Freelancing 2019: Ten Things I’ve Learned

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I find it rather scary to think that we’re already well past the half-way point of 2019. It doesn’t feel like that long since I was putting up the Christmas decorations!

It’s been an interesting and challenging year, and one that’s taught me that however long you’ve been freelancing, there are still big lessons to learn and lots of ways to improve and refine what you do.

With that in mind, I thought it would be fun to put together a little list of the realisations I’ve had so far this year. In truth, several of them could fit into the “depressing” column. However, I pride myself on an honest, “warts and all” account of freelance life, and hope I’ve managed to show at least a few silver linings in the clouds!

Let’s get started.

1. We are Very Fortunate in the Western World

There’s a huge amount of doom and gloom in the world right now. Hate and intolerance is on the rise, and economic indicators aren’t looking too great either, if you research beyond the spin from mainstream media and politicians. It’s easy for this to get you down, and I’ve certainly had my moments this year, as I discuss more below.

However, if you live in the developed world, it’s good to remember how good we have it. Every week, I chat to readers in places like Africa, India and South America, and feel sad that I have far fewer home working options for them than I do for people in the US and UK.

As my recent big feature on online jobs proves, there are TONS of options for people willing to work hard, do some training and put themselves out there. If you think there’s nothing out there for you, it might be an idea to have a word with yourself – as millions of people have it far tougher. This is a subject I explore more in this article about cultural differences.

2. Cafés aren’t a Great Place to Work

The idea of sitting in Starbucks working on a Macbook is a bit of a freelance cliché. But in an effort to get out of the house a bit more, I’ve tried to do just that several times this year.

Working in cafes

To be frank, every time I’ve tried it, I’ve found myself eager to get home. I want to sit somewhere undisturbed, with nothing more than the white-noise of my desk fan.

I was curious to find out if it was just me that felt like this, so I started a discussion on the subject on my private Facebook advice group. It turns out I’m not alone. While many people (me included) are OK to sit in a café checking emails, most find that such an environment isn’t great for doing anything that requires much concentration.

I increasingly wonder, therefore, if the main reason people get their Macbooks out in cafés is to take a picture for Instagram – which brings me onto the next point.

3. Being a Digital Nomad has its Drawbacks

There’s a ton of content online about the “aspirational” life of a “digital nomad.” Unsurprisingly, many people like the idea of earning a living whilst bouncing between beach resorts and hipster-friendly hostels.

I don’t doubt that some people make a genuine success of such a life. I know of one blogger who earns literally millions whilst travelling around in an RV and a yacht. However, I’m going to stick my neck out and say that I don’t think this is the norm.

Earlier this summer, I spent a week at a place in Amsterdam. It’s an interesting set-up, which has evolved from a youth hostel into a place with designer apartments and a new co-working space. It’s very cool, and VERY “insta-friendly,” and I’ll probably write more about it soon. However, the time I spent there, and some of the discussions I had, made me think that this “digital nomad” life has plenty of flaws.

Ultimately, if you’re going to be a successful freelancer, you need to choose a country where you’re going to be tax resident; You need a life that’s stable enough to allow you to commit to calls with clients and meet deadlines. When you get to my age and have children, you also need to think about their schools and their friends – otherwise you’re committing them to what is, in reality, an “alternative lifestyle.”

I’m by no means deliberately being down on the whole idea of being a digital nomad. But there’s a BIG difference between being a market-leading blogger in a yacht, and being a writer / designer / video editor who exaggerates about their career and scrounges drinks outside a hostel. Yes, I’m probably a little envious that I didn’t do that kind of thing when I was younger, but I suspect there are far more people faking it than making it with this nomadic lifestyle.

4. Freelancers Can’t Ignore Politics

I’ve decided to keep politics away from this site, as it’s not really the place for it. However, I will say that freelancers really do have to be aware of how politics can have far-reaching effects on their livelihoods.

I’ve taken my businesses through two recessions, and seen MANY firms go under as a result of them. Now, I find myself facing the uncertainties of Brexit, and it all feels depressingly familiar.


I personally think that Brexit is a terrible idea, and desperately hope it doesn’t happen. However, I live in the UK and earn most of my income in Dollars. With the Pound crashing, I’m actually benefitting from the chaos because my income is worth more and more in my home country. It’s like getting a pay rise every month, but it could all so easily be the other way around.

When you’re a freelancer, any difficulties for any of your clients can bring problems to your door. Trade wars and currency fluctuations have far reaching implications. As such, much as you might like to, you can’t ignore politics and finance. It always makes sense to think of how world events could affect not just you, but your clients as well.

5. Late Payment is Always a Worry for Freelancers

I’ve always prided myself on running a “tight ship” when it comes to credit control. Sadly, however, this year has reminded me that no small business is immune to the epidemic of late payment.

