Posted in Creative, Life, Study

Cool Careers: The Top Challenges Faced By Entrepreneurs And How To Overcome Them

It’s never easy to start your own blog or business, but it’s always helpful to learn from others who have gone through it all. That’s why I asked some successful entrepreneurs to share their experiences starting off their careers, focusing on the challenges they faced and how they solved them.

Welcome to the first post in my “Cool Careers” series, where I interview people from various careers, and compile their responses into a roundup post. You’ll discover the highs and lows of each profession, as well as how each person started up in their fields. Be sure to stay tuned for more careers in upcoming posts, and let me know in the comments if there are any you want me to cover.

For this first post, I’m featuring people who have launched their own business (something I’m interested in!). These stories will inspire you, motivate you, and equip you with knowledge that is sure to be helpful as you consider various career choices. Read on!

Top Challenge When Starting Off

We all struggle with different things as we start off, but here are some tips for the top challenges faced by entrepreneurs.

Maintaining Balance

Because businesspeople have loads to do everyday, it’s incredibly important to have balance. Racquel Guyton makes six figures with her event design company St Germain Events and Designs while spearheading several other initiatives, and she explains how she found balance: “What helped me find balance was looking in the mirror, having a long and hard talk with myself. Like, girl get your life together! I had to sacrifice some of my old habits such as procrastination and sleeping in… I purchased 2 planners and invested in a project management software.”

Although it’s hard, the first step to maintaining balance is often building self discipline in order to get rid of those bad habits. Look at any successful person – you’ll see that self discipline the number one trait needed to accomplish goals, and lead a healthy and happy lifestyle.

Changing Other People’s Perceptions

This is something many entrepreneurs face as they start up their own business or plunge into the freelance world. Abby Wallace, a graphic designer specializing in branding has reached close to 1000 Instagram followers in just a couple months, and she says that she had people doubting her at first. “I walked out of my 9-5 job on a whim as I could not stand it any more. I had people…wondering why I decided to start my own business with so little experience and have had numerous people suggest that I get another ‘real’ job.” But really, it’s all about mindset! “I know in my heart that this is what I am made to do. I personally don’t see the need to stay in a miserable job for 20 years just to get ‘experience’ – I would much rather learn as I go!”

Karen Ngai, a graphic designer who also has readers from over 50 countries on her blog says that a challenge for her was finding a tone of voice that was true to herself and suitable for her audience: “As a 20 something year old, I find people who are older who are, indeed, more experienced in life can undermine the advice you try to give.” But, she notes, “I also felt heavily responsible for what I write, because what I put in a post might very well influence someones thoughts and behaviour!”

Getting Prepared

Crystal Joey, a blogger with over 1500 Instagram followers emphasizes the importance of doing your research and being prepared before you dive in. “I didn’t know where to start and I spent like 5-8 hours studying about blogging, Instagram, Bluehost etc. everyday for two weeks. I always believe in the preparations. Be prepared before you start.”

Erica Walker co-founded and is the co-owner of, with over 2 million followers on Facebook and over 2 million site views per month. Erica started her blog 12 years ago, and says “The hardest part was having to figure everything out on our own. Everything we did was trial and error. We just did the best we could with what we had. We never gave up and we never stopped learning.”

Building Your Purpose

Rachel Schell helps entrepreneurs create their first online course. She believes that “it is all about the people you are trying to help. If you can truly provide a solution to their problems, then you no longer have a job – you are on a mission.”

Kimberlyn Racoma, who designs jewelry for her company Laola, says that her biggest advice for someone looking to start their own passion project is to simply do it. “If you are so passionate about starting something and can’t stop thinking about, it’s because you’re supposed to. It’s a long, difficult and stressful journey, but ask for help, and remember that you’re sharing your gifts, and don’t worry about 1 person might say because there are 30 other people who need you.”


Marketing is one of, if not the most important part of starting your own business. It’s how you get your clients and customers to find you, and choose you! One of the best ways to market your business is to take advantage of the internet! Door to door sales and telemarketing really can’t compare to it. Just think about how fast information spreads online!

Another method that has been successful for me personally (I run my own piano studio) is word of mouth. Emily Krings, who owns Quill to Keys Content Writing, agrees. “Make sure your product & customer service are top of the line. This will create customer loyalty and inspire your customers to talk you up to their friend and colleagues. The best form of advertisement is word of mouth. ”

Arella Swan, a lifestyle blogger and social media manager, says that networking was the big one for her. As much as the internet is helpful, connecting with others in person and building these relationships is essential to find/retain clients, and build your brand!

