Evan Weinberger of Illuminos: “Break the daunting project down into more manageable chunks”

Breaking projects down into phases that represent more manageable chunks is a great way to get past perfectionism. For example, when building a house, the entire house is not built overnight. The process starts by creating plans with an architect. Then there are several drawings made to address things like plumbing, electrical, etc. Then the […]

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Breaking projects down into phases that represent more manageable chunks is a great way to get past perfectionism. For example, when building a house, the entire house is not built overnight. The process starts by creating plans with an architect. Then there are several drawings made to address things like plumbing, electrical, etc. Then the builder pours a foundation and starts to frame the house. The process continues until finally the house is built.

Many successful people are perfectionists. At the same time, they have the ability to say “Done is Better Than Perfect” and just complete and wrap up a project. What is the best way to overcome the stalling and procrastination that perfectionism causes? How does one overcome the fear of potential critique or the fear of not being successful? In this interview series, called “How To Get Past Your Perfectionism And ‘Just Do It’, we are interviewing successful leaders who can share stories and lessons from their experience about “how to overcome the hesitation caused by perfectionism.

As a part of this series, I had the pleasure of interviewing Evan Weinberger.

Evan Weinberger is the CEO of Illuminos LLC, an academic coaching and tutoring company he co-founded with his cousin Wendy in 2016, after a decade of success growing the sister company he founded in Texas called Staying Ahead of the Game LLC. The focus of his program is helping kids build the executive functioning (EF) skills they need to be successful in the classroom and beyond. The core components include helping students with organization, time management, and influencing the perceptions of others.

Thank you so much for doing this with us! Before we start, our readers would love to “get to know you” a bit better. Can you tell us a bit about your childhood backstory?

I currently lead a very successful and growing academic coaching and tutoring company, but my path to get here was not full of sugar, spice, and everything nice.

My own academic struggles began in kindergarten. My teachers repeatedly found me alone and crying in my cubby because I had not realized my classmates had begun recess time. When I was five years old, my father, a renowned clinical psychologist, recognized my marked struggles to sustain focus and had me tested. As my dad suspected, despite scoring highly on an IQ test, I was diagnosed with ADHD along with reading comprehension and auditory processing delays. I began working with various therapies. My mother left her job and committed to staying at home with me. She worked with me daily to help me with organization, planning, following instructions, and study skills. She helped me build effective habits and routines full of checklists to get me through the day. These proved to be a central executive functioning skill for me to manage my learning differences, many of which I continue to use today.

Thanks to the unbelievable support I received, my performance in school was always good. I attended small schools with small class sizes and ready access to teachers. As the work intensified in middle and high school, I found it increasingly more difficult to keep up with the pace of the class. I spent countless hours in the evenings working through strategies to interact with course material, as I gained very little from reading and rereading my textbooks. For college, I attended a private, top-tier liberal arts school where my biggest class was 30 students. I used accommodations throughout my schooling, including extended test time and priority seating, to help me manage my learning differences and find success despite them.

My experiences in school led me to pursue doctoral work in psychology where I could position myself to help others in the pursuit of academic success. I founded Staying Ahead of the Game LLC in Houston, Texas, in 2006. The program I created incorporated my own academic experiences with my studies in industrial and organizational psychology. I recognized many students possess the intelligence to be successful, yet struggle in school and don’t know why.

After 10 years operating Staying Ahead of the Game LLC, I co-founded Illuminos LLC with my cousin Wendy to bring the program to the countless students who need help outside of Texas. I am proud to say I have now helped thousands of other students learn how to learn, and I look forward to helping many more!

Can you please give us your favorite “Life Lesson Quote”? Can you share how that was relevant to you in your life?

In college, there were various speakers who would come to the school and address the student body. One speaker in particular said, “Find something you love doing, and then figure out how to make money doing it.” The speaker explained how robust empirical research supports that this is actually the most direct formula for both happiness and financial success. This quote has always stayed with me.

While my friends were becoming doctors, lawyers, and bankers, I always kept this quote in mind and prioritized my passion above everything else. I ultimately entered the world of education, which is notorious for being largely absent of financial success. While the financial reward is certainly not my focus, I’ve been able to build a successful company and enjoy financial security along the way.

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

Stephen Covey’s “The Seven Habits of Highly Effective People” really had an impact on me. It wasn’t so much that the ideas in the book were super new to me. However, they represented validation for many of the concepts embedded into the very fabric of the program I created.

