the people who appreciate receiving a paycheck, and having money to pay their bills and spend on things that they like, but who don’t necessarily WANT to be toiling away doing what they’re doing.

They’re the people who are seeking to escape from work at the first opportunity and then go and spend their downtime hanging out with their friends and doings the things they REALLY want to be doing.

These people experience work and life as separate.

And then there are some people who simply don’t believe in wasting the precious moments that life gifts us. They believe in maximizing the experience of life itself.

I’m talking about the ones that do what they love and keep going until they have carved avenues into reality to receive money and resources for it.

For these people, there is no separation. Personal and professional dreams are inextricably interwoven and life is an experience of freedom and flexibility.

For them, there is no Plan B.

There is just, who they are.


If you’re someone who identifies as the first kind of person, but dreams of a life lived like the second, then in all likelihood you’ve probably already started feeling the circumstances building to an uncomfortable pressure and perhaps even started exploring alternative career options.

You may have already watched a bunch of YouTube videos from successful coaches, garnered a bunch of book recommendations from friends who you feel have got their sh*t together, engaged in a variety of different books, courses or programs to support you in finding your passion and life purpose.

You may even have researched and explored a bunch of vocational training programs that have peaked your interest and/or hold the promise of acquiring a professional qualification in something holistic or creative field that feels like it would offer a more enjoyable and laid back lifestyle.

If this comes close to describing your experience, then rest assured, you’re not alone.

The sad truth is that far too many people spend their days in jobs they just don’t like very much.

In a survey of 400 workers in Canada and the US conducted by Right Management, nearly two thirds of respondents said they were unhappy at work.

Only 19% reported feeling content.

That means that the vast majority of working people are unhappy.
So it’s understandable why millennial retention figures are so low, and why people are ditching the office and becoming self-employed in droves.

By 2020, there’s a study that estimates that more than 40% of the American workforce, or 60 million people, will be independent workers — freelancers, contractors, and temporary employees.

And from the position of being trapped inside a corporate prison, it’s understandable why the grass certainly looks greener out in the “free” world.

From inside a prison, someone who has the liberty to move around freely in the physical world, who can choose where they go and how they spend their time, looks free indeed.

But from this place, the place we’re having this conversation from, when we’re talking about employed or self-employed, it’s important to recognize that freedom is only really a relative term.

What do I mean?

What if, out there in Self-Employment Land, the things that confine us simply change?

Wouldn’t you want to know that before deciding the best and fastest route to your freedom?

Wouldn’t you want to avoid jumping out of the corporate prison, into a straitjacket of self-employment?

And if you’re confused about why I appear to be discouraging your flight for freedom, it’s because, ultimately, at Transformation Agency we want to invite you to consider the possibility of a more expansive definition of freedom.

One without invisible bonds.

And for that, it’s important to pull back the veil of illusion on the cultural definition that we currently hold and reveal the silent suffering of the self-employed.

So, let’s take an example.

Let’s say you’re an unhappy executive, professional or manager.

You’re ready to transition out of your current job and into something that gives you greater flexibility and freedom.

You find a vocational training program that offers a pseudo-professional qualification after a credible training program that’s delivered over a reasonable time period.

And you love the learning it provides.

And want to make a living out of that now.

Then what?

What do you know about starting your own business?

Do you know how to:

  • choose the right kind of business vehicle for yourself;
  • set up your finances and tax so that they can be managed easily and flow seamlessly; or
  • set up your basic tech, storage, email address and email signature?

These are some of the simpler A-B-Cs that people need to know when creating their own business.

And yet you’d be surprised how many people get stuck and get stymied in the early stages because they just don’t know the basics.
And why would they?

We don’t learn any of this stuff anywhere. Which is one of the things that a lot of people don’t realise when they first become self-employed.

We don’t learn it from our parents (or at least most people don’t).

We don’t learn it at school.

We don’t learn it at university/college.

Unless we actually engage in a business-specific degree, business post-graduate or paid coaching program:

No one teaches us how to set up our own business.

No one teaches us how to articulate our value.

No one teaches us how to have the money conversation with a client.

No one teaches us how to be in a healthy, balanced, working relationship with other people so that we can get the support we need in the areas we aren’t knowledgeable in.

No one teaches us how to consistently create content and value for us to share.

……or how and where to share it once we’ve created it.

….or how to leverage it what we’ve created to create a consistent stream of clients.

Heck, most us of have no idea that we’re even GOING to need to know these things when we start our own business. We simply don’t know what we don’t know.

And when we engage in our training, we don’t necessarily want to run a business, we want to deliver a service.

But you can’t do one without the other.

And without some kind of support in these “business” areas, or a reasonable amount of money to pay others to do these kinds of services for us, it is excruciatingly difficult to get anything sustainably off the ground.

Have you ever noticed how few vocational training programs will publish the success rates of their graduates a year or longer after they’ve finished the program?

I have.

I went looking and I didn’t find a single one.

And maybe it’s not fair or reasonable to expect the training programs to do anything other than train people in the particular skill that they specialize in.

But if you’re thinking about leaving your professional career to start your own business doing something that you love, then please just think carefully before you ditch your income and go into it full time.

Does this really sound like true freedom to you?



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Anna Margolis

Anna Margolis


As a former lawyer, Anna merges material world memories, tales of transformation and embodied experience in articulating the future of collaboration