Embracing the Challenge: Navigating Life's Transitions as a Full-Time Entrepreneur

Today, I’m opening up about my transition from kindergarten teacher to full time business owner. The plan was to write about this a lot sooner, but as we’ll begin to unpack today - life doesn’t always happen the way we plan…

I officially left my teaching career in May to do more for The Lovely Letter Co.  For the past few years, I’ve had dreams and aspirations for this little company, but life just kept pulling me into different directions. When I felt the nudge to pursue this business as my full time gig, I was so excited because it was finally time. 

It was time to put my time and attention on the things that I was passionate about. I was finally able to prioritize the needs of this business to serve my people well.

As I looked towards my future, I could see it all.  I saw myself doing everything for this business with such ease, beauty and gratitude. I even imagined having rhythms that supported my mind, body and soul (daily walks, morning devos, the whole thing). All I needed to do was make it through the school year, get to work and everything would fall into place. Right? 

Well, as I began my summer, I quickly discovered that this might not be the case. In fact, this new chapter wasn’t at all as dreamy as I envisioned. I was struggling… a lot. 

I felt overwhelmed by the pressure of having to run everything on my own. All those dreams and aspirations? Well, I had no idea how to prioritize them or put them into a system that supported my productivity.

I often found myself in a wrestling match with myself where in one moment I felt like I was on top of the world and then, in the next moment, I was drowning in failure and chaos. 

This is the life you’ve been dreaming of, this shouldn’t be that hard. You were made for this. 

Maybe this isn’t for you. You should just get a normal job. It would be more stable and more predictable.                 

I was stuck in this frustrating paradigm where I was kinda living my dream but it didn’t feel like my dream. I wasn’t sure how to feel or if I was entitled to have these feelings. This was an exciting transition I chose for myself. How could I complain about that? 

I’d like to pause here for just a moment to ask you if you can relate. Have you ever had a similar experience before where you’ve gotten to that next exciting chapter but it’s not at all like you pictured? Think about it.

Maybe for you it’s marriage. You’ve been dreaming of being a wife since you were a little girl and yet it’s hard because you don’t always agree with your partner on everything.

Maybe you recently bought a home and it doesn’t feel so much like home. 

Or maybe you recently became a mom, and while you love your child, there’s still a piece of you that misses who you were before.

As I’ve had conversations with other women, I’m realizing that it’s hard to admit that good transitions can be hard. There’s this pressure to celebrate them at all times because admitting it’s hard would mean we’re complaining, ungrateful or that we don’t actually trust Jesus at all.  

Ironically, I’m also finding that this mindset isn’t serving us at all. In fact, it’s robbing us of human experience. Mountaintop moments don’t always have to feel like we’re on a mountain top; Joy and sadness actually can coexist (Have you seen Disney’s Inside Out?)

I’ve found that when we finally start to admit that something is hard, and we acknowledge the feelings that come with that, something shifts. The blinders come off and we begin to see life in a new way. Our understanding of ourselves and of our situation becomes a lot more clear and we actually discover a new type of gratitude that is genuine.

How do I know? Well, I’ve experienced it.

As I’ve thought about myself, how I function and accepted the realities of becoming a full time business owner, I can’t help but have so much compassion for myself.  I’ve never done this before, so of course It’s going to be hard. No class, mentor, or even experience could actually prepare me for the novelties of running my own business. On top of that, I’m a human that thrives in routines and getting things right and yet none of those things are true at this moment. 

That’s hard.

While I’d love to tell you today that accepting my feelings and declaring “hard” has solved all my problems and cured my anxieties, I would be lying. The truth is that I still struggle most days. But instead of going down the rabbit hole of toxic thoughts (and job applications), I now know why I’m feeling this way. In light of understanding these things about myself and my situation, I can take control of my thoughts and speak truth over myself. Here’s what that might look like: 

Shoot, this project didn’t work out. I should’ve done x, y and z instead. Next time, I’ll know how to handle this better. I haven’t done this before. 

I’m so exhausted from the week, but I have so much to do. Maybe I should grind it out. Or I’ll do a brain dump and shelf it for later. No one is going to die. The business isn’t going to fall through. It can wait.  

Do you see the difference between these thought patterns and the ones I was having before?

We do more damage when we hold everything inside. We hurt ourselves and we hurt the people around us. The good news is that we can choose to live differently.

So as I sign off for today, I’ll leave you with some questions that should help you reflect on your circumstances and all the feelings that come with it. My hope is that this will guide you towards a place that is filled with more purpose and freedom. Think about these things. Share them with a friend. Share your experience in a comment below. We are here to support you on this journey.