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26 Things That Could Be Holding You Back From Freelance Success

Raj Dash

Freelancing can be a rewarding career, with many benefits over being a salaried employee. But success in freelancing means there are a lot of things you shouldn’t do - things I’ve done over the past twenty years and learned from the hard way.

Some of these are relevant to web workers, others to those of us that still visit clients on-site.

Are you making your freelance career tougher than it needs to be?

  1. Not defining success.
    What does success mean to you? Does it mean being able to work from home and escaping traffic jams or staying away from office politics? Or does it mean earning a lot more, after tax, than someone in a similar salaried position? We all have different reasons for wanting to freelance. Defining your reason makes it easier to believe that freelancing is the right thing for you.
  2. Not budgeting.
    Budgeting is crucial when you work for yourself. Freelancing work is often feast or famine, and this can be the single biggest factor pushing you back into a salaried position.
  3. Not distinguishing between need and want.
    It’s not easy sticking to a budget when you’re a one-person freelance business. It’s sometimes tough to separate personal and business funds. It’s even tougher to resist the temptation to indulge using business funds. However, the separation of funds is necessary if you’re going to stay sane through tax time.
  4. Not organizing receipts and invoices.
    You really want to do this as soon as possible. File them using a system that you feel most comfortable with. I like using large manila envelopes with the month and year written on them, then putting a year’s worth in another envelope, a box, or a filing cabinet folder.
  5. Not keeping a logbook or logfile.
    It’s not always easy to recall what a given receipt is for, and if you can’t catalogue it properly, you probably can’t claim it against taxes. If you don’t like scribbling in a day planner, try using a spreadsheet (desktop or web) to add notations for receipts. It makes filing taxes so much easier.
  6. Not having multiple skills.
    If you learn just one skill, you’re harder to market. Focus on one main skill, but also build up other skills. Recession happens, but you still need to work, especially if you’re bad at budgeting. If you can’t find work for your main skill, you have something to fall back on.
  7. Not saving.
    Saving goes beyond budgeting. A freelancer should make saving a key “skill”. The old rule of thumb is to save up 3-6 months of operating expenses - rent, debt payments, food, insurance payments, and other typical monthly operating costs. If you have a family to support, you should consider saving more than six months of operating costs. The reason for this? According to a survey of 3700 freelancers, 43% made less money and worked more since becoming freelancers. On the flip side, if you’re working from home, your day-to-day expenses should be lower, so earning less isn’t necessarily a bad thing - but not saving for the future is.
  8. Not investing.
    Put the money you’ve saved into an easily accessible liquid investment with minimal penalties for early withdrawal and optimal interest rates. One option is an online savings account. Investing safely helps you build up that emergency fund sooner. However, you should invest beyond that, for vacations, retirement or even a possible career change later on.
  9. Not reinvesting.
    Reinvest in your business, skills and knowledge. Reinvestment might include buying advertising, taking courses, or purchasing software and gear in order to offer new services.
  10. Not being pragmatic.
    It’s easier to be pragmatic about finding new work when you have funds saved. When you don’t and you’re looking for work, you might come across desperate or needy to the client. The irony is that when you come across casual/ indifferent - without being rude - you’re more likely to win a contract.
  11. Not seeking emotional support.
    If you’re already a top industry expert, you probably won’t want for work. But if you’re still building your skills and reputation, the downtimes might get you down. Don’t be afraid to seek a bit of emotional support and TLC.
  12. Not taking a break.
    When you freelance, you work for yourself, and time takes on a special significance. It’s not hard to fall into a state of mind where you feel you need to work long hours. The fact is, you cannot be productive for hours on end. Forcing yourself to work doesn’t necessarily get things done faster, and you miss out on the important things in life, such as family, friends, and relaxation. If it makes you feel better, take X hours off as a form of payment for the work you’ve put in.
  13. Charging too little.
    If you are working long hours, maybe it’s because you need to, or simply because you’re charging too little. Research your niche to determine what the rates are for various levels of skill, and set a new rate for your work. Charge new clients your new rate. If a former client comes back to you for more work, you can request the new rate as well.
  14. Taking on too much work.
    If you’re charging to little, you might be tempted to take on too much work. This is more of a problem when you work at home, because it’s easy to feel you’ll find the necessary hours. Don’t fall into the trap of taking on too much work, or else you could damage your reputation if you don’t deliver.
  15. Not tracking time spent.
    If you get paid by the hour, you have to track time. If you get paid by the project, you also have to track time - simply to make sure that you’re not earning less per hour, on average, than you think. If you’re screwing yourself over, you need to raise your rates.
  16. Not asking for deposits on projects.
    If you charge by the project, unless you know the client well and they have good track record in paying their account on time, it’s a good idea to ask for a small deposit up front. It’s common to ask for 25-33% at each project milestone (including contract acceptance and work delivery). How much you ask depends on how many phases there are. If something goes wrong, at least you’ll have received some compensation…
  17. Not building negotiating skills.
    It’s easier to raise rates for new clients, but occasionally you have to do it for existing clients - possibly the ones who’ve come back to you after an extended duration. Either way, it’s not easy asking for higher rates or for deposits. Negotiating skills also help landing contracts.
  18. Having a negative vocabulary.
    Good negotiating skills require casual confidence. The first step towards gaining confidence is ditching any negative or wishy-washy words in your vocabulary.
  19. Being too proud or too fussy.
    Work shouldn’t always be about the money. Consider taking a bit less pay for an interesting, stable, longer-term contract that you think you’ll enjoy. Just make sure to check your state/ federal laws about contract durations and the point at which you’re technically considered an employee.
  20. Not asking for help or clarification.
    Even a well-read freelancer doesn’t always know everything about a topic. It’s better to ask for help/ clarification from a client or their employee than to fake knowledge and do work badly. (Just stay away from the employee who thinks you’ve taken the job that they wanted.)
  21. Not remaining neutral.
    You’re a freelancer, not an employee. Be attentive in discussions, but don’t take sides in office politics.
  22. Mistaking politeness for friendliness. Freelancing can be a lonely business, but don’t assume that your client’s employees are being anything more than polite.
  23. Not applying the 80/20 rule.
    The 80/20 Rule (aka the 70/30 Rule) is also known as the Pareto Principle. It essentially says that 80% of results are due to 20% of causes/ efforts. The rule can be applied in many ways, especially for freelancers. Here are a couple:

    1. 20% of your clients will give you 80% of your revenues.
    2. 20% of your skills will earn you 80% of your revenues.

    You can probably come up with other applications. It doesn’t mean you should ignore the “20%” of something altogether. You never know when your clients or your skills will change their roles within the 80/20 rule.

  24. Not asking for referrals or testimonials.
    Here’s how you can apply the last item: Since 20% of your clients will probably give you 80% of your revenues, it makes sense to ask your current clients for more work. Do they have any additional work that needs doing? Or maybe they know another business owner and would be willing to give you a referral? At the least, if they’re happy with your work, they might be willing to provide a testimonial for your website. You have to ask to receive.
  25. No backups.
    While not having backups is usually a temporary issue, regularly ignoring the need could have damaging effects on your career. Some suggestions:

    1. Back up client project files regularly.
    2. Have a backup Internet connection, or access to one.
    3. Use a UPS (Universal Power Supply) box in case of power outages.
  26. Not controlling road-rage.
    If you do on-site work, you might find yourself in traffic jams from time to time. When you factor in high gas prices, high insurance rates, and the frustration of being stuck in traffic daily, it’s easy to want to vent when some idiot cuts you off. It’s fine to vent if you’re doing it in the privacy of your car - just don’t be too aggressive about it, and especially not within 5 miles of your client’s office. You never know who that idiot might be. Trust me on that one!

Do you have some tips for protecting your freelance career?


Raj Dash

Click here to view a bio plus other posts


Leave a Comment
  1. A little bit off topic but I noticed this article appeared in my RSS Reader last week. But when I tried to access the web-page received a 404 error. It was obviously held back in draft mode, but I was still able to read the article in the Reader. Maybe something to be aware of.

  2. Great tips. I went out on my own recently, I have a family… and I don’t have anything saved! We’re doing fine so far (plus my wife works a steady waitressing job), but when I read that, I hope I haven’t shot ourselves in the foot.

  3. Defining success is something that made a big difference in my freelance career. Success is about what makes you happy. Freedom, money, whatever it is that drives you. I do freelance web development on the side and for a while I was burning myself out trying to be the best developer in the world. Not a realistic goal, and it almost burned me out completely.

    Luckily I figured out my problem and have since changed my expectations. Web development is something that I genuinely enjoy, and I now define success on a smaller scale so it stays fun. Hopefully not everyone makes the same mistake I did about thinking they have to do it all to be successful.

  4. truth hurts.

    I can see at least half of the to 10 that I don’t do for my business that I would have automatically done in my last ‘real’ job. And writing that last phrase that popped in my head is an examle. If I am making money doing this - how is it not my real job?

  5. 26 items and not a single one dedicated to marketing. Freelancers who fail usually turn out to be freelancers who haven’t a clue how to market their services. If you aren’t networking, advertising your services, or taking some action on a regular basis to make sure the widest desired audience knows about your services, you’re somewhere on the road to a monster dry spell that could force you back into the “real world”. Even if you’re really busy now, that won’t always be the case if you don’t pump up your marketing.

