The Downsides of Freelance Work

Last week, if you would remember, I wrote a blog entry on the topic of ’The Perks of Freelance Work’ to describe some of the things I have enjoyed the most, so far, from being a freelancer over the course of last three years. While that post did not include an exhaustive list of perks, it gave me a pretty good opportunity to reflect upon what I have learned over the course of time, now that I’m getting pretty close as well to my 20th year anniversary in the IT industry. In it I also mentioned how I’d be writing another article where I would share across a number of other different advantages that didn’t make it into the first entry of this series, but I also wrote about creating a couple of different blog entries where I would be musing about the downside(s) of freelance work. Yes, that’s right, the ones no-one talks to you about, nor cares to admit they are going through themselves, mostly because of the lovely, rosy words we seem to impregnate freelancing with as the next big-thing (Remember the gig economy?), when, in reality, it might be everything but… 

The overall purpose of these blog posts talking about the perks and the downsides of freelance work is for me to try to share across a somewhat balanced view around my overall experience in an effort to, perhaps, help you folks understand whether freelancing might be something of interest for you, or not, who knows. At the same time, it’s also a unique opportunity to confirm for myself whether I am alone experiencing and going through some of these ups and downs of freelancing or whether it’s just me. There is that possibility as well. That’s why, with regards to the downsides of freelance work, I am putting together this first blog entry where I would like to explore ten of them and then over the course of time I will be picking each and everyone of them and describe in length how I get to overcome them eventually.

Thus, without much further ado, here are some of the downsides of freelance work, in no particular order, I’d want to share across for now and let’s see how much other folks can relate to each of these, if at all:    

• Uncertainty: If there is anything I have learned over the course of the last three years, as a freelancer, is money doesn’t like uncertainty. It runs away from it like the plague. So when we are going through this exhilarating, nerve-wrecking roller-coaster of tumultuous times, provoked by either global or political turmoils, you know you are bound to learn, and pretty quick, how to live with the uncertainty of not knowing what tomorrow is going to bring forward.

  Making plans ahead of time is not only a waste of time, effort and energy, but also a rather distracting activity, because, in most cases, you just don’t know what’s going to happen next week, month, or year! So, very early in the game, you realise that uncertainty helps you, through the hard way, to pretty much live in the moment, focusing on the tasks and work at hand without having much of an opportunity to focus on anything else, because, you know, it’s just not certain. The ever so much more complex times we live in will bring forward such uncertainty that will pretty much scare your customers away, specially, those with the budget to kick off your projects. But here is the thing about uncertainty that I like the most: it forces you to keep moving, constantly, without excuses, nor regrets, into striking the next lovely project work you will be doing with a potential client at some point in time. Now, I will be talking a whole lot more about it, but here is a tip of advice I learned about coping with the uncertainty: the moment you stop thinking about the what next that’s the moment when uncertainty wins. Don’t let it win. Keep moving! 

  [Like I have mentioned above already, I will be putting together a number of different blog posts in the near future where I will explain with much more detail how I get to tackle each and everyone of these downsides of freelancing, so you folks may learn some more about how I try to cope with them and how sometimes I succeed and how, in others, I don’t. But one step at a time …]
  
  

• Insecurity: With this one I’d want to encourage you all to think of it more as in job security than anything else. And here is a short story on what I mean with that. Three years ago, when I had already decided I was quitting my job at my former employer to start my own advisory firm around Social Business and Digital Transformation, I remember having a conversation with one of my managers where he was asking me what I was thinking about doing next as a freelancer. Back then, and without much thinking, I ventured to state I suspected plenty of the work I would be doing would be rather similar to the work I was doing for him, that is, advising and helping businesses make the most out of their Enterprise Social Networking platforms while embarking on their own Social Business and Digital Transformation journey, but do that work on my own. Going solo. 

  His response, after a long silence, was something along the lines of ‘Hang on, but where is the challenge in that? I mean, you would be doing pretty much what you have been doing for the last 14 years, so there wouldn’t be anything new for you to learn and enjoy in your new job and therefore you would still be stuck within your own comfort zone’. I remember how my initial response was fulminant and somewhat categorical. Alas, it had to come out. I remember I mentioned how, while I was working for him, I would be working really hard to my abilities (or not so hard sometimes) and still have the certainty at the end of the month there would be a paycheck. There always would be a paycheck.

