FOUR Heartbreaking Reasons Freelancers Fail (and how to address them)

  • April 11, 2022
  • Nick LeRoy

The Freelance Dream or Nightmare?

I firmly believe freelancing is a great option for many but is not the right solution for everyone. Since kicking this newsletter off last year I’ve talked to quite a few agency owners and they weren’t shy in sharing feedback. “I hope my employees aren’t reading it” and “you make freelancing look so easy when it’s not” are just a few of the many comments shared. Truth is, they aren’t wrong but they aren’t exactly right either.

I’ve previously written about freelancers and agencies working in harmony but I completely understand where they are coming from. Entrepreneurship, whether it be a brick and mortar store, building an agency, or even freelance services isn’t for everyone. Let’s talk a bit more about this…

Four Reasons You Will Likely Fail As A Freelancer (and how to address each)

Before we jump into this section I want to challenge you. If you currently fall into one of these situations below and you have your heart set on freelancing, PROVE. ME. WRONG.

The entire basis of this newsletter is to encourage people to not be afraid of freelancing. I truly believe I’m doing everyone a disservice if I were to only share insight and stories about how great freelance life is. These situations truly are freelance killers and the sooner you address them, the better.

P.S. My entire school/career was full of people telling me I couldn’t do this/that or wasn’t good enough. Fuck them – use this post as motivation. PLEASE.

1. You Lack The Skills To Execute The Actual Work

At no point in time in this newsletter do I ever intend to teach you how to build (nor execute) an SEO strategy. There are so many sites that do just this and are much better resources. For instance, check out the beginners’ guide to SEO by MOZ.

The #1 reason people fail in freelancing is due to not having the proper skills to execute their promised services. The barrier to entry in SEO is VERY low. This often leads to people taking on projects that are way over their heads.


Proposed Solution:

I highly recommend that if you are completely new to SEO or digital marketing that you work at an agency for a few years. Not only will you learn the basics behind SEO but you’ll also be able to execute tactics across multiple clients in various verticals and with different technology stacks. Agency world also gives you an introduction to working directly with clients which will also play a critical role in your freelance success.

Starting a freelance SEO career without the proper skill set is going to result in quick failure and/or a lot of clients getting little to no value for their hard-earned dollars. This is by far the number one reason I see freelancers fail.

2. You Lack The Soft Skills To Manage A Freelance Business.

I believe that the best SEOs in the world are ones that we will never meet. They aren’t on Twitter, they don’t speak at conferences and they certainly don’t speak to clients. If this is you and you can rank an affiliate site for “payday loans” then I hope you aren’t even reading this post. Keep on crushing.

I wrote last month about how effective communication is the key to freelance success. It doesn’t matter how knowledgeable and skilled you are if you can’t run the business side of a freelance career.

As a freelancer, delivering on a project is just the beginning. You also need to market yourself, pitch/sell your services and work directly with your clients. If you are unable to communicate what value you offer then it’s very unlikely you will secure projects. Any projects you do secure will require you to effectively communicate requirements to execute your strategy. Furthermore, you’ll be expected to regularly communicate with your points of contact about the larger strategy and overall results tied to your efforts (we’ll come back to this last point in a moment).


Proposed Solution:

Good news! You don’t have to master this skill before you start freelancing. There are opportunities to white label your work which will allow you to focus exclusively on the deliverables. However, I do not recommend that you use this as an excuse to avoid communicating with partners/clients.

Previous SEO experiences regardless of agency side or in-house will help give you experience in communicating. In both situations, you’ll learn to communicate your findings, establish your requirements, ask for resources and report out on performance.

I also find that networking is a great opportunity to work on your communication skills. Meeting unfamiliar people and talking shop allows you to practice in a relatively safe space.

Communication is so critical to freelancing that we all work to get better each day. It’s not easy and none of us are perfect. Continue to push yourself outside of your comfort zone and you’ll quickly find that SEOs (freelance or not) that can effectively communicate are the ones that companies are most likely to hire!