I continue to practice many of these ideas on a daily basis. The idea being proactive as opposed to reactive is something I think about at the start of each week. The notion of always having the end in mind helps inform the smaller decisions along the way. Whether I’m talking to a counselor at a school, a client, or a student, I always try to create situations where all parties involved have something concrete to gain. To this day, if there is a task that takes merely several minutes to complete, I follow Covey’s advice and do it right away.

This book is a must-read for all young adults and entrepreneurs learning to navigate the world.

You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?

  • Persistence

Schools and organizations can be very selective about the professionals to whom they refer. I recall a particular school in Houston, Texas, that prides itself on their elaborate vetting process. It took over five years to get a representative from the school to finally agree to meet with me and discuss our unique services for students. Fast-forward and this school not only refers dozens of students each year, they also bring me in regularly to do workshops for their faculty and staff about executive functioning skills. Persistence is key!

  • Resilience

Not every endeavor will be a resounding success. Failure is an important part of success. The important thing is to quickly learn from mistakes, adjust, and plow forward. I recall a presentation I did for students at a school for their interim term. They wanted to split their student body into several sections. I had several members of my staff deliver the same presentation to different sections of students at the same time. I was hoping the presentations would be similar. However, despite countless hours of practice, the presentations differed greatly. The students were frustrated, the school was unhappy, and I did not get invited back for almost 6 years. However, the mistakes that happened that day informed some important changes in our internal operations that has lead to countless presentations at other schools that were tremendously successful. These presentations helped to shape my company’s reputation moving forward. I wouldn’t be where I am today without that presentation that was a complete failure.

  • Compassion

It is important to operate with compassion both internally with staff and externally with clients. I recall a phone call into the office a couple years ago from a mother with little resources, but tremendous need. I knew we were in a wonderful position to help her child, but I knew there was no way this single mom could afford the suite of services her son would need in order to overcome his struggles. I decided to make concessions on our pricing in order to help her. Not only did we get her son back on a path to success, but it turned out this mother was involved in a well-funded nonprofit organization and invited me to an upcoming board meeting where we were engaged to help hundreds of students over the next several years. While we provided services to this nonprofit at a discount, the work we did over the next several years helped to get our name out in the community in a big way.

Let’s now shift to the main part of our discussion. Let’s begin with a definition of terms so that each of us and our readers are on the same page. What exactly is a perfectionist? Can you explain?

A perfectionist is an individual infatuated with the idea of flawlessness. These individuals want to feel flawless and want to appear flawless in the eyes of others. Unfortunately, flawlessness is largely subjective so individuals who are perfectionists tend to get lost in constant self-evaluation and self-doubt. Perfectionists tend to consistently let the perfect get in the way of the good. They often have a difficult time starting and completing tasks because they are relentlessly critical of themselves.

The premise of this interview series is making the assumption that being a perfectionist is not a positive thing. But presumably, seeking perfection can’t be entirely bad. What are the positive aspects of being a perfectionist? Can you give a story or example to explain what you mean?

Learning to manage perfectionism can actually turn the trait into a positive thing. Perfectionists set an extremely high bar for themselves. They are often mindful of not just following instructions, but also the entire visual presentation of a deliverable. Perfectionists have a unique ability to manage impressions that others form of them. They are keenly aware of the perceptions that others have of them. According to the movie, “The Secret,” perceptions are often more important than reality. Therefore, perfectionists have the potential to thrive where others struggle.

Several years ago, I worked with a college student trying to juggle school and an entrepreneurial endeavor with a close friend. He was constantly concerned he was not splitting his time perfectly between his schoolwork and his outside projects. Consequently, he consistently underdelivered on both his schoolwork and his side work. His parents hired me in part to convince him to drop any outside work and focus solely on school. However, as a fellow entrepreneur, I understood his deep desire to scratch his entrepreneurial itch. My instincts told me that he would begin overdelivering in both arenas if he improved his calendaring and time management skills. I helped him build the perfect schedule that represented the perfect balance between his schoolwork and his side work. During the global pandemic when all school went virtual, he utilized some connections he had made to deliver personal protective equipment to businesses, medical practices, and quickly entire hospital systems. He stuck to the schedule we made and began enjoying tremendous success both in school and in his new business. His business is now bigger than mine!

What are the negative aspects of being a perfectionist? Can you give a story or example to explain what you mean?