  However, I told him, when I start my freelance work I will be working just as hard, if not harder, day in day out, week in week out, and, unfortunately, I would not have any certainty I would be getting paid for that work. How is that for a challenge to shake your own comfort zone of having received monthly paychecks for the last 17 years without not knowing whether there will be a cheque anymore at the end of the next month? That is the kind of insecurity freelancers are constantly being exposed to. It’s not an easy downside to deal with I can tell you, as most other people would confirm as well, but, unfortunately, it’s going to be there from the very first day you decide to go independent and become a freelancer.

  How can you overcome it? Well, I will be talking about it in more detail at a later time on what I do myself to tame it, but my first piece of advice I have always shared with folks has been to have a substantial financial cushion that would allow you to live comfortably those months where either things are slow, or just not happening at all. And keep moving. The important thing though is not to live for too long under the assumption things will be all right as you deplete that cushion month after month hoping it will all turn around eventually. Well, it might not. At one point, you will need to decide what you may need to do to stop the bleeding, before it’s just too late and you end up in a whole lot of unwanted and perhaps unnecessary trouble. 
  
  

• Client Prospects: I know this may sound a bit weird, I mean, the fact I’m adding searching for client prospects as a downside of freelance work. Well, it is and those who may tell you otherwise may not be telling you about the untold costs of client prospecting. Because it does pay a toll, a huge one, actually. While you are doing client work (either with one client or multiple of them at the same time), your mind will always be worrying and preoccupying itself about the next client. Where are they? How can I find them? How can I reach out to them without sounding too aggressive, too desperate, too cheesy? How can I influence them to start working with me when there are millions of other freelancers out there? Will they be interested in the value add I can provide? What do I have to offer to that client that may be unique and no other people may be providing? How am I going to end up finding new clients when I’m terribly bad at marketing or selling my product? Where do I start? Jeez, why is it all so difficult? 

  I’m pretty sure plenty of the questions, concerns and uncertainties I have just shared in the above paragraph have gone through the minds of any freelancer over the course of time. Why is it a drawback? Well, because of focus. It’s a distraction. It’s a massive distraction from the work you are currently doing for your client(s). And here is the frustrating tidbit, that while you know you will want to work really hard for your clients and deliver 100% of your value add, that distraction, that lack of focus on finding the next client is going to neglect you giving that 100%. Ouch! It will hurt. You know you can deliver effortlessly, but the distraction is a killer.

  And while you may be wondering how to get around it, I can share with you all that the way I have done it is by creating in-between blank spaces where I’m not working with a particular client and, instead, do the prospecting. In short, that means I focus 100% on the client work I’m doing in the moment, delivering with the highest quality I can provide, and once the work is done, I will be spending some time (it usually depends, but it ranges from a couple of weeks to a full month) doing that client prospecting, knowing that there will be no income coming through, but it will help me focus on a single task at a time: serving my client(s) first, looking for new ones afterwards. 
  
  

• Trust: This is perhaps one of the downsides of freelance work that has hurt me the most over the last couple of years. And I don’t think it would apply only to people doing freelancing per se, but everyone, in general, whether you may well be in a salaried job or as an independent. Trust seems to be running very low all over the place at the moment, whether we like to admit it or not. And that lack of trust is causing infinite more trouble than one could have ever imagined. The thing is that if you are going solo trust is an even more critical component towards your own success working with clients achieving your various different goals, because, you know, you are on your own. There is no-one else out there supporting you, at least, initially. That’s what most clients would think about you and the work you do. 

  But there is also another component of trust at play, as a freelancer, which is when you connect and build personal business relationships with your ‘peers’, those people who, over time, eventually, become an integral part of your social networks, till you realise that what you thought of, and advocated for all along, as coopetition (i.e. collaborate openly to compete in a healthy manner) is just plain good old vicious competition. By the time you find out, the damage is already done. The horse has already left the building, indeed, at lightning speed.

