7 Things I Learned from Sober October 2019 + November’s Challenge

Another Sober October has come and gone. Insert cliche about how fast time goes here.

At the beginning of the month, I set out to not only challenge myself to complete sobriety for a month, I also added some other wrinkles. Here’s what I aimed to accomplish and how I fared:

Sober October Results:

  • No booze, no caffeine, no weed, no drugs of any kind: COMPLETED SUCCESSFULLY
  • Finish four 48-hour fasts: COMPLETED SUCCESSFULLY
  • Complete ten 1-hour boxing classes: COMPLETED SUCCESSFULLY
  • Read five books in their entirety: COMPLETED SUCCESSFULLY
  • Write 25 articles (500-word min) by month’s end: PARTIALLY COMPLETED (20/25)
A piece of paper with attempts at boxes representing my progress throughout Sober October

Overall, I’d call this month a success. *pats self on the back*

My lone shortcoming came in the writing department. I attribute this both to my initial resistance and the fact that I thought I only committed to do 20 (not 25). I realized I fucked that up when I checked back to the original article around October 21st, at which point it was too late to catch up.

At any rate, this was an extremely productive month and I learned a lot. Here are some of the big takeaways:

7 Things I Learned from Sober October 2019

I do more and feel better when I challenge myself

They say the way to build confidence and grow is to live at the edge of your comfort zone. When I have done challenges like this one and 75Hard, there is no doubt that I’ve pushed my limits and found new gears.

Some days are harder than others. But when I’ve pushed through my inner bitch and got stuff done, I’ve felt better and gotten more accomplished. I wrote more this month than the last three months combined. Boxing is the hardest I’ve trained since I was in high school.

I’ve been able to accomplish a ton because the monthly challenge structure gives me accountability, structure, and a finish line. Once I announce what I’m going to do, my identity gets wrapped up in success – there’s no turning back. The structure of the challenge rigidly defines success, so I don’t have to make tough decisions daily. And, by having a finish line, the difficult days are easier when I know I don’t have to continue indefinitely.

I’m definitely going to be using more challenges like Sober October going forward.

You don’t need drugs

This is going to sound like an advertisement for DARE, so be warned. There were very few points throughout my month-long sober experience in which I felt drugs would have enhanced my experience. 

In fact, in most cases, I saw the ill-effects drugs (primarily alcohol) had on people. As my friends got buzzed, I saw their eyes gloss over. Their behavior would shift and they’d become almost like a different person. I observed that most people have different personas – either heightened or dampened – when under the influence. 

Sober October made me realize how cringe most people are. I witnessed sad cat-calling, unrealistic business plans unfolding, awkward over-sharing, and other behaviors that sober, sane people would never be caught doing in a social setting. It was eye-opening and bizarre to see how people’s interactions generally digressed as they drank more and more.

Image result for drunk memes
Me during my partying heyday

I, on the other hand, didn’t feel left out. To be fair, I’ve cut back on my drinking substantially in the last two years, so I’ve had experience going out sober. For anyone starting to cut back on booze, I know the struggles, anxiety, and judgments that come with trying a new lifestyle. 

It’s not easy, but it’s worth it – if you’re pursuing sobriety for the right reasons. Like any habit or skill, it gets better over time. Stick with it. Because, at the end of the day, you don’t need drugs to have fun, be yourself, or relax. They just provide a short-term escape and illusion of enlightenment.

Drugs are a shortcut

At the end of The War of Art, Steven Pressfield speaks in-depth about the process and importance of separating your Ego from your Self. What’s the difference? Here’s one definition:

Self is that part of you that is connected to a higher being, while Ego is that sense of self-importance that you have when you compare yourself with others.

This is pretty heady shit, but the premise is that the key to creating great work and be fulfilled comes from destroying your Ego and developing your Self. This can be done through a variety of practices including fasting, meditation, exercise, or other forms of deliberate suffering. 

But the fastest way? Intoxication. Pressfield explains:

“Have you ever wondered why the slang terms for intoxication are so demolition-oriented? Stoned, smashed, hammered. It’s because they’re talking about the Ego. It’s the Ego that gets blasted, waxed, plastered. We demolish the Ego to get to the Self.”

Steven Pressfield, The War of Art

Sure, you can enhance the Self through the use of mind-altering substances. But they are simply a shortcut: you get the short-term satisfaction without the long-term benefits.

Image result for drugs meme
Truth

And, if I’ve learned anything in life, there are no free lunches. When you skip the hard work to get straight to the reward, there is always a price to pay.

Drunk people get hangovers. Most stoners lack mental clarity, have anxiety, or can’t find pleasure when sober. Caffeine addicts can barely keep their eyes open without a cup of coffee.

I’m not telling you to stop using drugs. I’m just suggesting you could benefit from a more thoughtful and honest look at how you use them. 

