How to keep your freelance dream alive

by Hazel Bird | 16 October 2024 | 0 comments

What was your dream when you first began freelancing? Or, if you're just starting out, what do you want to get out of this strange new adventure you're embarking upon? Think about what freelancing means to you and remind yourself of it on a regular basis. Keep your freelance dream alive and evolving.

Recently at a networking event, I was part of a great discussion with other freelancers about why we went freelance – and how to keep our freelance dream alive. I found it inspiring to listen to people just at the beginning of their freelance lives share their enthusiasm and excitement about the possibilities before them. And, with 15 years of freelancing behind me, I was able to share some of my insights on how to maintain that enthusiasm and make the most of what freelancing has to offer.

The pitfalls of freelancing (or, where the freelance dream goes to die)

I haven't always got this right – not by a long shot. At times I've worked too hard for too long (even to the extent of making myself ill), accepted work I hated, taken too long to 'fire' clients that weren't a good fit for me, made myself too isolated, and struggled to balance all the different 'hats' we have to wear as freelancers (marketing, tech support, admin, etc.).

When I began freelancing, I certainly wanted to be in charge of my own business – it felt like the right decision for me. But I also made the decision partly out of necessity as I wasn't coping well with a long commute. I was also only 24 so I didn't have much experience of the world of work.

In other words, I didn't really have a clear vision of what I wanted to get out of freelancing. It just seemed like the best option available to me, so I had to work the 'dream' part out as I went along. As a result, I often tended to treat freelancing just like an employed job.

Now, there is nothing wrong with this, and indeed this approach generally suits me quite well. I like having a routine. I like setting myself targets and achieving them. I like having a clear line separating work time from downtime (for me, it would be pointless to be working on a laptop on a beach in a sunny country, because I'd just hyper-focus on my work and the beach might as well not be there).

But that's the problem with being freelance. You have total freedom to do the things you want to do. And if what you want to do is be financially successful and feel proud of what you've achieved, then it can be easy for the boundaries to slip.

Controlled drift

Another fantastic thing about being freelance is that – as long as there is a market for what you want to do – you can do anything. Heck, if you're clever enough, you can even create a market for what you want to do.

You also aren't restricted by planning meetings or approvals processes. You can have a brand new business idea as you wake up at 7am and have launched a new page on your website offering the service by lunchtime.

So freelancing is naturally about embracing and even driving change. But it's important to control this change, or the drift may not all be positive.

The double-edged sword of freelancing

When you're freelance, every new idea you have is a chance to find something exciting and fulfilling that you want to do – but it also has the potential to royally mess up your work–life balance. For example:

  • A new client offers you work in a field you've been desperate to move into. It could let you pivot your business in a direction you've been dreaming of, but it will also mean working evenings for the next two months.
  • You decide you'd like to write a book to demonstrate your expertise to the world, but this will mean spending less time on a volunteering role you love.
  • You get offered a six-month contract that will pay very well, but the client has extremely tight, drop-everything-and-do-it-now turnaround times that will make it hard for you to plan your other work.

Freelance life is full of these double-edged swords.

Freelancers have complete freedom to accept whatever work we like, but this also means we have complete freedom to make faulty decisions about what we can handle.

Because we work on our own, often with no wiggle room to shift some of our workload onto others, every decision has the potential for massive consequences. I've got this wrong multiple times over the years. A single overly optimistic decision in January can literally leave me scrambling to catch up until June. If you'll permit me a terrible mixed metaphor, our double-edged swords can easily snowball.

If you want more reflections like this one, read my top 15 lessons from 15 years as an editorial freelancer.

What's your freelance dream?

At the networking event I mentioned above, I talked about what I do to try to keep my freelance dream alive, based on what I've learned over my 15 years of freelancing.

What works for me is to remind myself, every week, what I want to get out of freelancing.

