I’m A Business, Man: My First 6 Months As an Entrepreneur – The Good, The Bad and the Ugly

I recently realized that I’ve officially been in business as The Champ Media Agency for 6 months, and what a ride it has been. By now, you know the story of how my business was born in the first place, so I’ll save those pixels and get right into it and tell you that…

It’s hard.

No, really, it is.

And there’s no nice way to put that. It just is. But it’s incredibly rewarding, too.

I already knew (before starting my company) that being an entrepreneur required a lot of grit, but it’s never real until you have to exhibit some kind of resilience.

And honestly, it’s all fun, games, cocktails, wine-coolers and witty repartee when you’re networking to be able to say that you’re entrepreneur. It’s another total beast to actually live that life…every.single.day. It ain’t a game.

So, let me tell you what being an entrepreneur has meant for me in these last 6 months. Some of it’s good. Some it’s bad. Some of it’s just down right ugly…


The Good:

Helping people create, engage and nurture their online communities through copywriting, editing and social media.

I’ve been so privileged to do work that really feeds my values. Twice a month I get to have a front-row seat gleaning knowledge from some of the top people in their respective industries by facilitating Twitter chats for a great entrepreneurship livecast program, #MentorMonday. And that’s just one of the cool things I get to do. Helping to create and execute social media campaigns solely promoting value-added, positive content around personal development is something I’ve discovered that I love doing. I love being a key piece to the puzzle for clients who have online platforms connecting them to thousands, if not hundreds of thousands, of people. I get to help inspire people for a living and it really just feeds my soul.

 Building something of my own.

Despite the difficulties and challenges, creating my own media company from the ground up is SUPER gratifying. Just knowing that what I’m building is MINE does more for me than I ever knew it would. It’s like that problem child (if you’re a parent) or that old beat up car (that’s paid for and is the source of many endearing memories)…it may be ugly, chaotic, awkward, still in development…but it’s MINE. Yea, it’s scary knowing that if something goes wrong, it’s my responsibility to fix it, but the potential for its greatness far outweighs the worries I have about potential failures.

Building my character

Along with the previous point, I’m building far more than an empire (hey…gotta claim it, right?). I’m building ME. I’m building my character. Whenever I would be in the midst of doing something I thought was challenging as a kid, I’d whine to my dad (I was a daddy’s girl…and unabashedly so), and he’d always reply, without fail: “It builds character.” Now, I see just what he meant as I’m building my own business. And I think every entrepreneur would say the same. I’m testing my limits mentally, emotionally and intellectually, causing me to constantly re-evaluate and course-correct. This thing is definitely showing me what I’m really made of…everyday.

Oh, and my work ethic has been SUPERCHARGED. It’s unreal! Why? Because it gets real when you realize that you have bills to pay and investments in your company to make. Suddenly, slacking off on submitting that proposal, client estimate, or pursuing a lucrative, platform-building opportunity becomes unthinkable.

Doing what I love

In a world wrought with people trying to find their purpose and passion, I consider myself supremely privileged in that I know just what that is – and I’m doing it. Even if I have to work at the paycheck plantation fulltime, I feel like I’m doing exactly what I’m supposed to be doing, walking squarely in my purpose and getting gratification from that. I’ve said before that I was a reluctant entrepreneur. And, the ONLY way I’ve survived this long is because I’m doing what I love.



My God! The learning. I feel like I’ve learned more in these 6 months than I have in all my years in formalized education. Seriously. I’m like a sponge…soaking up information from everywhere, applying it, testing it and seeing how it works for my business. In many ways, I feel like I’m sharper than ever because I’m always learning something new and valuable. Experience is the best teacher, and I am getting my fair share of it.

Making connections and gaining opportunities

I really think I’ve networked and connected with more people now than I ever have – even when I was a fresh college grad knee-deep in the job hunt. I’ve managed to connect with so many other entrepreneurs who are grinding it out like me or who have successfully managed to go full-time with their entrepreneurial pursuits (like I want to). Learning from and “talking shop” with them has changed the game for me. I’ve written before about how important it is as a business owner to find your own entrepreneurial village and these folks constantly feed me, put me on to better ways to do business and look out for me on the DAILY with suggestions and leads. The camaraderie and community is unlike any other.