Both my wife and I have experienced late payment plenty of times over the years, and it can literally take you from spending with abandon to counting the pennies. Frustratingly, it’s often the biggest and most cash-rich companies who are the perpetrators.

We have articles here on raising invoices and chasing late payments. I’m sorry to say that however long you freelance for, and however strict you are with clients, the chances are you’ll need that second article at some point.

6. Life Gets in the Way: Resilience is Crucial

There have been FAR too many weeks this year where I’ve had to clear my “to do” list and pivot onto something else entirely. Google algorithm updates have been a big one, leaving me with tense weeks where I’ve not known how well my sites will hold up to changes in the rankings.

On a more personal level, I’ve had spells of poor mental health (in part thanks to the political uncertainty mentioned above!), tragic family news, and all the usual unforeseen things that happen to everyone – from water leaks to children’s sick bugs!

The point here is that when you work for yourself, you HAVE to keep getting back up – again and again. You don’t get to get signed off sick, or to throw the towel in with a website because Google have decided to push some other blog ahead of you in the search.

There’s been a LOT of “getting back up” this year, and at times it’s been really, REALLY tough. I’ve been freelancing for long enough to know the importance of resilience, but 2019 has brought it home to me once again – BIG TIME.

7. There are Some Funny People About

As I said in an article the other day, it’s almost a sign that a blog is gaining real momentum when you start having to deal with trolls. I’ve had my fair share this year!


The internet certainly puts you within reach of some…interesting people. I’m pleased to say that I find it MUCH easier these days to shake it off and move on. It’s made me realise that I used to waste a lot of time feeling affronted and determined to argue my point.

“Funny people” come in all shapes and sizes. It’s not just the trolls, but also the people who waste your time – enthusiastically pitching ideas before disappearing.

It doesn’t matter how long I’m in business, people still continue to surprise me!

8. Reliable Computers are Incredibly Important

Now this is a weird once, especially as I’ve been a freelance IT consultant for 15 years: 2019 has TRULY taught me the importance of having a reliable computer.

Late last year I spent a considerable sum on a new Macbook Pro. Then, at the start of this year, I had the keyboard issues that have inflicted thousands of users, resulting in lots of news coverage and even class-action lawsuits.

I won’t bore you with the details, but I ended up spending about six weeks on returns, replacements, arguments, emails to Tim Cook at Apple, a brief flirtation with a Microsoft Surface laptop, and a HUGE amount of frustration. It all cost a lot of time and money and seriously knocked my productivity. It’s made me further refine what I thought was already a perfectly well-planned technology strategy for my wife and I.

I’ll be writing more about this soon – but please make sure you have a computer you can truly rely on, AND a warranty AND a Plan B.

9. Podcasts and Audiobooks are Great!

2019 was the year I finally caught up with the rest of the world and discovered podcasts and audiobooks.

Podcasts and audiobooks

I’ve listened to internet marketing podcasts whilst falling asleep, heard business and personal development books whilst walking along beaches, and even got into the habit of switching between Kindle and Audible to listen to and read the same novel.

If you’ve not already, I’d highly recommend grabbing a free trial of Audible, and also finding some podcasts on subjects that interest you. It’s a great way to cram in more knowledge when your life is already very busy.

10. Exercise is Important

To end on a positive, 2019 will go down at the year I finally managed to exercise (semi) regularly. The turning point was reading a book called “The Power of Habit,” which taught me to start craving exercise.

It doesn’t take long to get to that point, and it now bothers me if I don’t regularly get out of the house for a walk or a bike ride. I’m never going to be a sportsman, but actually getting out and moving more has made a big difference to my life. I’d truly recommend the book if this is something you struggle with.

So, that’s what I’ve learned so far in 2019 – quite a lot really, looking back!

What have been your key lessons this year? Let me know in the comments!

5 thoughts on “Freelancing 2019: Ten Things I’ve Learned”

  1. hi! I follow your emails, semi-regularly. LOL.

    Am just about to venture into a formal online course with April and her VA school/course coming up Sept 15.

    We have windows 7 computers. Ugh, I know. No support at the end of this year. She says we need one with speed. She even recommended a gaming one.

    What are your thoughts? I would love to know, with your expertise.

    Thank you for just any help.
    Doralyn Bigelow

  2. Gosh, Ben, it has been a tough six months in some ways, hasn’t it. I have worked in quiet corners of cafes but I like the library better. I had to take my car for repairs recently and spent the whole morning with my laptop in the library and got so much done. Then got to go out for lunch which was a treat, given that I live in an isolated rural part of New Zealand. I’m with you on Brexit and laptops. Mine will have to go in for repairs shortly and I’m scared about how long that might take. But, on TV as I write, they are interviewing a man who was shot nine times in a terror attack and survived. So that puts my problems well and truly into perspective.
    Thanks for your unfailing honesty and I hope the second part of the year is much better for you.


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