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How NOT to Freelance
Portrait of Andy Leverenz
Andy Leverenz

August 9, 2016

Last updated November 5, 2023

How NOT to Freelance

Freelancing has become more and more popular for those looking to break out of the normal 9-5 day job regimen. Because of advancing technologies certain fields such as web design, web development and writing (all stuff that can be done with a computer) seek contract-based freelancers as opposed to full-time employees. The same is true teams working on large-scale projects which over time, saves on costs.

This growth in competition means finding and winning clients is becoming increasingly more difficult. Rising to a successful level (and maintaining it) is tough to do. In my own efforts over the years, I’ve found ways to best utilize my time to accelerate the process and avoid the obstacles.

This is my take on how NOT to freelance.


There isn’t much I haven’t tried in an effort to gain new clients. Some jobs I’ve taken have been real eye-openers while others leave me struggling to stay awake. After many years of learning about the good, bad, and ugly, I feel confident in offering advice to those new to the game. This post is a reflection on what working for myself means to me as well as how NOT to freelance.

Just Say No to Job Bidding/Freelancing Sites (the system is broken)

I can’t stress enough about how websites like Upwork, or Fiverr are poison for freelancers. In my opinion, the only people who benefit from these sites are the site owners themselves.

I get it, as a freelancer, you need money to keep the lights on. These sites help pay the bills if you can stand them, but I for one cannot and here’s why.

I’m almost 100% sure you want to grow your business(who doesn’t?). The truth about these sites are plain and simple: They won’t allow you scale. You may win a project here and there, have success with it, and get paid (less than your worth of course), but what happens from there?

On to the next one right? You are basically working for scraps just to get by. Do you enjoy it? My guess is no.

Take this sad example from a recent Upwork post I found:

upwork job posting

The job details are as follows:

“I have the picture for the logo THE ONLY THING YOU NEED TO DO IS CREATE UNIQUE FRAME FOR IT AND MAKE THE PIC VECTOR! THAT'S IT! Please note that this is a very simple job and I am only paying $6 since all you have to do is make the picture vector and create unique frame”

How would you like to work for $6 vectorizing a photo and making a frame for it as noted in the screenshot? Yes, I said, $6 USD. Note how the contractor wants expert level work for that rate as well. Are you kidding me?

Here’s the breakdown of how stupid this process is:

In this example, Upwork gets their cut(of course), the contractor gets a good deal(maybe even some decent work), and you’re left with little to show for it. In other words, you get screwed.

This is all not to mention the fact that you probably aren’t working on anything too exciting or at least something you would prefer to be working on. I know I wasn’t when I made the mistake of trying sites like this out.

The Misconception of Value

Websites like these are destroying the credibility of any and all freelancers. Even if there are decent-paying jobs available, they are too far and few between.

Those who are willing to work for such a low rate ruin it for the rest of us who need to charge professional rates to break even. I for one would love to see these sites go away.

Those who hire freelancers will always want the best deal and I don’t blame them, but the underlying issue is the value they receive for the amount they are willing to invest. People who aren’t used to hiring a contractor don’t know what to charge or how much your time is worth. Part of the problem isn’t the contractor but rather the freelancer for not educating those who have an interest in working together.

In short, a contractor wants to pay $6 for the project and be completely satisfied but in reality, for $6 you will get $6 worth of work. If they were capable of paying a fair rate for the designer’s time they would get actual value in return. It’s that simple.

The sad state of things

Unfortunately, these bidding sites screw the conception of value up from the start by allowing the contractor to set their budget so low without any consulting the freelance professional. In this way, the freelancer loses any bit of control over the project and is forced to succumb to whatever the contractor wants. It’s just so completely broken it leaves me dumbfounded at times.

I feel to properly fix the issue we (us freelancers) need to stop utilizing websites like this as it only makes achieving real success that much harder.

