It’s pretty often that I’m at a freelancer gathering or entrepreneur event and a conversation about business woes crops up. It usually goes something like this:

Person A: “I love what I’m doing, but I just want to work for bigger companies!”

Person B: “Same. It’s so hard to break into, though. I can’t wait until I’m working with [name of a huge, well-known company, like Nike or Disney].”

Person C: “Get that big paycheck! Hell yes!”

There seems to be a consensus among freelancers that working with small (or even mid-sized) companies is a steppingstone on the way to bigger (and, so the logic goes, better) things.

And if you’re a straight-up business owner rather than freelancer, I’m guessing there’s probably some of this going on in your own circles. What are you even building a business for, if not to grow it, hire more employees, grow it some more, hire more employees….?

The whole point of working for yourself is so that you can achieve enormous growth and wealth, right?  

Once upon a time, I used that line on my parents when they were concerned and confused about me no longer wanting to attach myself to one of those Big Name International companies. But that was, uh, a lie.

I knew pretty early on that I wasn’t interested in working for big conglomerates (whether as an employee or independent contractor).

That’s because—even with all their expensive branding designed to make them seem human—big companies feel like a concept. And concepts don’t inspire connection the way, well, people do.

Small businesses or single-person businesses are downright inspiring in every way. They’ve got complexities, grit, and honest-to-god-not-made-up-in-a-marketing-department passion.

3 more reasons why I love working with small businesses:


With small businesses, it’s not a matter of layering a voice over a concept. It’s a matter of drawing a real voice out.

It can be fun to create a voice out of thin air, sometimes. But after seeing and working on one or two branding projects for larger companies, it starts to feel manufactured. Whose voice is this? It’s a voice with nothing concrete behind it but a crew of marketing professionals.

With small businesses, there’s a single person, duo, or small cohort of people that are the lifeblood of the company. And they have a distinctive voice. It may be soft and vague, buried beneath attempts to sound how you’re “supposed” to sound, or just hard to put into words.

Drawing that flesh-and-blood voice out, capturing it, defining it, and spinning it into life on paper is unique to working small businesses. And it’s my favorite part of the process.

 Small businesses are down for one-on-one relationships.

I collaborate best one-on-one. Small business owners are usually excited to work this way.

On the other hand, larger companies tend to envelop their collaborators into their existing network of teams. That style of working often makes me feel detached from the big-picture goal or become overwhelmed by the numerous points of communication. …Which makes it more challenging to deliver high-quality work.

Truthfully, this one is really about how I crave a certain level of intimacy with my work. And that only arises when my relationship with my client feels more like a partnership than work-for-hire.

Small businesses have skin in the game.

Small businesses are full of people who have personally invested their time and creativity into the company. They bring energy and a drive to projects that has nothing to do with needing to please their boss and everything to do with wanting to make an impact.

I love this deep-seated belief in one’s own company. It’s what gets me out of bed in the morning and what makes this work feel meaningful.


You’re probably asked pretty frequently about your goals for your business. And if you run a small business or you freelance like me, you may sense a tiny bit of shaming in this line of questioning.

There may be a hint of “Aren’t you going to grow your business bigger, already?” trickling throughout the conversation. As though you can’t be successful or satisfied unless you’re scaling.

For me, I have no idea what my business may morph into over the years. But I do know that I don’t have a goal of becoming a household name—or working for a household name.

Instead, I aim to lead with my gut, leaning into the things that make me genuinely happy and following where those paths take me. So far, they’ve led me to dozens of partnerships with amazing small businesses. And I’m thinking I’ll stay on this path for a while.

If you own a small business or work for yourself, we'll probably get along pretty well.

Game to get to know each other over a quick video chat?