And since I’ve become connected with my “village,” I’m getting the opportunity to do more cool, platform-building stuff – all because I’m forging relationships with others who are like-minded. Without these connections, I highly doubt some key opportunities I’ve been offered would even be within the realm of possibility for me.

But…it’s not all lilacs and daisies. Uh uhhhhh. Remember the part when I said owning and building a business is hard? Welp…here’s (part of the reason) why (for me, at least)…

…or The Bad:


I’m learning as a newbie entrepreneur that in order to keep at least 50% of your sanity, you need to become play-cousins with uncertainty. Everything from financial woes (like chasing client checks even when you charge late fees or a client shaving off half of initial budget) to winning over a new client (devoting non-billable hours to creating a rock solid proposal with NO guarantee of closing the deal), you’ll never have a dull moment. And if you do, check the pulse of your business because something’s severely wrong!


The Balancing Act

This is the most difficult for me, personally. Especially because my “side hustle” has not yet shomoney’d it’s way over into “main hustle” territory. It’s almost like I’m living a double life…working the 9 to 5 by day and plotting to take over the media world (Pinky and The Brain style) by night. Because currently, the job that pays the bills isn’t really related to what I do as an entrepreneur…so exit strategy game is at one hunnid right now. I know that pretty soon this set up for me is going to be unsustainable (as I gain more clients), but right now, it’s one of those “ya do what ya gotta do things.” Build character, right?!



Didn’t I juuuuust write so glowingly about how cool it was to be building something? Well, that same thing can be a thorn in the side. Why? Because I’m impatient (I’m working on it). It’s not one of my strongest virtues, admittedly. Aaaand because it’s not fun. Building this thing brick by brick takes resilience because – newsflash – it ain’t always gonna be rainbows and sunny skies. Building a successful business is akin to running a marathon…or climbing Mount Everest…or jumping off the edge of a cliff and hoping that you deploy the parachute in time. It just takes time. And hard work. And grit. And all those other concepts folks tell you when talking about entrepreneurship. Yeaaa…I want to be Oprah status, but building that -ish? Gets rough sometimes.

The things I mentioned above are things that have to be managed on the daily. These here I’m about to share? Are occasional occurrences, but enough of them together (and if not handled correctly) are enough to make one want to shrink into a ball and hide out…

The Ugly:

Imposter Syndrome

Yep. I have dealt with this (and still do sometimes). If you’re not familiar, the imposter syndrome is feeling like you don’t belong where you are. It’s a running script your lizard brain runs when uncertainty abounds. It goes a little something like: “I don’t know what I’m doing”; “I don’t know enough about x”; “I don’t know enough people”; “this isn’t working, maybe I should do something else”; “I don’t have enough money”; “that client I really wanted rejected me? I’ll never get work.” And on and on it goes.


I honestly had one of these moments (to the point of shedding tears and crying on bae’s shoulder) just 2 weeks ago. I mean it was baaaaad. Like, questioning if I should even be doing this, bad. Like, wanting to cut my losses and send out some more resumes and work for somebody else, bad. And after I dried my tears and talked to someone (who is in business, too) about how I felt, I had a breakthrough, made more connections, took advantage of some more opportunities and got back on the grind again.

What’s important to remember is that if a certain set of circumstances are true (you really do know what you’re doing and you do a great job at it), most of the time the imposter syndrome is a bunch of dirty little lies that creep in during some of your most vulnerable times.

What do I do when it happens to me? I talk to someone I trust, meditate, pray, remind myself of the good work I’ve already done, and try not to make my current situation so catastrophic. It’s imperative to remember that there are times you WILL feel inadequate, but the key is to not wallow or stay there.


This is part of what feeds the imposter syndrome. Rejection is a beast to deal with…especially when you’re still in the building stages. Whether it’s voluntary rejection (having to walk away from a client/project that will not or is no longer serving your best interests) or just plain ole rejection from someone that decides to pass on your goods or services, rejection in any form can be unpleasant. And if I didn’t have a reservoir of resilience built up, I would have packed up my Macbook Pro and quit.


So, when these things happen, I give myself a day to get in my feelings, rant, punt kittens and then I get back to business. And I’m pretty sure that 24-hour “feels fest” will get severely limited to an hour MAX once I mature more as a business woman.

