7 Things I Learned Working out 365 Days in a Row

As of today, November 25, 2020, I’ve worked out 365 days in a row. That’s more than 300 Peloton rides, 100+ workouts with a trainer, lots of long walks, and moving for at least 30 minutes each day, closing all the rings on my Apple Watch. This is my story, things I’ve learned along the way, and some of the tools that helped me in my journey.
If you had told me that I would have reached a goal like this, I would have laughed at you and emphatically said, “NO WAY!!”
I’ve struggled with my weight all of my life. Growing up, I was the funny chubby kid that got picked last for every team in PE classes. I’m known for many things but being active, athletic, or consistent with habits of any kind is not at the top of the list. Throughout my 20s and early 30s, I was a pro-yo-yo dieter. I would work up some courage to start some new fad diet, find myself a trainer, and I’d go hard for a couple of months and lose weight only to burn out and gain it all back within a matter of months. It was a pattern that would repeat itself many times and something I never thought I would be able to overcome.
Before we get too far, let me be clear: I am all for body positivity and do not intend to fat shame myself or anyone else. I believe everyone is beautiful, and there’s far too much pressure on all of us associated with weight and appearance. Beautiful people come in all shapes and sizes, and a number on a scale doesn’t define us. It’s the weight of our character and the depth of who we are that truly matters. Unfortunately, society and social media do a great job of reinforcing ideas about how we “should” look, and that’s caused a lot of people, including myself, a lot of shame. I’m not for that at all.
That said, I do believe that we should all aspire to be the healthiest versions of ourselves that we can be. I believe that the excess weight I carried for so many years was symptomatic of other things I was carrying from my past: religious baggage, shame about my sexuality, and whole a host of other things I’ve been working with a therapist to process. For me, this journey wasn’t about trying to get a 6-pack or fitting into a particular size of clothes; it was about wanting to release what wasn’t serving me any longer and creating habits that would help me become the best version of myself in body, mind, and spirit.
After I moved to New York City from Chicago in 2018, I committed to making a fresh start. I joined a gym, started working out with a trainer, and went on a ridiculous diet where all I ate was basically chicken breasts, vegetables, eggs, and cottage cheese. I saw success, but it was quickly sidelined by a busy travel schedule, starting a new job, and falling back into old routines. I skipped the gym for a few months, started to put back on some of the weight, and ended up back with my trainer after a three-month hiatus, desperately trying to make up for the lost time.
He agreed to work out with me again but was very clear that I would only continue to have the same experience and results unless I learned how to make fitness and taking care of myself a habit. And he stressed that until I made it a habit, my efforts would be in vain. Those words stuck with me long after I had stopped going to the gym again, and I never really did believe I’d ever be able to make a regular habit of working out and taking care of myself. When any minor inconvenience came in the way: work, travel, being hungover, or just feeling plain lazy, I’d fall out of the routine.
As another year lapsed between my last fitness craze, I felt defeated.
In 2019, I took some pretty incredible trips. I was in Paris, Berlin, Munich, Capri, and London. During one of my trips, a friend commented on an Instagram photo that they loved seeing where I was but wanted to see me in the pictures. If you scroll through my feed, you’ll see I am barely in any of the photos from all of those trips. The truth is, I didn’t like what I saw when I saw myself in the pictures and didn’t want to be seen. If there were any pictures of me, it was with groups of people where my head would be poking out from behind the cover of other people.
I wanted to change but felt like being the funny chubby guy would be my lot in life. I’d tried and failed so many times already; why not just settle into the role and stop fighting myself?

Then, one fateful flight home from San Francisco, I picked up a copy of the book Atomic Habits by James Clear. My former’s trainer’s words about habits were ringing in my ears, and I knew that if I wanted to change my life, I would need to change the habits and the systems that had gotten me to where I was.
In the book, he says, “Every action you take is a vote for the type of person you wish to become. No single instance will transform your beliefs, but as the votes build up, so does the evidence of your new identity. This is one reason why meaningful change does not require radical change. Small habits can make a meaningful difference by providing evidence of a new identity. And if a change is meaningful, it is actually big. That’s the paradox of making small improvements.”
Approaching my 37th birthday last year, I decided it was time to make some small improvements and address the mountain ahead of me with small everyday decisions. My building had a gym with machines, weights, and a Peloton bike, and I started to go on a semi-consistent basis. To be honest, the idea of starting a new fitness journey made me want to quit before I even started. Knowing I was at the heaviest I’d ever been and knowing how much work it would take to get to where I wanted to be, I wasn’t even sure if I could put myself through the cycle again.

