How Journaling Can Make You a Better Entrepreneur and Leader

The most important words you write are ones no one will ever read.

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How Journaling Can Make You a Better Entrepreneur and Leader
Image credit: Sofie Delauw | Getty Images
VIP Contributor
Entrepreneur; Founder and CEO, JotForm
7 min read
Opinions expressed by Entrepreneur contributors are their own.

In 2019, I have written thousands of pages -- emails, memos, texts, articles like this one. Hundreds of thousands of words to communicate and connect. Most of them have an audience of at least one, even if it’s just a quick note to my wife. But not all of them. Every year, a few thousand of those pages are words no one will ever read.

Journaling can often be a difficult sell to productive people. Why would you spend time working on something that by design no one will ever see? But time spent journaling can pay dividends in both your personal and professional life. Journaling can help you organize your thoughts, prompt reflection and generate creative ideas. These processes are critical to being a successful entrepreneur and a happier person.

I started a journaling practice a few years ago. It was a major contributing factor in growing JotForm from a small idea to a company with more than million users. For me, journaling is a way to focus my thoughts into something clear and actionable. Whether I’m working through a new idea I want to test or reflecting on a presentation I wish had gone better, journaling helps me find the signal in the noise.

While journaling doesn’t technically result in a shareable document or an asset I can show the board, it makes me a better leader and entrepreneur every day, making it worth the time and ink 10 times over.

Related: Why It's Time to Dust Off That Journal

The Importance of Reflection in Leadership

Reflection is intentional thought dedicated to evaluating observations and experiences, considering alternative outcomes and interpretations and attributing meaning to inform decisions in the future. Research shows that people who engage in reflection are happier people and higher performers than those who do not. It makes sense. High performers and happy people learn from their mistakes.

Colonel Eric Gail says that reflection is what links our performance to our potential. Experience does not equal wisdom unless you consciously take time to learn from it. To reflect while journaling, I like to follow a structured set of questions. These questions can be general prompts to get the ball rolling or more tailored to the areas of personal and professional growth that are most pressing for me at a given time. A few guiding questions I like are:

  • What ideas or projects am I most excited about?

  • What am I avoiding?

  • How do I feel about my leadership?

  • What contributed most to my happiness this week?

By considering a standard set of questions, I make sure I’m focusing on my highest priorities and can see how my answers have changed. Just like I can track my companies growth with standard metrics, I can track my personal and professional growth over time, looking for patterns and opportunities.

I also found sticking with a template led to greater self-awareness day-to-day. After a few weeks of addressing the same questions, they’re never far from my mind. Each day brings more opportunities to learn from my experiences, and a regular journaling practice keeps those questions top-of-mind.

Journaling as Part of the Creative Process

Freewriting is writing with no prompt or goal. While this exercise may sound aimless, freewriting can help you break through a creative block and help you process your emotions and even boost your immune system. Though this sounds simple -- you just write! -- for people who are used to clearly defined tasks, it can be a bit daunting. How do you know if you’ve done it right or when you’re finished?

Luckily, there is no right or wrong way to freewrite. As far as how you know when you’re done, you can either go by time or length, writing for a set amount of minutes or pages per day. It’s okay if you don’t think the writing is any good. It’s not supposed to be! Freewriting is not meant to be a first draft of anything, but rather a practice that cultivates consistency and creativity.

Artist and creativity guru Julia Cameron created a writing exercise call Morning Pages, or writing three pages longhand of stream of consciousness, putting down whatever comes to your mind without editing or value judgement. She stresses the importance of writing your pages first thing before the rest of the day clouds your work.

If the idea of three blank pages is stressful, try writing for 15 minutes a day instead. Set a timer and write until it goes off. Try not to do anything else. Just write. The first few minutes can be frustrating, but by about halfway through, I usually find my flow and am disappointed to hear the buzzer. Afterwards, I feel energized and ready to apply my creativity to a new idea or problem I need to solve.

Put Down Your Laptop

Most of the writing we do now is digital. While there are definitely some benefits -- it’s faster, always accessible and allows for easy editing -- there are also some drawbacks. Most of us can type significantly faster than we can write with a pen and paper. While that comes with its advantages, being forced to slow down allows us to engage more fully with our ideas. Typing can get material down more quickly, but our processing of that information is less in depth, which impacts recall and learning.

Writing on paper also minimizes distraction. Writing this article, I’ve checked the news once and my email three times. Each time I leave and come back, I have to take time and energy to re-engage. Writing in an actual notebook gives me some distance from technology and lets me be fully engaged in the task at hand.

Related: Keeping a Daily Journal Can Give You Tremendous Power

Make It Work for You

Reflection and freewriting are valuable tools, but if you only use them before a performance review or during a brainstorming meeting, you aren’t using them to their fullest potential. By making journaling a regular practice, you can foster self-evaluation and creative thinking, skills you can apply to your work every day.

Find a notebook and pen you love (or maybe an app if handwriting isn’t for you). A quick Google search will show that people have very strong opinions on writing tools. Bullet journaling is a great tool for the more visually inclined. There are a million options out there. Find one that feels right to you.

In order to make the most out of journaling, I schedule time to freewrite into my morning routine. I put it on my calendar like I would a meeting to signify its importance. Once a week, usually on Sundays as I start to think about the upcoming week, I journal to reflect on how I’m feeling, what’s working and what I’d like to change. By doing both reflective journaling and freewriting at a regular cadence, I get a good balance of pragmatism and creativity, both crucial for successful entrepreneurs.

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