Noupe Editorial Team May 14th, 2010

Effective Tips To Start Freelancing Without Getting Too Comfy

By Andrea Austoni

There are many reasons to leave secure employment and embrace freelancing, from enjoying professional freedom to enjoying actual physical freedom. When you work for someone else, you spend eight (or more) hours in their office, and usually not just any hours, but those from 9:00 to 5:00, when everyone is awake and doing business. Don't you resent that? Of course you do! Who wants to wake up every morning to go spend their most productive hours doing something marginally engaging, listening to criticism from people they do not particularly respect and whose judgment they often doubt, just to make someone else's business grow?

Sure, your end of the deal doesn't look so bad: steady income, benefits, a job in your field of choice and being able to leave all your troubles behind when you go home. But if you're a creative type, this arrangement will soon start to feel either too stifling or too comfortable, or both. That's when you have to take a big risk and plunge into your own career.

(Image by xerones.)

Employee Work: The Scenario

Working in cubicles, anyone?
(Image by Tim Patterson.)

One of the good things about steady employment is the constant pressure on you to produce results and come up with ideas. You can't allow yourself so much as an hour to browse social networks, read blogs or, worse, "waste time" watching videos, even informative ones. Your boss could show up at any moment, demanding that you have something to show for the time that has passed since you were briefed earlier that morning. Some bosses (I've known a few) are sneaky enough to appear behind your chair out of the blue with some condescending remark like, "What are you doing on YouTube?"

Surely we should get rid of these people, because they limit our freedom and creativity. But something is to be said for getting cold feet from time to time. It keeps you focused. It's healthy.

What Happens When You Start Freelancing

Once you start freelancing, you rejoice at the notion that you control your own time and space. You don't have to show up on time (say hello to the wee hours). You don't have to be presentable (say hello to sweatpants and chenille robes). And you won't have to prepare three logo proposals in three hours (say hello to quality… finally!).

You don't feel uptight anymore—even if your boss was relaxed, sooner of later some kind of reckoning awaited you. But now that you work for yourself, that pressure is gone, and you are finally master of your domain. Now that drive you felt to produce results without wasting time might get lost.

It's way too easy to tell yourself that reading design blogs is never a waste of time because it gives you knowledge and inspiration. Of course, Photoshop tutorials are always beneficial! And Twitter is not a time-waster: it's a way to create business connections! Yeah, right. But everything has a limit. For those of you who find yourself stuck in this rut, here are 10 tips to get out of it and keep you from ever getting stuck again.

1. Turn The Alarm Clock Back On

alarm clock
Alarm clocks actually believe we want to wake up every morning!

When you worked as an employee, you woke up to the dreaded alarm clock every morning. If you turned it off when you started freelancing and are now experiencing productivity challenges, maybe it's time to turn it back on.

I'll share my experience with you. I use the alarm clock in my cell phone, which repeats Monday to Friday. On the last Friday of my job as an employee, I didn't turn it off. The following Monday, the first day of my freelancing career, the alarm went off at 7:30 as usual. I woke up and started what was, after all, just a normal workday. The only differences with previous workdays were that:

  • I didn't feel hurried because I had no train to catch.
  • The commute took about 10 seconds, the time required to clear the breakfast table.
  • As I sat down to the computer, I started working right away, instead of taking the first 20 minutes to gaze into eternity.
  • I loved that Monday, and each one after that!

2. Observe Regular Working Hours

Plan your working hours in advance.

Maintaining regular work hours is crucial to organizing your time. Even if you freelance, you still have to wake up every day and get things done; otherwise, where will your career go? Keeping regular hours doesn't necessarily mean working 9:00 to 5:00, Monday to Friday. The beauty of freelancing is that you can set your own schedule. Ultimately, how much is more important than when. Make sure you put in the hours, regardless of when they are, or you'll suffer the bitter consequences.

Don't fool yourself, though. You'll still be burning the midnight oil at times. You'll still have to skip a night out with your buddies occasionally to meet a deadline. But effective time management will help keep those occurrences as a rarity.

