The Sophomore Slump: Why My Second Business Totally Flopped

When I realized my second entrepreneurial venture – coaching creative solopreneurs on the logistics of starting and running a business – was a mistake, I developed a major case of What Will People Think. I’d sunk thousands of dollars into a business vision, a beautiful brand, a perfectly executed website. Would the brilliant creative firm behind the brand and the talented web designer be disappointed in my failure, ripping me from their portfolios while clucking their tongues? I’d paid a pretty penny for a Photoshop course so I could create branded blog images. Would my classmates – who had put their skills to good use building their online presence – think I was a quitter? And what would my friends and followers think after I’d teased the business on social media, then launched the business on social media, then gone dark on social media because I hated the work?

I shared my fears with a good friend, who just cocked her head and said, “What about you? What do YOU think? That’s all that really matters.”

Sage advice (what good friends are for). Though the truth is there are three responses to all of those questions: 1) my worries were super high school because NO ONE will care, 2) what I think really is all that matters because *I* have to run the business, and 3) never launch a business doing work you hate (even if you’re good at it).

That last one is the first lesson of entrepreneurship and despite the fact that I’m a fairly seasoned entrepreneur, I totally spaced on it. Running a business may be exhilarating and rewarding, but it’s also exhausting, scary, and uncertain – if you don’t like making what you’re selling, you’re in deep shit.

That’s not to say I love every ounce of my nearly-decade-old communications firm. In a nutshell, I write employee and marketing communications for Fortune 500 companies. While I’ve been writing since childhood and always knew I’d write for a living, this work isn’t exactly my passion. But I enjoy it, I’m good at it, I believe in what I do, and my clients are happy (and I like them). That’s incredibly rewarding. The business also affords me the freedom and flexibility to work alone anytime, anywhere; these are core business values for me as they allow me to do my best work – and all of that makes the challenges of solopreneurship worthwhile.

So why did I go sideways with my sophomore start-up?

1. I got caught up in a good idea. In trying to determine what I was an expert at doing, a friend pointed out that I was an expert at being a creative professional who was also a master at running a business. Not every creative can swing the administrative piece of the solopreneurial pie, but I can. So, glory be, let’s start a business teaching creatives how to do it! The problem was that I forgot to ask myself if I actually ENJOY the business side of things. And once I started teaching it, I realized I despise it. The trick is to figure out what you’re an expert at that you also WANT to do. Case in point: I’m the Russell Wilson of stovetop scrubbing after the preparation of a messy meal. I can make that shit shine like it’s never been used. But do I want to start a business teaching people to clean their stovetops? No f-ing way. The solopreneur coaching thing is a fantastic business idea, but I’m not the right person to execute it.
2. I forgot about my core business values. Back up a few paragraphs and you’ll find them: freedom, flexibility, and work alone anytime/anywhere. Coaching requires one-on-one interaction. Coaching requires scheduled meeting times. Coaching also requires believing you have sound advice and methods to share. And while I liked the idea of helping people nail the relatively concrete tasks and processes associated with running a business, the truth is I don’t believe there’s one way to do ANYTHING. I’m not convinced that just because something worked for me, it’ll work for someone else. So while I’m happy to share my success stories and lessons learned, if something didn’t work for a paying client, I’d feel like deep-fried crap. The business just wasn’t aligned with who I am and how I work.
3. I ignored the fact that my passion doesn’t have to be my profession. Here’s the thing: passion or no passion, my communications business works for me on many levels (see above). So why not take that for what it is and seek passion in life outside work? What about a side project? This is how I’ve come back to my core: writing stories. Because that’s what I’ve been doing for as long as I’ve been able to scribble a sentence: entertaining people with words – making them laugh, cry, and think. That’s what I’m an expert at AND what I love. It would be awesome if it put grub on the table, but it doesn’t have to. I just need to do it because I love it.

As for the sophomore slump, I’m over my case of What Will People Think. As a fellow solopreneur advised, “If you’re going to fail, fail fast.” So I did. I shuttered the doors after less than a year of operation. The beautiful business cards have been tucked away. The website is being retooled (yes, this one right here). My LinkedIn profile has been updated so it looks like this never happened. While most entrepreneurs will say their biggest mistakes were made during their salad days, mine occurred after I’d already seen success. Some people might think that’s a head-scratcher. Some might think my first business was a complete fluke, a stroke of luck. Some may think I’m flaky and self-unaware. I think I’m a solid businesswoman who simply got away from myself – my values, my expertise, my passion.

Yes, that’s what I think.

And that’s all that really matters.