Open Thread: What’s Your Least Favorite Part of Freelancing?

Okay, so we’re all freelancers here — let’s talk frankly. Freelancing may be one of the better things in life, but it sure isn’t perfect. In fact, some parts of freelancing just plain suck.

Come on, admit it. People asking you to work at all hours of the day? Collecting payment from clients? Dealing with someone who hires you and then forces you to do it their way? Keeping the books and filing taxes? Constantly trying to find new jobs and more work?

Miraculously accomplishing all of the above, while supporting your family, and still being treated with less respect than someone who has a job?

So, I pose the following question:

What’s your least favorite part of freelancing — and how do you deal with it?


  1. says

    The worst part was having to find new clients, luckily now I have returning clients so it isn’t as bad anymore. I get a lot of respect from my clients and a lot of them ask me to use my creativity wherever I can, I have had the occasional client who has been a pain in the past though. I like everything with freelancing, I’ve only ever had one job and it was rubbish and I was treated a lot worse than I do now so the little extra work like taxes and book keeping doesn’t bother me.

  2. shiido says

    “Miraculously accomplishing all of the above, while supporting your family, and still being treated with less respect than someone who has a job?”

    We love what we do, and we are free (or not) and the “real work people” envy that. Specially than ones that do the same thing during 20 years or more…

  3. says

    Oh definitely agree with @Tim Grahl the invoicing would have to be my least favorite part. Although I just found and it makes invoicing just a little bit easier!

  4. says

    If past FF articles are any indication, I can’t wait to see all the great comments that the readers offer up!

    First one to mind for me is the necessary evil of documentation for the client to use the CMS / site I have built for them. I know it is of benefit to me in the long-term as the number of “How do I….” questions will be reduced, and client satisfaction will go up leading to more referals and repeat business. But isn’t there a way I can just do a braindump and it all be converted into easy-to-understand terminology? Screencasts might be the answer, but don’t have the same gravitas as a printed document.

  5. says

    @Shiido — I agree with you, and my family agrees with you. I just wish my future in-laws could see it that way :-)

    And @JamieO, just bite the bullet and write up the docs. Took me a week of hard work to get everything well documented, but for months now I’ve been able to just point people to the instructions and not actually explain it over and over again. So worth it.

    Though it still doesn’t make TinyMCE any more reliable.

  6. shiido says

    @adelle i saw you talking about that app,, in twitter and i´m using it now ^-^ , i don’t do yet any invoices but i manage my clients there.

  7. says

    Hahaha, you’re absolutely right Shiido. Big house, shiny car, and maybe a swimming pool — that should do the trick. Oh wait, I guess I need to get back to work now :-)

    Oh man that gave me a good laugh…

  8. says

    @Mason: I have been doing that, but it doesn’t make the process any more enjoyable :P The larger challenge is that with each client / project has specific revisions that have to be made (screenshots, custom terminology, etc) which means it isn’t a process of write once / use everywhere. Though having a strong document base to work from means that process is more incremental / revisionary than starting from scratch each time.

    Anyone found an equivelent of CurdBee that is self-hosted for a PHP / mySQL platform? Free is great, but I tend to trust my own environments for data security over those of a company in any scenario if I can manage it.

  9. says

    @JamieO Look at the documentation as a way to stand apart. Build into your pricing payment for creating the docs then at the end of the job, hand over a nice folder with your branding on it that includes a disc that has screencasts on them (software: Snapz Pro X) and printed instructions on your letterhead. Also include in there your “thank you” note and request for referrals. Doing that will make you stand head and shoulders above everyone else because you took the extra steps that others wouldn’t. Plus, it’s a great final impression that can help clients overlook any previous missteps you made.

  10. says

    My least favorite part? Good question! Ok, I can’t say I like invoicing, taxes and all, but I do like to receive money (and I could use the shiny car and swimming pool hehe) :)

    But I’d say my least favorite part is when a client keeps changing the specs and adding stuff… sure that means I get paid more, but sometimes it just feels like it’ll never end, and if a project takes 2 months instead of just 3 weeks, that also means I have to put some things on the back-burner and tell potential clients I’m booked.

    How I deal with it is simple: I contact some of my good designer friends and send some work their way. It makes them happy, it makes me happy cause it helps free up my schedule a little and it makes clients happy cause they get what they want/need. Voila!