  I never thought I would be talking about this, but, like I have blogged a couple of months back, trusting people in this social age is a tough job, specially, when there is a lack of coherence between what people talk, preach and advocate for AND what people really do, letting hypocrisy, therefore, run the show while abusing your own good will. What did I do about this one? That’s a great question! I decided to move on with my work life, understanding I may need to work ever harder from there onwards towards building better, more effective, relevant tight social networks where the primary goal may well not be being poached around left and right. See why it hurt back in the day? Onwards and upwards! 

• Remoteness: This is one of those drawbacks you may not be able to see coming up front early in the game, till it’s, perhaps, too late and you may have experienced it firsthand already. What I mean with remoteness is, essentially, working remotely while freelancing and how, depending on the industry and the kind of work you do, it will become an issue that’s rather tough to overcome on its own. In this day and age of hyper-connectivity, of remote enabled collaboration, of networks and online communities as the new operating model, of digital technologies allowing you to transform work from a physical space (i.e. the office) into a mental state, it’s hard to believe that remote working in social business is pretty much dead, unless, of course, you would want to re-locate or work on-site 24x7x365. Then again everything you may have endorsed throughout your entire working life is bound to collapse on its own, because, you know, your words and your actions will no longer match. Two completely different worlds colliding with one another and you sitting right in the middle about to experience the clash. 

  That lack of coherence will eventually be your dead end, because how can you dare promote a different kind of working together? How can you state you are designing the ultimate new way of working while promoting an emerging set of digital technologies when you end up working in exactly the very same way you have done it in the last 15 to 20 years, if not longer? Why bother? Seriously. Why bother at all? It’s like as if you were heavily promoting the extensive use of all of these digital technologies at work to help improve the way you connect, learn, share and collaborate with others and yet your number #1 tool you still heavily use on a daily basis is *cough* email *cough*.

  I tell you, if someone would have told me, ahead of the time, what a huge challenge would be working remotely in the realm of Social Business and Digital Transformation I think I would have probably switched off a long long time ago and moved on to better things. That lack of coherence and dishonesty to our core beliefs are just killing us, social business evangelists, big time and, somehow, we just don’t seem to want to wake up and do something about it. Don’t worry, in an upcoming blog post I will let you all folks know what I am doing at the moment to overcome this particular drawback. Can you already hint what it is? 

• Lack of Discipline: Ok, let’s now move into the more down to earth, mundane downsides of doing freelance work and see what’s out there. Remember when I mentioned free time in a previous article around the perks of freelance work? Well, lack of discipline is one of its worst enemies altogether, more than anything else, because, unless you do something about it, it will manage to destroy your focus and dedication to your client work with a multitude of distractions that will be hard to beat till you realise it’s just too late. 

  That’s one of the reasons why I think plenty of freelancers are so keen on coworking spaces in the first place, because somehow there is a specific discipline in the air to get work done together but still separate, if you know what I mean, and therefore eliminate the urge for any kind of distraction or goofing off. The fact that others are working around you in the same space makes you give in to that thought of not wanting to slack off nor lazy around, to just go for coffee breaks whenever everyone else is having one (GREAT opportunity to converse and connect, by the way!) and to put similar amounts of work like everyone else is doing and eventually conform to an office-like environment where you know lack of discipline is no longer welcomed, nor encouraged.

  You may be wondering by now whether that’s how I have overcome that lack of discipline while freelancing, right? No, I don’t use any coworking space at the moment, even though there are a couple of them right where I live. What I have done instead is build a number of different routines I have developed over the years to help me focus on what I am working on at the moment. That’s why I depend so much on the Pomodoro Technique. That’s why I also rely quite heavily on the effective power of music, for instance, to help me eliminate distractions and really focus on what I need to do in the moment. And the list of routines goes on and on and on. I think I could probably write an entire blog post just on this subject, so I’m going to park it over here for now and come back to it with a follow-up entry at a later time. 
  
  

• Procrastination: Oh my, talking about writing an entire blog post on a specific subject! How about on procrastination itself? Yeah, I know, I bet plenty of you folks out there could write another article about it and how you try to beat it successfully. And yet, it just doesn’t happen. I think it would be silly at this point in time not to realise and acknowledge we all are professional procrastinators. The thing is that while you can certainly bump into dozens, if not hundreds or thousands, of articles, blog posts and whatever other publications about how you can stop procrastinating and keep working further along, over time I have learned about something else that works for me way way better: embrace it! Yes, that’s right! If we are all chronic procrastinators having mastered its art over time, why not try to make the most out of it?

