No One Listens to the Quietly Successful Entrepreneur

Gillian Sisley

Sorry, I’m not going to glamorize my entrepreneurial journey.

Photo by Jelleke Vanooteghem on Unsplash

I realized early into writing online that most aspiring entrepreneurs aren’t interested in my quiet style of entrepreneurship.

When I first started writing online, I had the intention to publish articles about 2 specific topics: writing, and entrepreneurship. Two subjects I’m qualified in and felt I could authentically write for my readers.

As a social media marketer, I also care about the data and stats. Mine were showing that:

  • My articles about writing were performing well
  • People really responded to my personal stories about sexual assault, womanhood and consent
  • My entrepreneurial articles weren’t doing so well

My fiancé and I were at a fancy restaurant a few years back to celebrate our 3-year anniversary of dating. We were 6 months from our wedding day, but despite our tight budget as we saved up for the big day, we decided to splurge on a romantic dinner.

Over candle-light, I watched my fiancé eat his panko-crusted parmesan salmon. I twirled some noodles around my fork, trying to catch a stubborn chunk of chicken at the end of my fork’s prong.

As an avid online reader and former entrepreneur himself, now a recently reborn 9–5er, my fiancé asks,

“How’s online writing going? Is it different than you expected?”

I consider his question for a moment, and nod slowly, “Yeah, it’s going really well, actually. I’m learning very interesting insights as I go along. Like, I started out expecting to write about writing and entrepreneurship, but…”


I take a deep breath and look at him pointedly, “I don’t think people want to hear about my style of entrepreneurship. I don’t think they’re interested in it.”

He furrows his brows and takes a moment before saying,

“I think you might be right.”

I couldn’t exactly be mad at him for agreeing with me because, well, beyond what my stats were saying (and numbers don’t lie), I read entrepreneurial articles online all the time and the authors who write them, well… they’re not sharing the same stories and realities of business ownership that I am.

It’s not all glittery unicorns and Instagram filters.

When I first started my business, there were others in my life who thought to themselves,

“Well, if she can do it, so can I! I’m starting my own business, too!”

And guess what… they never got very far.

Because there’s a misunderstanding of how easy it is to start a business. And by looking at a quietly successful entrepreneur, one might think that starting and running a business, and achieving a full-time income, is a breeze. They make assumptions without doing the research.

If they took the time to ask the questions, they would discover a very different truth.

Just because an entrepreneur is quiet, does not mean they aren’t working their butts off behind the scenes and making a solid living.

Barely-informed, aspiring entrepreneurs fail before they’ve even begun because they have deeply underestimated the amount of determination, commitment and 12-hour-days-for-a-year-or-more it takes to create a business from nothing and make it successful.

That’s not the realities they want to hear about, or read about. And I can appreciate that, because we all only want to daydream about the good stuff, and forget about the bad.

I’m not what most people expect when they hear “entrepreneur”.

I’m not interested in growing my business or my team.

Apparently, that’s a big entrepreneurial faux-pas.

But to be honest, and I know many quetly successful entrepreneurs who feel the same way... we just don’t really like working with people.

I love my clients. They’re wonderful human beings. I’m very picky with who I work with (I am blessed enough to have that luxury), and I always enjoy the banter before we officially start our meetings. I think humans, in general, are incredible beings capable of love and compassion and empathy and healing the broken world we live in.

But I don’t really like having clients.

And I would never hire an employee or outsource my work no matter how tedious I find the task. I prefer to work by myself, running my successful company from the quietness of my own home with my high-maintenance Shih Tzu and my yoga pants.

That’s just not the description you hear successful entrepreneurs with thousands of claps writing about in their Medium articles.

In such a glamorized entrepreneurial world, my style of business-owning might underwhelm people.

I’m not interested in making millions.

I’m not interested in growing my business beyond the limited capacity I can take on by myself.

I’m not interested in renting an office space and driving to that office space every day to sit there and think about how I wished I was back home — with my dog and yoga pants.

I am interested in reading a book in the accent chair in my living room during my lunch break.

I am interested in going for walks in the neighbourhood with my dog when I need to refresh my mind, whenever the hell I want.

I am interested in supplementing even a little bit of my income on Medium through monetized articles.

Because that way, I can go a whole day without seeing or speaking to anyone until my fiancé gets home and, quite frankly, I really like it that way.

And that’s not the kind of entrepreneur readers are interested in reading about online. The ones who are freedom-driven, rather than money-driven.

Quietly making a comfortable, reliable income just isn’t sexy.

The keeps-to-themselves kind of entrepreneur is underrepresented on this platform. I suppose because we’re not seen as much of an inspiration, and our story, isn't, well… sexy.

But we exist. And we live a reality similar to many other louder entrepreneurs who are preaching their stories on this platform.

Because at the end of the day, even though we are quiet and content and reserved, we are still part of the 10% of unlikely businesses to survive, when 90% of others fail.

I’m just a regular, introverted person who happens to have a successful business, a passion for writing and a belief in valuing my freedom and flexibility over all else.

And that’s just not the kind of businesswoman aspiring entrepreneurs are interested in reading about online.

Aspiring entrepreneurs want to read about the entrepreneurs who made big leaps and failed hard and got back up and leaped some more and then made millions and almost went bankrupt and rose from the ashes and now they’re sharing their story with you of how they got there and how you can too.

That’s just not me.

The bravest thing I did in my business was taking the leap of faith at 22 to start it. And at the time, that was a hell of a big deal. It was exciting and thrilling and impressive and ballsy. I thought quite highly of myself, and believed I had so much to tell and teach the world about being a “badass lady boss running her social media empire”.

Meanwhile, I’m writing about being a badass while updating my Instagram account in yoga pants and a hoodie with a tea in hand, lounging around on my couch. That’s what I thought I was supposed to do, because that’s what everyone did. People loved hearing from me then.

And I suppose that’s the point I’m trying to make — so much of entrepreneurship is glamorized online. There are entrepreneurs talking about how they’re living their dream and conquering new adventures every day and flashing their expensive cars (I can show you a picture of my 2009 Honda Civic Coup, if you’d like) or taking artistic shots of their coffee mug… but what they don’t show is the other 95% of the time when business is simply about putting your head down, doing tedious tasks and tackling administrative work out the ying-yang.

Because that’s not the entrepreneurial story people want to hear, no matter how true it is. They want the Fast & the Furious rendition of business-owning, without the hours of cut-outs and extras slotted in which, arguably, make things far more realistic.

This is why non-entrepreneurial readers or aspiring entrepreneurs can develop an unrealistic perception of what it’s like to actually start, run and successfully manage a business.

As for me, I’m happy to just quietly continue my entrepreneurial journey making good money, maintaining a good reputation, travelling the world with all the freedom and flexibility I could ever want and striving for a fulfilling, happy life in the suburbs with my high-maintenance dog, my incredible fiancé and a quality cup of proper English tea.

Because to me, a quietly successful and introverted entrepreneur, that is the absolute dream.

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