My Journey – why I did what I did (pre-30)
I found myself about to turn 19, and I was lost. I always knew what I was supposed to do. I was supposed to get good grades. Then I was supposed to go to college. It was never a question of “if” I went to college, but “where” instead. I honestly didn’t know not going was an option until I was almost 18. It’s just what our family did. However, at this point I found myself kicked out of college. I was suspended for a year, and I was at odds with everything in my life in a way I still don’t quite understand. I couldn’t go to school, but I didn’t want to leave. My mom told me I couldn’t go back to Virginia Tech where I started, but I was unwilling to give in. I had friends there. I made a commitment to go there and graduate there that I wanted to honor. I was simply in a place of strife. Before moving forward I’d like to spend some time on how I got to this place…
Growing up I was pretty much good at a lot of things. Sure I worked somewhat hard, but for me working hard to get As meant simply paying attention in class. Completing the work itself wasn’t hard. I just sat and did it. I was always a fast worker so the BIG project took me a couple hours. I also learned early on to read a grading scale. Every class has a different way of grading. If you figure out how that scale works you can easily pick which things you’re going to pay attention to. You can pick your battles to fight. This combined with the fact that I pick things up quickly meant school was very easy for me. I didn’t study for any tests until the 2nd half of high school. In addition I played sports and stayed out of trouble. In high school I played basketball for a year, lacrosse for 3, and football for 4. I skipped my junior year of lacrosse despite that being my best sport. I ended up with a weighted GPA > 4.0 when I graduated and had been a varsity athlete in 2 sports. I also ended up prom king. I wanted to go to Virginia Tech and was admitted early admission. Why does this matter at all though? Really these are just stats and things I’m hoping you can relate to. I hope it paints a picture of a pretty charmed life. In addition to this I had a solid family life. My parents were together, although they had admitted to me it was just for the kids. I had 2 younger sisters that I got along with. I can’t say we were close as we grew up… when we were little we were, but our interests diverged really as we got our own interests. All in all life to this point was simple and easy. I knew what I had to do and I did it. Simple as that.
Then I went off to college… it was AMAZING. The freedom was great, but to me that wasn’t the best part of it. To me it was about sharing of experiences and ideas. Please do not confuse this with an academic dreamland where we discuss academics. I’m talking more about stories of trouble we got into or good music. I’m talking about video games. I’m talking about different ways to pick up girls, or how to stay in shape, or sports, or whatever 18 year olds are interested in. The exchange of views of the world was fascinating to me. It was about little things… I made my first black friend. I don’t give a shit if that’s PC or not. He knows who he is and he knows he’s my first black friend. I loved asking him about what it was like to be black. I never heard that and could never know that kind of thing. The first thing I did after my parents left was setup my speakers. I had a really big sub for computer speakers and the whole thing was loud. I turned on some Notorious BIG pretty loud (I guess I’m that guy) and in walked this guy. He introduced himself saying “I’m Titus. You like rap music? That’s what’s up.” That’s my first black friend. I was in the world. I was doing things I could never do at home. I was living a life I didn’t know existed.
As I started to amass friends and acquaintances things started to become more fun. I’ve never had an issue making connections with people. I’ve never really had an issue finding friends, although it’s much harder as an adult. I found this environment much easier than any I had been part of before. My weekends started to get more fun. They were filled with sneaking booze into the dorm room then drinking it quickly/quietly before stumbling out into the world to find a party and meet some people. This was a ton of fun. I drank a decent amount my senior year of high school, but I started to drink more. It was the way of college. I was doing pretty well in school at this point. I found a pretty close group of friends pretty quickly. My roommate and I decided to pledge a frat. We pledged Kappa Sigma and the next couple months were a whirlwind. I look back at some of those times and see them as some of the most fun I’ve ever had in my life… silly things about the pledge process stand out to me. I won’t share a lot of details here because I do believe in the ideas of tradition. There were a lot of late nights. There were a lot of errands. However, there was a lot of brotherhood. It was well worth it in the end.