It’s especially hard when you’ve been so good at nearly everything you’ve done (was that a humblebrag?!). Entrepreneurship is different because you WILL fail, but the key is to fail fast to rebound faster. That’s where learning and course-correcting comes in. As they say, if you’re the smartest person in the room, you need to find another room. That said, as an entrepreneur, I feel like I’m a student first and with every rejection, loss or failure, I learn how to do what I do even better.

But you know what else I’ve learned from all this? I’m stronger than I often think I am and wayyy more resourceful, too.


I know I talked about the power of your entrepreneurial village, but there are simply times where you feel alone – especially if you’re a solopreneur like I am. I find that this feeling of loneliness happens when you think your entrepreneurial problems and challenges are unique to you. Granted, everyone’s business has its own set of hurdles, and being so head-down and knee-deep in them can cause you to really believe you’re truly alone – but honestly, most times you’re not.

And sometimes you are. Although it’s become a contemporary buzzword of sorts, entrepreneurship really is taking the road less traveled. And when you’re on that road, you sometimes will be by yourself – especially if you’re blazing a new path, or diving into blue oceans.

There are occasions where I feel lonely and overwhelmed as an entrepreneur. For the first three or four months in business, I felt like this was the way it was going to be – with only occasional pats on the back and patronizing words from peers to comfort me temporarily. But lately, I’ve been trying something new, this whole “closed mouths don’t get fed” idea of asking for help and advice. I used to think that if I asked, I’d be a burden, but nothing could be further from the truth. As an entrepreneur, I’m learning that if I don’t ask, I’m doing myself, my business and my clients a disservice because this journey was not made to go it alone all the time. Every entrepreneur needs a support system.

Burn out

For part of the summer, I experienced what I honestly believed was burn out. After grinding for nearly 6 months straight in earlier this year, I had a few moments of “eff this” and had to step away from the relentless “grind” for a taste. I was head down for so long in the following sequence: work (at the dayjob), gym, work (on the business)…daily…for months. I was my own living embodiment of that Kanye lyric, “lock yourself in a room doing 5 beats a day for three summers” and I didn’t have much balance. And because of that, when I did manage to take a break…I BROKE.


What I learned from that is how vital balance is. Just because you’re clocking more hours doesn’t mean you’re exactly being productive. I realize now that it’s not the end of the world if I’m not using every free second to do something business-related. In fact, I find that I operate better when I live my life and sometimes engage in activities totally unrelated. I find I come back refreshed, renewed and really ready to do impactful work.

This list is not at all exhaustive, but it does encompass many of the most important things I’ve experienced and learned about myself while in business. It’s certainly a labor of love. A couple things I know for sure: I won’t be the same in 6 more months and I’ll have so many more lessons learned.

Who’s in business? Can you relate? What have you learned thus far? 


Courtney Written by:

  • Gregory Kendrick Jr

    That impostor syndrome is real!! Thanks for writing this piece. I have experienced many of the same joys and pains in my first three months as a Executive Director of a small non-profit. I have learned to institute a day of Sabbath into my week so I can be refreshed for the other 6 days that I work. I have also learned that I can gain insight from those who are outside of my field and incorporate some of their practices into my work.

    • cherring09

      Ain’t it, tho? Thanks for reading! Yes! A Sabbath day is so essential for maintaining balance and your sanity. And you’re so right about gaining insight from others outside the field. You can truly learn from anyone! Hope everything is going well at the non-profit :)

  • http://www.strandedhhj.com/ TaiNYC

    So, this entire post is on point and had me nodding my head but when you talked about Imposter Syndrome, I had to make sure you weren’t in the room with me. I call it my inner hater because that broad has a LOT to say without saying anything. I’m working on listening to her less and letting my accomplishments, hopes, and dreams bolster my confidence. Thank you SO much for this piece. By the way, I love the name of your blog!

    • cherring09

      Thanks, TaiNYC! So glad you read it and even happier that you got something out of. Haha…that’s a great name for the Imposter Syndrome: “inner hater.” I’m gonna start using that. You’re so right. It’s like the angel on one shoulder and the devil on the other. Sometimes you just gotta flick that devil off and go about the business of building your business. What is it that you do? I’d love to follow you on social media!

      • http://www.strandedhhj.com/ TaiNYC

        I blog about hair, fitness, and my faith over at http://www.strandedhhj.com. You’re clearly awesome so I’ll be following back :)