5 Most Challenging Things About Being An Entrepreneur

Being an entrepreneur comes with its fair share of challenges, responsibilities, and rewards. Typically, my perspective on entrepreneurship is about being a ‘work-in-progress’ and knowing that it’s not about the ‘destiny’ but the actual ‘process.’

Truth is, entrepreneurship isn’t for everyone because it takes a ton of work and the ability to even hit $1M in revenue, let alone profit isn’t anything that is done overnight. The right mindset, work ethic, passion, self-awareness, and accountability all have to play well together. 

More specifically, I love GaryVee’s take as featured on Entrepreneur:

What we see on reality shows and social media is deceiving. Overnight successes are displayed as if it is the norm. Living a luxurious life without working seems to be becoming the new dream reality. And to go along with that, the new “thing” right now is starting a business. It is the sexy thing to do. People today are graduating high school and instead of going to college, going to grad school or saving for retirement, they want to start a million-dollar business. They want to be the next entrepreneur blowing up the Facebook newsfeed, yet they don’t know what is involved to actually get there.

When I decided to jump into the world of entrepreneurship, it was scary for me. I went from knowing that every month I’d get paid by an employer to legit having to find clients that were happy and would continue to pay for my services every single month. On the other hand, the ability to skyrocket my earnings didn’t have a salary cap. 

In today’s blog post, I’ll highlight five of the most challenging things that I continue to face as an entrepreneur, so let’s get to it.

1. Sales

What I absolutely love about sales is when I am able to hop on a phone call and really engage with a prospective customer on their marketing challenges. The part about sales that isn’t the most fun for me is the actual prospecting/hunting. This is where I have to admit it’s not my strongest suit because I feel self-conscious about doing cold outreaches. 

Although, that’s just mostly in my head and I do push myself out of my comfort zone because one of the things I keep top of mind is: “If you never ask, the answer will always be no.” So I march on and push to reach out to potential customers as much as I can. 

This is important to me because it’s similar to the strategy I take on with developing and publishing content. Yes, the content I push out provides value and with that value, I want to build a meaningful connection with my target audience so that we find a way to work together.

2. That Hustle Life

Remember how I said that being an entrepreneur takes a TON of work? Yeah, that’s what I mean by “that hustle life.” Personally, I truly believe that a lot of people who idealize entrepreneurship primarily have their eyes on the end-product — meaning, that false overnight success approach. 

Hustling to me isn’t about working nonstop and never taking time off to rejuvenate. It’s about being laser-focused on high impact and high return efforts. It’s about doing the things that really will move the needle for your business even when you don’t feel like it.


Again, it’s like sales for me. Sure prospecting can be challenging, but it is an absolutely necessity and what keeps the engine running at my company. It keeps me and my team from getting too complacent because truth is, not every single client is going to be one for life. 

3. Paperwork

Just as I mentioned in my Coffeeology post above, the paperwork definitely gets me. I’m not talking about actual paper that I have to file in a cabinet, but the processing of contracts, taxes, invoicing, etc. All of those things are important to the business and I never want to lose sight of them.

Here’s a real example: The first year I started running my company full-time, I was so pumped about growing the business that I didn’t think about everything I had to take into consideration, specifically quarterly taxes. 


I remember hiring an accountant to do my taxes for me. After it was all said and done, I had owed over $70,000 in taxes. That was my first year of running my business, and honestly it was less than a year. I mean I had an MBA and they never taught us about some of the practical things that would really matter if I were to run my own business.

The good thing was that I have always been very good with my money. I’m a very “live below your means” individual. Plus, my business finances and personal finances were separated so I had the money to pay off what I owed in taxes that year without having to go on a payment plan.

Outside of taxes, there’s the contracts between clients and the invoicing, etc. These things need to be organized extremely well. Yes, I do have help, but as I said, it’s also so important I keep a pulse on these too. I don’t want to delegate and forget because it is my responsibility to stay in the know.

4. Life/Work Tradeoff

I know for a fact that my company would have grown much quicker and I’d be generating a ton more in revenue as well as profit if #momlife wasn’t so important to me. Prior to running my company full-time, I fantasized about one day being my own boss and being able to be a hands-on parent where I didn’t miss milestones… where I felt like I was present for the growing years with my kids. 

That fantasy became a reality. I have two kids and I get to be there and enjoy the little moments when I take my quick breaks throughout the work day. 

This isn’t to say that this would work for everyone, but it works for me. This is my juggling act. This is my tradeoff too. 

I just know that once my kids are both in school and become more independent, my time will shift over to growing my business even more and I’m okay with sacrificing a few years of business growth for time with my kids.  

5. Consistency in all areas

Every week presents a new set of challenges with clients, sales, and just overall planning as well as executions. I’d be lying if I said I was always 100% in every single area with zero room for improvements. 

Again, entrepreneurship is always a work in progress. The process and journey itself matters more than just making money or trying to reach and surpass milestones. For this reason, I look at the work I push out as making progress versus trying to reach perfection. 

In a way, it’s much like diet and exercise… Some days I can go for a long seven mile run and feel fantastic. Other days, I might have a cheat day and run 4 miles. I’m still making progress and that’s the key to consistency. It’s the discipline behind it more than the big celebrations.

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