My first misstep wasn’t all that bad. About 12 of us were in a single room drinking beers watching VT vs. USC, and back in 2004 USC was a powerhouse. We were playing a pretty solid game and it was close. We were loud and ultimately a RA came in and caught us all drinking. We were underage so we all got JRs. This is what VT uses as their strikes. I don’t know too many people who ended their freshman year without a single JR so it’s not all that bad. Realistically after freshman year you move off campus so in theory it’s easy to stay out of trouble after that year. However, I wasn’t done with that first JR. I ended up with a lot more…
I don’t know if it’s a coping mechanism, a fact that I don’t really care, there was so much going on, or it was so long ago but for some reason I still can’t recall the right order of events for all the times I got in trouble. I remember them individually, but I don’t know the order. Basically 2nd semester was a shit show for me. My drinking went through the roof. My grades started to slip. I was having tons of fun, but not trending the right direction. At the end of the semester I ended up getting in trouble 3 more times: 2 drinking and 1 fighting. I get a lot of questions like “how did that happen?” I was just dumb and a little unlucky. 1 thing to keep in mind is that in Blacksburg if you get arrested for public intoxication and you’re underage it counts as an underage possession as well because you possess alcohol in your bloodstream. It’s a bit odd, but it is what it is. My first arrest, I believe, was from trying to sneak into a bar. My friends told me about a backdoor and I really wanted to hang out with them. The bar called the cops and they found me stumbling around outback. I don’t remember any of this of course. I just know I was drinking in the frat house and then I was in jail. Oddly enough I walked in and my friend was already asleep on the bench in the drunk tank. I slapped his chest pretty hard, which freaked out the cops, and he woke up quickly. We spent the rest of the miserable night talking and all in all it wasn’t the worst experience of my life. My next arrest was for assault and battery. This one is still on my record, and I still can’t get into some apartments because of it. It still has an impact 14 years later. Some people say that’s not fair, but I don’t care. It is what it is. I’d rather it wasn’t there, but I did what I did and it made me who I am now. I don’t want to get into the assault too much, but I’ll offer a couple things. No one was seriously injured. I did it for a reason that sits close to my core values. It is a misdemeanor. It’s over. That’s that.
If you add my second semester misdeeds to my first semester I was beyond 3 strikes… I was out. I was suspended for the summer and the next 2 semesters. It was going to be a long time before I was in school again. Suddenly that easy path wasn’t so easy anymore. I had no idea what to do. My dad picked me up and drove me home. I didn’t tell him about what happened until we got home. It was a tough conversation. My parents reacted different. My mom was embarrassed and my father was disappointed but supportive. I don’t know about you, but there are several defining moments in my life that I will always remember. Shortly after having a tough conversation with my parents I found myself in front of our computer in the living room. I don’t remember what I was doing, but my dad walked up behind me and whispered in my ear “I don’t care what happens. I will always believe in you.” I broke down, and even to this day I tear up writing about it. This was a defining moment in my life. He believed in me and I needed to as well. I needed to do whatever work would make this right. I mentioned earlier that things came pretty easy, but I put in a lot of work. I was an offensive and defensive lineman around 190 lbs. For context most of the guys I was trying to block were 230-280lbs. I was small, but I outworked and outsmarted 99% of the people on the field. I used to sneak into the weight room in high school and unlock a window so I could literally break in and lift in the dark. This is dangerous and I don’t recommend it, but for me 3 days a week wasn’t enough. I needed to lift more and they wouldn’t give me a key. I did what I thought I had to. Now was the time to do what I had to do. The next day I told my parents in no uncertain terms that I was moving back to Blacksburg in the fall when everyone else did and that I was going to get back into school and graduate. This didn’t sit well with my mother. She said she wasn’t paying for school anymore if I went back to VT (yes I had a totally free ride). I didn’t care. I had friends with jobs and loans and knew if they could do it I could too. I decided to go back anyway.
