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.

The struggles of being an entrepreneur or self-employed | Read more on The Girl Next Door is Black
My first “business” looked a little something like this | source

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.

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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.

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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.

The struggles of being an entrepreneur or self-employed | Read more on The Girl Next Door is Black

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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  • Kronda
    November 13, 2015

    Hi Keisha. Just found your blog via @DUNX on Twitter. I really feel for everything you’ve written in this post! I applaud your efforts and just want to encourage you to keep going. I got a great email from Nathan Barry the other day talking about how to monetize a blog. The gist of the answer was that a blog isn’t really a thing you monetize on it’s own–it’s a marketing channel for your products. And the easiest product to create as a blogger is a course.

    (And then he went on to plug his upcoming training about how to create a course, but I digress).

    That was probably the best explanation I had heard about how people make money blogging and it matches what I’ve seen. Darren Rowse (Problogger dot com) sells courses, photography tutorials etc. I don’t follow him closely so I don’t know all the details. Nathan Barry sells a course about how to write and market a book on your own. James Clear sells a courses about mastering your habits and dealing with stress. Hell, my wife bought one and she does NOT buy courses online!

    I finally jumped on the bandwagon and I’m creating a course for people who need to DIY their websites. It starts next week! I’m super excited. I never run out of things to write about now, because I just ask my subscribers (a small but growing list) what issues they’re having and write about those. (Referencing your writers block post).

    This is growing long, but a few things I wanted to share before I go. First, I created a timeline of my posts about my entrepreneurial journey, which you can find here: http://kronda.com/thread/tech-journey/

    One of the things that has been most helpful is finding community with other entrepreneurs. I’m particular trying to meet other Black and WOC who are doing this and I’ve found a few I’m now following on Twitter. And my friend Stephanie is making a list

    I’m a member of a few different mastermind groups and it’s nice to have people to go to who understand the business owner struggle!

    OK, I gotta make this popcorn and catch up on Grey’s Anatomy, but I just wanted to say hello and don’t give up! It’s a bumpy road, but it’s so worth it to be in control of your life.

  • cathleentownsend
    October 11, 2015

    Hey, Keisha,

    My husband and I own several businesses. We have a construction company, two rental houses, and a fishing boat. And when that’s not enough, like you I do day gigging and substitute teach. I hate it, but that’s reasonable. Lousy pay, and when anything goes wrong, it’s your fault. Blame the sub.

    And now I’m trying to make a go of writing. And when people ask, the expression on their faces is probably similar to those who ask you about blogging. *shrugs* It is what it is.

    Nothing wrong with having a job. I think starting a business is better because you’re making a job, even if it’s only yours. But then it makes sense that I’d feel that way. 🙂

    • The Girl Next Door is Black
      October 13, 2015

      Wow, several businesses; I like it!

      I just told someone a few days ago that I decided to pursue my interest in writing and she raised her eyebrows so high they almost left her face!

      Much success to you and your husband!

  • Mrs. AOK
    October 6, 2015

    Kudos to you, my dear friend!! We can do whatever we put our minds to!! You can do it! {Yes, I said that in the corny “you can do it voice”}
    I really do have faith in you…. you have passion and that passion is going to take you! Keep that fire in your belly.
    I’m trying to make a living from writing and blogging, I need to make this work. I want to make this work.

    • The Girl Next Door is Black
      October 8, 2015

      LOL, I say “You can do eeeeet!” from time to time. Great minds… 😉

      Thanks so much for your continued support, A! I’m so glad we met in the blogging world!

      You are a talented writer and that’s half the battle. We can do it!

  • JoulesDellinger
    October 5, 2015

    I loved meeting you at BlogHer this year and I love reading your thoughts. I especially love that you think of yourself as an entrepreneur — because you truly are. So many times us bloggers are made to feel like we are less important and this isn’t a ‘real job’ except for the few who make it super big. I juggle my full-time job (I’m good at it, health benefits are excellent and it pays the mortgage), consulting side-work (hustle, hustle) and my blog (hustle, hustle, hustle) and I can tell you they are all REAL jobs because they take a lot of REAL work. =)

    • The Girl Next Door is Black
      October 8, 2015

      Joules! My BlogHer pal! I’m so glad we met! 🙂

      I admit I didn’t realize all that I was getting into when I started blogging more seriously. I quickly learned we are definitely entrepreneurs (and often solopreneurs). You are absolutely right, we do a lot of work running these blogs!

      Thanks for your comment and continued success to you in all your hustles. We got this!

  • Markita
    October 4, 2015

    Ok now that I’ve discovered your blog I can’t get enough! You are an amazing writer and I just LOVE your perspective! I really hope that you keep going…it’s definitely going to end well 🙂

    I have a full time gig and a (very neglected) blog. I totally feel your pain. Another frustrating perspective I’ve found is ironically from the blogger/startup community, as I have been trying to establish myself. When they don’t recognize my blog name or realize I don’t have thousands of Twitter followers, I’m totally dismissed. Then if I mention I work for XYZ company that they recognize, they’re interested. But that’s the very thing I don’t wanna talk about! Very frustrating but those people will always be there so I’m learning to deal.

    • The Girl Next Door is Black
      October 8, 2015

      Thanks so much for your kind words, Markita!

      I have encountered some of the blogging snobbery you have, which i think is unfortunately par for the course in any industry. However, I’ve found the blogging community to be more welcoming and less competitive than other arenas I’ve been in. There’s room for many of us. Besides, we all have to start somewhere and no one starts out with a huge following.

  • Heather
    October 3, 2015

    I’m also trying to be an entrepreneur with blogging and make money with other things as well. Blogging is what I’m more passionate about though.

    • The Girl Next Door is Black
      October 8, 2015

      Sometimes figuring out what your feel passionately about is the hardest part! As the saying goes, “Follow your passion and success will follow you.” Here’s hoping that’s true for you and for me! 🙂

  • Liz
    October 3, 2015

    Thank you for sharing your story. I’m stuck in a full time stable career but want to really dive more into blogging. So happy I read such a relatable post this morning 🙂

  • Oumayma Legraini
    October 3, 2015

    Proud of you!! I don’t know if I’m supposed to say this cause I’m only 19 years old. You’re really inspiring!! respect!

  • Baydian Girl
    October 2, 2015

    Where do I even start? At the moment, I’m a serial entrepreneur, running a business, blog and a blogging movement. Crazy enough, though, I love it! However, like you, I’m experiencing the transition of going from an office job to working for myself and I’ve found what you’ve found. Everyone wants to know what the next job is going to be versus how my business is doing. It’s been tough and I really have to curb my tongue but I’m not giving up. I hope you don’t either! The race is for the persistent and if everyone could do it, there would be no such things as the outliers (like us).

    • The Girl Next Door is Black
      October 4, 2015

      I’ve seen your hustle and I’m impressed. I’m always happy to see hard working people get theirs.

      You’re right, it’s not easy and if it were it probably would be less appealing!

      Here’s to ditching the office jobs! (No disrespect to office job-loving & hiring folks. 😉 )

      • Baydian Girl
        October 4, 2015

        Aw thank you! and yes lol let’s do this!

  • Laina Turner
    October 2, 2015

    Amen to this! It is hard for others to understand why we don;t want to work the traditional job which would, in many instances, be easier. Keep on your path:)

    • The Girl Next Door is Black
      October 2, 2015

      Yes! I have often wondered why I can’t just be happy with what many people are fine doing.

      Thanks for the encouragement, Laina! Your blog has been helpful to me during this process. 🙂