It's Important To Dream Big

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One thing I hear a lot of people say on teacher transition forums is that they can’t go back to school. As someone with $60,000 in student loan debt and two kids, I can appreciate that! But Dan Woodman isn’t one of those people. He took a deep dive and went to law school. While it might not be a path for everyone, his insights and insistence on dreaming big and not selling yourself short are.

On a personal note, this is such a fitting interview to run this week, as I’m finishing up my own MFA app (to a fully funded local program!), which is a dream I honestly thought had passed me by. As a mentor tells me, “If you tell someone your vision and they don’t laugh, it’s not big enough.” Thank you Dan for taking the time to write out these answers and for reminding us to dream BIG.

Introduce yourself! Give us your name, location, number of years you spent teaching, what subject and grade level you taught, and number of years since you’ve left teaching.

My name’s Dan Woodman. I graduated from Penn State (Go, Nittany Lions!) in 2014 with my BS in Secondary Education with a focus on English. I got my masters from University of Virginia in education, as well. 

I spent two years teaching middle school. I taught in a school with nearly a 90% free-and-reduced lunch student population, and I’d say about half of my students were ESOL students.

Upon my divorce, I left the country to teach in Brazil. I taught English and History and absolutely loved the experience. I’d highly recommend teaching abroad to anyone considering it. 

When I came back from Brazil, I taught ESOL in high school grades 9-12. This was at a great high school that was valued by families and the community. It was the kind of teaching position that teachers dream of. However, the politics behind closed doors were absolutely life-draining. In disbelief, I realized, This is the best school the education community has to offer. So when quarantine hit, I took my stimulus check and studied to take the LSATs. I got in, and here I am four years later. 

What brought you to teaching? Why did you become a teacher?

I became a teacher for the salary! No, I became a teacher because I really bought into the “follow your heart” dream. Society told me that I’d have meaningful relationships with students and make an impact on their lives. I bought into that belief.

Briefly describe your experience teaching. What did you like about it? What did you find challenging or unfulfilling?

Let’s step outside the classroom to set some context. During my time as a teacher between 2013-2020, the government was pushing No Child Left Behind in every school. The focus in the education community was to get students to pass a multiple-choice standardized test, and nothing else. 

I had the students for no more than 60 minutes a day. During that time, I was supposed to teach standards and objectives that half of my students wouldn’t meet for one reason or another. The push from administrators was to drill, drill, drill. 

I found myself so overwhelmed with lesson planning and meeting objectives that the promises of the “follow your heart” dream never had the opportunity to develop. I was being overworked given the resources I had, and I wasn’t building meaningful relationships with students. 

Some students, parents, and faculty were amazing. I can’t discount the good relationships I had with them because to do so would be dishonest. With that said, I took a lot of crap from students, administrators, parents, and society as a whole.  I didn’t know it at the time, but I’ve since learned that the way I was treated as a teacher wasn’t right. Today, I’d label it as abusive. That’s a heavy word, so I don’t use it lightly. It wouldn’t be until I took a job in another career where I was respected that I’d come to call my experience in teaching as being abusive. 

That abusive relationship is what made leaving teaching so hard for me. Society had sold me the belief that I was following my heart and this was the meaningful road. In reality, I was constantly disrespected and used as a scapegoat. I was told that my students were underperforming because of me, when in my heart I knew that often wasn’t the case. I was gaslighted into believing that students with long histories of acting out in every class were acting out only in my classroom, and it was my fault. I was being forced to teach standards, some of which I knew the children would never need in their lives, all of which were coming from lawmakers who weren’t in a classroom. I needed support to deal with these challenges, but all I got was blame. 

What brought you to the decision to leave teaching? What was the breaking point?

It wasn’t so much that I made the decision to leave as much as the opportunity presented itself. I had time off during quarantine and the stimulus money to do what I wanted with, so I decided to prepare to go to law school. At the time, it was just a curiosity more than anything. When I applied and saw that I actually got into some law schools, that’s when I made the decision to leave; it wasn’t until I had that safety net that I made the jump. 

What plans, if any, did you put in place before transitioning out of teaching? How and to what extent did you prepare for your transition? How did you research and decide on your next move?

I really walked into law school blind, and to be honest, I’m glad I did. One of the most difficult things about going to law school for me was that I didn’t come from a family of lawyers. Everything I wanted to build, I’d have to do from scratch. There was a lot of trial and error. A lot of expensive mistakes. I’ll concede that I couldn’t have done it without the help of my parents. They supported me towards the end of law school. 

What emotions came up for you in leaving teaching (fear, grief, guilt, relief, etc)? How did you manage and move through these feelings?

If anyone is considering leaving teaching, and they don’t have fear, grief, guilt, and a full gamut of emotions to go with it, I’d say you’re a sociopath. It’s totally normal to have these fears. I can’t pinpoint what fears I had because I had them all, and whatever emotion I was feeling just depended on the day, or sometimes even the minute. 

I didn’t always handle those emotions the right way. Sometimes I turned to the bottle. That was another symptom that the lifestyle I was living wasn’t healthy, and that included my career as a teacher. 

I did, over time, learn how to cope with those emotions in a healthy way. I started therapy. I work out a minimum of three times a week to naturally release stress. I meditate (me! meditating!). I carve out time in my schedule to hang out with friends and gossip about pop culture. I play with my dog every day. These things in my life are non-negotiables that I need to do to stay happy and healthy.

I will say that four years later, those initial fears about leaving teaching have dissipated. Once I took my first job out of law school, I felt like I had finally landed.

Tell us about your first year out of the classroom. What lessons did you learn? What successes did you have? What challenges did you face? What, if anything, would you have done differently?

