I Became an EntrePreneur Because Clearly I’m a Glutton for Punishment

I built my first business at 6-years old – a bakeshop, because when you’re that age, having your own store full of delectable sweets seems like the best idea in the whoooooole wide world. I lovingly designed the awning with alternating red and white blocks that stretched across the windowed storefront. I made the best damn paper cupcakes in Brooklyn and my mother was my favorite customer, exchanging the fake currency I’d cut out from green construction paper for inedible treats with an amused grin.

When I shared a version of this memory with the career counselor I sought guidance from a couple of years ago, she said, “I really think you are an entrepreneur. So much of what you’ve told me about your past and all the organizations you’ve started and your ability to lead people reminds me of my entrepreneurial clients.”

I dismissed her idea fairly quickly as I contemplated all the moving parts involved in running a successful enterprise. “No, no. I haaate having to sell and do the marketing. I don’t want to have to deal with numbers and managing money. Plus you’re not guaranteed a steady paycheck. Who needs the headache? I just want to get paid to think. To research ideas, study society and write about what I think. Where’s that job?”

I could tell my answer exasperated her. She clearly saw something in me that I didn’t or couldn’t.

Last summer, after the “shady layoff of 2014“, I recalled that conversation when I realized I’d been bestowed with an opportunity to make a significant career change. That fall I experienced a light-bulb moment: “Hey dumbass, you have that blog that you put a whole lot of work into for free because you like it. Why don’t you do something with that? People keep saying you should.” So, I did.

A year later, I’ve:

• transitioned from a hosted blog to self-hosted
• redesigned the blog interface
• registered as an LLC, with trademark approval pending
• tripled my social media following
• doubled my blog subscribers
• been paid to write for the first time ever
• been hired by brands to promote them
• attended two blog conferences as an official blogger
• discovered an additional passion for speaking my thoughts as well as writing them, thanks to a radio and podcast appearance.

I am running a business. I have become the entrepreneur my career counselor glimpsed.

Many of the items above seemed unattainable when I started out. Yet, I rarely take the time to stop and appreciate the results of my efforts. I’m proud of these accomplishments, but I still have a long way to go. With what I’ve achieved so far, I cannot yet say: “I make a living through writing, speaking and teaching.”

It’s a difficult undertaking. I’ve wondered many times if I’m making the right choices. Who the hell decides to walk away from tech paychecks to become a writer and blogger? Do people even read beyond 160-characters anymore? I hit 40 in a few years. I’m “supposed” to be firming up the foundation of my career now, not starting over.

 

I only confide in a few people about my doubts. As I’ve discovered, being an entrepreneur is at times, quite a lonely existence. In my experience, those who chose a more traditional career route, such as 9-to-6ers, have the most difficultly relating to and understanding what it is I’m trying to achieve. They don’t always get it. I didn’t fully get it myself. It took months of unlearning the working world view I’d held for so long before I became more comfortable with the idea of moving in a less stable direction.

Some will casually ask, “So are you still blogging?” as though it’s just a passing fancy and all the work, energy and money I put into it, as well as the fears and tears is just something trivial I’m playing around with. It’s insulting. It’s like they’re saying: “Are you done goofing off yet and ready to come back to the real world? Be chained to your desk like the rest of us!”

Earlier this year, I took on a contract job in my former field to pay the bills. The company is a well-known startup and a few years ago I would have had a greater appreciation for having their name on my résumé. However, at this point, I’ve seen what’s behind all the free food, fancy perks and “unlimited” vacation and I no longer buy into it. I’m here for the money, not to pretend like when the board members, C-levels and stockholders make stacks of bills, I see even a 1/100 of it.  I’d rather work just as hard – if not harder, since I’m the only employee – and actually feel connected to the results of my work, as well as get paid what I’m worth.

Family and friends have asked, “How’s work?”

Knowing they mean the day job at the startup, I’d respond, “Oh the blog? It’s going. I’m making progress day by day.” Of course, they press further, “No, the startup.”

I give a speedy summary of the office perks, grumble about the coldness of the environment and end with, “It’s just a day job. I am grateful for the opportunity and the paycheck, but it has little do with my future and I hate every day that I have to go there.”

I get it though. Tech startups are fascinating organisms; I’m just jaded.

Returns aren’t fast and easy when you build your own business. As many a successful entrepreneur will tell you, few people blow up overnight. There are often years of toiling, tweaking and struggling behind what may appear as “overnight success.”

However, if you’re not making sustainable living right away, it seems as though in the eyes of some, you’re failing and again, it’s time to give up the dream. It’s like: “Hey, you’ve been doing this for 6 months. Can you quit your day job yet? No? Well, maybe you should think about doing something else?”

I realize I’m projecting some of my own fears onto others, but much of this stems from actual conversations I’ve had.

I’m not always sure what my next steps are – because in this life, the path is more uncertain, but I’m dedicated to what I’ve set out to do.

I don’t know if I’ll achieve my goals of being self-employed and retiring early, so I can really devote my life to issues that matter, but dammit I’ve got to try. If not in this life, when? The other way of life was killing me softly and life isn’t worth living if that’s what it’s about.

Do you own a business? What challenges have you faced as a business owner? Why did you decide to become an entrepreneur?

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