Jesse Stoddard

Life After High School: Interview with Isaac Gregg

Today’s interview with Isaac Gregg is part of my ongoing blog-to-book project: Life After High School: Secrets To A Successful Life By Those Who Have Had Twenty Years To Think About It (or) What They Didn’t Teach Us Gen Xers In High School. If you missed the last post, click here, otherwise, you can start at the beginning here.

Isaac Gregg

Anacortes, WA

My Life In High School

Isaac Gregg AHS 1996

Who were you in High School and how did you feel about it?

I changed who I was multiple times; fitting in with what felt comfortable at the time. Even though I was a tall guy and could be perceived as intimidating, I was mostly a gentle person that thought the only way to be liked was to come off as “hard”. I felt good with my persona but that’s because I didn’t realize how unimportant it really was. I was, in effect, a poser.

What did you think your life would become when you graduated?

I had no idea immediately after graduation—then I realized that while I was just hanging out doing nothing, everyone else around me had been making plans. College, internships, and life. This scared me to death so I followed my stringent religious upbringing and left the state for theology school. This seemed like the safest bet at the time.

My Life After High School

Isaac Gregg

What happened in your life to you, for you, and by you in the last twenty years (how have you used your time and who have you become)?

I left in 1998, landing in Dallas, TX near the end of the summer. It felt like I had landed in a foreign country.  It would be the longest I had been away from home ever (as is true for probably everyone at that time).

The first thing that struck me was the heat; like a wall of humidity just hit me in the face.  I remember sneaking out of a friend’s apartment that night to smoke. (I had to sneak because they don’t allow smoking on campus). I saw a cockroach for the first time and it was the size of a cigar as it scurried towards my feet… I must have jumped 5 feet in the air!

I was pretty lonely those first few weeks, and leaned pretty hard on another person that had come from Anacortes but learned quickly she was trying to branch out.

I had sold my treasured GMC Truck to help pay for school so I was on foot everywhere, I took DART (Dallas Area Rapid Transit) to work most days, sometimes scoring a ride with someone that worked in the area.

I used to wander around at night because one thing I have always loved was exploring. I ended up on a bus going the wrong way and I was the only white person on it. A group of guys behind me was rappin’ from Tupac’s last album, and as they got past the chorus I joined in (uninvited mind you)! They flipped out! It was hilarious!

They were shocked I knew Tupac’s music. One of them asked me what I was doing in that neighborhood. I told him I got turned around. We exchanged more conversation, but not before he warned me to be careful around there at night. I thought nothing of it—again I just assume no one will mess with me due to my size.

I headed over to the light rail station to head to work and as I was waiting, this kid approached me and asked what I was doing down here. I said, “Where? here?? I’m waiting for the train!?”

“Whatchu doing ’round us!?” At this point, 3 other African American teens had gathered around me. I didn’t notice his fist was cocked and I chose to ignore him and turned my back, he sucker-punched me in the nose, I went down and he jumped on top throwing blows to my head.  I don’t know that I even felt the hits as I jumped up and all of them scattered. I chased but didn’t catch anyone. This was the day I started to realize I was on my own.

I continued onto work bloody-and-all and my co-workers (all bellmen at the Adam’s Mark hotel) chipped in their tips to help me out as I had all my books stolen.

This would be a turning point for me. At this point, I had only been in Dallas 3 weeks, and the cloud of depression started rolling in. I didn’t know what depression was! I hadn’t felt it before (being in a cloud of Marijuana smoke keeps you happy).

As the school year moved forward and I got into the business of life, each month would seem even darker. CFNI: Christ For the Nations Institute. This is the school I went to—it had been recommended by a friend of a friend, it was an easy admission, non-accredited school, but I told myself that didn’t matter because I was going to be in the ministry!

I attended school from 7 AM to 12 PM Monday through Friday and worked every evening from 3 PM to 10 PM. I jumped jobs a bunch of times; waiter at chili’s, security officer on campus, a server at American Airlines Center, Starbucks, a gelato shop, part time DJ (that lasted 3 gigs until I changed my prices).

That “poser” issue I had in high school? It was playing out in the real world too! During my 2 year program at CFNI, I had attended many churches, all different denominations but had gone to one more than others; Trinity Church of Dallas.

Trinity was exactly what I thought I wanted—a younger congregation with a small mixture of 40+, a blossoming youth ministry (my specialty) and a passion for reaching all nations for Jesus.