My first year out of the classroom was law school. That’s an entirely different topic. For the record, I loved law school and would do it again in a heartbeat. 

I did struggle to get through law school. I had to take a semester off to substitute in the Philadelphia School District. I was a certified teacher with a master’s degree from a semi-Ivy League university being underpaid as a per diem sub. It sucked, but it got me through another year of living expenses for law school. You’ve got to do what it takes to make the dream happen. 

What are you currently doing for work? What do you like about your current career or job?

Currently, I’m a lawyer. I work for a judge. All of the cases that he sees come to my desk first. I see a lot of domestic abuse, divorce, and custody cases. I’ve taken an interest in domestic abuse cases because legislation doesn’t protect victims as much as I think it could, and I’m trying to figure out how I can change that. 

What I like about my job now is I get to help people when they’re in a tight spot. When people are in a crisis, they call a lawyer. As a teacher, when it came to student’s personal lives, I knew a piece of the puzzle and nothing more. As a lawyer, all of the “dirty laundry” so to speak gets aired out. I thrive in that kind of environment. I love helping people make life-impacting decisions. I can confidently say that I do more work helping people now than I did as a teacher. 

Last week, a group of FBLA students came to watch jury selection. I got to talk to them. They were so interested in what I had to say, in a way that students weren’t interested in me as a teacher. Just yesterday a principal called me with police officers in her office to get my help figuring out a high-conflict problem. She didn’t know I used to be a teacher. 

I just accepted a job as an adjunct professor teaching upper-level literature in an English class at the local community college. I cannot wait for this next chapter because I have the know-how of a teacher paired with the work ethic of a lawyer. I plan to be the hardest-working teacher these students have ever had. I cannot put into words how excited I am for this job. 

What skills and knowledge from teaching were you able to utilize in your new career? What gaps in skills or knowledge did you have, and how did you address those?

I walked into law school knowing nothing that I know today, and that’s okay. Just today my boss asked me to do something, and I have no idea where to start; I’m going to have to ask a colleague for guidance. That’s okay! 

I’ve developed a lot of skills since leaving education. One skill that I’ve developed is my ability to take rejection. Because I don’t fear rejection, I feel confident in taking risks. If I’m not scared of being rejected, what can’t I do? I would’ve never developed a mindset like this in teaching for a gamut of reasons. Confidence like this has become such a good skill to have.

Another skill I’ve developed is thinking outside the box. This goes concomitantly with rejection. When faced with rejection, is there another way I can achieve the same objective? Overcoming that obstacle is such a rush. 

What, if anything, could have kept you in the classroom? What, if anything, could ever lure you back?

What kept me in my classroom was purely logistics. I was worried about supporting myself and making ends meet. I chose to have my next steps planned before making the jump, and that served me well.

Today, I’m $300,000 in student loan debt and am paying both rent and a mortgage at the same time. My dad is helping me make ends meet. This has been a feeling I’ve had hanging over me for the last four years, and that’s not a small feeling. My fear of finances today are trumped by what I’ve developed in self-confidence, self-esteem, and self-respect. The finances will come later, and they’ll take a long time to work themselves out. That’s okay. I invested in myself and my education, and that’s something no one can ever take away from me.

Mentorship is luring me back to teaching. I was in such a sad place with teaching. In addition to what I’ve already described with the teaching environment, on a personal level, I came from an abusive background as a child and suffered with substance abuse as an adult. I decided to leave this entire life behind by looking straight into the fire, walking through it, and not stopping until I was on the other side. My education is what got me out of that mess, and I feel a burden to share what I have with others. I know that there are many teachers stuck where they are who can find hope in my message. 

Finally, what advice, tips or wisdom do you have to share with current teachers considering a career transition into law or law school? Is there anything in specific you wish you’d known or prepared for?

To get through law school, I had to tap into a source of strength I didn’t know I had. I pushed my boundaries and limits in so many ways that I never imagined I could. That’s not a skill that I can share with you in words and sentences. Believe me, I wish I could. 

My advice is this. Before you even consider law school, you should dream. Dream big. What kind of life do you want? Teaching didn’t let me do that. Teaching made me feel small, and because of that, I sold myself short at times throughout law school. 

Then whatever your dream is, work at it. I learned quickly how to work hard. There was no other way to work but to work hard. I didn’t know how to work hard as a teacher. I’m not saying teachers don’t work hard; I’m just saying I didn’t know how to work hard. 

The problem then became that law school was the dream. I didn’t dream big enough. Once I graduated, I felt a little hollow. I wish that I had allowed myself to properly dream beyond law school.

My new dream is to open up a solo family law practice. Some of this is fueled by my desire to get out of student debt. I also want to write a book. I figure, I’m studying three-to-five hours every day, so when the bar exam is done, I’ll put that time I used studying and use it for writing a book. One day I’d like to be on the board of a rehab and be hands-on in building a facility from the ground up that can help addicts and alcoholics long-term. Those are the dreams I think will come true. 

My wildest dreams include writing legislation for the Pennsylvania Department of Education that will impact ESOL students. I want to write articles for women on how to prevent domestic abuse. Since going to law school, I’ve become a huge feminist and love doing work that empowers women. Will I be fundamental in opening up a domestic abuse shelter one day? Maybe! Anything and everything is on the table. 

If there’s nothing else you take away from this, take away this: I think that it’s important to dream big. I regret selling myself short because I didn’t know my own potential. With that confidence, stare the fire in the eye, walk through it, and don’t stop until you’re on the other side. That’s how I moved through my career in teaching and a substance abuse problem. My life is all the better because of these obstacles I had to overcome, and I’m grateful. 

My email is [email protected]. Feel free to ask questions, and I’d be happy to share more of my experience. You can also find me on my Instagram page @lawwoodman.