I had seen a couple of people in my building’s gym working out with trainers, and I posted to our message board, seeing if anyone could recommend a trainer to work out with me. Anthony replied to me, and our first workout was on November 25, 2019, my 37th birthday.
Like my former trainer, he was insistent on this new journey being grounded in goals that weren’t necessarily about a number on the scale but about a life I was trying to create for myself. He would push me in the gym, but it was on me to do the work outside of the time we were together to support myself on my journey to wholeness.
The following day, I woke up and decided to hop on the Peloton for 20 minutes. The day after, since I already had a streak going, I went back downstairs and did a walk on the treadmill. I dusted off my Apple Watch and decided I should use it to start tracking my progress.
The next day I did a workout with Anthony, and the day after that I got back on the Peloton.
Two weeks in, I was already wondering how long it would be before the streak would be broken, and there were indeed a lot of obstacles in the way: namely traveling home for the holidays and then work travel that would resume at the start of the year. If two things were the biggest hindrances to my goals, it was traveling and being out of a routine.

I knew the only way I could succeed was by having a plan for how I’d stay on track while I was home for the holidays. I packed workout clothes and shoes and mapped out how I would workout each day. I found a hotel with a Peloton bike and joined a $20/month gym by my parent’s house and committed to myself that I would keep moving. The only hangup would be Christmas Day: no gyms were open. I ended up going to a walking trail, and when I got the notification on my Apple Watch that I closed my rings, I realized it was December 25: I had made it an entire month!

As 2020 kicked off, I was more motivated and believed this would be my year. The longest I had ever gone with a fitness streak was about 4 months, so my short-term goal was to make it to April. Then I’d know this was a serious change. (Little did I know what would happen in March.)
In addition to the daily workouts, I started journaling and meditating each morning. I had a handful of books I’d read, I’d give myself 10–15 minutes to be still, and I would take some time to journal my thoughts and express gratitude. I later added the habit of not looking at my phone for the first 30 minutes I was awake. Working on my body was one thing, but I knew there was inner work that needed to be done, too.
At the end of January, I traveled to San Francisco for work and knowing I had survived a trip home without breaking the streak, I was confident I had this one in the bag. I booked SoulCycle classes with some co-workers and hit up the hotel gym for the week, and successfully made it through another trip.
I coasted through February, amazed that I had made it three months. I started to notice a difference on the scale and in my clothes, and I was excited about my progress.
Then, March rolled around, and the world started to change. I remember the day my trainer showed up at the gym wearing a mask and hearing we may be going towards a shutdown. If there was ever going to be anything to stop me in my tracks, this would be it. If the building gym closed, that meant I couldn’t work out with my trainer or ride the Peloton, and I knew that would be the end of the streak for me.
The day they did announce that NYC would be moving to stay at home orders, I ordered a Peloton, thinking I would return it within 30 days once things were “back to normal” (wishful thinking). My trainer and I shifted to virtual workouts over Zoom, and I was able to order a kettlebell and yoga mat for in-home workouts before they were out of stock on Amazon.

I’ll be candid, if there was ever a time in all of this where I could have justifiably given up, it was in those early weeks of the pandemic in March and April. I was scared like everyone else; New York City came to a screeching halt, I had no access to the tools that I had been depending on thus far, and I was only 4 months into my streak (when my usual fitness habits tended to die.) But, I had made it this far and wasn’t going to quit now.
After a couple of weeks, my trainer and I started to meet outside in a park or my rooftop to workout. We both wore masks and kept socially-distant and made do with what we had available to us. The outdoors became my gym for the next six months, and the Peloton and all of the amazing instructors became my community of coaches and cheerleaders.

In June, I welcomed Matias into my life. I was desperately lonely and decided it was time to have a dog. Getting him added another layer to my daily routine because he needed to get outside and walk. His energy level was (and still is) through the roof, and he’s made me more of a morning person and added more activity to my day outside of my daily workouts.

In August, gyms opened back up in New York City, and I decided it was time to mix things up a bit. I found Tom via Instagram, and we started working out in a real gym. It was a game-changer to be back in a gym and have access to weights and machines. Being in the gym also brought me into a new community of friends who have supported me and encouraged me in my journey.

Over the last three months, I’ve kept consistent, continued to see progress, and have taken on new challenges — like running! — and have found that this habit is now a part of my everyday routine. It’s no longer as much of a challenge to get moving every day. Even with the possibility that gyms may shut down again, I’m not scared of falling out of my routine because I’ve done it before and know I can keep going. Taking time for myself and working out is something I look forward to now and is part of my daily routine, like brushing my teeth or having iced coffee in the morning. I can do it without thinking about it.