Many freelancers admit they work longer hours than when they were employees. I believe this is more a consequence of loving what they do and devoting more time to it than anything else. Your mileage will vary.

3. Dress And Behave Like You Still Work In An Office

Don't wear slippers! Especially these ones.
(Image by mrbill.)

You've set up your workspace to be all spiffy and trendy. You've brewed a fresh pot of strong coffee. Now, be professional. Wear something other than pajamas or sweatpants. Because regular clothing is less comfortable, it enhances the office experience even when you work from home. Wearing shoes instead of slippers helps, too.

Sit properly at a desk instead of slouching on the couch (or worse, lying on the bed). Not only does correct posture benefit your health, it separates the business "you" from the private "you." Just because you're your own boss, doesn't mean you can just leave the office in the middle of the day to walk in the park! Take five-minute breaks every hour, and then get back to work.

Keep yourself on your toes.

4. Devise a Reward System

Treat yourself when you're good!

Reward systems work. People go to extreme lengths just for that big final payoff. Just look at the ridiculous things men do to win women's favor.

If the thought of finishing or even starting a project doesn't seem to shake you out of procrastination, then set another goal, one that's not work-related. Is there a certain movie you're dying to see? Don't see it unless you cross a certain item off your list.

Three years ago, when I moved to Poland, I could have easily installed an Internet connection in my apartment. I could afford it. Instead, I chose to wait until I found a job. Only then did I connect myself, and I felt proud. I deserved it.

5. Devise a Penalty System

Sentence yourself to house chores when you're not productive.
(Image by walkn.)

Penalties work, too. Write a fun list of little chores that you'll sentence yourself to if you don't do your work. People you live with can help you with this (and they'll love it). "Didn't work on that website? Here's the mop!" "Forgot to go through last week's mail? Clean that chandelier!" Instant productivity.

6. Prioritize Your To-Do List

"I would prefer not to" is a good answer.

The concept of structured procrastination has been explained brilliantly before. Apply it to your to-do list. Prioritize your assignments according to deadline and importance. Never postpone deadlines, but address the most interesting and important items first.

Once your priority is set, just do as follows: don't feel like tackling the first item? Move on to the second. Don't feel like doing that, too? Move on to the third. And so on. If you reach the bottom of the list and still don't feel like doing anything, maybe you're in the wrong profession. Or you might simply need a boss. See the next tip.

7. Have Someone Pose As Your Boss

Your fianceè could double as your boss.

You read that right. You still need a boss. If you can't make yourself work productively, then you'd better give your significant other the job. Just have him or her demand a report from you about your daily accomplishments.

  • "Did you complete today's to-do list?"
  • "Did you make that phone call?"
  • "Did you submit that quote?"
  • "Did you start that new project?"
  • "No? No soup for you!" (See tip #5.)

This "boss" should be someone who knows you well and whom you trust. Someone who's close enough to you to be able to call you on your little schemes to get out of work.

8. Optimize Your Lunches

Mmm, pasta.

If you work from home and cook your own lunches, like me, cook larger portions to last you a few meals. Yes, eating the same dish two or three times in a row is boring, but it's time– and cost–effective and helps you better manage your eating breaks.

When lunch hour comes, opening the fridge and finding yesterday's left-overs ready to be warmed up is great. Quick and delicious, the meal won't take longer than the usual half hour to eat, and you'll be back to work. Mind you, rotating a few dishes during the week doesn't have to dull. Do your research; ask knowledgeable friends; find new easy recipes to increase your gastronomic arsenal. Food can be inspirational, too!

On a personal note, I really enjoy being able to warm up my lunch after having spent three years in Polish office spaces, where microwave ovens are hard to come by. Being Italian (and hence, obsessed with food), this deprivation contributed big time to my distaste for employee life.

Keep the complicated dishes for the weekend, and make sure to show them off by hosting dinner parties and Sunday brunches!

9. Keep Yourself Busy And Inspired

There's a beautiful world outside. Go out and it will inspire you!