If you are in this boat, the best advice I can give you is to avoid these types of sites at all costs. You may think that in our competitive market you will struggle to get noticed and need to sign up for these sites and accept this type of fate.

To that theory, I respond by saying stop being lazy and utilize your network or even your locale to find prospects. You’d be surprised how much a bit of optimized SEO on your website can help attract new clients locally thanks to Google or Bing searches. Being more proactive rather than just settling for devaluing jobs.

I promise you that if you position yourself correctly these bidding sites will never be a consideration for you going forward.

Spec Work

I would argue that there are a time and place for spec work. My own policy (and advice) is if you are working for free then it should be on something that will potentially earn you work later. I feel it should also be work that you have complete control over like an unsolicited redesign or something of that nature.

A couple of years ago I did an unsolicited redesign of LinkedIn to fill up my portfolio a bit. I did a project such as this because many of my clients required me to sign a Non-Disclosure Agreement. That basically meant I couldn’t publicize any work produced for those clients. That issue sucks if you need to show your abilities in your portfolio and it happened often for me.

I figured a redesign would allow me to reach a wider audience and demonstrate a few areas of skill and knowledge my portfolio wasn’t already showcasing. To my surprise, my redesign got quite a bit of press. In fact, the senior design lead at LinkedIn at the time got a hold of me about the possibility of me working for them. It was pretty neat how it all unfolded.

Spec work you shouldn’t do is work for clients who want to pay you in other ways or not at all. This type of client will probably say they just don’t have the budget when they really do but are too cheap to value your offerings. Avoid these projects at all costs. You’re better than working for free unless it is a project you are truly passionate about or if it's to somehow help someone in real need.

Cold Calls

Nobody likes to be cold called. It has a high unsuccessful rate. The plus side is that it does sometimes work, even if it isn’t instant. It’s rare that I cold call (or cold email) but once in a while the opportunity presents itself to reach out to network and try to win new business.

If you are new to freelancing I wouldn’t start off by cold calling but rather utilizing your network no matter how big or small as a starting point. From there, you can be put in touch with leads that may not know you yet until you get in touch with them. Sometimes this just has to happen unannounced to work.

When cold calling here’s my bullet list of advice/tips to keep in mind:

  • Never seem too desperate
  • Get to the point (No one wants to read or hear a novel. Get straight to the point. Realistically you’re looking for a yes or no answer)
  • Be clear as to what you can offer and summarize it. (Don’t list your skills like every other freelancer. People come to you because you are good at something. Make sure they know it’s that of which you offer)
  • Always seek the decision-maker. Lower-level employees at a business can’t make big decisions in a company. Seek the decision-maker (usually the CEO or president) to win leads.
  • If you start with email, eventually set up a time to actually speak whether by phone or in person. People won’t trust you as much otherwise.
  • You’re going to get more declined offers than accepted ones. Don’t get discouraged and keep trying.
  • Consistency pays off. If you set a cold call quota, maintain it on a monthly or weekly schedule.

Portfolios: The Do’s and Don’ts

Portfolios are necessary no matter what contracted role you have. Designers, developers, writers and all those similar will need to showcase a collection of their best work. This work represents their abilities to the public eye. It’s absolutely essential to have a portfolio. An online portfolio is almost a must-have anymore.

