When freelancing fails: 5 questions to ask yourself

November 1, 2010 by Dean Rieck
Filed under: Freelancing 

fail at freelancingI didn’t want to write this post. But I felt I had to.

As this blog becomes more popular, more people are sharing their personal freelancing stories with me. And one recent theme has been freelance failure.

You almost never hear people talk about this. Most of the freelancing information out there is upbeat: “Freelancing is great. You should start freelancing now.”

But for some people, there’s another side to freelancing: “I tried it. It didn’t work out for me.”

My heart goes out to these people. I know how hard freelancing can be. I started with nothing. I had no money, no job, no contacts, no clue what freelancing was or how to make it work. I began my freelancing career in desperation and out of necessity. It worked out for me, but it was a hard road.

So I cast no blame, nor do I make any judgments about those who couldn’t make freelancing work.

But if you’ve gone through this, if you’ve tried it and failed, I think it’s important to take a little time to figure out why. That way you can do it better next time. Or you can learn once and for all that freelancing just isn’t for you.

So here are 5 questions to ask yourself:

  1. Did you get into freelancing for the right reasons?
  2. Did you start freelancing at the right time?
  3. Did you plan your transition carefully?
  4. Can you identify what went wrong?
  5. Are you really the freelance type?

Let’s look at these one-by-one.

Did you get into freelancing for the right reasons? There are a lot of myths about freelancing. The most alluring is the idea that you’ll make lots of money with very little work. It’s the old, get-rich-quick lie that so many e-books promise.

The truth is, freelancing takes work, persistence, and skill. It’s not a quick road to riches. It’s like any other service business. You get out of it what you put into it.

If you got into freelancing to escape the responsibilities of a job, you’ve similarly been led astray. Freelancing actually comes with more responsibilities than most jobs, because you not only have to do the work, you must get clients and manage a business.

Did you start freelancing at the right time? In a way, anytime is a good time to start freelancing. There’s always work out there and a demand for skilled freelancers. In another way, some times are better than others. Today’s down economy has hurt many industries and dried up some of the demand.

It all depends on your skill set, your specialty, how much freelance experience you have, and a host of other factors. It also depends on your personal situation. If you’re going through a divorce, just lost your job, have no savings, face foreclosure on your house, and your dog is sick, it’s probably not the best time to think about freelancing.

Did you plan your transition carefully? Many people start freelancing at a moment of change in their lives. They don’t plan to freelance. They just start, out of frustration or blind hope.

But you’re much better off if you plan ahead and prepare. Set a date for when you’ll leave your job. Build up your savings account to pay the bills during the early months of your freelance business. Create your website. Design your letterhead. Set up your home office. Start working with clients in the evening and on the weekends.

Doing all these things after you’ve taken the plunge skyrockets your stress level, wastes your time, and lowers your odds of success.

Can you identify what went wrong? Sometimes you can do many things right, but one big thing goes wrong that kills your freelance business.

Was it fear, panicking when you realized how significantly your life had changed? Was it lack of discipline, missing deadlines and failing to keep to a daily schedule? Was it lack of action, sitting around waiting for something to happen instead of advancing your business on a daily basis? Was it a lack of skill, discovering that you really couldn’t handle the work you had promised to your first clients?

Be honest. It’s not fun to admit your own shortcomings, but it’s the only way to learn from the experience.

Are you really the freelance type? Earlier this year I wrote about the pros and cons of freelancing. As I said then, I can’t tell you if you’re best suited for a job or for freelancing. But there is a right answer for you.

I never liked the jobs I had. I have never been the corporate type and never seemed to work well in a rigid 9-to-5 office setting. But there are others who thrive in this sort of environment.

When you freelance, you’re on your own. You have to find paying projects. You spend a lot of time working alone. The cash flow can be irregular. And you must be able to multitask with clients and projects. There’s a certain chaos and uncertainty about it that doesn’t exist in a full-time job.

This is another question that demands honesty. Some people are cut out for freelancing, others are not.

So if you’ve tried freelancing and it didn’t work out, don’t beat yourself up. Congratulate yourself for taking a risk, something most people never do.

And if you’re convinced that freelancing really is for you, figure out what went wrong. Maybe you can give it another go when the time is right and you’re better prepared.

Do you have a story about freelancing not working out? What happened and what have you learned?

Related posts:

  1. $#!* Happens! A dirty story about freelancing success
  2. Okay. Okay. I’m writing a freelancing book.

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Smart Comments

20 Comments on When freelancing fails: 5 questions to ask yourself

  1. Alyson Kiel on Nov 1st, 2010 11:36 am
  2. Thank you very much for this post! As one of those who went back to a 9-5 after a full-time freelancing stint, it was really helpful to have the list of questions to determine if maybe freelancing full-time is in my future down the road.