Sober October made me realize how big of a crutch marijuana was in my life. I would use it as an escape from my boredom instead of finding ways to fill my life with things that kept me entertained naturally. I still plan to use weed to enhance some experiences, but I’m going to be more intentional going forward.

It’s good to start new things

I was recently encouraging a friend to start stand-up comedy. This guy is one of the most naturally funny people I know and has talked about trying comedy for years. But he still hasn’t gotten on stage. Why?

He’s afraid of making an ass of himself.

Look, someone smarter than me once said: if you’re not willing to look like an idiot, you’re never going to become great at anything.

The reality is, everyone sucks when they first try something. Sure, the best of the best of the best were probably amazing the first time they tried something (e.g., Lebron, Tiger, Hendrix, etc). But the majority of successful people were awful before they built momentum and improved.

Steve Harvey talked about living in his car for years before getting his break. The greatest basketball player ever didn’t make the varsity team during his first tryout. Everyone thought Joe Rogan was off his rocker when he put all of his time and energy into a weird new technology. 

Everyone looks crazy before they look like a genius. 

This is why I find it valuable to try new things constantly. It helps expose you to the judgment and emotions that come with sucking shit. The key is to feel the discomfort and stick with it long enough to push through and see progress.

This does two things for me. First, it helps tame the aforementioned Ego. It humbles me and reminds me that there are still so many things I can improve upon, no matter how badass I think I am.

Also, it gives me confidence. When I see myself improving at something I knew nothing about even a couple of weeks ago, I am reminded that I can learn anything with enough effort.

Boxing is a great example. I am afraid of fighting. And I didn’t know the first thing about throwing a punch. My Ego definitely took a massive hit when people way more coordinated and athletic than me cruised through the first classes while I struggled with simple combinations.

Comin’ out swingin’

But ten classes later and I’m starting to get the hang of it. I’m no longer the worst boxer at each class. That’s the beauty of fitness: you can see the benefits fast.

It’s good to start and stick with something new – it humbles you and builds self-confidence.

Writing feels good

Since I was in seventh grade, I’ve wanted to be a writer. I figured there’s no better time than now to dust off my dreams and give it a go. It’s more viable than ever to be a content creator, so let’s give it a shot.

In order to give myself a fair chance, I knew I would have to start writing a fuckton more. This month was the first challenge to get my feet wet again…and it has felt amazing.

Writing is like lifting weights for your brain. There’s almost nothing harder to do when you don’t want to do it, but it feels so good and natural once you build momentum.

I struggled during the first ten days of the month. I wrote nothing. Despite knowing that this is the one career path I’ve always wanted to pursue, I couldn’t motivate myself to start. 

Finally, the pressure mounted and, knowing I had to crank out a ton of content in a small period of time, I started a daily practice. I wrote – when I wanted to and when I didn’t. Eventually, the habit formed and it became easier.

I’ve got a loooong way to go, but I’m happy that Sober October reconnected me with my passion.

It really is about the little things

Not eating for 48 hours can be an emotional journey. By the time dinner rolls around on the first night of fasting, your mind starts to play tricks on you. It pulls out every conceivable rationalization, trying to convince you to throw in the towel and grab a burrito. 

But if you can push through the resistance, there are a lot of perks to fasting. For example, the exercise has many health benefits – including reducing inflammation, improving blood pressure, and weight loss – and improves cognitive performance.

While the well-being and longevity components of fasting drew me in, it’s the unexpected byproducts that will keep me coming back. 

See, when you temporarily deprive yourself of one of the few things you need to live, it makes you start to appreciate the little things in life. By not eating, all of your senses are heightened. All of a sudden, music sounds better. You start to notice the simple beauty in trees and sunsets. You start to find humor in trivialities.

The blue, red, and green looked really nice when I was 40+ hours into a fast

Then, once you finally get to the point of breaking fast, food has a whole new meaning. Those first bites aren’t about quelling your hunger or curing your boredom – they are about fueling your body. Fasting transforms your relationship with food and hunger in short order.

I usually break my fast with fresh fruit and, believe me, nothing tastes better than a juicy apple after two days of eating nothing. Once I become satiated, my perspective on eating shifts significantly – at least temporarily. Instead of constantly shoveling calories in my mouth when I’m idle or the slightest bit hungry, I start to eat with intention and gratitude. 

In fact, I felt more grateful, patient, and grounded throughout this entire month and I believe the four 48-hour fasts played a large role. 

If a book sucks, put it down

You ready for me to brag? Ok, here we go: I’ve read 40 books this year. I know, I know, I’m an overachieving nerd. 

Image result for bragging book reading memes

While I’m happy with my focus on reading this year, I still am likely to fall short of my annual goal: I wanted to read a book each week in 2019. Why have I fallen off track? My Ego has gotten in the way (yet again).

