Pairing Start-Up Journaling With Intentional Business


Do you keep a journal? I do. I write letters to myself.

When I decided to start a company last year, I knew from the beginning that it would require some kind of self reflecting platform in order to keep my thoughts clear and keep my goals for the business moving forward.

Journaling is not a new form of self reflection. In fact, there are now notebook products designed for journaling that include bullet style formats, goal tracking, daily progress documenting, and more. In my experience, though, writing letters to myself is the most effective form of self reflection. The practice tends to guide me in establishing that much needed self awareness as a business owner.

I consider my start up journal a personal narrative with chapters, with titles like:

“Too Quiet”

“The Chase”


“Evaluate + Simplify”

I’m sure you can see the arch of my narrative here; it’s your typical business growth and self-talk as I meet professional goals and assert expectations for the business I am building. But to me, these journal entries are so much more than business insights. These personal reflections create vision and perspective.

Patience and Motivation

Most new ventures start with fear. My first chapter was that in a nutshell. Reading the words back to myself months after I’d written them, I felt proud that I’ve come so far from my initial feelings of doubt and insecurity around my skills and expertise. My first few months of business revealed the need to be grounded, and also revealed the detriments of overcomplicating my business practices in order to fulfill an unattainable ideal. Gratitude became my core motivating force, which gave my professional endeavors the forward momentum needed to succeed in my first projects as a business owner. I stopped trying to see the results, and trusted myself to just DO!

Keep Going

It’s interesting because the chapter titled “The Chase” focused on experiences I’ve had when it was in my company’s best interest to turn down business. This was something I was not trained to do. I had been exposed to work cultures throughout my career that pretty much consistently encouraged me to say yes, take on any new business out there, and approach it with a “we’ll figure it out later” mentality.

The freedom I found from saying no early on in my business’s history is something I’ve decided that all honest business owners deserve for themselves. My deepening skill sets and the growth of my services have benefited from this clarity, and my clientele are all incredibly wonderful businesses that understand and need my services. I’ve deliberately selected each of them, and that is something I take pride in.

“The chase isn’t about finding business or selling services, but rather, it’s about connecting with people who want to work with me because of who I am, why I do what I do, how I do it, and who I do it for.”

This lesson increased my passion and love for my chosen occupation, making it less scary to go after the client relationships and brands that once intimidated me. Saying no to new business when it wasn’t my specialty gave me and those doing business with me a newfound respect for my business practices. Being intentional about the clients I choose to serve also helps me to efficiently create the high quality results my clients deserve.

From this chapter came an important affirmation: “You are going to build a company people admire, trust, and believe in. Keep Going.”


Re-evaluating The Why

Things like journaling always take the back burner when you need them most. My business is growing. We’re booked up. I’m struggling to find balance. How do I have time anymore for my own brand as my client list and responsibilities continue to expand? Shouldn’t clients always come first? This is where my head was at; clients came first, while my own brand and personal needs were reprioritized to the bottom of the list.

I felt the brand identity that I had intentionally crafted slipping away from my business, and furthermore, I was beginning to feel that loss of identity in my personal life, as well. I wondered to myself, “why do I want to be working all the time?” I knew it was time to start journaling again!

Once I began journaling, I realized that it had only taken 5 months for me to start losing myself, and I frequently caught myself using my most loathed word: BUSY. In my opinion, this is the word that kills sustainability. So, I started an exercise of quarterly reviewing my WHY, or the intent behind my business choices and actions, versus just trying to stay busy.

I gave myself personal assignments, which included reflecting on the following questions:

Why should clients and partners continue working with me?

Why should I create a team, and not a company?

How do I define the alternative to “busy?”  

How can I find meaningful ways to replace “busy” tasks with purpose, reason, clarity, innovation, elevation, and advancement?

How can I find less complicated, more direct solutions?

How can I practice kindness, while still being honest?


The Need to Simplify

With growth comes stress. It’s normal. This is what I told myself, but I decided this fact was not my truth. This is a continuous lesson that I will most likely always have to manage, because of my inherent desire to make everyone happy. Choosing to be aware of this quality has allowed me to gain perspective that I desperately needed at the time.

So how did this translate in my work and client relationships? I decided to focus on the client’s why informing each task and project, versus just delivering a service. Reminding myself of the goals or larger strategy behind each moment I spend working on behalf of my clients creates meaningful work. This journal “chapter” showcases a lot of bad habits that I was able to identify and change.

A few interesting truths I’ve discovered through my journaling practice:

Stop multitasking; it’s unproductive, not more productive.

Stop creating over complicated answers to satisfy a desire to have an answer.

WAIT and learn to trust that the right answer can’t be forced instantaneously.

Let go of the pressure to meet unreasonable internal deadlines.

Stop adding to your to do list.

All these truths were amazing revelations, but my favorite discovery by far is:

Rushing and stressing is useless. It changes nothing, hurts creativity, and it sucks you into mundane, and often fruitless, tasks.

So.. just don’t stress and you’ve already simplified. Being an effective business owner should not cost your happiness or well-being. How is that sustainable?

What’s Next?

I will continue to pursue journaling as a form of self reflection and a way to identify problems in my business and operations. As I approach the coming months and years, I know I will face new challenges, continue to develop my expertise, as well as discover new ways to stay in love with my work, engaged, and innovative. I look forward to reading the letters I write to myself in the coming months, and I encourage you to start documenting that conversation you have with yourself as a business owner, too. Happy journaling!

Company UpdatesCasey Nifong