    And thank you for the encouragement about being brave enough to give it a go – I’m also one of those that beats myself up for “not being able to cut it” and maybe I just need to give myself a break. I hope that others can find the same kind of encouragement as I just did! :)

  3. Dean Rieck on Nov 1st, 2010 11:52 am
  4. Alyson,
    I’m glad you found this useful. I really just wanted to get across the idea that freelancing is an option, not the ultimate goal for writers. So it’s important to find what’s best for you.

  5. Andrew B. on Nov 1st, 2010 1:42 pm
  6. Hi Dean,

    Great questions — very thought-provoking. I’ve read your questions a number of times in an attempt to apply them to the notion of freelancing on a very part-time basis, but I don’t think they totally apply.

    I’d love to get your thoughts: Is freelancing on a very part-time basis (like 6 hours a week) something that’s feasible? From the standpoint of doing the creative work and the writing, it absolutely is. But from the perspective of client service, needing to meet face-to-face during regular business hours, or even taking anything other than a 30-second phone call, I’m not sure.

    In addition to my 8-to-5 job, I’d love to do another 4 to 8 hours a week of freelance writing. What’s your opinion? Is that too minimal? Is that realistic? Or is that just stupid? (Be honest, Dean. I can take it.)

  7. Dean Rieck on Nov 1st, 2010 2:05 pm
  8. Andrew,
    I see no reason why you couldn’t freelance a few hours a week. You don’t need in-person meetings (I almost never do that). As long as you can juggle your job and a few on-the-side clients, go for it.

    The only problem may be your employer’s feelings about your doing this on company time and equipment. You’ll probably have to limit your daytime freelancing to the occasional call, and save the writing for evenings and weekends.

  9. Andrew B. on Nov 1st, 2010 2:35 pm
  10. Absolutely — I would never do it on company time or equipment. And that’s the rub: If I’m not available during the typical 40 or 45 hours that my potential clients might want to be in touch with me, is there hope for a strictly after-hours/weekend type of business?

  11. Dean Rieck on Nov 1st, 2010 2:52 pm
  12. Andrew,
    You’d have to find a way to communicate with clients during business hours, assuming you’re in the same time zone. Or find clients willing to work with you purely by email.

  13. Lucy Smith on Nov 1st, 2010 4:41 pm
  14. I can really relate to the part about setting things up before you start. Because I began out of necessity, I had some savings and that was about it (apart from the good fortune of having a partner who has a web development business). It’s very discouraging to hear of people who walk out of a job, start freelancing, and almost immediately start making more money than they did in their job. What’s almost never mentioned is that those are probably the people who walked out of their jobs with a client base, rather than starting from scratch.

    There have definitely been times where I’ve started combing the job ads, but really I can’t see myself having to be at work by 9 and dealing with office politics ever again. But if I don’t want that, then I have to learn not to get down and sulky when it’s not working out, and do something about it!

  15. Dean Rieck on Nov 1st, 2010 5:02 pm
  16. Lucy,
    Well, I made more money right away from freelancing, but that’s only because it was a long time ago and I was earning a low wage. I had nowhere to go but up.

  17. Allison Marquardt on Nov 1st, 2010 6:01 pm
  18. Dean,

    I’m wondering about the role of the web and social networking in freelancing. I’m a working writer, but I’m curious about what you think about these things as a promotional tool for freelance writing.

    Should I spend time with these things first, or should I just try to get some more work? Things like Linked In, Facebook, Twitter, creating my own blog, etc. I mean, I could spend hundreds of hours bringing these things up to par in an effort to get more clients. Or maybe they aren’t so important. Can I get clients without having 100 connections on LinkedIn, a big Facebook presence and my own daily blog? Do most clients expect to find you on LinkedIn and Facebook? Or don’t they really care, as long as you do good work and meet their deadlines?

    Is a good electronic portfolio adequate these days, or is full participation in the social media game a necessity?

  19. Dean Rieck on Nov 1st, 2010 7:42 pm
  20. Allison,
    Wow. That’s a lot of questions. And all good ones. Maybe I should write a post on this to answer it.

    The short answer is that you can promote your services and find clients in many different ways. It all depends on who your clients are and what works for you.

  21. Tombee on Nov 2nd, 2010 7:37 am
  22. Dad was an extremely successful freelancer, with years of blue-chip clients and London agency work under his belt. He even travelled the world on the back of his portfolio – stopping off in places like Hong Kong when the bank account was looking low… because of his portfolio he found it easy to stop somewhere he could find work (like Hong Kong) and build up his funds again over a year or two before jetting off on more adventures.

