The tough road to starting a business

Organized Jane, The tough road to starting a business

From the outside, my life might seem wonderful. I have a book, a mantra, clients, and a healthy Instagram account. But how does that translate into a business?


As you can probably tell, I love organizing everything, from objects to processes and everything in between. When I’m working on organizing challenges, I barely feel like I’m working, or that it’s even a business—that’s the beauty of passionate work.

Yet, making your passion your business also has its drawbacks. For a long time, I didn’t treat organizing as a business. I downplayed the importance of what I could offer people and I still sometimes struggle with this. At first, asking people to pay for something I love doing seemed crazy and unfair. Over time, my passion had transformed from mere hobby into a well-honed and researched skill. Without really realizing it, I’d become an organizing expert. And experts in a field deserve to get paid for that expertise. But, as we all know, what we deserve isn’t always what we get—more often than not, we need to fight for it. And in that fight, your own worst enemy is sometimes yourself. 

Even before I joined the corporate world, I had the mindset of a die-hard businesswoman.

Throughout high school, university, my MBA and then, finally, within my corporate career, I was always working hard, and constantly chasing my larger goal, which I thought was to be a VP or CEO in the corporate world. I don’t think chasing this goal was the wrong thing to do, and I won’t rule out going back to it someday. But I do think it was wrong to think this was the only logical path that would make me successful—or happy. In my 20s, I was sure becoming a VP or CEO at a large company was the only way to truly be respected by my friends, family, peers, and society. Keep in mind, this was the early 2000s. Lifestyle blogs, social networks, and tech start-ups existed, but weren’t the rage they’ve become. Back then, being an entrepreneur in the lifestyle field wasn’t looked on as fondly as it is today. 

I’ve always known something of what it takes to be an entrepreneur. My parents were hard-working entrepreneurs, first as organic farmers, and then as owner-managers of a fishing resort. Through them, I saw the constant stress, hard work, and extreme dedication it takes to make an independent business successful. For decades, my parents had no weekends off; they were constantly working and dealing with unexpected variables and crises. On the flip side, however, my parents were always happy; there was never a time they weren’t passionate about their work and focused on building the kind of life they truly wanted, one where hard work is rewarded both financially and emotionally, through the satisfaction that comes from knowing you’re responsible for your own success. So why did I think I had to be different from my parents—why did I think I needed to be a manager in the corporate world to be successful? I’m not sure—it’s something I’m still working out.

Many people have asked me: What was my turning point? What inspired me to get outside my comfort zone, and overcome my belief that I needed to become a corporate world CEO to be successful? My turning point was gradual, the cumulative result of surrounding myself with a tribe of positive mentors, mostly through books, courses, and coaching, and through interactions with the business bloggers I followed over many years. Before I had this tribe of mentors, I started and abandoned the exact same business I have now.

Looking back, it’s obvious why my first attempt to start my own business failed.

After completing my MBA, and with a few years of work experience under my belt at corporations in the insurance and construction sectors, I thought I was ready to start my own organizing business. So I did all the usual things: I registered my business, completed my website, prepared content, and was ready to market myself. Or at least, I thought I was ready to market myself.

Intellectually, I was comfortable with the fact that I would have to be the face of the company and drive my own profit. But emotionally, I was terrified.  Also initial reactions from a select group of corporate mentors scared me enough that instead of seeking out advice from a variety of sources (which is what I should have done), I just got discouraged. Looking back, I cringe thinking about how quickly I gave up. If I’d had the support that’s so much more readily available today, from Girl Boss Empowerment coaches and online communities of successful entrepreneurs, or if I’d been pro-active enough to look for that support back then, I probably wouldn’t have given up.

Everyone needs a good network to support them, and I’m no exception. I owe so much of my current success to the wonderful and inspiring growth of lifestyle businesses, so many of which are led by amazing men and women driven by an insatiable need to make the world a better, more welcoming, and—in the case of some of my favorite mentors—a more organized place.

10 years after abandoning that first business, I faced a more direct turning point, one that forced me to question my belief that success could only come from within the corporate world.

