By Georgina Laidlaw

Are You Living the Freelancing Dream?

By Georgina Laidlaw

Before they start freelancing, many imagine themselves rolling out bed at midday, doing a couple of hours work from a banana lounge, and being paid so handsomely for it that they can knock off at 3pm, in plenty of time for a surf/ski/margarita.

You and I know the reality is different, but for me, at least, there remains a ghost of that expectation. I saw freelancing as a path to the sort of freedom that I could never attain while I was a tenured employee. Every day I’m conscious of enjoying that freedom, yet between client meetings, deadlines, and deliverables, I can forget to look beyond this, to (cue: dramatic music) The Bigger Picture.

Let’s face it: we freelance because it’s meant to be more fun. The question is, do you simply want your work to be more fun, or do you want your life to be more fun, too? Freelancing doesn’t only affect what you do between the hours of 9 and 5 (or 9 and 9. Or 9 and 12, perhaps?) — it impacts your whole lifestyle.

Or it can, if you let it.

In the early days, it can be difficult to believe this, as you focus on keeping your head above water and getting the work you do land done on time, to a high standard. You may also have unconscious carry-over behaviors from regular employment — thinking you need to work the same number of hours every day, that you can’t take holidays, and so on.

But as you find your feet as a freelancer, and you relax a little, it’s a good idea to check every so often to make sure this gig is living up to your expectations: to make sure you’re living your dream (or close to it). To give you some examples, here are a few of the aspects of my approach to freelancing that I’ve rejigged in recent months, to more closely align my life with The Dream.

1. Projects, or days?

Initially, I saw myself as freelancing full-time. I was at my desk eight hours a day, which, I eventually realized, was eerily like having a full-time, tenured job. Now, I see myself as a project worker. I work on projects — in chunks of hours — rather than x days a week.

2. Workplaces

A key reason I wanted to freelance was to get away from the office environment, yet when I started out I spent all my time at my desk. I almost felt guilty when I wasn’t there. This is no recipe for joy. These days, since I see my work as projects, I can — and do — work anywhere I like, whenever I like. So long as I can get my projects done to the standard I want to achieve, the choice of workplace and time is mine.


3. Clients or colleagues?

This is one I still struggle with. I freelance because I want to work with people, not for them. Although I didn’t realize it, breaking out of the client-supplier mentality was part of the dream for me. Nowadays, I prefer to think of myself as working with contacts, rather than for clients. Adopting this philosophy has made my personal and professional lives much less stressful, and far more enjoyable.

4. Breaks

I’m the first to admit that I don’t have ambitions to build my freelancing into a world-beating super-business. I just want to do cool projects and enjoy life. Knowing that, I recently made a conscious decision not to work full-time, and to plan a few holidays. Purists will gasp: Holidays! What person who’s serious about working for themselves can afford to take a holiday, let alone a few of them?! But, well, that’s part of my dream.

What about you? What’s in your freelancing dream? And are you living it?

Image by stock.xchng user winjohn.

  • Paul

    Its hard… been freelancing 3 years now and STILL in that workplace mentality. I think I need to keep that mentality to keep motivated.

    I’d be worried of slipping if I didnt focus 100% of the time. Do I enjoy it? Probably not – there are obviously some freedom perks, but generally I work more hours than I ever have, have constant cash flow worries and whilst I’ve made (what I consider) a success of freelancing, I’m not sure its everything its cracked up to be.

  • Sheila Muir

    A fantastic reflection. Absolutely. I’ve just started this fantastic yet tough journey to FREElance land, and I feel excited but exhaused. I do often picture myself having a fantastic holiday whenever and wherever I feel like in the world because I’ve created a fantastic job for myself that will allow me to do this. Neverthelss, for the time being, I do spend too many hours sitting in front of screen, completely by myself working on that dream…If I was an employee I would be looking for another job but being myself the boss, I have no choice but to comply with my own rules. It definitely helps me to thrive!

  • Martin Dubé

    My freelancing is about being listening to when speaking in meetings. I’m no longer “a ressource” but an asset in the eyes of the administration. I get a lot more respect and gratitude as a person.

  • T-racer

    I’m just about to move to a beachside location in another country to try to realise this dream and to hopefully achieve some work / life balance. I’m going to attempt a working holiday of sorts. Luckily my clients have been very supportive and through the wonders of technology it should pretty much be business as usual as far as they’re concerned. I, on the other hand, will be enjoying ocean swims, eating fresh fruit and generally looking after myself – hopefully not working myself into the ground like I have been doing.

