Wins and Losses Series: Drew from FI Introvert – “You’re broke. You have nothing”

Wins and Losses Series: Drew from FI Introvert "You're Broke and You Have Nothing"

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Hi, Team!


Welcome to another edition of MikedUp Blog’s Wins and Losses Series, where we interview a generous participant about 4 of the best and worst moments of their life. The point? To learn from the past so that we can improve in the future!


If you are are interested in participating in the series, please send me an email and we can talk details. 


This week’s participant is: Drew from FI Introvert


Drew has recently become a blogging friend of mine and I’m so glad that he agreed to take part in this series. Why? Because everything I read from him carries with it either a great lesson or some solid information. Drew went all-out with what’s below and I’m so excited to share this with you now! Take it away, Drew!


(Photo courtesy of MKulp Photography)




I struggled for years to decode why going to work, socializing in loud places, and taking trips with large groups were so draining. Finally, after gaining an understanding of introversion, I started to progress professionally and socially. Coupled with my newfound knowledge of introversion, the concept of financial independence was the motivation I needed to improve my life.


The goal of my blog is to help 1,000 introverts step onto the path of financial independence.


I created my site to marry life-enhancing best practices for introverts with financial independence strategies. Gaining a better understanding of these two concepts has had an outsized positive impact on my life. I believe that other introverts will feel liberation and motivation from intertwining the two ideas.


My blog documents my journey and the journey’s of other introverts, lessons learned, and strategies for a meaningful and fulfilling life as an introvert in an extroverted world.


Thank you to Mike for providing this platform for me to share with you a few valuable lessons from my life. My “Wins and Losses” stories revolve around one car and two dogs. Let me explain.


Two Worst Moments

You Can’t Escape Your Past


My past caught up to me in rush hour traffic. Life had not turned out the way I planned. Strike that. Life had not turned out in a way to which I felt entitled.


At 31, I was working making $40,000 while going to grad school. I’d busted my 401(k) to scrape by. There was enough there to continue paying the mortgage on a condo I purchased at the near height of the real estate market in 2007.


Class-by-class I piled on student loan debt from a prestigious university. At the same time, I kept the guillotine from my neck by transferring debt from one credit card to the next.


It was under these circumstances that one of the worst moments of my life unfolded. Crawling along in bumper-to-bumper traffic, the blue lights of the law flickered in my rearview.


What the hell? I’m going two miles an hour. Why is this guy pulling me over?


I maneuvered the car through the commuter traffic to the shoulder of a bridge. The police officer diligently followed. Crap!


In the past, when I’d been pulled over I’d known the verdict before the officer read the charges. But speeding was out of the question. So I waited.


“Sir, have you ever had a DUI?”


“Yeah,” I replied, “ten years ago.”


Ha! This must be some mistake. Boy is this overzealous officer going to be embarrassed!


“Sir, you need to step out of the car. You are driving on a suspended license.”


What in God’s name did he mean? I’d been driving for ten years with this license. I’d gotten a speeding ticket or two in those ten years. Why was he bringing this to my attention while I drove to my crappy job, late for a meeting, and life already out of control?


I don’t think the police officer enjoyed the situation. I was bent on self-destruction and the officer could have arrested me for the way I was talking to him. He seemed to not fully understand it either. His computer showed what it showed. He did his best to keep me from getting in more trouble by being patient and not allowing me to escalate the situation.


It seemed like an eternity. I stood on the median while thousands of commuters went about their day. I emailed my manager and told him I’d be late. Go ahead with the meeting without me.


A second police car arrived. Then the tow truck. I watched as my car disappeared to an impound lot. The second officer offered me a ride to public transportation. Maybe she was being nice. Perhaps she could identify when someone was in a state of mind not to be left alone on a bridge.


Thirty-one years old. Sitting in the back of a police car. Overeducated. Overprivileged. Underemployed. Underachieving.


Ten years earlier, I was an arrogant college student that thought the rules didn’t apply. I was pulled over on campus leaving a party. A cup had fallen off my bumper. When the police officer said that one of my passengers had thrown a drink out the window, I objected, not knowing anything had fallen off the car.


That interaction didn’t start well. Didn’t end well either.