  6. I would also like to add: Being willing to fire a client. Several reasons: not paying the invoices, too high maintenance ( which could be good), but my big one is; negative or unhappy with my work ( typically to bring down the price). Maybe this could come under negotiating skills. But my best marketing tool is a happy client. And I want those around me to be happy.

    I just lost some images created on software I don’t have (any more, or want): I know backup on several devices. Every time I loose something I realize how important my work is.

  7. Excellent article.

    Freelancing can be a dream come true, as long as you keep your legs on the ground. You work harder, you might earn less, but the satisfaction is far greater than in being a hired employee.

    Thanks for the post!

  8. I have freelanced for 15 years as a pianist and teacher. I want to turn my hand now to web marketing and local art scenes - build a small business painting local topography and creating my designs as cards, coasters, calendars, mugs, T-shirts, coffee table books and mouse mats which I will sell locally, and nationally on the internet.

    This is what I really love about being freelance: you can come and go as you please, change direction as you please, wear what you want…can’t beat it, I say!

  9. Well, i definitely agree with some of your points, and i admit that i wouldn’t implement some of this but anyway, thanks a lot for sharing your own thoughts and i know that everyone of us have different way in working and surviving in freelancing but it’s just how you will do which you think works for you

  10. not taking a break is my biggest mistake. i tend to become a workaholic. i feel like if i turn down work or leave for more than a day, that all my clients will magically disappear.

  11. I think I’m guilty of many of them!!! Great post!

    I’ll work on my mistakes ;)

  12. yes yes yes! excellent blog post. this works as a great checklist to look into every month. i think i’m going to print this off and put it on my wall. at the end of each month check the items that i have committed to that month.

  13. Only one thing to add - realize that the internet does not make you invisible. Some clients (or enemies, for that matter) may go to great lengths to find out information when your name is brought up for a project.

    Make sure you’re Facebook/MySpace/Blog is private or completely anonymous - and even if it is, make sure there’s nothing in there you wouldn’t want your clients to find. It’s always possible for someone to print something off and hand it to the wrong person (accidentally or intentionally).

    Be cautious, as some folks will be jealous of your success - I learned this lesson last week.

  14. It is a very helpful article for every freelancer. Thanks!

  15. Great Post!!

    I think that you have pretty much outlined a blueprint for success here. Mostly how well people do is more to do with their organisation and processes than their creative excellence.

    I meet a lot of peniless genii with superb creative ideas with no idea of how they will capitalise on their skills.

    Having a few well executed average ideas is better than a plethora of unsued spectacular ones.

    Very useful indeed

  16. Riki: Thanks for the heads up. It’s a problem with my understanding of the new WordPress 2.5 panel and my inability to figure out why it’s such a pain to create a draft mode article. So the article got published and I pulled it back into draft mode.

    Kyle: It’s nice if you have someone else in the family pulling income, of course. If you don’t, well…

    MattC: How did you change your definition, in order to help you?

    Richard: Good point. It’s sometimes hard to realize that freelancing can be a “real job”.

    Andy: Marketing is my great failing. I’m not good at singing my praises. I always used to rely on word of mouth or using “headhunters”. But very good point. I guess I took it for granted, now that I’m working mostly online and my writing and screencasts across the blogosphere are my “marketing” efforts, by default.

    Jack K. Yes, very true. In the past, I didn’t turn anything down - offline and online. It’s a bit easier once you establish yourself.

    Revital: So true - freedom and satisfaction is what I love about freelancing. If you can weather the downsides, you’re set.

    Zowoco: Don’t neglect exploring web video to help market your products and services. Simple lessons on how to play piano, etc.

    Philipines Freelance Web: Share with us some of your tips for coping.

    Melek: Yes, fear of losing your clients sure puts a damper on things. I’ve had the same problem, but I think once you’ve established yourself, you might feel differently.

    Pablo: Good luck :)

    Bugsy: Cool :) Good luck.

    Laura: So true. I’ve had a big mouth in the past (though a misunderstood big mouth), and I know that some of my past offline clients, were I to approach them again, might balk were they to see what I’ve said. Live and learn. And jealousy, yes. Unfortunate but true.

  17. Hoooweee, there are lots of “not” in this post!

    See #18 Having a negative vocabulary.

    ;-)

    Thanks for the good tips.

  18. I think inner demons such as laziness should be numero uno. Shit its holding me back from eating let alone success :S

  19. Jaden: Agreed, but it would be kind of hard to write this post without those “nots” :)

    Tofu: I didn’t want to open that can of worms :L

  20. Wow, it’s the best set of advices for freelancers that I’ve ever seen… Thanks!

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