How to love your sweet little freelance self

I was going to call this edition “How to know when you’ve levelled up”, but when I realized this would go live on Valentine’s Day I thought I’d go a little more thematic with it (ironically, I hate capitalism, but I love Valentine’s Day).

One of the things I’ve been thinking a lot about lately is the fact that freelancing lacks a lot of the success landmarks that are sort of baked into traditional employment. Take raises, for example: If you get a raise at a j.o.b., you might call your mom excitedly or go out with friends to celebrate. But as a freelancer, landing a bigger contract or negotiating better pay isn’t as straightforward. After the exhausting process of figuring out how much to charge, convincing the client to agree (sometimes even bartering for what you’re worth), the feeling isn’t exactly celebratory. It’s more like profound relief, followed by the realization that now you have to deliver on the promises you made in said contract.

I know I’m not alone in this. Meg Wilcox, who I interviewed last edition, put it perfectly:

”One of the biggest pinch points for freelancers is trying to figure out what your next step is. There’s no boss coming and doing a six-month review with you. So, how and when do you decide to level up…or that you have levelled up?”

I’ll talk more about when to level up in the next edition with insights from the equal-parts-generous-and-talented Tim Nguyen. But today, let’s focus on deciding you’ve levelled up—because this ties back to my original question: How do you show yourself love as a freelancer?

Why is it so hard to celebrate freelance wins?

Maybe it’s the hustle culture, or the ever-present looming threat of instability, but even the natural celebration points in freelancing—a published project, industry accolades—can feel fleeting. It’s like if you pause to appreciate your success, you’re somehow falling behind. Take podcasting: A season launch is a huge achievement! But if you stop to soak it in, you’re suddenly behind on the next episodes barreling toward you.

A couple of years ago, at the ripe age of 28, I was diagnosed with ADHD (Attention Deficit Hyperactivity Disorder, which is kind of a misnomer – probably part of why I didn’t get diagnosed until later in life). I’ll be writing about this more in subsequent editions (actually, let me know if you’re interested in that!) but the reason I bring it up here is because neurodivergence fits into my hypothesis of why it’s hard to celebrate wins in freelancing.

There’s loads of research on ADHD and creativity, or “outside the box” thinking – but my personal experience is that most of the people I know who work in my industry are either clinically or self-diagnosed as some variety of neurodivergent. My own diagnosis was eye-opening in many ways, but one thing that really changed how I see myself was thanks to something that my shrink told me about ADHD and self-esteem.

He pointed out that despite being an accomplished, driven, well-educated small business owner, I had incredibly low self-esteem. Like, diagnostically low. And a lot of that probably stemmed from some hallmark ADHD traits that tend to perpetuate low self worth:

• An intense (to the point of paralyzing) fear of failure

• A preference for working with others, but often choosing to work alone to avoid rejection or criticism

• People-pleasing tendencies and weak boundaries due to a need for external approval

One of my favourite people (who also happens to be ADHD) has an amazing phrase for when you need to stop spiralling and just get to the bloody point: “Okay, land the plane.” Land the plane, Jess.

Do I think every freelancer has ADHD? No, that would be statistically improbable. Do I think neurodivergent people are more likely to end up freelancing? Yes—and both research and personal experience back this up.

The grind of freelancing makes it harder to celebrate wins…and maybe the kind of person who’s drawn to freelancing also struggles with valuing themselves the way they deserve.

If I was going to express this problem in my favourite kind of chart, it would look something like this:

Okay, so why am I low key bullying you, fellow freelancer, about self-love on Valentine’s Day? BECAUSE I LOVE YOU. And because I am also trying to love myself, too (please tell my therapist I said this, it’s part of my homework).

One of the hardest things about changing self-perception is breaking a pattern you’ve spent years, if not decades, reinforcing. “If I just work a little harder, I can tell myself I did a good job” is a well-worn path in the freelance brain—a groove so deep, it’s easy to slip into. But what’s harder (and well worth doing) is recognizing that pattern and choosing to step out of it.

Even if it’s just for today, try this instead:

“I’m doing the best I can.”

“That last big step was tough, and I’m really proud of myself.”

“People like me for who I am, not just for the work I do.”

“I’ve come such a long way from where I started – that matters more than how I think I measure up to others.”

“Just because my wins are small doesn’t mean they’re not important.”

If you’re like me, these are hard things to believe…but the more you practice, the easier it gets. From one freelancer to another, Happy Valentine’s Day – I hope you can take a second to love yourself.

x Jess

Here’s me with two of my biggest lessons in unconditional love (Rooney & Indigo) in Waterton Lakes National Park. Photo by my endlessly patient partner, Ryan.