Freelancers: Thinking Small is Actually a Viable Lifestyle, If It’s Right for You

Jim Dee
Jim Dee
Apr 12, 2019 · 6 min read
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Photo by Michal Ico on Unsplash

As a self-employed individual for a decade, I’ve found my way onto scores of email lists that have to do with growing one’s business — a skill that, admittedly, self-employed professionals need to survive. But, one thing I’ve noticed lately is that there’s a theme of “nonstop growth” inherent in so many of the messages I receive, as though everyone’s goal should be to hustle 24/7 toward becoming a giant corporate entity.

Everyone wants you on the big highway, when in reality there are small paths and trails out there that are surprisingly pretty rewarding. (See pic, above!)

One guy sends me a regular email newsletter about how to “grow my agency.” Sure, it has its decent business development points inside, so I read it sometimes. But, occasionally, I’ll pick up on messaging that, if you’re not shooting for building a giant business (tons of clients, tons of employees, all of the normal corporate-think stuff out there, etc.), then there’s something wrong with you.

Corporate America Middle Management Hell

My experience was this: Unending meetings, sitting in traffic, thinking about office politics, having little freedom or time to pursue personal interests, being places I didn’t want to be, at times I didn’t want to be there, working overtime, suffering the wide-ranging idiocyncrasies of bosses and heirarchies — or, hell, even working full-time at all, to be honest.

Sure, someties I got free golf. Everyone loves golf in the corporate world, right?. But, I get bored after maybe 9 holes. It’s just not my jam. Maybe if corporate networking happened at rock concerts, I’d have taken to it more.

All for the security of a decent salary and a couple of weeks of annual vacation, right? Livin the dream, they say.

It wasn’t for me, though.

Somehow, I escaped the corporate world after two grueling decades of ladder-climbing, soul-crushing, nine-to-five-plus-overtime-plus-commute-time, suit-wearing, meeting-going monotony. Trust me: The last thing I ever want to do is to be in that mode ever again. I sure the hell don’t care to rebuild it myself, as everyone advises!

What I Stopped Doing

So, I dropped everything and moved to Portland — somewhat famous, as Portlandia famously portrayed it, as “the place young people go to retire.” I took on freelance marketing and web gigs as I built up a client base.

When I had work, I did it, and luckily it was enough to get by. When I didn’t, I wrote blog articles to help drum up business. I preferred that to insanely overpriced advertising, hard-selling cold calls, or other types of pain-in-the-ass marketing techniques I’d learned in the corporate world.

Yes, I reluctantly “networked” a bit, but to be honest had grown tired of the superficiality of that whole scene, too. Classic corporate burn-out, I suppose.

I literally gave all of my suits away, threw out all of my ties, let my hair grow wild, and stopped wearing business casual, even. I went straight to jeans, rock and roll t-shirts, hoodies, and even a bandana on my head — in other words, just my own dress style in which I felt (and still feel) most comfortable.

What I Started Doing Instead

I attended client meetings dressed this way (and still do!). And, in Portland at least, the clients were (usually) more dressed down than I was! Sure, many clients were still in that suit-wearing, corporate mode. But, they didn’t care how I presented myself outwardly.

It was strangely liberating. I always felt one had to “dress for success,” as though wearing a suit (which I always hated doing) was critical. (I suspect back east, dress matters a bit more than on the West coast, admittedly.)

I walked into huge, respectable corporations that way, and walked out with deals. It wasn’t the superficialities people responded to after all — it was the substance. If you know what you’re talking about, people will hire you. It turns out professionalism has more to do with communication style and technical ability, in my world.

I stopped going to “client-building” types of networking meetings — all of those annoying groups where you join up solely so that people can refer business to each other, always meeting up at some vanilla chain restaurant at like 7:00 a.m., everyone eager to show one another how much of a go-getter they are.

Instead, I started hanging out with my own peers — other web developers and marketers from around town. Instead of talking about leads and boring business headlines, we talked about HTML, PHP, CSS, and CMSs. We shared actual, useable tech tid-bits. And, guess what? We referred each other to prospective clients because we got to know who’s good at what.

Over time, my business grew organically, simply via referrals from colleagues and clients. If I had too much work, I’d pass opportunities along to colleagues I’d gotten to know around town or online, and them to me. We still do that.

What I Missed Out On

What I could have done, if I’d listened to so many voices in my inbox, is to hoard all of those clients as they came in, accepting them even if I didn’t have the capacity for it, and farming out the work, project managing all of it instead of doing it myself. And from there, I’d simply expand that concept until I had freelancers doing everything, and from there slowly convert those to in-house employees.

Except… Fast forward 5 years, and you’re sitting in an office spending your mornings hashing out HR issues with Jonathan, your office manager, and trying to wrap your head around financial reports from your Brittany, your CPA.

I’m not saying that’s not a respectable business model, of course. But, it wasn’t me. I have zero ambition to grow my business into a giant agency, no matter how synergistic the in-house pinball machines are or the kombucha on tap may be.

Why We Do This

We stress constant growth because we’re Americans, I believe. That’s our model, and the world knows it. It’s tough to extricate yourself from this deeply ingrained line of thinking, actually, if you’re an American. We have big dreams for success, media-fueled ambitions for luxury consumerism, and social-media fueld ambitions for personal fame.

Ironically, I didn’t even realize we Americans do this so intuitively until I lived out of the country for a while. For example, in India we met a painter and, upon seeing his work, we offered him nonstop ideas for building up a business selling his works. We fired off one idea after another at the man, and it came naturally.

But, the guy finally looked at us and said, “Thanks … but we’re okay. We like doing things the way we do them now.” There wasn’t any world-domination ambition in the guy and, frankly, he really was doing okay is it was.

I think that experience helped me accept my own opinions on the matter — that you don’t have to strive for some giant thing. You can be okay with simply making a decent living.

Life of the Small Player

I’ve often called myself “The Dude” of web design, simply because of my own laid back approach toward growth. I pass on opportunities all the time, if they’re not in line with the type of client and/or work I actually want.

Being “The Dude” doesn’t mean I don’t know what I’m doing, or that I’m poor, or unsavvy about anything in particular. It’s not for everyone, either. So, don’t @ me — I’m not disparaging you if you’re super ambitious!

But, actively managing my approach toward growth also offers me freedom that I cherish. I can (and do) spend time doing all sorts of things I could not do otherwise. So, all I’m recommending is to take a minute from time to time and consider if where you’re at, and where you’re going, makes you happy work-wise. If you want to be Mark Zukerberg, that’s cool. But, you can also be absolutely content without such business ambitions.

🐱 ✍🏻 Jim Dee maintains his personal blog, “Hawthorne Crow,” and a web design blog, “Web Designer | Web Developer Magazine.” He also contributes to various publications. Find him at, his Amazon Author page, Facebook, Twitter, Instagram, LinkedIn, Medium, or via email at Jim [at] His latest novel, CHROO, is available on If you enjoy humorous literary tales, please grab a copy!

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Jim Dee

Written by

Jim Dee

Web guy at; author of books & blogs. See:

Web Designer / Web Developer Magazine

WDWD Magazine features articles on web site design / development, internet marketing, social media, SEO, and topics like marketing, communications, business development, etc. Editor: Jim Dee of Array Web Development —

Jim Dee

Written by

Jim Dee

Web guy at; author of books & blogs. See:

Web Designer / Web Developer Magazine

WDWD Magazine features articles on web site design / development, internet marketing, social media, SEO, and topics like marketing, communications, business development, etc. Editor: Jim Dee of Array Web Development —

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