The most glaring negative aspect of being a perfectionist is struggling when starting and finishing tasks. If compensatory skills and strategies to circumvent or push through these issues are not developed, perfectionists can experience many more negative outcomes. In addition to poor performance, perfectionist can begin to suffer from serious instances of anxiety, depression, etc. However, by getting help and by incorporating some of the suggestions above, perfectionists can turn this obstacle into a driving force for success.

I personally worked with a sixth-grade girl for almost three years who struggle with perfectionism. We started our relationship by talking about the importance of “the process” when tackling tasks. We talked about how the perfect process for getting to the perfect work product involved drafts along the way that, by definition, were imperfect. We developed specific strategies such as writing “DRAFT” at the top of her papers that reminded her that perfection at this point was not expected. In other words, the perfect draft contains mistakes. We even joked about making mistakes perfectly. While it was a long process to solidify compensatory skills and strategies such as this one, she now performs tremendously well in school and earned admission into her college of choice. I am very proud of her!

From your experience or perspective, what are some of the common reasons that cause a perfectionist to “get stuck” and not move forward? Can you explain?

Many perfectionists struggle to get started. I have found this to manifest differently across perfectionists. Some struggle because they want to wait for the perfect time and place to start something, which just never seems to happen so they never get started. Others can sit down to start, but then obsess about every word of every sentence. Yet others can begin and even get close to completing a task, but struggle to turn it in because there seems to always be room for minor enhancements. Since this experience is excruciating, many perfectionists start to develop anxiety around the entire process of executing a task. This further complicates executing tasks in the future, turning the process into a vicious cycle!

Here is the central question of our discussion. What are the five things a perfectionist needs to know to get past their perfectionism and “just do it?” Please share a story or example for each.

Break the daunting project down into more manageable chunks

  • Breaking projects down into phases that represent more manageable chunks is a great way to get past perfectionism. For example, when building a house, the entire house is not built overnight. The process starts by creating plans with an architect. Then there are several drawings made to address things like plumbing, electrical, etc. Then the builder pours a foundation and starts to frame the house. The process continues until finally the house is built.

Write “DRAFT” at the top of the paper to relieve pressure

  • Just writing “DRAFT” at the top of a paper can help relieve some of the pressure of creating something perfect from the start. For example, if a student struggles to create a title and start getting thoughts on paper, knowing it’s a draft implies imperfection and can get the ideas flowing. Once things are on paper, it is much easier to add, eliminate, and elaborate. It also creates an opportunity for feedback to increase confidence in the quality of the final deliverable.

Outline all the execution steps in bullet form

  • Outlining the steps to any task at hand can be tremendously helpful in overcoming perfectionism. Doing this in bullet form removes the anxiety of creating perfect sentences from the start. From writing an essay to designing a nursery for a new baby, outlining the steps that are involved helps to get the show on the road. It also prevents unnecessary oversights and improves the final product.

Set a daily goal and plan a small treat for yourself when it’s accomplished

  • Creating an incentive in the form of a treat when a certain amount of work is accomplished can you help improve productivity. This will certainly manifest differently for different people, but having a carrot helps with focus and staying on task.

Use a visual timer and remove all other distractions when working the task

  • Creating your own palace for productivity with the proper tools around you can you help get things done. There is an increasing amount of research about the power of visual timers where you can see time elapsing as you focus on the task at hand. The latest research indicates, we can focus all of our attention on a specific task at hand for one minute for every year of age. Therefore, a high school student should be able to set a visual timer for 15 to 20 minutes and focus 100% of their attention on the task at hand before needing a brief brain break.

You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be?

I would love to inspire a movement to introduce more life skills classes for students at all levels. Most working people report using less than 10% of what they learned in school in real life. I would like to see executive function skills incorporated more deeply into the fabric of education at all levels. This would include more robust courses about financial responsibility, etiquette, social skills, etc. I see too many students graduating from school with tremendous subject mastery and knowledge, but lacking the real life skills to secure gainful employment and manage both personal and business relationships.

Is there a person in the world whom you would love to have lunch with, and why? Maybe we can tag them and see what happens!

I would love to have lunch with Andrew Rosen, the Chairman and CEO of Kaplan, Inc. In addition to being a leader in the standardized test preparation arena, Kaplan has grown to be a broad global educational enterprise. I would love an opportunity to discuss more precisely how they grew to be a global leader in helping individuals achieve their educational and career goals.

How can our readers follow you online?


Thank you so much for sharing these important insights. We wish you continued success and good health!

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