Expectation vs. Reality: What You Learn After Your First Year of Freelancing

Freelancing has fun expectations, but if it’s something you’re considering, be sure you’re self-sufficient.

When I first heard of freelancing, my first thought was “Freedom!” And oh boy, was I right. But with great freedom comes, cliche as it might be, great responsibility.

As technology races forward, thousands of us are connecting with people online, buying food and items for our homes online and taking up a career online. I know, because that’s my life. If you’re in the shoes I was walking in a few years ago and are thinking of quitting the rat race to be a freelancer, this could be your turn to take the first step! Let me help with some of the challenges you should expect before you take the leap.

Working Whenever You Like

Flexibility can be a ‘dream’ way to work, but it can also be overwhelming for beginners. Your newfound flexibility won't necessarily solve your procrastination habits, addiction to coffee, or fear of rejection. It's both a blessing and a curse. Unless you’re extremely proficient at managing your time, it’s easy to either become addicted to work (night owls, do you hear me?) or descend into being less productive near the comforts of your couch and fridge.

However, the flexibility of working at home has some serious perks. At the office, I used to submit a leave request for a spontaneous holiday, only to be rejected. At home, I’m my own boss and can work out my own vacation schedule, depending on my ongoing projects and impending deadlines. I can swap around my work hours to grab groceries, visit sick friends in the hospital, or collect friends from the airport without needing to check in with a boss or team.

Staying at Home

Not having to commute to the office sounds great in theory. So does working in your pyjamas. However, it turns out that working from home can be fairly distracting. After all, you’ll only be a twenty-second walk to the fridge or TV.

Working without getting dressed is better in theory than in practice, too. Working in pyjamas can easily result in comfy but unproductive days. I didn’t want to wear anything uber-formal like suit jackets, but a favourite dress or sweater with smart jeans always helps to shift me away from lazy morning mode, especially if I’m not feeling well.

I chose to set up a clean, clear office with neutral colours, comfortable chairs, and as few distractions as possible, apart from my Samoyed puppy calendar and a baby palm plant— I think it’s always good to have a little bit of nature indoors!). I use the Pomodoro technique to work in 25-minute slots, with 5-minute walks around my house. This has helped greatly with the jitters I get after concentrating for long periods of time.

The Lack of Social Contact

If you’re thinking about going into freelancing, you might think that you’ll have a lot of freedom. In a way it is true: you'll be able to go to as many coffee dates as you like. Unfortunately, there are plenty of days that I don’t leave the house or see anyone at all.

There are ways around this, like using coworking spaces. If you take advantage of spaces like this, you can discover a whole beautiful community of fellow freelancers or start-ups working on interesting ideas too. You’ll just have to make sure you’ve got the motivation to go out and make an effort to speak to people.

Working in your pyjamas sounds like a good idea, but you can get complacent and not be your most productive.

The Need for Self-Motivation

You’ll probably need to be even more motivated than you might expect. If you’re not, you’ll quickly find that your work takes three times the length to complete as it did in the office. There’ll be days that you’ll want to stay in bed or watch television all day, but doing so will put you at a disadvantage.

However, there’s a plus side to having to motivate yourself. Once you’ve figured out how to do so, you’ll be at an advantage in your life. Motivation is incredibly important and knowing how to find it is a serious skill in today’s world. Once I had learned how to motivate myself, I found that it helped me in my own personal projects. Learning a language or practising an instrument much easier when you’re motivated.

Running a Business on Your Own

Finding new clients can be a nightmare for new freelancers. They're responsible for customer satisfaction, with no guarantee of future work. Work can also be wildly inconsistent.

This does get easier. Along the way, you’ll learn the best ways to find clients. Gradually, I built up a client base through word-of-mouth. You might also want to use an accountant for your first year, so you have one less thing to worry about.

Many freelancers love running their own businesses after things have settled down a bit. This way, they have complete control over their work and clients.

Ready to start?

Freelancing can be a lucrative choice. You’ll need plenty of self-control, discipline, and dedication to achieve quality results. Being your own boss, among other advantages, might just be worth it, though – only you can decide.

Based in Dunedin, New Zealand, Cloe Matheson enjoys how her freelance writing career has allowed her to combine her love for writing and travelling – two of her greatest passions! She has previously collaborated with various blogs, sites and businesses such as Keith Andrews. Visit Cloe’s blog to see more of her published work.