My father drove me down to my new apt and we didn’t say much. When he left he told me he believed in me again and gave me some $$ to help me get on my feet. At that point other than my father and my sisters the rest of my family had largely disowned me. They were embarrassed and didn’t agree with my decisions. That squeaky clean record didn’t exist anymore and to them that was the worst thing that could happen to the family… not to me, but the family. It was about them. Anyway, I found myself jobless, carless, and with very little $$. I needed to find a job. I started applying which took longer than I thought it would. I wasn’t going out and doing much because I didn’t want to get in trouble. However, 1 night I went to the frat house for a party. I didn’t drink that much, but had a few beers. Halfway through the party there was a girl who was too drunk to stand. I carried her outside and called our DD then found one of her friends. The DD got there and I carried her to the car and put her in the front seat. Her friend got in the back and she was on her way home… safe and sound. I turned around and started to walk back into the frat property. I was about 1.5 feet away from the property line when a brother handed me a beer. As soon as the beer hit my hand another hand grabbed my arm and pulled me away. It was an undercover cop. I was once again busted with an underage possession. I was beside myself. I didn’t know what to do. I begged for leniency. I told the man my story, but he didn’t care. He told me he would let me off if I would wear a wire and help him bust some people selling fake IDs. He knew there were new fake IDs hitting the street, but didn’t know where they were coming from. He didn’t know that I knew who it was, but I did. It was a friend of mine. My good friends were in the process of getting fake IDs from him. I wasn’t interested, but I told him I might be able to help. I was faced with a dilemma… do I rat out my friends and save my own ass or do I take this blow. I didn’t know what this meant. I was sure I would be expelled. At that point, 19, it was the end of my life. The plan wasn’t going to work. The path was ruined. When it came down to it I couldn’t trade my friends for me. I didn’t do it. After a few days I called him and I said I couldn’t do it. He was mad, but at that point there wasn’t much he could do. One interesting thing is this was literally the first time I went out or drank that year. I’d watched people do it dozens of times and decided not to. Then I go out 1 time and get arrested 1 time, and I think I was doing the right thing helping that girl. I was dumb. I did it. I got caught, and I was in a world of trouble.
The next steps happened pretty quick. Hell I had been through this 4 times already so I knew the process well. I ended up in front of a woman. I can’t remember her name, but I can remember her face. I told her the story and even drew a diagram of the frat house and what happened. I told her I really wanted to go back to school and graduate. She needed to think about this situation a bit more. She wanted me to come back the next day. I don’t think I was ever as nervous, before or since, as I was walking into her office that day. I sat down and she told me a few things… she told me she believed in me. She told me she thinks I did the right thing, even though I shouldn’t have been drinking. She told me she used to go to the Kappa Sig house when she was in school. She then told me the greatest news ever: I wasn’t expelled. I was put on “deferred expulsion”. I asked her what that is and she told me she simply made it up. It didn’t really exist. I guess it’s kind of like double secret probation. What it meant is that as long as I didn’t get in trouble again I could return almost on schedule. She did add an extra suspension of the summer on. That wasn’t a big deal for me though. I could return the following fall as planned.
So where does this leave me? At this point it was very clear that alcohol was my enemy. Volume didn’t matter. Behavior didn’t matter. I was ready and willing to give up the sauce forever. I doubled down on looking for a job. I had been doing that throughout the above ordeal, but not very aggressively. I ended up applying to 30+ jobs. My 1 advantage was that I could work anytime. I had no classes or commitments. I was just there. It took about 5 weeks to find a job. By that time I had essentially run out of money. I was making choices about whether to pay rent or whether to eat. I had to pay rent because once again I wouldn’t trade me for my roommates. They were hard working college students and friends, and I couldn’t let them know I was in trouble. I found myself unable to afford food as I looked for jobs. I lost a little over 20lbs in a few weeks simply because I wasn’t eating. I would sneak a bite here or there from my roommate’s food when I thought I could get away with it. I don’t know if they knew and didn’t care or never noticed. I think they knew and knew I was too prideful to ask for help because they’d offer me food when they cooked. Either way it was a tough time. Then I got a call back from a restaurant… The Boston Beanery. After a short interview explaining that I had 0 skills they needed, but I needed work to feed myself they hired me. This place would be a cornerstone of my life. It ended up becoming my new home and another family… more to come on that later.