When I was working for someone else, the thing that depressed me most was waking up every morning full of ideas but not having a way to pursue them until much later in the day. Sadly, after at least eight hours of work, commuting back home, taking a shower, cooking and eating dinner and doing some house chores, I was so tired (more psychologically than physically) that I just couldn't bring myself to revisit those ideas. Never again! That's why I quit my job and began freelancing.

Before, I was on perfectly straight paved roads, but I only trudged. Now I'm on shaky ground and winding roads, but I'm strolling along nimbly at an ever faster pace.

There's nothing better than being able to reach for the computer to try out a great idea that just came to you. And now that you're freelancing, you can afford to do that because your schedule is suddenly free. Alas, freelancers get lonely and fall into ruts easily. To keep the creative juices flowing, you need a steady intake of inspiration. Read books and magazines, play music, exercise. Leave the house, meet people, go places. When you come back to your work space, you'll feel refreshed and full of ideas.

You'll also need a lot to fill your days. In fact, we seem to accomplish more when we're busiest. Without taking on more jobs than you can handle, try to discriminate between your tasks. If you spend too much time on a job, you will get bored and sloppy, and the quality of work will suffer. Break down complex tasks into simple bits, approaching them on different days. This will keep you objective and enthusiastic.

10. Look Back On The Old Times And Chuckle

Yes, remember back when you were a mere employee, trudging your way through endless weeks of dull assignments, baffling meetings and forced laughs at your boss' jokes? You can look back on those times and sigh with relief. It's all over now. Muahahaha!

You had the strength to quit steady employment and concentrate on your career. Now you owe it to yourself to make it take off. Get to work!

Further Resources

Here are some further articles and related resources:

  • Freelance Switch
    These resources for freelancers are a must-visit. The contents are grouped into clear sections: getting started, dealing with clients, day-to-day productivity, etc.
  • Freelance Folder
    Another great resource for new and seasoned freelancers alike. Both this and the previous website have interesting communities to which you can contribute by using the forum and submitting articles.
  • Productivity articles on
    Blogging superstar Leo Babauta shares his insights on productivity.
  • Structured Procrastination
    The original essay that inspired this effective productivity method.
  • Quick and easy recipes on
    A good collection of recipes, grouped by preparation time: 15-minute meals, 30-minute meals, dinner in an instant, etc.
    One of the best image bookmarking websites around. Great for inspiration. So great, in fact, that it could eat up precious hours. Use with caution!
  • StumbleUpon
    Everyone knows about this amazing service. Inspiration is just a click away. StumbleUpon is also a fantastic source of traffic for your blog and portfolio.

About the Author

Andrea Austoni is an Italian freelance designer currently living in Krakow, Poland. He specializes in icon design and illustration. He runs Cute Little Factory, his personal portfolio and blog.


Noupe Editorial Team

The jungle is alive: Be it a collaboration between two or more authors or an article by an author not contributing regularly. In these cases you find the Noupe Editorial Team as the ones who made it. Guest authors get their own little bio boxes below the article, so watch out for these.


  1. Nice article – I also work from home a lot, and I agree it is very important to keep to some sort of regular schedule, but some good time out is important especially to keep those creative juices flowing! – And I did laugh at the slippers reference (NO I do not wear them – thank you!:)

  2. Good tips, I’m currently in the last year of my design school and I’m not sure what to do next, work with a boss, study more or go freelance.

    I’m curious about the amount of work I can get and if the economic crisis has any effect on the amount of work there is. Maybe someone has some insights about this ?

    1. Tom, my advice to you is do not start freelancing right out of school. I would suggest gaining valuable knowledge that you do not learn in design school in a full time design job. I have been in my current position for almost four years. I have learned triple what I learned in my four years of design school. I am building clients by working freelance at night and will be moving to full time next freelance next May. You will know when the right time is step out on your own, but I would suggest you gain some experience first. Good Luck!

      Andrea, loved the article. I always enjoy your articles and tuts!

