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Four reasons why freelancing leaves me lukewarm

I remember when I was nineteen and reading Jack Kerouac, On the Road, for the first time. This book touched me deeply in more ways than one; not least of all it made me reflect on writing and the privilege, and responsibility, of being a writer. This is where the main character, when asked how to be a writer, said:

‘You have to persist; you have to persist with the persistence of a drug edict.’

This book also opened a different path of literature for me; I could easily and without regret forego the flower power of the 1960s, and the ‘happening’ kind of creativity of the hippies – they were not my cup of tea. On the other hand, the Beat Generation of the 1950s were a different matter – they were intellectual and quirky; they were challenging and quaint.

Anyway, this somewhat more profound effects aside, reading On the Road also got me into a very bizarre ritual; every 100 pages or so I’ll get up and start/continue packing my backpack. Of course I didn’t hitchhike around Europe – there was too much studying to do, books to read, knowledge to acquire and degrees to complete. But the longing for the freedom that would allow me to just pack and go still lingers in my soul. Probably because of this I chose to stay in academia – before the neo-liberal onslaught of the last decade or so, academics had quite a bit of discretion regarding teaching, reading, writing and, more generally, touching the future.

Lately, I have been lusting again after the freedom that not being employed by an organisation brings with it. And no, I am not talking about retirement – who wants to retire anyway. What I would like is to be able to focus more on work and contributing value rather that on employment and the terms of my contract. Hence I have been pondering the advantages and disadvantages of freelancing.

In my mind, the advantages are fairly obvious:

a)      discretion over what I do and how I do it (within the usual constraints);

b)     freedom to decide when, where and how I work (yes, if I feel like writing while being in Granada living with the gypsies, so be it);

c)      wearing what feels comfortable (well, I did spend my sabbatical in tracksuit bottoms and cosy fleeces and it was very productive); and

d)     no limit to learning and earning.

This list can no doubt be expanded but these four are really what does it for me.

Despite all these I am not planning on leaving my job – well, not in the next five years, anyway – and going freelance. Why? There are four main reasons why freelancing leaves me lukewarm.

The hassle of hustling

To generate decent income as a freelancer one has to hustle like mad. Here ‘hustle’ is a shortcut for something rather unusual for my generation: work nomadism. This involves the continuous generation and commercialisation of ideas. There are different names for that but Tim Ferriss talks about ‘muses’.

The working life of a freelancer consists of a continuous cycle starting with an idea, moving through the dream, plan, strategy and product, and successfully going to commercialisation. Not too taxing, right? Wrong!

To begin with, statistically only two out of every ten ideas are likely to work; which doesn’t even mean they will generate decent income. Assuming that these ideas generate income, the work nomad has to move on immediately to working on the next idea. This is what I call ‘the hassle of hustle’.

Yes, I am an innovative person; but could I sustain this nomadic work life for the next 20 years? Could I do this till I am 70?

All the trimmings

When people see what a freelancer may charge or earn per month (or week) it seems a lot. What people don’t realise, and freelancers tend sometimes to forget, is that this is gross pay, not take home pay. It has to cover all the trimmings that come with employment like – pension contributions (the part of the employer as well), national insurance (or similar depending on where in the world you are), all kinds of insurance (I have decent insurance as part of my employer’s pension scheme, for instance) and this is when one really needs to build serious savings reserves – most employers still pay redundancy which of course is void if you are a freelancer.

In brief, after covering ‘all the trimmings’ freelancers may find that suddenly making £1,000 per week ($1,600) is not as much as it seems and they have very little left to live on. To top it all, being a freelancer means complete change in the way we manage money.

So the question is: can I make enough to cover ‘all the trimmings’, have decent income to live on and develop the fortitude to cope with high level of uncertainty? After all, I do belong to a generation that was raised to be employed and suffer, and enjoy, all that goes with it!

You want to borrow; how much does your job pay?

Today I was filling in an application for a 0% credit card; and no, it is not so that I could borrow irresponsibly. It is just that having access to 0% borrowing can be handy in variety of ways, so I’d rather have the option. Why am I telling you this? Because one of the questions was ‘How much do you earn from your employment?’.

The application form didn’t at any point ask ‘how much you pay taxes on’ but all the questions were about employment and earnings from it. In fact, I remember that recently J.D. Roth, the man who built and sold Get Rich Slowly, was discussing that he is not too keen on buying an apartment for cash since the cash makes more when invested than he will pay interest on a mortgage. Snag is, he can’t get a mortgage because he is not employed. Go figure! But it is a fact of life: borrowing becomes problematic for the work nomads, or the freelancers.

