What’s Preventing You From Growing Your Freelancing Business?

Pitching paralysis? Fickle clients? Imposter syndrome?

I love my job.

I don’t wake up dreading the day ahead. I have the power to design my schedule as I see fit. I set my own rates, choose client gigs as they arise, and can explore an infinite array of passion projects.

It took a long time to reach this point, but starting my own business was a worthwhile, life-changing investment.

That said, freelancing is still a job — there are aspects of our work that we’d hardly call “work” and then there are other responsibilities that are, admittedly, not enjoyable. And since we serve as both the “employer” and “employee” (and everything in between), we have to wear many hats, ranging from data analyst, writer, and editor to CEO, CFO, and CMO.

These hats are hard to balance on one lonely cranium, which introduces unique challenges that only freelancers can truly understand and relate to.

So, with that spiel in mind, I have a question for you:

What Are You Struggling With as a Freelancer?

Seriously, I want to know — and help if I can.

Why?

The short answer: I wholeheartedly enjoy talking (and writing) about my time in this profession. So much so that I kept a journal of my first year freelancing and turned it into a book.

The long answer: I’ve been a freelance writer for the last 5.5 years, experiencing my fair share of learning lessons, missed opportunities, good fortune, mistakes, unbridled adulation, and suffocating imposter syndrome. I cold pitched, albeit briefly, and endured never-ending stretches of digital silence. I lived invoice to invoice, adhering to a strict budget until I “made it” and started earning more than I did when I worked in investment banking. I’ve written viral articles, guest posted on a dozen niche websites, and contributed content to a few of the world’s biggest financial publications. I’ve learned how to sell myself, keep my own books, network with other entrepreneurs, and hold myself accountable.

But the challenges of freelancing don’t disappear once you reach a point of comfort, confidence, and stability — they evolve alongside you and your business.

To give you some inspiration, here are a few of my current challenges:

Consistently posting on social media

I’ve watched several of my self-employed friends amass a small nation of social media followers — Niharikaa Kaur Sodhi is a prime example. While I’m incredibly proud of her, I’m also a tad jealous.

The not-so-secret formula to building a following is time and consistency. I’ve learned this after writing 175 Medium posts since August 2020, growing my readership to 8,900.

Growth was slow, but eventually exponential — some call this “hockey stick” growth.

As business owners, maintaining a social media presence is a necessity (in my opinion). There are three reasons for this: (1) to spread the reach of your content, (2) to connect with clients, and (3) to connect with peers. Unfortunately, my Twitter and LinkedIn activity has slipped through the cracks lately. That’s a problem.

Narrowing my focus for personal projects

Creative flexibility is a blessing and a curse. I want to experiment with an impossible number of projects, a desire that’s akin to juggling bowling pins (and I suck at juggling).

I’ve written a book. I actively write an investing newsletter. I’ve started Medium publications. And lately, I’ve toyed around with the idea of writing a book/guide or even course on growing a freelance business without cold pitching.

If I would just prioritize one, the odds of it succeeding would likely increase ten-fold.

Sticking to a structured schedule

Freelancing is inherently volatile, which makes it difficult to create a routine. Life gets in the way too.

In a recent post, I shared my latest attempt at devising a streamlined schedule — and it worked…for a little while.

I dealt with some back issues (standing desks and core exercises are your best friends when you work from a computer all day), leading to hours and hours of physical therapy and doctor visits. This, coupled with an escalating pile of client work, caused me to stray from my state-of-the-art schedule.

That’s not good for productivity or personal projects.

Telling my biggest client I’m raising my rates

Raising rates is a challenge every freelancer encounters. It doesn’t help that money is an awkwardly delicate subject in general.

The beauty of the corporate ladder is, in a way, that it’s a ladder — promotions and raises are somewhat systematic. When you call the shots, it’s on you to increase your rates. I haven’t had a problem doing so, except for my biggest client, who accounts for 70% of my monthly income on average.

It’s easy to say I’m waiting for the right moment, but there’s a fine line between strategic patience and costly procrastination.

Would This Help?

Whatever challenges you’re facing, please feel free to tell me in the comments. You can also fill out this survey if you want to remain anonymous.

On a related note, would it help if I gave you insight into my monthly finances? I’m considering starting a profit report, overviewing my business operations — my rates, cash inflows, cash outflows, time inputs, goals, etc.

(In case you’re thinking, “Uhh, Carter, didn’t you just say you suck at juggling?” — yes, but this is different since I already track my monthly activity for my own personal benefit, so this shouldn’t be too difficult.)

Money isn’t everything, but it matters, obviously.

If you think I should do this, can you do me a favor and take 15 seconds to answer the poll below?

And if none of this appeals to you but you’ve made it this far anway, thanks for reading.