Being boss doesn’t have to mean that you hold the ranking of “head honcho” in your business. You can be just as boss as every single entrepreneur out there even if you aren’t the employer, but are instead an employee.

Being boss is a lifestyle and a mindset, not an occupation.

For those of you that don’t know what I do—aside from editing the Being Boss podcast and website, allow me to give you a little background. I started working for Emily (co-founder and co-host of Being Boss) in 2013 at Indie Shopography as her client support guy when her business was still relatively young. She gave me my big break in my website development career. Two years later, Emily brought me in to work on her new side project: Being Boss.

Just last year, I was also hired by A Practical Wedding to be their on-staff website developer and tech support. For our long-time listeners, you heard APW’s founder Meg Keene on episode 59 of the podcast, where she talked about finding balance in business and life.

Working for three small businesses and supporting the entrepreneurs behind them over the past year has reignited the entrepreneurial passion that I’ve had since I was too young to grow facial hair. Heck, I’ve been obsessed with the idea of being my own boss ever since the days when I wore velcro sneakers and I played with Hot Wheels in the sandbox after nap time.

During my early years of college, I even owned and operated a successful video game news and media website with a staff of 20+ writers and half-a-million readers a month. That stint as an editor-in-chief, working for Indie Shopography, and getting my Computer Information Systems degree in 2015 were supposed to be stepping stones to my nearly lifelong goal of opening my own website design and hosting company.

Life is funny, though, because sometimes it presents you with opportunities that you never could have imagined but are ultimately better than even your biggest dreams.

Working for these creative bosses has opened doors for me that I never thought would be possible in my early 20s. I’m just 24 now, having only been out of college for a year…and I am happy with my career. I get to do exactly what I love to do on a daily basis, but I get the added bonus of not having to worry about the red tape and responsibility that comes with being the employer behind the whole operation.

I get to live my dream of coding and maintaining websites for a living. I get to make my own hours. I get to take on new projects whenever I want so that I never get bored. I get to work from home, which means that I rarely have to change out of my sweatpants. And best of all, I get to play with my dog whenever I feel like it.

I’m not the owner of any of the three companies that I work for, but I take ownership of my job. Click To Tweet

Despite the freedom that my bosses give me, I own what I do. (Emily is probably laughing after reading that because of how often I forget to do something.) I’m not the owner of any of the three companies that I work for, but I take ownership of my job. Emily is my boss at Indie, but the website development is my specialty and nobody else’s. She and Kathleen are my bosses here at Being Boss, but no one else on the team can edit the podcast episodes like I can. Meg is my boss at APW, but whenever the staff has a tech question or problem, they come to me for the answer or the fix.

The details and scenarios may vary from person to person, but my point remains the same:

You can be a boss even if you aren’t THE boss.

I would be lying if I said that my roles at Being Boss, Indie, and APW weren’t stressful at times. There have been many times where I’ve pulled all-nighter’s to meet deadlines or to fix a broken site. There have been times—like in any job—when the to-do list piled up and I nearly cracked under the pressure. But if that doesn’t sound like a boss, what does?

Above all else, I’m being boss because I’m helping my bosses live their dreams. Part of that is just my ego talking, but the sentiment is still valid. I give maximum effort at my jobs so that my bosses can run successful companies. Helping to grow the Being Boss brand over the past two years has been one of the most fulfilling experiences of my entire life, and I did it all for Emily and Kathleen (and obviously to be a part of something cool).

Emily has told me and everyone listening to the podcast that her business would not be where it is today if she hadn’t brought me on to her team. Indie Shopography is obviously Emily’s baby, but I can take some pride in knowing that a part of that success was because of me and what I was able to contribute to the company.

Successful small businesses are often more than just the work of one person. Click To Tweet

My point in telling you all of this is simple: Successful small businesses are often more than just the work of one person. If you are working as an assistant for a creative designer, or as a social networking manager for a photographer, or as a receptionist for a small flower shop, or as a website developer for several online businesses, you are still vital to the success of that business. You are being boss because you chose to work for a boss.

I’m being boss at my job, and my bosses love me for it.


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In addition to developing and launching dozens of websites for creative clients as the website developer for Indie Shopography, Corey Winter is also responsible for editing the Being Boss Podcast and developing the website. He also moonlights as a freelance website developer. Some of his freelance clients have included and He has even turned his passion for drumming into a world championship-winning gig as a drumline instructor.