And here we are today, day 365. There were days in this journey that I never thought I’d make it to this point, but I did, and I’m so grateful. I’ve done something I never believed I could accomplish, and I’m freaking proud of how far I’ve come. I still have a ways to go, but know that if I’ve done this, I can literally do anything.
So, what did I learn through this process? Glad you asked.
1 — You can work out and eat healthy as much as you want, but true health and wellness involves body, mind, and spirit.
As much as I would like to say that diet and exercise are all it takes, that’s only half true. The one thing I’ve learned about myself in the last 365 days is that proper health and wellness involves all areas of our life. In addition to working out, I embraced a mediation practice, found ways to turn down the noise in my life, learned to say no to things and people that weren’t pushing me toward my goals, and faced things in myself and my past that I would typically want to overlook. I was fortunate to find a great therapist and added weekly sessions with him to help me look inward and see how my past impacted my current circumstances and how I could work toward creating a new vision for myself and my future.
2 — I know I’m worthy of being loved just as I am.
I’ve known the pain of self-rejection, have dealt with feelings of shame and suffered from severe body image issues all of my life. I didn’t know how to love myself or the person I saw in the mirror. Through this process, I’ve learned that what makes me lovable isn’t anything external or a number on a scale, but truly embracing all of the parts of me and learning to be my whole, authentic self. It’s not about being some version of myself that I think others want me to be, but learning to be my full self and not apologizing for it. I’ve still got a lot of work to do in this space, but my daily practices help keep me focused on the art of self-compassion. I know I am just as lovable now as I was 365 days ago; the only thing that’s really changed is how I see myself.
We are all worthy of being loved — stretch marks and all.
3 — Routines will keep you grounded.
I’m very grateful I started this streak 3 months before the pandemic. I really believe having the daily habit of moving kept me grounded when so much of life was in chaos this year. Taking time for myself every day in whatever form it looked like helped keep me focused. In addition to working out, journaling, meditating, and reading, all helped me look inward when the world outside was spinning out of control.
So much of our life is routine, even when we don’t realize it. Routines keep you grounded and focused on your goals. Having control over your routines gives you the power to create the life you want to experience.
Want to change your life? Change your daily routines. It’s honestly that simple.
4 — Find something you enjoy doing and do it often.
I never played sports as a kid and never really liked much physical activity for that matter, but I recognize now that it’s so important to find something you enjoy doing that keeps you active. I’ve discovered I love indoor cycling. Getting a Peloton has been a game-changer for me, and it’s something I really do enjoy. I love the classes, the instructors, the theme rides, and the supportive community on the platform. And who knows? Maybe I’ll be brave and start cycling outdoors in the future.
Even after a year of working out, the gym isn’t necessarily my favorite place to be, but I love being on a bike — it’s something I enjoy that doesn’t feel like work.
Find your thing and go do it!
5 — Surround yourself with a supportive community
Finding a supportive community isn’t always easy, but it’s so necessary when you’re on a journey like this. For me, sharing my progress on Instagram was a way to hold myself accountable and receive a flood of encouragement from friends and family following me. Especially in a year where I haven’t been able to travel or see many people, I cannot tell you how much the encouragement I received from friends (and strangers!) on social media made a difference.
You can’t make a journey like this alone. You won’t succeed. Find your tribe, find your people, and lean into them. Don’t be afraid to ask for help and call in professionals when you need it.
You’re only as strong as the people you surround yourself with, so choose your close companions wisely.
6 — Eat the damn carbs and drink wine without shame
Nutrition is so important. I’m not a dietician, so don’t take my advice, but having done so many restrictive diets in the past and I will tell you that life is too short to not enjoy what you enjoy. Cutting out foods, guzzling shakes, eating prepared foods, counting calories or points, and every other method we’ve tried to watch what we eat is just bound to end in disaster, for me anyway. Through the last 365 days, I have become more aware of what I eat. I’ve learned how to cook. I’ve been more disciplined about what I eat, but I have still had carbs, wine, pizza, and everything else. And guess what? I still lost weight. In the end, you have to find what works for you and be aware of how food impacts your goals. Diet and nutrition matter as much as how much you move and workout. Just learn to be kind to yourself.
7 — Don’t measure success with a scale
When I started out on this journey a year ago, I did have a particular number that I hoped to see on the scale. I didn’t make that goal. I’m not far from it, and I’m okay with that. I am the skinniest I’ve been since I was 21, so I’ll gladly accept that. I’m wearing pants that are 4 sizes smaller than when I started and have gone down 2 shirt sizes. I could say how much weight I’ve lost, but I never want this journey to be about a number.
For me, I feel like I’ve gained so much more than I’ve lost. I’ve gained confidence — I set a goal that seemed impossible, and I crushed it. I’ve learned to take risks and try new things. I’ve pushed myself to keep going when all I wanted to do was give up. And I somehow managed to lose and keep weight off during a global pandemic. That’s something to celebrate. To me, that’s the ultimate success.
In conclusion…
If you’ve made it this far, God bless you, and thanks for reading about my journey. Like I said about 3,400 words ago, I’m the last person in the world that would have ever believed that I would have achieved a goal like this, and trust me when I say that if I can do it, you can too!
What’s next for me? I’m going to keep going. In a lot of ways, this is just Day 1. I’ve got more work to do, and I’m going to set some new goals for myself built on the habits I’ve created in the last 365 days.
I’ll close with one more quote from Atomic Habits:
All big things come from small beginnings. The seed of every habit is a single, tiny decision. But as that decision is repeated, a habit sprouts and grows stronger. Roots entrench themselves and branches grow. The task of breaking a bad habit is like uprooting a powerful oak within us. And the task of building a good habit is like cultivating a delicate flower one day at a time.
Here’s to Day 366 and beyond.