I spent the night in jail, mostly watching Silence of the Lambs in a holding area while other men were being maced and beat up in a cell 25 yards away.


I guess I felt this was punishment enough because I never took a court-mandated alcohol awareness class. It turns out that was the cause of my suspended license.


The police officer ten years later had it in his computer that my license was suspended. Maybe the computer systems got more integrated. Who knows? But I hadn’t done what I was supposed to do and it caught up with me.




From this experience, I learned that my past would compound, positively or negatively, by my actions. Though it took ten years to feel the pain of skipping out on an obligation, it came at a time when I was already reeling and it knocked me down.


I also learned to diligently take care of my obligations, especially when it involves the law. For example, I don’t mess around with taxes. I get them squared away and done right. No creativity.


Lastly, I learned to build a strong foundation in as many areas of my life as possible: emotional, financial, social, and physical. Self-imposed suffering is going to enter my life due to my own choices and random suffering, like an illness or death of a loved one, will also enter. I can’t stop that. But I can try to fortify other areas so that everything isn’t weak at once when life strikes particularly hard.


When It’s Over, It’s Over


My mom called me and told me to come. It was time.


I drove the thirty minutes to her house trying to guess at what kind of a person I was. How would I handle the situation?


I got to the house and there she was, sweet as ever but clearly struggling. My dog, a lab who had been with me since I was sixteen, lay on the floor in her own piss with her arm locked out. She must have had a stroke and lost control of her bowels.


I carried her in my arms as I’d done a hundred times before. The weight was different. I had her wrapped in a towel. I laid her in the back seat. My mom got in the back as well.


Several weeks earlier, we had put down my sister’s dog


I remember going with my sister, a doctor. She was calm and reassuring to the dog as the doctor gave her the lethal injection. My sister listened to her dog’s heartbeat, and then, like a doctor would, told us when she was gone.


As I started the car, I reached back to hold my dog’s paw as we drove to the same vet to repeat the awful process.


I got angrier and angrier as my mom talked to my dog in the back seat. I don’t know why. I guess I wanted to be the one back there with my dog in her final moments.


We got to the vet. My mom left my dog and me alone. My anger subsided as I was able to talk to her for a bit by myself.


But our talk was partially lies. I had no idea if it would be okay


I told her I loved her and that she was the best dog in the world. And that was all true. But I didn’t know what she understood or what she didn’t. If she was calm and ready or just being brave and stoic.


Inside, I simply repeated what I’d seen and heard my sister do. It wasn’t me. I was method acting.


And then it was over. On a cold linoleum floor, the dog I’d been with for twelve years was dead. We just left. They told us she’d be cremated in a separate crematorium as if that made any difference. It was BS. But what could we do? We left her there. Alone with strangers. Yeah, she was dead, but it didn’t feel right.




This was a terrible day.


Similar to the story above, I learned that the micro-decisions of my life had a way of catching up to me in the finality of my dog’s death. When it is over, it is over. There are no more walks to take or balls to throw. I couldn’t get back when she asked to go for a walk and I was too busy playing online poker. I had to live with the finality of the choices I made in the time we were given together. And it ends suddenly.


Two Best Moments

Chance at Redemption


Eight years after the death of the dog I’d grown up with, I hesitantly decided to look at adopting a dog. My finances were in a good place. I was older and didn’t go out late much. It was time to experience the joy unique to developing a bond with a dog.


In my mid-thirties, single, and rather introverted, I was used to going to places alone. I can’t say it didn’t make me anxious, but being anxious about going to a new place was kind of like looking up the right trains to get where I was headed. It was just a normal part of going out.


The day was cool for August. After work, I took the train out to an area of town that was hip (and therefore I was not familiar with it). Walking by the young, confident happy hour crowds, I had a tinge of regret. What exactly was I doing going to a fundraising event for an animal shelter alone in this part of town?


Right. I’d seen a dog that would be at the event that I thought might be a good fit


By this time, I’d seen a dozen dogs. You just kind of know if you’ll be a good fit for each other. It hadn’t worked out yet.


I arrived at the fundraiser. Sure enough, I was greeted by several dogs looking for a home. They had eager volunteers attached to them.


I honestly, and kind of sadly upon reflection, don’t remember if I ever met the dog I came there to see.