  11. says

    What I hate about being a full-time freelance writer:

    1. Not being able to say no to a project even though I have a full bin
    2. When people assume I can work at the drop of a hat – I do have a family and work specific hours.
    3. When I have to hire other writers to help me! Sorry, but it never seems to work out well.

  12. says

    @Jon — I was just talking with Steven Snell about the importance of having a good network, and your comment reinforces this even more. Having a group of colleagues to help out in a bind can be great for friendship and business.

    @Qoska — Read more SmallFuel Blog! We’re doing our best over there to make marketing easier :-)

  13. says

    I agree with Jon about having to refuse clients because an existing job spec has changed…

    My least-favourite thing about freelancing is collecting payment. What irks me is that payment shouldn’t have to be ‘collected’ – in theory, it should just arrive … on time.

    I’m forever boggled by the irrelevant explanations offered for late payment, ones that an in-house worker would never, ever face – or accept. Can you imagine working in-house and not getting paid because the accountant’s on holidays? How about a whole company getting paid a day or two late? It’s only a couple of days, right? It’s pretty unthinkable.

    That said, we’re all pretty content to do what we do. :)

  14. says

    I have to agree with Dave Navarro on this one. I get the constant “could we try this” or “could you do this really quick”. The worst sentence a customer can send me is “this should only take you an hour so can you just toss it up for me” …. how the HELL do they know how long it should take, and regardless, an hour is a billable hour.

    #2 pet peeve – lack of stability in cash flow. Yes, I am saving money, and yes, it’s getting better, but damn, I’d love to have a weekly payment schedule where I KNOW what’s coming instead of planning on getting 3 payments and only receiving 1 because the other two are late.

  15. says

    The admin, the admin – invoicing, chasing clients for late payments, renegotiating payments because the client has changed the specs, and all forms of paperwork. I love writing, and I love getting paid, but the other tasks are necessary evils.

  16. says

    Dealing with clients who have been burned (or think they have been burned) by another designer.

    I can’t tell you how many times I have heard – “Well I have this logo…but…” or “I have this website…but…”

    @Mike Smith – Ha! So true, so true. “Hey, can you try this instead real quick?” – like it’s EVER that easy.

  17. says

    There are many great ones here, so to be different I’d say:
    Learning a client’s preferences.

    There is always a growing period where you test the waters, and if communication isn’t handled well through this time it can sour up the mood of a project fairly quickly. Once you find their style, and break through that tough business demeanor, it is all cake.

    And if I could add in another one:
    Clients that can’t express themselves but hate everything.

    You can either be relaxed and let us handle it, or you can be hyper picky about the shade of green and I won’t care either way. But you can’t have zero opinions up front and still be hyper picky come concept time.

  18. says

    @Mason I’m been reading Smallfuell for a week (discovered in here) and it’s an amazing resource of marketing tips and strategies. However, I still suck on anything marketing related :)

  19. says

    For me the worst thing about being a freelancer would be the fact that I always feel pressure to finish things on time and pick up more gigs. Not that I necessarily have to pick up more gigs to be able to pay my bills or have deadlines that I’m struggling with… It’s just that I always want to finish more projects within tighter timeframes simply to be able to make more money. It’s so stupid because in the end you are just more stressed and enjoy life and work less… damn freelance freedom! ;-)

  20. says

    Isolation: The isolation of not working in an office and interacting with co-workers. Granted I love being able to work my hours and do my own thing as a freelancer but I miss working in an office with other people that I can talk to when I need a work break.

    Also, having friends who are not freelancers and don’t get the freelancing thing is not fun either. Working from home in pajamas does NOT mean I’m taking the day off. It means I have a “relaxed” dress code in MY office.

  21. dschibut says

    I began this discussion to evaluate public available web proxies:

    Which are really anonymous?

    Which can unblock facebook, myspace etc, in other words: are fresh ?

    Which would you recommend?

    Thanks for your help,

    P.S.: In my land, the freedom of speech is somehow constrained, please give me a hint, if you are not sure about your recommendation.

  22. says

    I know this is an old post, but I just found it today. I’ve been thinking of assembling all the tricks I learned to freelancing into a book, specifically how to manage cash flow.

    Does something like this sound interesting? What is the most difficult “how to make money at freelancing” question you’d want answered?

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