This place had another appeal for me: Money. A good number of staff and parishioners were plugged into the financial markets, real estate, art scene, etc. I felt like I as in the right place. I could finally get some order in my life.

I was fast approaching my mid 20’s and I figured this was it—I would commit my life to this mission and Trinity would be the place! Trinity was in a transition period while they were coming into the oversight of Morning Star International (later to be changed to Every Nation Ministries due to legal problems, corruption, charges of emotional abuse, etc).

These Morning Star folks were like the Marines of the Christian non-denominational churches—soldiering through the nations with the good news of Jesus Christ, planting churches in “illegal countries” like China, Myanmar, Morocco, Iraq, Afghanistan. Their leaders Rice Broocks was plugged into NFL players and celebrities, he had been to the white house and consulted with President Bush. I thought these folks were the end-all-be-all of leadership!

The church was mandating that all member get accountable with God by being accountable to church leadership for their behavior. We had special “Purple Books” that had the discipleship mandates for the church and we were to follow those, study those, then disciple others to do the same.

My meeting with my “discipler”—usually an older “wiser” man would consist of me confessing my sins and telling them about my problems in the desperate hope they would have and an idea of how to help me. You see, this is also about the time that the other side of my mental issue started to surface.

Bipolar 1. When I was depressed I was just depressed. I would stay in a lot (which was easy because I was poor), not leave the bed, lose interest in being around people, then be ashamed because of the latter.  For the longest time, I thought it was shame connected to being a sinner! See how that works?

Anyway, the mood swings became an issue for me. I would be super tuned up and ecstatic around people—even manic—and folks just thought I was fun to be around, then become worried when they wouldn’t see me for a few days. This mostly stayed under the radar until I became a volunteer staff. I helped launch a ministry that targeted at-risk youth in South and Central Dallas.

It was around that time that the confrontations in my discipleship meetings became more aggressive. My discipler would make demands of me, like not going certain places, or being with certain people for my own good—at one point taking the DSL line out of the apartment so I couldn’t get online. They thought they would make “sinning” difficult for me.

Concurrent with my own agonizing existence, my best friend and roommate (who was on as paid staff for the church) was instructed to disassociate with a girl he had been seeing. A romantic relationship completely non-sexual in nature was being squashed because church leadership disagreed with it.

Well, he disagreed with their assessment and I had to sit there in a meeting while they notified all of us that we were to have no contact with him whatsoever; no phone calls, texts, cards, anything! This is what is called “Church Discipline”. It’s an effort to “turn them over to the devil for the destruction of their flesh”, in a sense to give them as much pleasure as possible so they will see the destruction and return to God like they do with AA and intervention.

He eventually “saw the error of his ways” and returned to the church. He was welcomed back but things were never the same for him or me.

The threads were starting to unravel and soon I would be back in Anacortes to tend to a family crisis that would span a year and a half of my life—something that I feel like I am still recovering from.

The bipolar got worse. The medication didn’t help and neither did the counseling. My family’s drama would only compound the desire to take a tumble off Deception Pass.

There is much more, but I feel like this is a good stopping point, because of the subject matter. While I am totally willing to share, it will take longer to write, as it is agonizing to recount how close I came to ending my life. Let me know if you want more.

My Life Lessons

What were the major life lessons and wisdom that you gained during your journey over the last 20 years?

Don’t put all of your efforts into one thing, one passion or desire until you are sure that’s where you belong, or you will end up like me: almost 40 and still confused.

My biggest success was overcoming an illness you are not supposed to be healed from. 🙂

Letter To My High School Self

If you could write your 18-year-old self (or however old you were when you graduated) a letter, and send it back in time, what would you say? What lessons, wisdom, encouragement, or warnings would you give yourself?

The letter would read:

Stay at home a little longer. While you may have wasted your time during high school and not figured out what you wanted to do, there’s no shame taking a little longer to work on it.

Don’t be motivated by the fear of not knowing. You have to live with every decision you make so you shouldn’t make life choices off of religious obligations.


In the next post, I will kick off chapter 12, called STUPID TAX.

Are you from Generation X? I want to hear what you think! Please comment below and participate in the conversation about What They Didn’t Teach Us Gen Xers In High School. What do you wish someone told you when you were eighteen?


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