I did it. The first big step. I could now afford to feed myself and with my employee discount I realized I could eat 1 pretty good meal a week. The rest of the time I had to live on cheap food. That was good enough for me because I was trending up. I mentioned defining moments earlier… I had another one after I finally got established in my job/life. I don’t remember the day, but I remember where I was. I was walking home from work up a hill listening to music. I realized I wanted more in life. I realized I needed more. On that day on that hill I vowed I would do whatever I needed to do to live a good life, but what did that mean to me at the time? To me that meant by 30 I wanted an established career, an established relationship, and a house. If the house had a pool it was a bonus. I wanted the pool, but I could be successful if I didn’t have it. This is what I wanted, what I needed. As I sit here at 32 years old typing this on my fiance’s computer in our 5 bedroom house with a pool before going to my far above average job (career) I realize just how impactful that moment was. I did it, but even that doesn’t answer why I do what I do… that answers why I did what I did. I’ll work up to why I do what I do.
Following that moment the next couple years are pretty boring. I worked a lot. I lifted a lot. I studied a lot. I did really well. I ended my freshman year with a 2.7 GPA and that first year back in school I posted a 3.9 both semesters. My parents decided to pay for school in the end, and they even wanted me to not work to focus on school. I quit my job at the Beanery for a little while, but I found myself halfway done with the semester’s work in a couple weeks. I was reading ahead and doing work on my own. I was lifting daily. I was bored. I needed something else so I went back to work. My parents offered to pay me not to work so I could focus, but I declined. I needed the activity. I needed to work.
So far these things I’ve written about are the tactical pieces of life. They exclude a lot of the social and personal growth aspects. Through these 2 years a couple big things happened that changed my perspective on life completely. First, there were a lot of deaths in my life. I found myself going to a funeral on average once every 2 months. I lost my grandmother, friends parents who had helped raise me, and even a couple good high school friends. It was a rough time in that regard. People were leaving that I wasn’t expecting. I had never experience 1 funeral and then I went to a half dozen in a year. This changed me. My relationships and my focus on people was my #1 thing. In addition I met my best friend Nick. He had a way of thinking about the world that I had never seen or heard. He stood up for himself in a way I had never seen or heard. He ended up working at the Beanery after I vouched for him, and he subsequently forgot to show up for his first day. He really taught me the importance of people… not just having relationships, but having good ones. I started to develop a focus on having the right relationships with the right people. It wasn’t about having 100s of friends. It was about having relationships that enhanced your life in a real way and enhancing others’ lives in a real way. I was still hyper-focused on my goal at 30, but I was also enjoying everyday. I look back at this time fondly.
I don’t want to spend much time recounting my college life. Maybe I’ll do that later, but for the purposes of sharing WHY I do what I do most of those details don’t matter. My early career is also inconsequential from an event perspective. What is important for this piece are some conclusions and realizations that came as part of that journey. I’m going to share them now. We’re getting close to the end.
I started work in 2009 in a rotational development program. After a month of training I started my first real job. I had a solid boss and a solid project. I was essentially a 1 man project. I had to build out a reporting database and UI for some internal metrics. After the first week of being lost I came in on Monday and sat in my office, yes I had an office somehow, thinking about what happened the prior week and what to do this week. After about 30 minutes of sitting, staring, and doodling something dawned on me that has profoundly shaped my professional view ever since… THIS IS ALL MADE UP. We didn’t discover business like we did gravity. Somebody made it up. How we get work done is completely made up. Then it also dawned on me, in a very cocky way, that I’m smarter and more capable than the average person. That means that it is statistically likely that the world I’m operating in was made up by a less intelligent less capable person. From that moment rules became optional to me, and not just that by their very nature of existing I immediately categorized them as silly until proven otherwise. Is this really the best strategy? I don’t know, but I like it. 10 years later and I find the pattern fits VERY well.
