During my first coaching session with Chrissy, a special education teacher, she told me her big idea: to create empowerment binders for her students. She would guide students in using these binders to collect their learning tools (graphic organizers, anchor charts, etc.) to use as resources when they move on to high school and beyond. But she wasn’t sure where to begin. 

What idea has been begging for your attention? Often the obstacles that prevent us from making our dreams a reality are those inner obstacles, a term I am borrowing from the W.O.O.P. strategy. It might be fear—fear of failure, fear of hearing “no,” fear of judgment. By defining our inner obstacle, we can remove a hurdle preventing us from that daunting first step. Perhaps if we reframe the challenge as a series of steps instead of one big chaotic ball of stress, we can surprise ourselves.

Try these five strategies for tackling your big dream:

1. Identify your inner obstacle. 

Is it fear-based? If so, the three simple steps of the Hot Mess, or Pre-Mortem, Strategy is your new best friend. For best results, use this strategy with a team since varying perspectives can help identify a wider range of potential challenges. 

  • Write out a step-by-step plan for ideally, and realistically, implementing your vision.
  • Imagine each step of the new strategy, model, or project from the point of view of what could go wrong. Next to each step, record, rather than attempt to fix, any potential obstacles.
  • Review the plan and modify it, taking into account these possible conflicts.

2. Practice what you preach. 

As you facilitate goal setting with students or educators, join them by setting your own goals. Pick a goal setting strategy designed to prioritize action steps and coach your students to make them timely and achievable as you do the same. 

3. Break your big idea down into a series of smaller, sequential steps. 

Take action on the simplest steps first. Once you gain momentum through progress, you’ll begin to embody an implementation mindset and you will be ready to take on the bigger pieces of the puzzle. 

4. Experiment with different types of to-do lists. 

Try Google Tasks, color-coding, or even a dry erase board. These action items must be simple and specific. Think “select 3 topics to use for report card comments” rather than “work on report card comments.” Enjoy the fun of crossing those items off of your list. Some people thrive by giving themselves deadlines for to-do lists, others are more likely to procrastinate with a deadline. One size does not fit all, so do what works for you.  

5. Find an accountability partner with an objective point of view. 

This is where a BetterLesson Instructional Coach can come in handy. When a school counselor told me of how overwhelming her plan of handing over social-emotional learning lesson plans to classroom teachers felt, she acknowledged that she wasn’t sure where to begin. Together we used Google’s Jamboard to list out each potential action item on a digital sticky note. We then put them into three categories: short-term goals, long-term goals, and immediate next steps. Every other week when we met, we shuffled the sticky notes, sometimes adding more, often putting a few in our new, and favorite, category: “completed.” Our scheduled meetings gave her natural but flexible deadlines. Each time, we would use the visuals to recognize her progress, and that was motivating in itself. She also knew I wouldn’t judge her if she didn’t complete a task. My job was to support and empower her, and I was able to do so objectively since my own opinions about her school weren’t getting in the way.

Just like with the counselor, Chrissy and I gained momentum by first listing the steps she would need to take to reach her goal. Together, Chrissy and I made a plan. Rather than sit in the “what if,” Chrissy took action by scheduling a meeting with her administrator to discuss her idea. Next, she ordered supplies. Finally, in what she describes as the most important step, she designed an introductory lesson with the purpose of getting buy-in from her students. She knew she could get the idea off the ground, but without their interest, it would be difficult to maintain. Now, here we are five months later, and her students have taken ownership over their binders and are coming up with new, enriching uses for them beyond what Chrissy originally envisioned.  All because of a “Wouldn’t it be incredible if…?” moment and that first step.  

As you lace up your shoes and prepare to take that dreaded first step, channel your inner Chrissy and choose an action step. You might choose a small step or a giant leap; either way, you are moving forward, and that is what it’s all about. 

Remind yourself of a time you stepped out of your comfort zone. Did you learn from the experience?  Did it open any doors to relationships or opportunities? Did it help you evolve as a person? If even one of your answers is a yes, it sounds like it was worth it then, and will be worth it the next time you step, hop, skip, or even stumble into your next big idea.  


Jenna Gilfillan, M.Ed., BetterLesson Instructional Coach

Jenna Gilfillan is an ever-evolving educator committed to developing inclusive solutions that result in lasting, equitable change. In addition to her work in education, she is a mother of two young children and enjoys hiking, yoga, gardening, baking cookies, and reading. You can find her on Instagram at @msjennagil.


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