Every week, I try to set aside the last half-day purely for non-client work. One thing I do in this time is to read through a set of reminders I've made for myself over the years that are designed to keep myself on track. A post I wrote a while back – on ruthless balance as a freelancer – came out of this.

The idea is simple: I remind myself why I'm freelance and the sacrifices I need to make to maintain my freelance dream. Because what you'll notice from the three examples I gave in the bullet list above is that all of them require a sacrifice, whichever option you choose. You either have to give up the business opportunity or give up something else you value.

I also keep a log of my slip-ups, when I pursued a business opportunity and regretted it. Every now and then I read through them to remind myself of when I was over-enthusiastic, over-optimistic, too blinkered or just plain stupid.

Writing your freelance vision

I was inspired by the networking chat and the process of writing this blog post to come up with a formal version of my freelance vision. Everyone's will be different – and, importantly, I'm not here to shame anyone for working long hours or accepting work with types of client that others might prefer to avoid. If that's your plan for meeting your life goals and you're comfortable with it – go for it.

Here's my vision for my freelance dream:

  • Full days off: I will have at least three in four weekends totally free of work.
  • Evenings: I will keep at least three in every four weeks free of evening work.
  • Mealtimes: I will never eat at my desk. Ever.
  • Work–life split: When I have a holiday, I'm fully away from work. I won't check emails or go on social media.
  • Non-client work: In addition to doing ad hoc non-client work throughout the week, I will set aside half a day minimum each week for uninterrupted non-client work, to ensure I have dedicated time to consciously set the direction for my business.
  • Project priorities: I will prioritize projects where I can truly add value and build a great relationship with the client.

This is the vision I've used for several years, and it works for me. (Incidentally, note that it says nothing about how I’ll use my downtime. That’s a whole separate question. The point is just to set boundaries that protect my downtime, so it’s not swallowed up by work.)

I don't adhere to my vision perfectly, but I'm pretty close most of the time.

Is it a bit boring and unglamorous? Yes. But I'm now at the age where I understand that dreams are built on boring foundations. If you want to achieve something big and exciting, you have to understand the mundane little things that will allow you to get there.

Your vision might be totally different – and it may well change over time. The point is just to have a realistic template for your time that you can use to determine what a business opportunity might require you to sacrifice.

Of course, you can always decide that the sacrifice is worth it and pursue an opportunity even if it contravenes your vision. You can also kid yourself that the opportunity will be less work than is actually the case. And you can honestly miscalculate the effort an opportunity will require. But in all these situations, by creating your vision at least you'll have improved your chances of making an informed, deliberate decision.

Establish your freelance dream now

Whether you write it down formally or just keep it in your head, I'd encourage you to establish your freelance dream now.

You might not feel you need to understand your dream at the moment. Perhaps you're just starting out as a freelancer and are loving the buzz of getting your work done. Or perhaps you're coming out of a dry spell and feel you have to accept any and all work that's offered. Or perhaps everything is ticking along nicely and you don't feel your boundaries are being especially challenged.

But trust me: it's incredibly easy for good intentions to drift and to kid yourself that your good habits aren't as important as you once thought. It can be easy to forget the pain of over-committing, especially when things get hectic or you're under pressure to accept an amazing contract.

Freelancing is hard. We do it mostly in isolation, and we are just as free to make mistakes as we are free to do what we love. Without a manager or direct reports to provide helpful questioning or a sounding board, we have to face those mistakes head on, which means consciously acknowledging what went wrong and then putting in place a structure to avoid it happening again.

Setting out a vision of your freelance dream – and then reminding yourself of it regularly – can help you to choose the opportunities that will prioritize balance, joy and health in your life.

About Hazel Bird

Hazel delivers editorial services that empower non-profits, charities, businesses and authors to confidently share their expertise and impact. An editor since 2009, she aims to see the big picture while pinpointing every detail. She has been described as ‘superhuman’ and a ‘secret weapon', but until Tony Stark comes calling she's dedicating her superpowers to text-based endeavours.

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