  This may sound a bit too weird, but mastering the art of procrastination has helped me, over time, become much more effective and creative altogether. If anything, it’s helped me understand how there is good and bad procrastination and how, over time, I have become a huge fan of learning ‘how to procrastinate well’. Have you tried it out yourself? Believe me, it just works! 

• Self-pity: You know those times when things are running far too slow in terms of clients asking for your help, support and guidance or when freelance work just doesn’t come up often enough and you start wondering about whether you really have it or not? You know those times when you are on the brink of giving up on freelancing because you keep thinking you are not good enough for it, or you don’t have the right skills, expertise, mindset, networks (to help out and assist where appropriate), etc. etc. Or perhaps you even thought you made the wrong decision about going freelance in the first place and you should be doing something else elsewhere? Well, folks, that’s when you’d know you are entering the world of self-pity. Welcome to the club!

  I tell you, I don’t know a single freelancer out there (me included as well for sure!) who may not have gone through that phase of self-pity, specially, when there is no paid work coming along for an extended period of time. It usually comes in the most unsuspicious ways: thinking too hard too often. Thinking about your current situation; about why you are not getting enough client work any longer; about why hardly anyone comes to you anymore and asks you to speak at an upcoming conference event or to write an article for an online publication, for example; about why no-one asks you to help them, where you can, with their own projects collaborating together; finally, about why, all of a sudden, it feels as if you have disappeared entirely from the scene as if you never existed. My goodness, self-pity can have such a destructive flair to it, can’t it? Well, it doesn’t end up there. 

  Then there is the doubt. That same doubt about whether you may have made the right decision in the first place when you decided to go freelance, as I have already mentioned above. Or when you start questioning your own skills, experience and expertise thinking that perhaps you may not have it after all and that it may well be a good time to move on to other things whatever those may well be. Or when you think you are living in a bubble that has got its days numbered and it’s about to burst, if not already! Or even when you think that some of your most innovative, refreshing, new, profound radical thinking just ends up in the same gutter as everything else. Or, even worse, when you start questioning whether loneliness is harming you more than whatever you may have  thought of in the past. Loneliness as in ‘Who is going to hire this person who goes solo?’ Why is he / she not working with an agency? We only do work with consulting agencies anyway, right? So why bother? 

  Gosh, I know what you are thinking, self-pity can have such a destructive power of the self that it’s just mind-blowing. And while I surely agree with that sentiment, doing some self-pity every now and then shouldn’t necessarily be something negative. On the contrary. It helps you to constantly question AND challenge what you do, to confirm whether we feel we are on the right track, whether we have made the right decisions, or whether we need to perform a number of different changes before we move on. The issue with self-pity though is when you dive into it for far too long that you give up on either moving on or making some changes. Well, whenever that’s happening, the best thing one can do to revert course, move on and get back in business is to eventually rely on your own social networks, more than anything else because they know you better than anyone else and at the same time there isn’t anything more satisfying than relying on their power to get you out of such black hole as self-pity. So handle it with care and whenever you feel you are just going down on a spiral of negativity, reach out to your trusted networks, because, if anything, they are the ones who care the most about you. One conversation at a time. 
   

• Payment Methods: This particular drawback of doing freelance work may not necessarily apply to vast majority of freelancers out there, at least, as far as I can see, since most of them have got a very clear payment method based on either an hourly rate or a daily one. If you work under either model I don’t think payment methods would be an issue other than, you know, getting paid on time, which certainly can be one of the most poignant disadvantages of freelancing by itself as well, as I keep reading different reports on taking between 60 to 90 days to get paid. Ouch! 

  However, that’s not the main downside I’d want to highlight in terms of payment methods. To me, it’s slightly different. You see? I don’t usually work with either the hourly or daily rates. I much prefer to set my fees based on the overall outcomes of the project or its different deliverables, but also within a timeline manner. The drawback is that most firms are not very much used to that kind of payment method resulting in a good number of unnecessary bureaucratic paperwork that sometimes can delay a project for a certain amount of time. And while I usually explain straight up front why I don’t work with hourly or daily rates (mostly due to time constraints, which I will develop further in an upcoming blog entry to explain more in detail how I work through payments), it’s still a bit time consuming helping folks understand new ways of doing work and getting paid accordingly. 

