Want to avoid drifting into mediocrity? Start journaling

“The First-Year Freelancer,” shares tips and lessons I’ve learned in my first year as a solopreneur. Join the conversation on LinkedIn or Twitter.  

Home office? Check.

Laptop? Check.

Business cards? Check.

Personal journal?

When you’re piloting your own ship, it’s important to have all the tools necessary to do the job. A journal is one of them. Mine has kept me motivated and on-track more times than I can count. It also helps me avoid the slow drift into mediocrity, the death knell for any self-guided venture.

I’m currently using two journaling techniques for my professional life: Daily Success and WAWD. The latter is a semi-regular exercise I use to assess my long-term trajectory, and the former focuses on more immediate concerns. Let’s break both of these down.

Daily Success

I usually start my morning by defining what success will look like in the coming day. What would my best self do today? What do I need to accomplish to count the day a success?

My work life is always evolving, so every day’s list is a little different. A typical day’s list might look like this:

  • Be highly engaged and present for each ESL class I teach this morning.
  • Get my writing work done by 2 p.m. so I have time for a walk.
  • Plan tomorrow’s classes with special attention to increasing student output.

This exercise helps me get my head screwed on straight in those critical first hours of the day. I can also review it at the end of the day to see where I’ve hit my targets. This practice helps me see where I am making progress and where I’m consistently falling short.

Success is always a moving target, and its definition changes depending on my priorities in the moment. For that reason, it’s important for me to define what success looks like and set measurable goals for achieving it.


WAWD stands for “Wither Are We Drifting?” I stole this phrase from an episode of Dobie Gillis, believe it or not. In one episode, Dobie’s wise but crotchety high school teacher asks his students to write an essay on this subject. The phrase stuck with me. In the mad scramble of life, it’s easy to drift mindlessly, unaware that the current is taking you far from your destination. A quick but regular check-in with yourself can prevent you from drifting too far off course.

In my WAWD reflection, I ask myself questions about where I am and where I’m headed. These questions include:

  • What new changes or developments have transpired in my work?
  • What possible changes or threats might be on the horizon?
  • If I continue on the present course, where will I end up? Is that where I want to be?
  • If not, what course corrections should I make now to change my destination?

These questions help ensure that I’m in charge of my destiny and not simply drifting with the tide.

The bottom line

Journaling may seem like a frivolous use of time and energy in your business. But, believe me, it’s not. The work people commonly associate with self-employment — sending invoices, doing your own taxes, and the like — that’s the easy part. The hard part is setting your own trajectory and maintaining it over time. Journaling is a powerful tool for doing just that.

Plus, it’s fun. Your journal allows you to observe how you change over time. You gradually see yourself gaining confidence, taking bolder risks and growing greater trust in your own abilities.

Working for yourself is one of the greatest adventures you can take. You’re going to want to remember the journey. Do your future self a favor and write it down now.

Do you use a journal for your professional development? If so, how has it helped you grow? Leave your thoughts in the comments. 

Photo credit: Gratisography


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