Holding Space to Talk Negatives Of Entrepreneurship

I’m writing this as I’m sitting outdoors at a local coffee shop – I feel like being here is the norm lately (I come here a couple times a week) and it’s stemmed from a lack of motivation and uninspired feelings with entrepreneurship. Believe it or not, there’s negatives of entrepreneurship that aren’t talked of often.

I’ve seen it a lot recently on my Instagram and maybe you have too –

“Anyone else feeling unmotivated to work?”
“Working from the couch today… I just can’t focus!”
“Meeting with a friend today for a work date – I’m so excited!”

There are times when entrepreneurship isn’t what it’s all cracked up to be and we need to hold space to talk about it.

Don’t get me wrong – I love my job, I love owning my own business and dictating when I have to work and when I can take time off. It’s not that..

It’s also not the fact that I dislike who I work with or the clients we take on – that’s actually the best and most rewarding part of my job. I love my team and making connections with clients is so life-giving.

What I think it boils down to is the loneliness, the comparison, the constant work-ethic and the “more” attitude that this space can bring.

Something I’ve spoken about on our Instagram before is how lately I’ve struggled with the “more” mindset – I’m constantly searching for what’s next within my business, how I can expand it, make more income, reach more people, do more things. I have an Enneagram Wing 3 (Hi achievers!) and it’s hard to tell this point of me to dial it down and just be satisfied!

When honestly, I just want to reach a contentment point in my business.

Being a Christ-follower, I’ve brought this before the Lord in prayer to help me in my contentment and showing my heart the path I need to go to avoid constantly searching for more. This is a hard thing to get over when social media plays a huge role in the marketing of Chloe Creative: I have to be active, I have to engage with potential clients, I have to showcase our work. Which leads to the destruction point:


I know in my heart that social media is merely a highlight reel of those around me: it’s an obvious point that everyone isn’t going to show their lowest of lows in front of everyone to see… because we all know that just makes us a failure (cue my sarcastic tone here – because that is SO not true).

But that’s what we believe because the Enemy is hard at work in our minds to make us believe these lies.

So what do we do about it? That’s what I’m trying to figure out!

I think for me, the first starting point is sharing your perspective. Share those losses. Share the fears and the scary moments. This is where breakthrough happens, because you’ll start to notice there are many individuals around you who feel the exact. same. way and have been praying for someone like you to share their story so they can share theirs.

As I’ve mentioned above, entrepreneurship can feel very lonely because you are often working from home by yourself, without many people to discuss everyday activities with other than your clients or your direct team (if you have any), or your family members/spouse when they get home from work.

So, to try to battle this loneliness, sharing your stories = community. Community can give you hope that you aren’t alone in your battles. What’s a better feeling than being able to resonate with someone else and say, “Hey, I feel that, too!”?

I’ve had the opportunity to make connections with many wonderful women in my entrepreneurial journey (my photographer, my team, other business friends) but as an adult (I’ve learned this via experience) you really have to work to maintain friendships.

“You’re telling me to do more work?”

It’s not like we are in elementary/middle/high school where you just see your friends everyday and can socialize with them. Nope, if only it were that easy 🤪

You’re telling me along with my busy days, cooking meals, walking the dogs, and all the other responsibilities, I have to meet up with friends?

Well yes 🙂 Community should be a priority to avoid those feelings of loneliness that are bound to come at a certain point in your entrepreneurial journey. Here’s what I’d recommend:

  • If you’re like me and struggle to respond to people’s texts in a timely manner, get an app like Voxer, Slack or just your Apple Voice Notes to have actual audio conversations with your people. This has worked wonders for me because I don’t feel the pressure of actually typing out texts and can just have a genuine conversation back and forth.
  • Schedule a monthly meet-up with a friend and talk about work! For me, I wish I had someone in-person to chat about work things with and relate to the crazy parts of business. It’s a struggle for me to make the time to meet up with someone last minute because client meetings will always be a priority (trying to shift my mindset for this too!), so I thrive more in routine. For example, plan to meet with your work friend every 15th of every month to chat about work wins and losses!
  • Schedule a weekly meeting with something non-work related. In college, this was a small group for me. Every Tuesday night, I met with 10 college aged-girls, with 2 leaders to expand upon a book, a scripture reading, certain topic, etc. This was so life giving and something I really miss having!

Now that we’ve gotten the comparison and loneliness covered, let’s chat more around the constant work-ethic.

You’re an entrepreneur because you have good work ethic. It’s not easy to start your own venture.

But, let’s face it: this is also a negative.

Honestly, who wants to constantly be an over-achiever, working hard to do the “next big thing”? Because I sure don’t. That’s super tiring.

I know that because I’ve been there before and it constantly creeps back to me.

For me, this is the hardest thing to combat because it’s literally changing part of who you are – so instead of thinking about “changing” something about myself, I instead try to “reframe”.

Ask yourself this: where are you placing your purpose?

For achievers, this answer can often be work.

And if you are a Christ-follower, that’s a hard pill to swallow because we fully know our purpose isn’t found in our works. It’s found in Jesus.

It takes a lot of reframing work to figure out where your purpose lies and ensure it’s aligned with your values – for me, I know that I want to place Jesus in front, in center, all around my life to structure my thoughts. So when I struggle with placing works > Jesus, here’s what I do:

  • Talk about it. This can be with a fellow over-achiever and Christ-follower so they can relate to you 100% and share their struggles and reframing skills with you, too. This also includes talking about it to Jesus. Express your struggles and ask for God to help you – He will pull through. 😁
  • Read and educate yourself to grow. When I was right in the middle with this battle, I read “You On Purpose” which really helped me to learn why these thoughts may be in my head and how I can fix them. Think I might need to pay this one a revisit 🙂
  • Stop working. Let me remind you that you own your business and you can dictate the amount of work you do. Although we often don’t want to not take clients on because that affects the income we bring in, it’s often necessary to get back on track with your purpose. This is why we do not take clients in December and we often will have months where we just don’t take on anything additional. I’m working on reframing my purpose.

I can talk years about this topic because I have loads to say and know I always will. But I wanted to share because I wanted to arise conversation about it in hopes someone else can say, “You know what? I feel that exact same way!” and provide a sense of relief.

If you are feeling any of these things, know they are valid and I’m right here struggling with you.

Entrepreneurship isn’t always rainbows. Don’t believe that lie any day of the week.