  How do I break free through this downside? Usually, through one or two additional conversations with the client explaining the advantages of the pricing I enjoy using the most, which is the one that allows me to focus on the work to be done for the client without not necessarily worrying too much about the time constraint, but, instead, focus on the quality of the overall outcome(s). If there is anything I have learned over the course of time in the area of Social Business and Digital Transformation is that you just can’t hurry things too much, because, after all, we are running a marathon here, not just sprints, and some times you need to allow enough time to take place before you can show and demonstrate the real impact of the work you are doing. A single week, month, quarter won’t cut it, I am afraid. So why the time pressure of working through the ruthless law of either hourly or daily rates when we could instead focus on change programs where the quality of the deliverables becomes much more important than the time spent executing on them? I wish I were more effective in being able to communicate why I prefer this payment method over others … Still tons of room for improvement on this one, I can tell you. 
  
  

• Free work: And, finally, the last, but not least important, of the downsides of freelance work for this time around. One that I am pretty sure would come up on the Top 3 pet peeves for most freelancers out there. One that annoys plenty of people to no end, if anything, because of the lack of respect for one’s rights to get a decent payment for the work one gets to deliver on. Of course, I’m talking about the constant requests to work for free for other people. Yes, I know, 2016 and it still is a thing. 

  Somehow there seems to be that expectation that whether your are in pursuit of cheap, or whether you are just getting started with your freelance career, or whether you would want to ask for a few minutes of someone’s time or pick someone’s brain, you name it, you will always get asked about working for free for people, even if you know things just don’t work that way anymore.

  The exposure economy can only take you up to so far, I am afraid, before you realise you can no longer pay the monthly bills. At that point, and thanks to those many many requests still coming through to work for free, you know you are in (big) trouble, because people would still expect you to work for them for free, as it will be good exposure for you, while the unpaid bills tend to accumulate. And before you know it, you are doomed. Freelance work should not be like that. We should pretty much respect and treasure people’s time, hard work, effort, energy and, overall, their own lifetime work experience and get paid accordingly. It’s the least we could all do to recognise and appreciate both people and the good work they do. Anything else is an open call for even bigger trouble.

  Of course, I, too, have been asked to work for free as a freelancer in numerous occasions, although things have slowed down a fair bit at the moment with perhaps two or three requests per week. Mind you, I fully realise it’s very difficult to break the chain of working for free. And don’t take me wrong, it doesn’t necessarily imply I won’t be doing any kind of free work, on the contrary, I’m rather keen on doing it as long as there is a single premise in place that would give me the heads up: that is, I know you really really well and I truly love what you are doing. Anything else would need to be discussed and settled down for payment. No exceptions, I am afraid. Just like everyone else, there are plenty of bills to pay month in month out and that’s something that we all ought to respect and acknowledge for everyone, even freelancers. 

  There is a blog draft I’m putting together to talk at length about this particular downside on its own, more than anything else because it’s an important topic we only keep hearing about from one side of the story without getting the other and I feel, as I am getting closer to my 4th year of freelancing, it needs to get the word out and have a conversation about it, as opposed to just take things for granted. We shouldn’t. We should just take a moment to understand the context and the circumstances as to why people do the work they do and eventually appreciate and recognise it accordingly. It’s not that difficult, nor challenging, right? 

And that’s it! Those are some of the downsides I can think of at the moment about doing freelance work. And while I fully realise this blog post may be coming across as somewhat negative, it’s not meant to be. By far. It’s more about exposing some of the issues, the drawbacks, the disadvantages, the challenges, but also the opportunities about freelancing we all have in order to start the conversations on how we can all improve the state of the present of work today to then perhaps still have a future tomorrow, specially, if we all keep claiming the so-called future of work is the gig economy. Is it? If so, we still have got plenty of good work to get done! So let’s get down to it, please!

Here is a final, open reflection for you folks out there who may have been reading this article thus far: What’s the main downside of doing freelance work you may have experienced yourself in the last few months? Or to put it in other words, if you could address a single disadvantage of freelancing, which one would you choose right now and why?