    • rickydazla

      I just got back from three months in India. Got myself a Tata broadband USB modem and an apartment looking out over a beach in Goa. Working from a hammock was bliss! My wife and I escaped the majority of a Michigan winter, I covered all of the trip expenses, we ate curry until came out of our ears and we saw some of one of the most interesting (IMHO) countries on earth. We will be going back again this winter or next to do the same.

      It can be done. Good luck!

  • indianer3c

    Hi :)
    I’m a trainee for application development from Germany. In my free time I developing websites for small business. After my education I want to further on develop websites. My freelancing dream is work on sustainable projects and I can decide when and for how long I work. Live in work-life balance

  • Annie Mous

    I worked freelance for a lot of years. I worked weekends and took off 2 weekdays. Dual advantage: stores were open when I was off and clients don’t call on weekends == MORE productivity. Sigh, I needed partners with skills I don’t have, thus am tied to desk/office scenario now.

  • Rich

    Nice Article! I’m a 100% freelancer (I do internet marketineng for small businesses). It’s allowed me to live in Ireland for 6 months, a beach resort town in Sicily, and enjoy my life here in South Beach Miami.
    I love how this business gives you the ability to work from ANYWHERE you can link up to an internet connection.

    My problem at first was that I took EVERY and ANY job at whatever price. This burnt me out and I soon realized that there MUST be a balance. You’re right though..there was a point where I found myself working harder & making less money than I did as an entry-level employee. Talk about depressing! :)

    Best of luck to all,


  • Bert

    I freelanced for 5 years out of school, worked at an agency for 9, then went back to freelancing. Guess which occupation nearly destroyed my sanity? My clients adore me, they pay me, and I love what I do.

    As a matter of fact, I feel more secure now than I did working for a worldwide branding company. By getting away from those sociopathic knuckleheads I’ve improved my life tremendously.

  • Patrick Samphire

    Excellent article. I’ve only recently started freelancing, and like you, I have absolutely no ambition to create a world-beating agency. I want to do a few cool projects that I can really believe in and which allow me enough time to follow my other interests. I don’t expect to get rich this way, and I know I’d make more at a 9-5 job, but I actually think this is the freelancing dream.

  • Will

    Great post.

    I’m taking the day off tomorrow and this post has made me feel less guilty about that!

    I definitely work more now that I freelance, but overall I enjoy it more. I really need to take on board some of the advice given here and not feel guilty if I decide to go and play Squash during the day, or take a few hours out here and there. I tend to worry though that if I’m not at my desk I’m going to miss an important email or an important call.

    I’d love to meet a freelancer who has struck that illusive work life balance.


  • Dennis Vieira

    My wife and I both worked in corporate offices. Which we believe to be the worst environments to work in. They are creatively unstimulating and oppressive. So we decided to ‘slim’ down our lifestyle and prepare for a freelance world.
    Currently we are a freelance web and graphic design duo, traveling and working form our RV. We work from anywhere we can get a wifi connection. We keep life simple and keep our cost of living down so we don ‘t have to work so hard and so much. It’s all about what you want and you just have to make adjustments in your life to get there.  We started by cutting unnecessary spending, getting rid of cable tv, not being over consumers, reducing clutter, and using that money to set aside a padding to help us get started.
    We’ve been at it for a little over a year now and I couldn’t even imaging sitting in a cubicle again. The ever changing workspace environment keeps us fresh and creative.

  • John Tabita

    There were definitely many perks when I was self-employed. I could take my son to the park in the middle of the day. When I relocated across the U.S., the entire cost of the move was deductible as a business expense.

    The downside is you have to eat what you kill. It always felt like I was one lost bid away from financial ruin.

    There’s a bumper sticker going around that says “Livin’ the Dream,” but it’s crossed out, and underneath is scribbled, “Plan B.” The reality is often different than what we had hoped for.

  • saradeviva

    I don’t know what I THOUGHT would happen when I launched my own design business to be home with my newborn, but hammocks certainly aren’t involved. Freelancing is not for the faint-of-heart!

    For me, the work exploded almost instantly – I was working 9am to 2am for MONTHS! I really started to lose my mind… It has settled down considerably, and now I enjoy the creative freedom, and more importantly, the trust that my clients have in me (which was lacking when I worked for another company).

    I still feel like I’m playing hooky if I grab a coffee and peruse the bookstore at mid-day. But, overall I’m working much harder now than I did in a cube, and the payoffs and job satisfaction are much higher now.