    I have though about going freelance but the one thing that puts me of is having to work at getting your work. I asked if him how he found his clients and he said there is no secret – it’s just a case of pounding the pavement and knocking on doors with your portfolio. A case of throw enough mud and right place right time. It’s a sheer numbers game.

    That kind of put me off trying for myself, but that was a different generation as he’s long retired now and living in the sun somewhere exotic – do you think it’s easier finding work now thanks to computers and the internet? I’m still stuck in the gloomy UK you see.

  23. Eddie Gear on Nov 2nd, 2010 8:12 am
  24. Hi Dean,

    Fantastic Post! I have asked myself the very same questions. Initially I was under the impression that I could make lots of money with very little work! But now, I know different. I feel that most people hate their 9-5 jobs sooo much that they think freelancing is the answer to all their troubles.

  25. Rebecca on Nov 9th, 2010 10:34 am
  26. I think #1 is so crucial to making the switch from 9-5 to freelancing. I work ten times harder now that I’m a freelancer than I did when I was a cubicle rat. It’s because now my name and reputation is at stake. But I honestly like that. I like that now, when I do my best work and put out a quality product, I get the reward. And I like knowing it’s no longer an option to slack or provide anything less than my best. It’s actually liberating to work harder. Funny as that sounds.

  27. Dean Rieck on Nov 9th, 2010 11:08 am
  28. Rebecca,
    I know exactly what you mean. It’s kind of sick. But completely true.

    [...] few weeks ago, Allison Marquardt commented on the post When freelancing fails and asked some great questions: I’m wondering about the role of the web and social networking [...]

  29. Deborah on Jan 12th, 2011 8:07 pm
  30. I am considering going back to work part-time until I can get more residual income coming in. I have to work so hard now just to keep the bills paid. I feel like I’m making minimum wage, even though I’ve never really figured out how much I make per hour.

    I have a real self-discipline problem as well, so maybe I’m not the freelance type. Maybe I should just do it to earn enough money so I don’t have to work full time. I don’t know right now, because it’s all I have, so I have to just keep plugging away.

  31. kosta on Jan 17th, 2012 7:11 pm
  32. Thankyou for your insightul post. I recently had troubles with a failed freelance project and it came down to a lack of project management and stress. I had to tell the client that my days of developing for them were over after over a year of development and several applications. Needless to say, they were disappointed but i had to let go my worries. I had been worried that my reputation would be in ruins but knowing that it had been an experience I can learn deeply from helped.

    In the future, if I was to take on freelance work, it would be managed much more professionally. For now, I’m happy in my 9-5 job. It pays well, its secure and its stress free.

  33. Dean Rieck on Jan 17th, 2012 8:16 pm
  34. kosta: What’s most important is that you find what works for YOU. Still, don’t give up on freelancing. It can take time to learn how to work with clients successfully.

  35. Jeffrey A. Lubbers on Mar 12th, 2012 1:13 pm
  36. I’ve read a few books on freelance copywriting, but none of them ever gave me a clear idea on who to contact — where to get started. The authors typically suggested doing pro bono work, but when I contacted volunteer organizations, they had never heard of anyone doing freelance writing.
    I’m interested in doing this part-time, to see if I like it, but I don’t know where to get started. Again, the places I contacted had never heard of anyone doing volunteer writing.

  37. Bob Collins on Apr 16th, 2012 1:36 pm
  38. My own “business writing service” (me freelancing for local non-profits and ad agencies) didn’t fail, so much as I quit it when a client list I had inherited dried up. A local writer developed cancer (eventually fatal) and asked me to take over her clients whom I had been assisting her to serve. Gradually, over a five year period, those clients moved on – some closed down, some hired full time writers, and a couple of the NPs retained volunteers who did my work for free. I moved on to manage my own nonprofit program for families and have been doing that for a dozen years.

    Now I am considering re-entering the business writing business, but feel very out of touch with … anyone or anything related to what I used to do. I am quite apprehensive about jumping into the water again. This is exacerbated by my financial needs (read: desperation for money) which has developed over a dozen years of near volunteer work at a mission I love dearly.

    Now, I am worried about how to get back into the race when I’ve been removed for so long. I know I did it before, but all my contacts are gone, relocated (or dead, God rest her!), and out of my circle. My portfolio is aged, I have aged, and the world has become very digital since I retired my iMac in 1999!

    Being broke has both benefits (driving need!) and problems (no money to hire professional help, such as a coach or agent). Any thoughts, anyone?