My corporate job was moving me—yet again—to another country. The old Jane would have moved anywhere, anytime, to climb the ladder to the next role. But after more than a decade in the corporate world, I’d travelled so much, I was starting to wonder if my home was really a home, or just somewhere I stayed for a few days or weeks between business trips. I’m also terrified of flying, so unnecessary plane travel—like flying from Zurich to Singapore for a one-day meeting—isn’t exactly my idea of a good time.

Don’t get me wrong: I’m definitely grateful for my corporate experience, which has given me truly global business skills and the ability to work with a diversity of cultures on both large and small-scale projects, restructures, divestments, etc. Plus, many of the people I met in the corporate world are still my close friends. Being forced to travel and adapt also widened my perspective on organizing, and informed my development of a simple, structured process that could be applied to a variety of situations and lifestyles. However, 12 years of being constantly at the beck and call of a huge corporation ultimately left me feeling burnt out. The fact that my new role would have required me to spend 50% of my work time travelling provided the push I needed to finally follow my true passion—which involved resurrecting that long-abandoned organizing business.

Thankfully, in my 30s, I’m a lot more confident than I was in my 20s.

This confidence is informed by my many corporate successes and, of course, my occasional failures, including the failure of that first organizing business.

I’m also thankful that today, it’s mainstream to market yourself on social media. These days, if you don’t use social media, then you don’t really have any marketing at all. I sometimes wish I could go back to my younger self and tell her not to care so much what people thought about her. But even though I don’t have a time machine, I can pass this message along to others who have the same fears and doubts, and hopefully make a difference in their lives.

The moral of this story is that whatever product or service you’re selling, if you believe in the benefits and are proud of it, it should never be considered less important than more traditional businesses. Different things are important to different people, and chances are, if there’s something that’s really important to you, it will be important to someone else, too (and, if you’re lucky, many someone elses).

Today, we see plenty of successful businesses that a lot of people might have been scoffed at not so long ago. Blow dry bars, for instances, have become a 70-million-dollar business, while lifestyle bloggers sometimes earn seven figure salaries. And if you ever think your idea is stupid, think of the pool noodle—who could have predicted such a simple invention (with such a silly name, to boot) would become ubiquitous?

The life coaching business has also exploded. The younger me would have scoffed at the idea of hiring a coach, but now I’m so grateful I did, and promote it to everyone I meet. Coaches not only keep you accountable, but can truly help you achieve your desired outcome. Now, I feel silly for doubting the concept, especially since I’ve come to consider myself a type of coach.

To illustrate the depths of my confidence problems: When my first book, Organizing for Your Lifestyle, was released in 2016, I was so proud, and shared it with everyone I could. Well, almost everyone; I still found the need to hide it from my corporate circle, scared my work colleagues wouldn’t think the subject was not “professional” enough. The irony is that the exact opposite is true—the more organized you are, the better you can succeed professionally!

Instead of promoting my book to my extremely large and well-connected corporate network, I actually downplayed it. This turned out to be one of the stupidest moves I’ve ever made. Two years later, when I finally did find the courage to promote the book to my entire network, almost everyone was extremely supportive—much more supportive than they’d been ten years before, when I’d created that first website for my original organizing business. In fact, most of my business has come from my corporate network, and connecting my organizing life to my business life has improved my skills in both spheres. It’s also, of course, invaluably informed my 4-step process

Take it from me: Whether your passion is a side hustle, a full-time business, an idea for a business, or even a hobby, never discount its value or think it isn’t worthwhile.

Most passionate side hustles or hobbies teach you plenty of transferable skills, and they almost always help you grow a network of people who want to see you succeed—which is the best kind of network to have! If you’re not fully self-employed, there are a few side hustles and hobbies that may be a bit too “out there” for some employers to handle. But in the vast majority of cases, you can spin your passion in your favor, to show employers—or just the world at large—that you’re interesting, hard-working, creative, and, of course, worth investing in. If you don’t tell your employer about your side hustle, chances are they’ll find out anyway. So better to be upfront, proud, and make it a benefit to both your current role and your business!

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jane stoller