6 Things Successful Freelancers Regret Not Doing Sooner

Becoming a successful freelancer takes years of practice, refinement and good old fashioned trial and error.

However, those who make it to the freelance big-times often share the same stories of screw ups, mistakes and regrets of not doing certain things sooner. Let’s explore a few.

Regret #1: Not Taking the Leap into Full Time Freelancing Sooner

There is opposing advice on this issue.

For instance, my friend Joel Klettke openly admits:

“One of the best things I ever did for my freelance career was keeping my day job.”

Jumping into the deep waters of freelancing without at least knowing what lies ahead could indeed prove fatal for your business but so could waiting too long to get started.

Here’s the thing.

Sometimes you need to get in over your head so you’re forced to dig yourself out.

Often times, getting started is the most difficult step to take. However, once you’ve made the decision to go full-time and are willing to put in the time, energy, and effort to make it successful, you’ll regret not doing it sooner.

Why you ask? Because there is an opportunity cost to not getting started. Waiting months, if not years, to launch your business deprives you of numerous learning opportunities, experience, and project revenue. Not to mention the valuable relationships you would have established.

Once your part-time freelance business begins to grow, you’ll quickly find yourself facing a serious dilemma – do you reject profitable projects due to your full-time job commitments?

At some point, you’ll be forced to make the hard decision as to whether you take the leap.

Regret #2: Not Marketing Their Businesses

Call it whatever you wish but the fact remains:

Your freelancing business is exactly that, a business.

And in order to support it, grow it and make it profitable, you need to market it properly.

But many freelancers, especially at the start of their journey, focus exclusively on delivering the client work and skip promotion.

Now, I admit, doing great work that spurs referrals is one of the best ways to market your business. But, at the start, when you don’t have enough clients, you should focus on building authority and shaking hands and kissing babies.

So, instead of putting in extra hours on a low paid project, invest your time into marketing:

  • Start a blog,
  • Attend networking events,
  • Build relationships online,
  • Build up your portfolio,
  • Start a newsletter,
  • Get active on Linkedin or Twitter,
  • Create a video introduction (or video course),
  • Record a podcast and learn to do millions of other things that could help you onboard new clients.

Regret #3: Not Developing Business Processes

I’ve spoken a lot about the importance of developing business processes here on FBG. So just to reiterate:

Processes organize and help you control your business.

Every time you fix silly errors, you waste time you could be spending on billable tasks. Processes help you keep your business organized and reduce the amount of errors or omissions.

They also help you simplify complex operations.

Processes that define every action needed to complete a task simplify the entire delivery of your services, making your business much easier to run and manage.

Not to mention they speed up the delivery of your services and make you appear more organized and professional.

But, many freelancers never develop processes to organize their businesses. Or wait too long before doing so and in turn, lose clients, projects and revenue.

Regret #4: Not Specializing

There’s an ongoing debate over whether freelancers should specialize.

Some people say that being jack-of-all trades is the better solution. You can take on more projects, attract more clients and thus, earn a greater revenue.

But then there are those who claim that it’s specialization that helps you to achieve it all.

My stand on this issue is simple:

Specialization makes you unique in the market – the purple cow, to use the Seth Godin’s analogy.

As a specialist you are more likely to get picked up by better clients, typically big companies that hire freelancers only for particular aspects of a project and value specialization. You can also charge much higher rates and deliver associated services for which you could also charge top dollar.

And here’s the common trait of almost every successful freelancer I know. Once they discover their specialization, they suddenly regret not finding it sooner.

Regret #5: Not Firing Awful Clients

Bad clients are like the infected zombie arm that needs to be speedily hacked away before it infects the rest of your body.

Gruesome, I know.

But here’s the thing about awful clients, not only are they stressful to work with, they also cause you to lose time, and money. Yet, it can seem hard to fire them because you’re afraid to lose the income they provide.

Bad clients typically offer no prospect for your future growth and prevent you from working with amazing clients who respect your work, pay on time, and refer you to other awesome clients.

Ask any seasoned freelancer and they’ll tell you, they regret not learning the benefits of dropping problematic clients early on.

And many admit that once they did, their work has become more enjoyable and business shot through the roof.

Regret #6: Not Hiring Help When Needed

Lots of freelancers, myself included, can get caught in the hiring trap. Being too busy to manage all the client projects on your plate, but feeling apprehensive about hiring a full-time employee, and taking on the added overhead.

However, if you continually provide excellent work and keep marketing your business, soon you’ll become overwhelmed by projects. And, you’ll need an extra pair of hands to help.

Many freelancers avoid hiring help, even if it means working long hours and putting regular all-nighters.

Here’s the catch.

Hiring help, even if it is part time (or another freelancer you simply outsource to) could allow you to propel your freelance business’ growth. You could, for instance, delegate tasks you don’t enjoy to that person and focus on what you’re the best at. And if you structure the relationship with the employee correctly, it could also make your business more profitable, paving the way for the development of a micro agency (which is exactly what happened to me).

In summary

It’s common to fear making a regrettable decision about your freelance business, career, and income. However, with this list, hopefully you’ll have fewer regrets and more success to show for it.


Written by: Calin Yablonski

Calin is a freelancer, local search marketer and founder
of the Freelance Business Guide.


  • 王睿麒

    Thanks! I am beginner in freelancing job, this article eliminate the some worries from my life. I will keep this working way in my country! – Ricky @ Taiwan

  • Calin Yablonski

    That’s great to hear, Ricky. I’m glad it was of value.