Freelance Life: The Reality of the Ups and Downs

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EDITOR’S INTRODUCTION: I’m delighted to introduce this great post from a new writer discussing her first experiences of the freelance life. The highs and lows she describes are all but inevitable in the early days – making this essential reading for anyone thinking of making the jump to freelancing

Introduction – Freelance Highs and Lows

You’ve cleared out the spare room and made yourself a nifty home office. But are you psychologically prepared for what comes next?

When I began my freelance writing journey earlier this year I was so excited – terrified but excited.

I had been thinking, dreaming and planning it for so long, I could hardly believe it when I finally took the plunge into the freelance life. I felt that I was ready. I’d done my research, taken a couple of courses and come up with a plan. Now it was “go time.” Following a passion? What could go wrong?!

For a few weeks, everything was great. I created a couple of websites, learned a bit about SEO and started blogging.

I learned some basic marketing and improved my social media presence. I was reading and writing and creating every day and loving it. I was building something of my own, on my own terms – everything you think the freelance life should be.

But then I hit a wall.

One morning I just didn’t want to get out of bed and that’s not me. But not to worry, it was just one lazy day.

Until the same thing happened the next day, and the next.

A week of little to no productivity followed. I was worried. I started to think that maybe I’d made a mistake.

Maybe I didn’t have what it takes to succeed on my own? Maybe I didn’t want it enough? I thought of going back to the 9 to 5, the regular pay cheque and my comfort zone. The thought made me sad beyond words.

Ever the introvert, I decided to turn inward and have an honest look at what I really thought and felt about freelancing. I knew I wanted to write. I just needed to find out what was holding me back and how to get around it. After a bit of a rummage, I came up with three major stumbling blocks that seemed to be getting in my way: unrealistic expectations, a poor attitude to time and not taking enough care of myself.

(Note that there are some links above that lead to articles giving advice on some of these issues).

Managing Expectations

As a perfectionist and one who suffers from an almost crippling fear of failure, I had some pretty high and unrealistic expectations of myself.

In the beginning, I spent a lot of time comparing myself to other more experienced and established writers.  I wanted to be them but I felt so unpolished and unprofessional by comparison.

I would think: why am I even bothering when they are out there doing it so much better than I can? I somehow forgot that even they had to start somewhere. 

Freelance worries

The reality is that I am just starting out, so I am exactly where I should be when it comes to my level of skill and professionalism. To get where I want to go I just have to keep moving, take every opportunity, develop my skills and build my experience. I have to accept that this takes time and there’s no way around that.

Another thing I had to make my peace with was my fear of failure. We all have it to some degree and it’s a bitter but necessary pill to swallow if we are to do anything of worth with our lives.

I began freelancing with a ‘failure is not an option’ mindset. It felt like too much was at stake to spend time being anything but brilliant. But, of course, that’s impossible.

No wonder I was finding it hard to get out of bed! The reality is that I have to be prepared for setbacks. In fact, I should probably expect to fail at least as often as I succeed – perhaps even more! It’s an ongoing battle but I’m beginning to see that when I fail it’s an opportunity to learn and grow, and not confirmation that I’m not cut out for the freelance life.

Taming Time

One of the most appealing things about becoming a freelancer is the reclamation of your time.

After years of giving my time away to other people to manage, I finally had it all to myself. I had all day to get things done; all night too, if I wanted.

But all of a sudden I had so much time that I didn’t really know what to do with it. I felt kind of “untethered,” and days just ran into one another. I pretty much did what I wanted when I wanted and thought that was my right as a freelancer. It’s all about being ‘free’, isn’t it? Well – yes and no.

The freedom freelancing brings comes with a price. I am beginning to understand that it isn’t for the faint-hearted or the undisciplined. That sexy life you see online about working a couple of hours a day from the beach and still making squillions probably doesn’t exist, and if it does, that life is more than likely earned by putting in the hard yards first.

I had to rethink my attitude to time if I had any hope of being productive. It was my most abundant resource and I had to use it wisely. I had to invest my time with all the care I would have invested my life savings, had I any to speak of! I had to get real with the unsexy side of freelancing and introduce some structure into my days.

Thankfully there’s a lot of advice out there about how to manage your time and I won’t waste yours now with yet another example. It’s actually a very personal thing that will probably take a while to get right.

My schedule is still a work in progress but it is definitely worth the effort. Having a more disciplined approach to time not only helps me feel productive but it’s a great motivator too. I’m more likely to stick to a task when I’m on the clock, rather than think that I’ll have the time later to pick it up. There’s a sense of urgency now that keeps the momentum going and I have no option but to keep moving forward.

Being a Better Boss – Key to a Healthy Freelance Life!

I think I learned pretty quickly that working by yourself and for yourself is both a blessing and a curse.

We are often our own harshest critic and probably an even harder taskmaster!

Be a good boss

In those first few weeks, I was pretty hard on myself. I felt I had to work all the time to justify my new career, and when I wasn’t making any money for my efforts I berated myself that I wasn’t working hard enough or taking it seriously enough.

When I wasn’t physically working I was thinking about work or, if I’m honest, worrying about work. It was relentless and – in the end – counter-productive.

No boss I had ever had ever expected me to work and worry like that so why was I doing that to myself?!

I had to learn that it was OK to switch off and have a weekend or an early night or even the odd day off.  Being good to myself was going to be good for my work as well.

I had to prioritise my physical and mental health. I went so far as to actually schedule some time to play. That seems weird, but until it became a habit or until I was more comfortable going easy on myself, I would have to officially make the time. Now I walk most afternoons and do yoga or some meditation in the mornings. And I have the weekends off like everyone else I know (usually!).

I think I now have a much healthier approach to this freelance life than I did when I began. I would love to say I am richer and more successful since wrestling with my demons, but I think that’s going to take a little more time. Right now I’ll settle for being happier and more productive.

EDITOR’S NOTE: I can’t help but think that Natasha is rather far forward in organising her freelance life to have worked all this stuff out already 🙂 I’ve been doing this for well over a decade and still need to learn to be a better boss to myself! However, this pleases me because it’s exactly what I wanted this site to be – a place where we can all learn from each other. 

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