  • Georgina Laidlaw

    Hey there :)
    Great stories, guys :) The thing that comes across loud and clear here is that quite a few of us experience some anxiety around how much we work (or don’t), and how we work — two things that freelancing is, in many people’s minds, meant to make non-issues!

  • astrotim

    I’m about to take two weeks off to get married and in addition to all the things that need to be organised for such a trip, I have to try to get a bunch of project across the line before I go to avoid client contact as much as possible while I am away. I’m definitely under the pump and I’ve been pulling my fair share of 9am til after midnight sessions

  • goldfidget

    Constant cash flow worries, inability to plan holidays and trips due to aforesaid worries, and the ever present fear that something might break in the middle of the night, and the buck stops with me!

    That balanced against the ability to learn, to do what I like when I like, the thrill of the ride, etc etc.

    So far I have swapped back and forth between paid employment and running my own show. Currently I’m a part time employee with freelance gigs on the side. That regular monthly paycheque clears all my bills, then anything extra is mine to keep. It’s a good balance.

  • anna


    + clients have much more respect about your work and time spent on their projects – less unnecessary hours and no exploitation
    + One is asked when he/she can work on a project, and not the other way round: “may I take a few days off?”
    + open future: one can take whatever projects he/she likes, as you they are not bonded in one company and working field
    + huge diversity and therefore more inspiration
    + no dumb feeling every day because your day today wont look like the one in a year
    + work from everywhere, every time (go skiing during the day, work in the evening)
    + freelancers are more awake then employees since they have lots of options.

    – financial insecurity: but this makes life somehow more exciting
    – no paid vacation or days you’re ill
    – in case of a pregnancy / baby life gets a bit tougher – but you can still be at home and earn your money
    – no social contacts during extended home office projects

    I would say..
    You live your life and work additionally – and not the other way round..

  • Dorsey

    My reason for working freelance is that I have no choice. I’m 61 years old and can’t find a full-time job due to my age and appearance (I wear an eye patch due an accident). I have no problem finding freelance work, however, because my work speaks for itself and I sound much younger over the phone. When I walk into an office for an interview, I can feel the “who’s the old guy?” looks, and it only goes downhill from there. This has been the case for me since 2000.
    I would love to return to a full-time office job. I like being around people, lunching in the cafeteria, meeting to share ideas, and just getting out during the day. Also, at the end of the day, work was done and there was a clear difference between work and home life. That phase of my life is over.
    At this point, being “retired in place” in a cushy office job is extremely attractive, and it kills me when I hear stories from people with full-time jobs who produce 1/5 the output I do while receiving generous benefits, feel no pressure to meet deadlines, and simply have to show up every day to collect a check.
    In any case, too many people fail at freelance work because they don’t take it seriously and have the wrong priorities. You’re working from home, and that requires some mental adjustment – don’t take two hours for breakfast, leave the TV off, avoid distractions. It’s very easy to spend more time running errands, doing chores, and stretching breakfast, lunch, and dinner simply because you’re not in office surroundings so that at the end of the day, you’ve only put in four hours and not the eight that the work requires.

  • ram

    Hi to all freelancers,
    Nowadays, the cost of living has become unbearable, unsustainable, so i thought of doing freelancing as a part time job. I am happy that after my full time job, i go meet my freelance clients discuss with them, go home and design the client needs and send them an email and after they approve i give the source of design in a cd or dvd for their printing purpose or i upload the files to the server and make their site go live. By this i earn few more extra money so that i can spend for holidays, medical needs, and other desires.
    But at last i would like to say what ever you do, do it with your heart. Thats what really gonna make you feel happy and satisfied.
    Thanks freelancer to stopping by and reading my comment.
    May god bless all the freelancers.
    bye bye
    take care


  • Thanks for a great article. It changed my way of thinking about what I do. After reading your comments I reworked my website to focus on the positive aspects of hiring a freelance graphic designer. I’ve been billing myself as a small design business because it sounded better to me than saying I freelanced. But in this economy being a one person operation might have more appeal to those companies that don’t want to pay for the overhead of a larger organization.

    Over the years I’ve had a lot of great clients. Many of whom have become friends. Because my clients’ businesses are all very different I’ve had to learn about each one in order to accurately represent their product or service. All of this keeps life interesting. Each day is different.

    I’ve recently moved closer to my aging parents and having the flexibility to help them out when they need it has become really important. So when I have a project I put in the hours to meet deadlines. And when I don’t, I find something equally worthwhile to do.

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