      1. I agree with Luke, experience is very important. However I started freelancing while finishing university and I gained valuable experience about the business. I later worked as an employee and I learned how not to run a business from my bosses so I went back to freelancing.
        Tom, my advice is to just work as much as you can however you can.

  3. Nice down to earth advice. I am currently freelancing and I have to admit, as I write this on my work laptop, in my office, in the middle of the working day, I am wearing slippers.

  4. I would like to think of myself as a successful freelancer and I happily break many of these rules most of the time. The whole point of going into freelancing was to get OUT of thinking like a corporate drone.

    I don’t set my alarm, but I do wake up around the same time every day (usually when the sun comes through the window). However, if my body feels it needs an hour extra of sleep, I let it have it. And you know what? I usually have a more productive day because of it.

    And I ALWAYS wear slippers around the house. Usually with a t-shirt and jeans. Because no one is going to see me. And you know what? I can still get the work done, no matter what I’m wearing. Dressing up for work was something I always hated to do, so why do it now? I want to enjoy my job (and you know what? I do. And in enjoying it, I do a better job).

    Almost every freelance advice suggests these things, but I don’t feel they’re necessary. Because each person has their own way of working and being motivated and I really would love to see an article discussing that.

    Also, there is no way I’d have someone pose as my boss. Honestly, if you can’t supervise yourself, you probably shouldn’t be freelancing to begin with. That’s the #1 thing you need to be able to do if you’re going to make a living at freelancing.

    For me, I set myself a goal of accomplishing at last five tasks per day, including one time-consuming task. And once I’m done with those tasks, I decide if I want to get a little ahead or if I want to call it a day, no matter what time it is. I like that flexibility and it’s all the more reason to want to be a freelancer. Time management is key.

    I’ve been doing this and paying my bills successfully for the past five years, so I think I at least sort of know what I’m talking about.

  5. Excellent advice all-around. I do have to say that, when working at home (I have a couple of clients where I work on-site), I do so without shoes (we take them off when we walk in the door). dirty shoes + light carpeting in home office = upset wife/boss. Also, I’d recommend (I’m sure it has already, but I’m too lazy right now to read all the comments) eating lunch or spending a few minutes outside every once in a while. It’s good to get a change of scenery, not to mention the interaction with other people.

    Thanks again for a good read.

  6. I agree with Robin. While structure is a good thing to keep you on task, the flexibility of working for yourself is one of the reasons I do this. A couple of days a week I go out for a 2-3 hour mountain bike ride. The exercise helps clear my mind and I simply work into the evening on those days. If you can keep your clients happy and keep work coming in then there’s no reason to stick to a rigid schedule.

  7. I am reading this article on a bright sunny afternoon, thinking I wish I where outside making the most of it and part of me is now feeling guilty if I do so ! – nice plain to the point article thanks.

  8. I agree, there are advantages there are disadvantages as well … everything is back on ourselves. Keep the spirit became a freelancer.
    Great post, thanks for share

  9. Freelance life is really good. I like numer 8: cooking food is one of my favorite hobbies as freelancer.

  10. Andrea, I like many aspects of this article but have a little problem accepting all your advice without creating a nagging, self-inflicted pit in my stomach. :-)

    If I really need to find a virtual boss to nag me, cook less healthy because it saves time, set the alarm the same as my old job, or wear shoes instead of slippers in my shoe-free house, then why exactly did I leave my old job? My question is a bit facetious; I understand the part about being able to optimize and focus on more rewarding projects which is a good thing.

    But in my opinion, freelancing survival should not require reshaping the home into a clone of the old work environment. If it does, then there may be other issues for that person to dig more deeply into.

    Still, I acknowledge that you’ve provided many good, thought provoking ideas that will resonate with your readers.

    1. I didn’t say anything about cooking less healthful food. On the contrary cooking at home is definitely healithier than eating fast or packaged food.
      As for the other tips I realize they may seem extreme but but sometimes people need to be kept on their toes. These are tips to start freelancing and find your rhythm. Of course these measures can be eliminated once you got it going. And as with everything your mileage may vary.

