Freelance Advice: Your Experience MAY Mean Nothing!

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This particular freelance advice article is one that’s been percolating for some time, so I thought it was about time I sat and wrote it.

Fundamentally, it’s about establishing your services and winning clients, especially when you first embark on your freelance career, and especially if you’re moving from full-time employment.

In the course of running HomeWorkingClub, I get an awful lot of emails from new subscribers seeking freelance advice. Something that’s surprised me over the past few months is how often I read detailed run-downs of really rather auspicious past careers, and then find myself trying to diplomatically explain to people that their experience could be completely meaningless in the world of freelancing.

Let me give a couple of (fictional) examples:

Perhaps you’ve been involved in writing for several years – let’s say technical writing. You’ve produced manuals and “how-to” guides for your company, been involved with editing the work of others, have a small team, and a great looking resumé.

In this position, you might reasonably assume you’re in a good place to embark on a career as a freelance writer?

Or, let’s say you look after the website for a huge company. You’re highly competent in coding HTML and PHP, and there’s nothing that could go wrong with that site that you wouldn’t be able to fix.

On that basis, surely a lucrative career as a freelance website builder should be easy to aim for?

Unfortunately, in both cases, you’re not really that much further forward in the freelance world than a total novice. And that’s still the case if your CV’s scattered with household-name companies. It’s still the case if you have impressive letters after your own name.

You see the thing is, people taking on freelancers only really want to see a few things:

  • How much you charge
  • What previous clients have said about you
  • Some examples of your work so they know what you can do for them

People hiring freelancers rarely want to see a full resumé; In many cases, they don’t care to know much about you or your life; They just want to know that they can get their work completed, reliably, for a rate they’re happy to pay.

Is this the Most Depressing Freelance Advice Ever?

So why am I telling you this? Am I trying to hint that moving from full-time work to freelancing is too challenging to even attempt?

Of course not.

But what I am keen to get across is that you may well need to adjust some expectations. This is especially true when it comes to any assumptions you may have about how much people value your past experience.

It’s easy to become a “big fish” when you work for a company. Perhaps you’ve become used to being “schmoozed” by the agencies your firm employs, or are at a level where you’re accustomed to business class travel or fine dining?

Well, I’m sorry to say that however big a fish you may have been in the world of traditional employment, everyone in freelancing starts out as a minnow.

A Personal Example

Success in a single job can actually, in some cases, become detrimental to long-term freelance success, and I’m going to illustrate that with an example.

For the few years before I started HomeWorkingClub, I’d been working a lot with one specific client. I’d started off just writing occasional articles, but the company grew rapidly, and I ended up (despite being freelance) in a management role that took up the bulk of my time.

I enjoyed it for a while, especially when the company still had that “startup phase” vibe. However, I became less and less happy as things went more in the direction of corporate talk, structures and PowerPoint presentations!

Anyway, as I began to grasp my desire to step back from this client and re-establish a much more diversified and varied freelance lifestyle, I started to realise that getting so involved in something that was more like a “job” had been a bad plan for the long-term.

As I started to update my writing portfolio, I realised much of it looked woefully out of date. One annoying thing about writing for the web is that the content is rarely there forever. It’s a terrible shame when you find some of your most impressive “clips” are no longer out there to show off to the world.

The point here is that I’d put myself in a position where I had a very impressive-sounding LinkedIn profile, but a far weaker profile as a genuine freelancer. In essence, that’s often exactly the position you’re in when you come out of full-time employment and move into freelancing.

What to do about it

Obviously, everybody’s experience here is slightly different; If you’re moving from a high-end management role into doing “day rate” consultancy, these kinds of issues may not be such a concern.

However, if you’re moving from – for example – a leadership position into freelance writing for the first time, a crucial piece of freelance advice is that nobody cares about how big your team used to be or how prestigious your MBA is.

Really, this applies to anything remotely “portfolio based.” Want to apply for a writing role? The client will want to see examples of recently published work. Want to become a Pinterest specialist? The client will want to see some analytics showing how you’ve helped past clients to increase their exposure.

Ultimately, the important thing is to ground yourself and start to work towards the career you want, rather than remain attached to the career you had. The freelance lifestyle is about many things; For me, it’s about being able to spend quality time with my children every day, having time to cook, barbecue, do the garden and enjoy my home, and being free of management BS, power struggles and office politics.

But you have to give things up for that; You have to give up the Business Class lounge, the posh coffee, the kowtowing suppliers and the general sense of status.

There’s plenty you can do to mitigate the issue of not having a portfolio of work. Planning a gradual migration to freelancing is often a good idea, as you can start to build up the things potential clients are going to want to see. (The first thing I did once I knew I intended to step away from my main client was to look at ways to get my work and my name back out there, regardless of whether doing so made any meaningful money).

What seems to prove more difficult for some is coping with the bump down to reality. Sometimes when I receive emails, I can tell from the tone that I’m dealing with a person used to the perception of “being important” in a business environment! (To be clear, I also receive plenty of emails from people with PhDs and incredible career histories who’ve completely grasped the way things are, and gratefully and graciously accept the “beginners’ guides” I send to them).

The irony is that it’s those who are willing to slow down and learn how the world of global self-employment works who have the best chance of achieving success and enjoying the freelance lifestyle. Sadly, I suspect some others will find themselves remaining in the traditional workplace, enduring the daily commute with a taste of bitterness and a strong sense of “don’t you know who I am?!”

So, I’ll end this short burst of freelance advice by posing the question of which person you really want to be. If the status, the title and the kowtowing are important to you (and you’ll know the real answer to that if you’re honest with yourself), moving to freelancing is going to feel like quite the adjustment; It doesn’t mean you can’t, but it deserves more serious thought.

I know which emails I enjoy receiving the most: The delighted ones from people who’ve just picked up their first regular writing gig, or their first couple of jobs on Upwork. These are the grafters, the humble,  and the realists. They’re also often the very happy people who’ve suddenly realised that all they have to do is repeat the formula X more times, and they have exactly the life they want.

Then I get one of aggressive “I only want to hear about the big bucks and I’m not willing to work for peanuts” emails, and think about who I’d rather be.

It doesn’t take me long to decide.

Thinking about moving from employment to freelancing? I suggest reading this article. 

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