5 Years Later: Freelancing Lessons I Wish I Knew Sooner

Last Friday marked the fifth anniversary of my leap from banking into the world of freelancing. Reflecting on the whirlwind of these past years, I can’t help but reminisce about those early days.

My “pain points” were much simpler in July 2019. I was incorporating my fledgling business, setting ambitious goals, connecting with my initial clients, and just basking in the novelty of working from home with a wide open schedule.?

While I'm still thrilled to be freelancing, my hurdles look quite different. So, in honor of my fifth anniversary, I’d like to spend today talking through five current pain points and lessons I’m grappling with as I continue scaling.?

Navigating Retainers Without Scaring Away Prospects

Transparency and near-term predictability are rare in the freelancing world. While retainers can fix that, they also pose a commitment that might intimidate new clients. One way to relieve that hesitation is to start with a trial period or project. That way, both parties can test the waters without locking into anything long-term.?

They can see how valuable your services are, while you can uncover red flags that you wouldn’t necessarily be able to sniff out ahead of time, like poor communicators or harsh editors. In turn, you can account for these in your actual contract, or move on.??

Avoiding Unwanted Payment Methods

It’s 2024 and I still have clients that pay via check. In case you don’t have clients who pay you this way, let me break down why it’s a problem.?

1. Firms often batch their check writing, which means there can be a delay between invoicing and check processing.??
2. Mail can take one to two weeks to arrive.?
3. Mail can get lost (it’s happened to me more than once).
4. If I’m ever traveling, I can’t check my mail or deposit checks until I return.?

Suffice it to say, checks are a headache. So, I started mandating online payments in my writing agreements. Those who are adamant that they can only stroke physical checks (which I have a hard time believing) will pay a convenience fee.?

The Compounding Value of a Portfolio

Okay, this isn’t exactly a pain point anymore, but it’s something I’ve been thinking about.?

In retrospect, could I have committed more hours to prospecting in my early years? Yes.?

Would it have led to more work and, thus, more money? Probably.?

Is it also fair to say that prospecting is a comparative breeze thanks to the projects I can showcase from year five versus year one? Absolutely.?

In short, it helps that I can lean on a portfolio that’s been honed through years, not weeks or months. To put that another way, it’s easier to land strong clients when you’ve already had strong clients.?

Setting Boundaries Is Essential for Success and Sanity?

This year, I started prospecting regularly for two reasons — first, to have more control over my pipeline and, two, to mitigate my client concentration risk.?

The flip side is now I have to manage more project timelines and expectations. Setting boundaries has been integral to my sanity. While my typical turnaround time for a project is five business days, I’ve had to set the expectation that my timeline doesn't start until I have capacity; a client can’t drop a project on me out of the blue and expect me to turn it back to them in a work week.?

Subcontracting Takes Months to Actualize?

In my opinion, the key to next-level growth as a freelancer is through subcontracting. In a way, this turns you into an informal agency and allows you to increase your pipeline (and profits) without overloading your schedule.?

The trouble is that this system takes time to establish, particularly vetting freelancers and ensuring the right writer-client fit. It’s slowly coming together, but this has been a work in process for the last seven months.?

For those of you who are deeper into your freelancing careers, what have you found to be the greatest challenge?