      1. I’m sorry Andrea, I was making a judgment call about pros and cons of batch cooking meals, but you’re correct there are healthier ways to do this too. Thanks

  11. These are good tips, especially the one about getting dressed for work. I’ve noticed that the way I’m dressed effects my productivity

  12. Very good article indeed. People tend to forget that starting up a business is not a joyride and even though you’re not doing 9-5 you still have to put in the effort and maybe more since you are the one running the whole business

  13. thanx

    though freelancing environment is not the same in every part of the glope , you can change how some peoples think

  14. Thanks for this post, i am a brazilian webdesigner and i am really looking forwarding to be a freelancer full time, actualy i start a fell days ago i have some clients so i am safe, but this tips really helps me.

  15. Show this list to your partner too if you’re married or living together. It is equally important he/she follow the rules.

    One baby is usually still manageable. It’s when baby two comes around, you start to question the above tips.

    No need to draw up a penalty list. Life will deal you enough punishment by then. House chores never stops. With the kids taking up a huge chunk of mummy’s time, house chores are yours whether you like it or not.

    Forget about regular working hours. Spending hours in locked in your home office sanctuary? Sure if you are alright leaving your 18-month-old toddler alone around the house while mummy is tucking in his 1-month-old baby brother in the baby room.

    When parenthood arrives, you will have to have top-notch time management and organisation skills to cope with the never-ending interruptions. If you fail to do so, I bet you’d regret why you left that comfy 9-to-5 job.

    Think twice before going freelancing from home.

  16. Interesting article by Andrea as usual :) Freelancing is indeed very fun. Keeping oneself motivated and focused is one of the biggest challenges in it though.

    May be we can see a “How to manage a web development start up company” article by you some time soon? What say Andrea? :)

  17. Very inspiring! Described almost every thing that I go through at my office everyday….

    I wish I could get ready sooner to quit my job to be a freelancer!

  18. Yes, been there so many times – really good pieces of advice though :) Observing Regular Working Hours really works for me:)

  19. Nicely done! If my slippers are kittens instead of rabbits, do I at least get props for creativity? No, in reality I wanted to say that I gave up a lot of money for freedom and it’s much better for me, because I am one of these creative types you were mentioning. One of the great benefits is wearing jeans and actually–barefoot is the truth–no slippers. To keep from slipping, I have had a journey to discover the pieces of structure I need, and some of them are like the cubicle world, and some of them are my own. One of the most important things I did was figure out what things were torturous that I never wanted to do again, like wake up before dawn. It was freeing to feel like I could choose whether to do something or not do something–it was not to curb media addictions but to gain freedom. Basically, the great thing about independence is figuring out what works for me as a person, without having to “align” (corporate word) myself with the goals of groups that often act in bad faith. (But I am bitter from enacting the profit motive, and not everyone is.) My prayer to the silicon god: May all of us working for our own creative souls build a critical mass that turns this world away from its current destructive pathways!!

  20. Excellent article, a brilliant read. I freelance two days a week at most (sometimes get called in to the office) so I haven’t fully made the plunge, but some of these tips are definitely very on point in regards to effectively working well at home as a freelancer. I agree mostly on the part about being able to explore creative ideas. When I finish work, as you said after you get home, have dinner etc. etc. you are too exhausted to visit the ideas that you want too, but when you’re working from home you can visit them as soon as they pop into your head.

  21. I’ve been self employed for around 6 months now, and I love it. There is alot of freedom, but the hardest part for me is pursuing new clients, but its always worth it.

    As far as not having a boss… each clients is your boss. If you seek to please every client you have to the best of your ability, then serving will not get lazy.

    Its when you seek to please yourself and lose site of the fact that your business is to serve the needs of others that you start to get lazy. Theres tons of design work out there, you just have to dig.

  22. Wonderful article, pretty much based on real life facts. Been there, done that too. Also enjoyed reading the Structured Procrastination article. It’s brilliant indeed.

  23. Thank You Man! I really like this one, the best thing about it was you dont have to go outside from your home. Better than others.

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