Doing the research for this article I did find some loan brokering for bad credit loans who are prepared to offer deals to freelancers as well; with no fees but a representative APR of 62.1%.

Can I guarantee that I’ll never need to borrow again?

How about a coffee?

Last but not least, the aspect of freelancing that leaves me lukewarm is the loneliness of it. Today, in the time of ‘connectivity’ one can build ‘virtual tribes’ and web-based bee-hives. And for a period it is fine – I was rather happy last year during my sabbatical to just sit in my study and write. Well, almost – I also travelled, met my colleagues from time to time and made good use of Skype.

But I know that eventually, the virtual life won’t be enough for me. I like being able to knock on someone’s door and say: ‘How about a cup of coffee? I know this great coffee bar.’

Don’t argue! Having a virtual coffee, in a virtual coffee bar is not the same.

Final words

If you have poor credit and need a loan, by all means: there are times in life when a little on time, even at high interest, can save the day when borrowed responsibly. But freelancers are different; most of them don’t have bad credit: they are just the forefront of a wave of work nomads who may be the foundation of the tomorrow’s economy.

As to me, I have to think a bit more about this and prepare the transition better. There is a work nomad trying to get out of this respectably employed academic!

19 thoughts on “Four reasons why freelancing leaves me lukewarm”

    • @Krant: You see, I have a bit of a problem. Throughout my life so far, I am either too young or too old for things. I would like to be in a position not to be have to be employed if I don’t want to in five years time. This means that we either have to build very serious investments, or develop freelance businesses or a combination of the two.

  1. I’ve thought about taking on some freelancing or staff writing gigs, but I’m not really sure it’s my cup of tea. I don’t believe I’d enjoy doing it full-time as I enjoy running a website more. If anything, I’d look to buy more websites and go about “freelancing” that way.

    • @Jason: It seems that together we may make a perfect internet entrepreneur – I have no idea obout running webistes (John does all that including hosting, speeding up and designing TMP) but my gig is writing. In fact, we were just invited to write for another site and we accepted. Let’s see how this one pens out (it is realtively small though). I still have a very demanding day job (which may become even more so in the next three months).

  2. There’s another point which should make you even more lukewarm: when you’re a freelancer you have to spend time on all of those benefits, also. At a company, there’s usually an HR department that has already made those decisions on your behalf. The older I get, the more Time is my greatest weapon, and the thing I treasure most.

    • @AverageJoe: Yeah, thanks for reminding me. This really is likely to tip the scales and I am staying put! Who knows I may reach a level of intellectualism when I belong to the world so it doesn’t matter anymore whether I am employed or freelance – the freedom will be there :).

    • @TheFirstMillion: This is interesting. My guess would be that people who are now in their mid- to late twenties (most of them anyway) won’t have a choice – they will have to learn to be work nomads. Then again, I may be wrong.

  3. Virtual coffee bar, great idea for a new business! You make valid points, I made sure to get a mortgage before leaving my day job, borrowing in the future sure won’t be easy. 

    • @Pauline: Tell you what, Pauline. Let’s go for it – the virtual cofee bar, I mean. We split fifty-fifty. How about that? As to the mortgage – smart. The next step would be for your business to get so large that you could appoint yourself as the CEO and pay yourself a wage.

  4. I have thought seriously about freelancing myself but there are some many things to consider like you mentioned. The biggest for me is benefits and gross income. I get a pension, benefits, etc. where I work now at a great rate. Trying to make that up myself would be very difficult. At this stage in my life where I haven’t even started a family yet, I don’t think I should try it. I need stability for a while.

    • @Miss T: Exactly! In the UK we still have very good conditions in the public sector (I have a wonderful final salary pension scheme which is getting ruined for the ones coming after me but…). So, my take on this one is that I’ll make a go for creating the conditions to leave within five years time but then it would all depend on how I feel. Nothing firm!

  5. Relying solely on a freelance income is a hairy situation and yet even those employed in previously stable sectors are facing challenges due to economic instability. I feel you are making a wise decision by working for another couple of years until you ultimately decide which path comfortably to pursue (and financially you will be in a better position to manuever there as well!)

    • @Brent: It is good; mainly I am feeling very flattered. Most people apply for this positions I was asked; this make me really think of myself as a writer. We shall see what happens next.


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