See, I’m a competitive and overly self-critical person. This disposition has helped me accomplish important tasks and projects, but when it comes to reading books, it has its drawbacks.

Because I hate admitting defeat, I sometimes soldier on through books that don’t have my full attention. I try to power through even though I constantly lose focus and have to reread paragraphs.

Sober October helped me realize how foolish this behavior is. There are more amazing books published now than you can ever read in your lifetime…and countless more are released daily. So when you choose to struggle through a book that doesn’t fascinate you, you’re robbing yourself of the opportunity to dive into a book you’d love.

There is nothing better than cozying up with a page-turner you can’t put down. A book that keeps your mind engaged and delivers “aha” moments, suspense, memorable stories, and new perspectives is invaluable. And there are countless waiting for you to read!

At the end of the day, life is too short to be stuck reading a book you’re not passionate about. If a paperback you’re sitting down with doesn’t draw you in within the first 50 pages, don’t be afraid to set it aside. You can always revisit it. 

Do your best to only read things that get you excited.


Life after Sober October

Now that Sober October has ended, I need to evaluate my usage of drugs and see how they fit in going forward. My gut tells me that alcohol and caffeine will not play a role in my life for the time being. 

Sure, I’ll probably have a beer or cocktail here and there, but binge drinking is a thing of the past. I will also limit my caffeine intake to one green tea or decaf coffee per day. I enjoy those beverages but see no upside to using excess caffeine.

Cannabis is an interesting one. I’ve smoked a lot of weed in the last couple of years, especially as I’ve decreased my alcohol consumption. I find it to be a helpful tool for relaxation, creativity, and introspection.

Sober October has shown me that I need to be more careful with how I use this substance though. I have a tendency to smoke weed too frequently and fall into ruts. 

As for the other habits, I plan to continue with my boxing work. I want to continue to build on the fundamentals and develop more endurance. I plan to incorporate at least one prolonged fast each month, as well.

Writing and original content creation will definitely be a focus of mine for the foreseeable future. I’m starting to hit my groove and want to see how far I can go. I love reading, so that’s not going anywhere either.

As I mentioned earlier, I thoroughly enjoy the monthly challenges like Sober October because they have an end date and accountability built-in – they’re a great way to test drive new habits. So, for the month of November, we’re going to keep it going.

The November 2019 Challenge

Fitness: Run at least one mile each day

One of my favorite YouTubers did this 30-day challenge a few months ago and raved about it. As someone who has been traditionally bad at cardio, I think this is a worthy way to get back into running shape without torturing myself. Plus, there a ton of health and cognitive benefits to running, especially early in the day.

Fitness: Do a minimum of 20 minutes of heavy bag work 15 times

I picked up boxing this month and have had a great time. It’s been fun to improve and push myself through some intense workouts. This goal will be my way of continuing to improve, stay in shape, and practice the sport. 

Creation: Create, edit and publish at least 10 YouTube videos

I’ve been thinking about starting a YouTube channel for a couple of months now. I think it would be fun to create videos that accompany the blog posts I write and help teach what I’ve learned in entrepreneurship, podcast production, writing, and other endeavors. The hardest part seems to be starting, so here’s my pledge. 

Creation: Write 500+ words daily

I’m happiest when I’m creating, even if it’s garbage. This past month, I challenged myself to write 20 articles and reconnected with my passion for writing. This month, I’m going to take it even further and turn it into a daily practice. I’m going to commit and “go pro” as Steven Pressfield would say.

Creation: Rewrite and publish 20 blog posts

Last month, I wrote a lot of stuff. All of it needs more love and attention before it’s released. I’m going to rewrite, edit, and publish 20 blog posts this month. Most of them will be published here, on my personal blog, so stay tuned. 

Friendship: Write 30 handwritten notes to friends

Staying in touch gets harder each day that passes. Yet, my favorite moments are spent connecting with people I love. Nothing is more valuable. My aim is to show thirty friends how much I appreciate their companionship. 

Connection: Start a conversation with 30 strangers

Even though I live in a large apartment complex, in a big neighborhood, in a massive city, I often feel disconnected and lonely (working from home doesn’t help my cause). I feel more energetic when I’m social, so I’m going to do my best to get to know thirty new people I cross paths with. These can be Uber drivers, baristas, waiters, people on the train, or whoever is up for a quick chat.

Service: Volunteer at least four times (minimum of two hours each)

I’m the most selfish person I know. So, in an effort to distance myself from my narcissism and give back to the local community, I am going to dedicate some of my time to help those less fortunate than me. I’m not sure what this is going to look like just yet, but I’ll be sure to report back my experience.


I think I may have bitten off more than I can chew with this month’s commitment, but if you’re not scared, you’re not trying hard enough.

Let’s get it.

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