This realization fostered a spirit of bravado in me that has really carried me through to now. It’s definitely gotten me in trouble, but it has continuously put me in a position to be some kind of change agent. I’ve managed support, dev, and QA teams. I’ve had transformation roles. I’ve built partnerships with other companies. Really what happened is I’ve become very good at finding the right problems to solve given unknown situations. Developing a new thing is difficult, but we have a pattern. How do you build a relationship that works on a business and technical level with another large company? That doesn’t have as much of a pattern. The reality is though that since I’ve always looked at the rules and patterns as silly I’m very used to forging my own path so I naturally see developing a new thing in the same light as building a new partnership. My general disregard for rules & process has honed my skills in creating new paths forward because that’s the only way I’ve approached work since that realization a few days into my first job.
This bravado was fueled by something else, which in hindsight is much more powerful. As you sit and read this there are many possibilities in front of you. Can you imagine the worst one? What does it look like? It probably entails getting fired, losing friends and family, and having to rebuild. When I imagine the worst case (I throw out things like an apocalypse) for me it looks a lot like getting put on deferred expulsion. It looks a lot like calling my parents and telling them I messed up again then hanging up and being hungry. It looks a lot like the life I lived. I lived in a small apartment. I started working at $6.50/hr. I lost friends and family in the literal death sense. I was disowned by most of my family. If I lost everything tomorrow I could still get a restaurant job and a small apartment and rebuild. I’ve done that already, and as I mentioned I look back on those days fondly. For the most part I’ve lived the worst case scenario. What that gives me is a view of work and career as optional. I TRULY don’t care if I get fired. I don’t yet have any dependents, but even if I did I think I could rebuild. My skills and what I can offer are far above $6.50/hr at this point, and in reality I don’t need possessions to be happy. This true lack of fear of getting fired enables me to say things to people others cannot. It’s not necessarily for the better. Maybe if I played politics I’d be further (whatever that means). What it does enable me to do is play the game of work on my own terms. Everyday I do what I want and what I think is best. That’s it. I honestly think this is my true edge if I have one. In the long run in reality I TRULY don’t care about my job. I never have. It certainly has it’s down side… there are days I say fuck it and leave early or slack a bit. I’ve been doing a lot of work on that lately.
Where it’s led me is that by 30 I was in a great place with my career. I was far ahead of the curve on “the ladder” for my age, and I could write my own ticket. I had accomplished what I set out to accomplish with my career on that hill in Blacksburg, Va when I was at the lowest of lows. It was done. I also met someone amazing… Kelli. We’ve been together for ~7 years and we’re getting married soon. She is my rock. She’s my home base. Together we bought a house right before I turned 31. It’s 5 bedrooms with a pool. I MADE IT. From that crazy place of not knowing what to do I hit my goal…
So now what? I’m only 30. Where do I go now? I based my goals on pretty tactical/material things. What’s next? At 30 I reached what I had been going after for 11 years. I had no idea what to do next until I came up with the question that would rule my life for the next 2 years…
A lot of great insights here. I completely agree with the success that can come from not caring about your job. I took a pay cut when I started my first career job and always knew I could replace my income which gives a great bit of freedom to make good decisions over safe ones.
Now with myself and 3 others dependent on my income I can quickly see how people struggle to no longer care about their job. That said I’ve managed to keep our bills low and our savings high enough to keep the freedom to succeed.
I also like the insights that business is made up and it’s not gravity. It points to a good reason to do the best thing over the safe thing even if you are worried about your job because this kind of challenging is the only way to make a real change.