Why freelancing is challenging to master (and why hiring out is key)!

Freelancing is challenging to master, but when you build up your trust in others and delegation skills that's when you can truly begin to grow.

I’m my own boss. I’m self-employed. I can choose to work whenever I want, on my own schedule.

That’s what we read in blogs, from other freelancers, and from ourselves. Yet as that honeymoon period comes to a screeching halt, burnout and a growing lack of motivation washes over you.

The truth is, yes, we can all freelance, get our first clients, and feel rewarded. After that? How do we grow? How do we delegate (if we could even bring ourselves to do it)?

The million-dollar question is- how do we make the leap from a side hustler to a full-time freelancer?

As I ventured into freelancing as a web developer, it wasn’t some of these reasons or worries that swayed me. For me, I just wanted to take a step back and “do my own thing”. After working for a company, all I really had to do was take my skills and offer them up to clients. My tools, skillset, and experience got me the initial gigs.  

But after that? I found out the hard way. Trying to cobble together an income with few clients wouldn’t work and getting more and more while avoiding burnout was another matter altogether.

That’s when panic crept in. How did this happen?

Skim through some of the main problems that make freelancing less easy than it looks…

PROBLEM ONE- How do I scale and grow?

Personally, I have a love/hate relationship with freelancing. There are zero barriers to entry, but almost everyone runs into a wall pretty quickly when it’s time to scale and grow their business.

At any given time, most freelancers have a client, maybe two. But it’s going to be tough to get by on that alone. When they realize this, they know that they have to “scale up”. They go out and get handfuls of clients at a time, because, well, more clients = more money? Right?

Nope. Unless they were actively looking for sleep deprivation, anxiety, or burnout, those freelancers would be in for a terrible few weeks.

Essentially, freelancers are on their own. We’re not a multi-employee agency, so we shouldn’t take on as much work as them, but we shouldn’t shy away from scaling either.

In my case, I thought scaling would be a complete waste of time, and that I would lose money on top of that. I was content with the clients that I had in my self-employed life.

In truth, scaling isn’t bringing on more and more clients, until you’re struggling mightily under the weight of the work.

Once you’ve got more work than you can handle- it’s time to delegate.

PROBLEM TWO- What on earth is delegation?

Maybe you’ve got too much on your plate. Or maybe you’re scaling up, and it’s time to hire out some projects. For whatever reason you choose to delegate, you’ve made the right choice in your freelancing journey.

Over the years, I’ve worked with various other full-time freelancers, from those who do all the work by themselves, and of course, those who have some contractors that help them out.

If you’re just starting out, or getting into the groove of a routine, you’ll probably be reluctant to hand over work to others. But for your freelancing to scale into something that you can do full-time, delegation is key.

After all, you’re just a freelancer, doing what you love. If you spend hours on hours sending quotes and invoices, communicating with picky clients, and marketing your services, is it really an enjoyable way to work?

Still a little skeptical about why you should leave your comfort zone and hire out? Here’s what happened to me!


In 2013, I was freelancing, and I had it made. Money was flowing in like never before, and I believed that I was working under my own schedule and being my own boss. Going to bed at 4 a.m. for two hours of sleep? No problem.

At least until… burnout hit. Hard.

After this, I saw freelancing in a different light, and hiring out was the ultimate solution. Freelancing isn’t the utopian “vacation-from-home” scenario it’s usually made out to be.

It’s work, just like at a company. And a ton of it at that.

From sales to marketing, billing to quoting, communicating to revising, I found myself buried under stuff to do- all of which could have been avoided by hiring out.


Us freelancers, we automatically shy away from hiring others, because, well, we just don’t feel ready.

I told myself things like:

  • I can do it quicker than them (with five projects at a given time?)
  • I’ll save money that I’ll have to pay them (by turning down high-paying clients because you’re swamped with work?)
  • I have no idea how to delegate or hire out (that’s why you’re reading this blog post)
  • What if I don’t have enough work for them? (you have too much work, not just enough)

Still worried? Seriously? Were my skeptical statements not enough?

In the end, though, a freelancer won’t be going about projects alone. Whether it be a virtual assistant, an advisor, a contractor, or a partner, delegation is the main way to level up your freelancing game.

Even as you do this, you’re going to have doubts, but you’re well on your way to this next level of business.


At the end of the day, freelancing is the dream life of many, but you have to keep it from turning into a nightmare.

If you constantly avoid growth and change, it’s going to be tough nurturing your business, because freelancing is a business. The biggest problems you’ll face will be around your workload. This goes both ways.

We don’t get a monthly paycheck- if we take a week off to find a client during a dry spell of work, we won’t get that week back. You always have to be on the hunt for new gigs and finding your balance will be a challenging aspect of your experience.

Freelancing’s hard, but you’ll thank yourself for embarking on this path.

You’ll probably look back in a couple of years, with your tight-knit team, and think-

“Why didn’t I start sooner?”

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