Here’s what Racquel has to say about marketing her event design company: “Initially, I registered on directories like the knot, wedding wire and thumbtack. I got some of my first bookings from advertising on those sites. Those avenues opened doors for me to get into the industry.”

Cherie Oduwole offers virtual assistance services, and has a 75% conversion rate for her email list, but she notes that she stressed about finding clients before she launched her business.”I was scared it wasn’t going to work out but I kept reminding myself I’m doing all of this for a purpose. I reassured myself everything was going to be fine before I went to bed at night and that enthusiasm solved the problem!” Cherie advertised through Facebook (where she got her first two clients), and a local job listing website. “Even though I had limited means of advertising, I posted everywhere I could.”

Abby uses Instagram. “If you are a business owner, Instagram will open you up to a whole new community of potential clients and friends all over the world. Especially as my services are business to business, I find it so much more effective to network and strike up genuine friendships with other business owners, rather than going for the hard sell. As long as you are putting yourself out there, being yourself and being a 100% genuine on social media – your ideal clients will come!”


Search Engine Optimization is probably one of the hardest concepts to get a good handle on. It can be really confusing, or too “techie” for some people to understand. Here are some tips that can help improve your ranking on Google.

Keneshia Raymond runs Curvy Unicorn Bridal which designs gorgeous wedding dresses for plus size women. She explains her strategies to get seen: “I have found that using keywords and making sure to name my photo’s and add alt text has helped a lot. I am also in a very niche section of the wedding industry which is good and bad. So I use all of my keywords thought my website as well in the descriptions.”

Karen focuses in on the posts: “It took me a while to learn this, but writing evergreen/cornerstone posts! These are long posts that ideally will have more than 1000 words. You don’t need a lot of these, but they should be the posts you always link back to, making them the foundation of your blog. These not only help you set the foundation for the topics you want to cover, but also helps Google bots find the most significant piece of content from your site.”

Balance Between Work and Life

We often like to devote loads of time into building our business, but what about family time? How do we become successful in both?

A common tactic was to plan out your time. Allot time to write and create, but put it on hold once it’s time to do something else. Another strategy is to carve out certain days and reserve them for family. Racquel and Keneshia, for example, both put aside Sunday for family time.

Caitlin Houston, a Connecticut based life and style mommy blogger who has been blogging for 10 years delves into how she handles this: “I carve out specific time during the week and weekend for blog related work now when I ONLY do that. Then when I am done with my blog work, I put my phone on the charger and focus on my family.”

Abby makes the most out of her time. “Something had to give, so I upped my prices which made me more in line with my perfect client and also meant that I had to take on less jobs each month.” In order to cut off business time to focus on life, she turns off her devices. “I turned off all social media notifications on my phone so as soon as my laptop closes at night, I am off duty and I started scheduling all of my social media content so that I wasn’t scrabbling around for something to post each night. It can be hard to switch off from your business when it is literally your heart and soul, but it is so necessary to avoid the inevitable burnout.”

Erica shares a great metaphor – she doesn’t call it balance, but rather a juggling act. “Each ball, even if for a brief moment, is being held in your hand and has your full attention. You are never really holding ALL the balls at one time, yet somehow, by juggling, you are able to keep them all up off the ground. When you juggle, holding more than one ball in your hand at a time can be extremely detrimental. In life, we call that “multitasking”… and multitasking is rarely productive and more often than not, it is actually counterproductive. It is best to keep your tasks separated and in motion. This way you aren’t ever multitasking. Instead, you are are being systematic. You are switching tasks when tasks need to be switched. You are tossing one item in the air so you can catch the next item.”

Hopefully, by reading the stories shared above, you have learned a thing or two about the starting a business. There will always be challenges, but power through them, use the tips above, and never forget – it is moments like these that make you stronger and better!

7 thoughts on “Cool Careers: The Top Challenges Faced By Entrepreneurs And How To Overcome Them

  1. These are so cool, Hedy! Where do you get to contact them? Woah, like I know not a lot of entrepreneurs (except my father, ofc😂) What do you think would you like to be? I’ve always wanted to start something of my own. This helps.
    Ju xx.

    Liked by 1 person

    1. Thanks Juhena! I just reached out to some people online; I posted a survey to some Facebook groups with entrepreneurs and people who wanted to be featured replied. I’m planning on featuring some other careers in future posts as well. As for a career, I’d like to go into business and start something of my own in the future too! So happy that this was helpful for you. 🙂

      Liked by 1 person

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