The Do’s
  • Do have your own portfolio - It doesn’t have to be state of the art but it needs to be branded with your personal or business’s branding. I’m not a fan of portfolio sites that are essentially themes for you to choose from. I think if you’re a designer that tells me instantly you’re incompetent even if you just really have no idea how to code. Chances are you know someone who does code you can hire or you can even just hire someone you don’t know to help you develop your own site. It’s truly worth the money and effort as your portfolio is how anyone will judge you going forward. Make a good impression from the start.
  • Do show how you got from point A to point B - Work samples are great but most people looking to hire you may want to know more about your process rather than just the finished result. A portfolio consisting of case studies is a great way to tell a story of how you started and ended a project along with the successes and failures along the way. My new micro agency called Couple of Creatives puts focus on this with case studies for each new project. The case studies themselves are in the form of a blog post with visuals to tell the story.
  • Show only the work you want to be working on - If you like designing websites and only want to offer that service it wouldn’t make sense to show logo designs in your portfolio. Keep it clear and focused to the user.
The Don’ts
  • Don’t show too many examples - We don’t need to see 40 examples of projects you have done. Choose your best work and showcase it. It doesn’t need to be a set amount but if you get feedback from prospects asking for more examples it’s a good sign you need to add more.
  • Don’t list your skills with ratings - Okay, this just may be a pet peeve of my own but the skill charts are absolutely ludicrous to me. A prospect may need to know if you know a certain skill but I highly doubt that’s the sole reason they would hire you. Focus more on what problems you solve for people rather than the tools or languages you use to do so.
  • Don’t overdo it - If you’re a designer or developer you may have a tendency to want to build something abstract that ultimately becomes hard to understand or use for people not used to such a thing. Be sure to just keep it simple and let the work you do stand out rather than being hidden by the busy/noisy presentational layer you may have constructed.
  • Don’t forget contact information - Always give your users a way to contact you. I would recommend having your contact information highly visible on all pages at all times on your portfolio. It is after all, how you get new business.


When prospecting you may likely meet and discuss new opportunities with potential clients. Doing so eventually leads to submitting a proposal for work they may require and work you may recommend.

There are a few things to keep in mind when prospecting I wouldn’t recommend doing:

  • This probably seems obvious but don’t act like a know it all. Clients come to you for help, not to be ridiculed for their lack of knowledge on something.
  • Don’t over promise. You can easily shoot yourself in the foot by committing to more work than you budget for and end up working for free as a result. Take time to factor out all the details of the project. Ask plenty of questions before submitting any type of proposal.
  • Charge what you are worth. I have found that if the price I charge for work seems a little steep to me then I’m usually charging enough. A good way to figure out if you charged enough is to see if the client immediately accepts your offer or asks if there’s room tweak the budget. If they immediately accept you haven’t charged enough. If they walk away, they are just pricing around. If they are still interested but ask if the budget can be tweaked you’ve got the best chance at business.
  • Only submit a proposal if you think it’s worth the time - Creating a proposal is time-consuming. You may very well have a template but there still needs to be some thought as to the project’s objectives, timeline, and budget. Factoring all these things up takes time and if you think the prospect won’t even give it the time of day it’s probably not even worth pursuing.

Time Limits Matter

If your website is set up correctly you may get inbound prospects interested in working with you. This is always exciting because you didn’t have to “hunt” to find possible new work. Those who inquire usually submit a general request for help with something you specialize in.

In my past, replying to these requests as soon as possible has yielded better results than waiting a day or two. People looking for help with a problem rarely have the patience to wait around for you to get in contact with them. If you put yourself in their shoes you probably wouldn’t either.

If you do happen to get a response back you’ll want to then set up a time to speak with the prospect. Rather than continuing via email, you leave a better impression by actually introducing yourself and speaking to them. This goes a long way if they decide to put trust in you to have you help them with your problem.

Now, this doesn’t mean you’ll get the job nor does it mean each and every prospect is worth a phone call but those that could be lucrative will definitely be worth the fuss if you can manage.

Closing thoughts

Freelancing is hard. More people do it than ever before. I started out knowing nothing, scouring job boards and hoping clients would come to me rather than I hunt them. I quickly found in order to get clients to come to me I need to position myself well, build a solid portfolio I am proud of, and ultimately charge what I’m worth.

Doing this combination of things has allowed me to work on more projects I actually like working on not to mention earn more for doing less.

There is no secret to achieving success. It’s going to forever be trial and error. Hopefully some of what I shared connected with you and will help you along your own freelance journey. Share your own success and failures in the comments. I’d love to hear how others go about living the life of a freelancer.

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