3. You Are Unable To Measure/Demonstrate ROI

Every single SEO engagement should start with a conversation about the client’s goals. Any client who tells you they want “more traffic” is lying. More likely, those who request traffic as a success metric simply aren’t putting enough thought/time behind this question. Fumbling this part of the engagement can have a very real impact on future contract(s)/earnings.

As a freelancer, it’s your job to work with your clients to determine project KPIs. Every company invests in marketing with the expectation of making money from their investment. You, as the “investment” need to take control of KPIs and ensure that you are able to measure and provide data to support a positive return on their investment. I always aim to provide (at minimum) a 3-4:1 return on my SEO services meaning that if my fees are $5,000/month then the client is earning $15-$20,000 in sales.

Clear KPIs and a process to measure/report on ROI is your strongest “guarantee” to keeping your clients happy and regulay payments hitting your bank account.


Proposed Solution:

As mentioned above, the first step to taking an ROI-based approach to your services is to ensure you discuss with your clients what success means AND price your services accordingly. If you pitch your services at 10K/m and the client sells $1 products then they will need to sell 10,000+ incremental products just to break even on their investment (your costs). Many freelancers fail simply because their fees and success metrics don’t align.

The second step is to make sure you are experienced with third-party measurement tools. In many instances, knowledge of Google/Adobe Analytics will suffice. However, many times you may also need access to call tracking or even a CRM.

“But Nick, my client isn’t eCommerce so I can’t track product sales” — no problem. Talk to the client about the value of a lead and the average sale of their product/service.

With this information, you can regularly report on the amount of leads/conversions that the organic channel is driving. The average lead/conversion value will give you a monetary value that you can multiply against the lead/conversion value.

If, in the end, you aren’t able to provide your client a multiple on their investment, you aren’t likely to maintain that client for long. Measure your SEO efforts and report success in $$$

4. You lack the confidence to leave the stability of a 9-5 job

I made every single excuse possible to avoid freelancing full-time. “I’ll miss my co-workers”“I’m giving up an easy paycheck” and “I can’t possibly afford health insurance for a family of five on my own” were just a few that I often share.

While it’s all true (healthcare insurance is flipping expensive) they are what they are, EXCUSES. In fact, had I not been fired during COVID-19, I can’t even say with 100% certainty that I would be writing this post right now. Crazy how the world works, right?

I wrote back in November about the costs of leaving your 9-5 gig to freelance full-time in an effort to add more transparency to both sides of freelancing full-time. It’s not a decision to take lightly.

Freelancing doesn’t need to immediately need to replace your 9-5 income. I highly recommend that anyone who has an interest in freelancing start by doing it part-time, to begin with.


Proposed Solution:

A part-time freelance commitment allows you to experience each of these four situations that typically kill a freelancer’s career with very little risk. You may find that freelancing part-time is the best solution and allows you to make a few extra bucks. I know many who tried it out and absolutely hated it which allowed them to fully commit to the 9-5 lifestyle. For the rest of you, freelancing part-time may become a gateway to fully committing to the full-time freelance lifestyle.

If you are risk-averse but still committed to a full-time freelance career, I’ve included a few additional suggestions.

  • Pay off your debt. You’re likely to make less than your 9-5 at the beginning. Keeping your expenses to a minimum allows you a longer runway to find success.
  • Create an emergency fund. Bad months happen. If you can save 6 months of your expenses that will allow you to push forward during the rough times. As you tap into this account replenish it ASAP as funds become available.
  • Keep your expenses low. Expenses may be deductions but it is not free money. It’s tempting to buy a brand new computer/desk and sign up for all the software subscriptions you dream of. Freelancing, especially in SEO has a very low overhead cost (check out what it cost me to freelance in 2021). As you build up your savings and contract more work you can invest in more luxuries.

Do You Have The Itch To Leave The 9-5 Behind?

Freelancing is an amazing experience that has personally opened up a lot of opportunities I never had before as a 9-5 employee. Is it the right choice for everyone? Absolutely not. However, if you get past the four hurdles outlined above you will be in a significantly better situation to find success.

Keep Crushing!