But I did gravitate toward one dog. He wasn’t looking for attention. In fact, he was sleeping under a bench. He had no littermates with him like some of the other dogs.


He was yellow, like my old dog, but male and looked to be a pitbull lab mix. Given my experience with adoptions, it was strange that a yellow lab mix was not scooped up right away by some family looking to recreate an L.L. Bean Catalogue.


I sat with him awhile and chatted with the volunteers. He was laid back, sweet, but not needy or overeager.


“Why is this yellow lab mix not adopted yet?”


“It’s August. All the families are on vacation.”


Ding! Usually I am very deliberate but sometimes I know an opportunity and act quickly


I filled out the required paperwork immediately. I picked him up two days later. That day, he pooped twice in two different pet stores and peed as well. He’d do it in my condo dozens of times over the next few weeks as he transitioned from kennel to permanent home. We had our growing pains but finding and meeting my dog was one of the best days of my life.


My dog grounded me. He got me to get out of my own head, to be less selfish, and meet new people. With a dog, I naturally engaged in the best way to meet people, Social Collision. I made new friends, got perspective at work, and had more dates than I knew what to do with.




We’ve been together for three years. I’ve loved watching him grow up and develop a personality. He’s allowed me to learn to care for and love a living being all on my own.


From this experience, I learned that life can present amazing opportunities and l have to take care of myself in order to seize on them responsibly. If I don’t take care of myself, I cannot take care of a pet, spouse, children, a business, my neighborhood, town, city, country, or world. It starts with me as an individual.


I believe the same concept applies to financial independence. Once I was able to get rid of debt, I could start saving. Once I had savings, I could take employment risks and advantage of investment opportunities. When I reach financial independence, I can start a donor-advised fund and the world becomes full of opportunities to change lives. But if I never take care of myself, I can’t help anyone else in a meaningful way. This holds true for finances, health, and emotional stability.


You’re Broke, You Have Nothing


The auto mechanic looked me squarely in the eye and said, “You’re broke. You have nothing.” He was helping me get my car back on the road after an engine failure. Through several conversations over a few days, the mechanic began to understand the dire financial situation I was in.


At the time, I was at least $21,500 in credit card debt from online poker and spending more than I was bringing in.

I had taken out loans for grad school at an expensive private university that amounted to approximately $75,000.


I was living in a condo I bought at the height of the real estate market in 2007


I had a $10,000 loan obligation to my Dad from a failed side hustle in my early 20s.


Oh and let’s not forget the $4,000 or so I owed on the car that was sitting dead in the mechanic’s garage.

That day, I realized that my actual identity – no matter where I grew up or what schools I went to. I was broke. And not just financially.

Having a stranger bluntly articulate my situation stunned me into action. I’ll never forget that man sort of laughing in disbelief and flatly saying that to me. That was definitely one catalyst that made me realize I was in a huge life hole and needed to make changes. I started to say what I wanted and go after opportunities that would enhance my financial situation.


I have to say, as bad as the situation was that day, it was one of the best days of my life. I had a perception of myself that because I had fancy degrees from fancy places the world would eventually hand me what I deserved.



This day, I learned and faced the hard fact that not only was no one coming to save me, no one cared whether I succeeded or failed except me. It was my responsibility to pull myself out. There was no “they” out to get me and no “they” coming to my rescue. It was on me.


It took several years to dig myself out of this situation but I am stronger and smarter for it. I am sure I would have had the realization, but for some reason that guy, with his facial expression and disbelief I didn’t get that I was broke, was the catalyst for change that I needed.


Thank you!


I appreciate Mike getting me mic’d up on this interview series. If the above resonated with you and you’d like to talk more about it, I’d invite you to drop me a message or Tweet me. To fellow introverts, no small talk. I promise.



Reader’s Input


(Mike again) See what I mean? Drew didn’t hold back up there and I know that I took a great deal from his life lessons. What did you take away and can you relate to any of what he went through so far in life? Let us know in the comments below and we’ll keep this discussion going.


Thanks for reading!


If you’re interested in discovering a better version of yourself – whether with fitness, finance, or family – then subscribe below to MikedUp Blog’s FREE newsletter and let’s improve together!


I’m glad you’re here. Thanks again and talk soon!



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